- Fatty acid-indole fluorescent derivatives as probes to measure the polarity of interfaces containing gangliosides
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The fluorescence emission properties of three indole derivative probes N-2-(3-indolyl)ethyl-tetradecanoyl carboxamide (N-myrTAM), 2-tetradecanoyl carboxamidyl-3-(3-indolyl)propanoic acid (N-myrTRP) and 11-N(2-[3-indolyl]ethylamino)-9-en-methyloxy carbonyldecenate (11-TAMundec) were studied in solvents of different polarities in pure lysophosphatidylcholine micelles (lysoPC) and in total brain gangliosides (TBG) micelles using steady-state and phase-modulation fluorometry. By comparing the fluorescence emission spectra in solvent mixtures with the spectra in lipid micelles it is concluded that the probes detect a more polar environment in TBG compared to lysoPC micelles. Quenching experiments with acrylamide indicate that the indole group of N-myrTRP and N-myrTAM are more exposed to the aqueous medium than the indole group of 11-TAMundec both in lysoPC and TBG micelles. Quenching of the indole fluorescence with brominated fatty acid at the position 9-10 of the acyl chain is in the following order: 11-TAMundec > N-MyrTAM > N-MyrTRP in lysoPC micelles whereas in TBG micelles only 11-TAMundec fluorescence is quenched. Based on the results of accessibility of the probes to the aqueous quencher and the dielectric constant calculated for their environment, we estimated the surface to core polarity gradient of the micelles. The polarity gradient is higher in TBG micelles compared to lysoPC micelles.
- Bagatolli, Luis A.,Montich, Guillermo G.,Ravera, Mario,Perez, Jorge D.,Fidelio, Gerardo D.
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- Synthesis and biological evaluation of fatty acyl ester derivatives of 2′,3′-didehydro-2′,3′-dideoxythymidine
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A number of 5′-O-fatty acyl derivatives of 2′,3′- didehydro-2′,3′-dideoxythymidine (stavudine, d4T) were synthesized and evaluated for anti-HIV activities against cell-free and cell-associated virus, cellular cytotoxicity, and cellular uptake studies. The conjugates were found to be more potent than d4T. Among these conjugates, 5′-O-12- azidododecanoyl derivative of d4T (2), displaying EC50 = 3.1-22.4 μM, showed 4- to 9-fold higher activities than d4T against cell-free and cell-associated virus. Cellular uptake studies were conducted on CCRF-CEM cell line using 5(6)-carboxyfluorescein derivatives of d4T attached through β-alanine (9) or 12-aminododecanoic acid (10) as linkers. The fluorescein-substituted analog of d4T with long chain length (10) showed 12- to 15-fold higher cellular uptake profile than the corresponding analog with short chain length (9). These studies reveal that conjugation of fatty acids to d4T enhances the cellular uptake and anti-HIV activity of stavudine.
- Agarwal, Hitesh K.,Loethan, Kelly,Mandal, Deendayal,Doncel, Gustavo F.,Parang, Keykavous
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- Pyridinium based amphiphilic hydrogelators as potential antibacterial agents
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The numerous applications of hydrogelators have led to rapid expansion of this field. In the present work we report the facile synthesis of amphiphilic hydrogelators having a quaternary pyridinium unit coupled to a hydrophobic long alkyl chain through an amide bond. Different amphiphiles with various hydrophobic chain length and polar head groups were rationally designed and synthesized to develop a structure-property relation. A judicious combination of hydrophilic and hydrophobic segments led to the development of pyridinium based amphiphilic hydrogelators having a minimum gelation concentration of 1.7%, w/v. Field emission scanning electronic microscopy (FESEM), atomic force microscopy (AFM), photoluminescence, FTIR studies, X-ray diffraction (XRD) and 2D NOESY experiments were carried out to elucidate the different non-covalent interactions responsible for the self-assembled gelation. The formation of three-dimensional supramolecular aggregates originates from the interdigitated bilayer packing of the amphiphile leading to the development of an efficient hydrogel. Interestingly, the presence of the pyridinium scaffold along with the long alkyl chain render these amphiphiles inherently antibacterial. The amphiphilic hydrogelators exhibited high antibacterial activity against both Gram-positive and Gram-negative bacteria with minimum inhibitory concentration (MIC) values as low as 0.4 μg/mL. Cytotoxicity tests using MTT assay showed 50% NIH3T3 cell viability with hydrogelating amphiphile 2 up to 100 μg/mL.
- Brahmachari, Sayanti,Debnath, Sisir,Dutta, Sounak,Das, Prasanta Kumar
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- Synthesis of the enantiomers of 13-methylheptacosane, the sex pheromone of pear psylla, Cacopsylla pyricola
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An efficient and gram-scale enantioselective synthesis of (R)- and (S)-13-methylheptacosane, the sex pheromone of pear psylla, has been developed. The key steps of the approach included Evans' chiral auxiliaries and Wittig coupling of chiral phosphonium salt with aldehyde.
- Yuan, Gucheng,Yang, Yuxiong,Liu, Jiawei,Bian, Qinghua,Wang, Min,Zhong, Jiangchun
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- Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids
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We develop a palladium-catalyzed H/D exchange reaction with 8-aminoquinoline as the directing group as well as D2O as the source of deuterium atom and solvent. This reaction achieves selectively H/D exchange at the ortho-C-H of aromatic amides and the β-C-H of aliphatic amide. Ortho-deuterated aromatic acids and β-deuterated aliphatic acids are obtained by removal of the directing group. And a possible mechanism is also proposed.
- Zhao, Donghong,Luo, Haofan,Chen, Binhui,Chen, Wenteng,Zhang, Guolin,Yu, Yongping
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- Temperature Control of Sequential Nucleation–Growth Mechanisms in Hierarchical Supramolecular Polymers
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Upon cooling insolution, chiral triarylamine tris-amide unimers produce organogels by stacking into helical supramolecular polymers, which subsequently bundle into larger fibers. Interestingly, circular dichroism, vibrational circular dichroism, and AFM imaging of the chiral self-assemblies revealed that monocolumnar P-helical fibrils formed upon fast cooling, whereas bundled M-superhelical fibers formed upon slow cooling. The mechanistic study of this structural bifurcation reveals the presence of a strong memory effect, reminiscent of a complex stepwise combination of primary and secondary nucleation-growth processes. These results highlight the instrumental role of sequential self-assembly processes to control supramolecular architectures of multiple hierarchical order.
- Osypenko, Artem,Moulin, Emilie,Gavat, Odile,Fuks, Gad,Maaloum, Mounir,Koenis, Mark A. J.,Buma, Wybren Jan,Giuseppone, Nicolas
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- Homologous, long-chain alkyl dendrons form homologous thin films on silver oxide surfaces
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As suggested by X-ray crystal structures, homologous, long-chain alkyl dendrons with three carboxyl groups form thin films on silver oxide surfaces, which give reflection-absorption infrared spectra that show a linear increase in intensities of methylene C-H stretching absorptions. The Royal Society of Chemistry 2005.
- Williams, Andre A.,Day, B. Scott,Kite, Brett L.,McPherson, Melinda K.,Slebodnick, Carla,Morris, John R.,Gandour, Richard D.
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- Synthesis and In Vitro Evaluation of Inherent Properties of L-Glutamic Acid Based Dendritic Lipopeptide Oligomers
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Purpose: The present study reports synthesis, characterization and in vitro evaluation of physicochemical and biological properties of dendritic lipopeptide oligomers comprising L-glutamic acid dendrons and myristoyl tails such that termini of the molecules carry carboxylic ester, carboxylic acid or alcohol functions, which account for nonpolar neutral, polar anionic and polar neutral surfaces, respectively. Methods: Reactions adopted in the current work were fairly rapid, moderately simplified and required fewer coupling reagents. As inherent physicochemical and biological properties depend upon structural details, synthesized compounds were tested for the presence of foaming, nanoparticle formation, antibacterial and anticancer potential, if any. Results: The synthesized nonpolar molecule demonstrated potential to form self-assembled polymeric nanoparticles, whereas the polar molecules demonstrated surfactant-like properties. None of the synthesized molecules demonstrated any inherent antibacterial activity against gram-positive as well as gram-negative bacterial strains, but compound with hydroxyl termini showed anticancer activity hint as a result of preliminary screening. Conclusion: The synthesized molecules demonstrate potential for their application as drug delivery materials and hold scope for further investigations.
- Hegde, Namita,Juvale, Kapil,Prabhakar, Bala
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- Synthesis, characterization and mixed micellization study of benzene sulphonate based gemini surfactant with sodium dodecyl sulphate
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Herein, we have shown the mixed micelle formation between anionic benzene sulphonate (viz., sodium 4,4′-(16,25-dioxo-15,17,24,26-tetraaza-hexatriacontane15,26-diyl)dibenzenesulphonate [BSC14-C6-14CSB]and sodium 4,4′-(18,27-dioxo-17,19,26,28-tetraaza-tetracontane15,26-diyl)dibenzenesulphonate [BSC16-C6-16CSB])with conventional anionic surfactant (sodium dodecyl sulphate [SDS])by conductivity and fluorometry methods. The conductivity measurements were done over a range of mole fractions of SDS at different temperatures to study the mixed micellization and thermodynamic parameters, while fluorescence measurements were performed over entire range of mole fraction of SDS in order to observe the aggregation and micro-polarity. The conductometric study confirms the synergism in all mole fractions of SDS with [BSC14-C6-14CSB]and [BSC16-C6-16CSB]at all temperatures. The Rubinghs regular solution theory (RST)was employed to evaluate micellar mole fraction, X1, ideal micellar mole fraction, Xideal, interaction parameter (β), activity coefficients (f1, and f2)for both mixed micelles systems and Gibbs excess free energy (GE). The GE values are negative for entire mole fraction range suggesting the formation of stable mixed micelles. In addition to this, other thermodynamic parameters like Gibbs free energy change of micellization (ΔGmic), enthalpy change of micellization (ΔHmic)and entropy change of micellization (ΔSmic)were evaluated. Also, the aggregation number (Nagg)in micelles was calculated using pyrene probe fluorescence measurement. The binding constant, dielectric constant and micropolarity of mixed systems of SDS + [BSC14-C6-14CSB]and SDS + [BSC16-C6-16CSB]binary mixtures were obtained from the ratio of peak strength (I1/I3)from the pyrene probe fluorescence emission spectra.
- Wani, Farooq Ahmad,Khan, Abbul Bashar,Alshehri, Abdulmohsen Ali,Malik, Maqsood Ahmad,Ahmad, Rabia,Patel, Rajan
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- Synthesis of New Lipophilic Cyclopentafullerenes from Long-Chain Alka-2,3-dienoates
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Abstract: Long-chain alka-2,3-dienoates were synthesized via the Wittig reaction fromthe corresponding fatty acids, and the subsequent triphenylphosphine-catalyzed[3+2]-cycloaddition to fullerene C60 afforded newlipophilic cyclopentafullerenes.
- Biglova, Yu. N.,Mukhametyanova, A. F.,Nugumanov, T. R.,Sakhautdinov, I. M.
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- Synthesis and characterization of gemini ester surfactant and its application in efficient fabric softening
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Cationic surfactants with ester groups are considered as an important class of hydrolyzable and biodegradable materials utilized in multiple fields. In this work, a new type of gemini cationic surfactant containing two ester groups, N1,N1,N4,N4-tetramethyl-N1,N4-bis(2-(hexadecanoyloxy)ethyl)butane-1,4-diammonium bromide (TBDB), an 18-4-18 type gemini surfactant, has been successfully synthesized in a three-step reaction from natural palmitic acid, thionyl chloride, N,N-dimethylethanolamine and 1,4-dibromobutane. The maximum yield reaches about 94% under the optimum reaction conditions. The structures of the final product were characterized by FT-IR, 1H NMR and mass spectra. The critical micelle concentration (CMC) and surface tension of its aqueous solution are ~3.09 × 10? 5 M and 38.4 mN/m at 25 °C, respectively, and the gemini ester surfactant shows high benzene solubilization capacity. When treating cotton fabric, it can effectively retain the whiteness and surface hydrophilicity of the fabric while exhibiting a higher fabric-softening ability than the corresponding monomeric surfactants, due to its more efficient adsorption onto the fabric surface. The discovery suggests that this kind gemini ester surfactant is promising with potential applications in the fields of surfactants and coatings.
- Liu, Dantong,Yang, Xin,Liu, Peng,Mao, Taoyan,Shang, Xiaoqin,Wang, Liming
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- Characterization of the molecular packing, thermotropic phase behaviour and critical micellar concentration of a homologous series of N-acyltaurines (n = 9–18). PXRD, DSC and fluorescence spectroscopic studies
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N-acyltaurines (NATs) are amides of fatty acids that can be structurally related to endocannabinoids. They show interesting physiological and pharmacological properties. We have synthesized a homologous series of NATs with saturated acyl chains (n = 9–18) and investigated their supramolecular structure and thermotropic phase transitions by powder X-ray diffraction (PXRD) and differential scanning calorimetry (DSC). The d-spacings obtained from PXRD increase linearly with chain length with an increment of ~0.847 ? per additional CH2 moiety suggesting that NATs adopt a tilted bilayer structure with similar packing in crystal lattice. Results obtained from DSC studies indicate that the endothermic transition temperature (Tt) of NATs showed a gradually increasing trend with increasing acyl chain length. The enthalpy (ΔHt) and entropy (ΔSt) of transition show odd-even alternations with odd-chain compounds having higher values than the even-chain compounds. The critical micellar concentration (CMC) of NATs was determined in water at room temperature by fluorescence spectroscopy by monitoring the spectral changes of 8-anilinonaphthalene-1-sulfonic acid (ANS). The CMCs of NATs were found to decrease with increase in acyl chain length. The present results provide a thermodynamic and structural basis for investigating the interaction of NATs with other membrane lipids and proteins, which in turn can shed light in understanding how they function in vivo (in biological membranes).
- Arul Prakash, Sukanya,Kamlekar, Ravi Kanth
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- Synthesis and Properties of 4,4′-Di(n-Tetradecyl) Diphenyl Methane Disulfonate Salt
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The gemini surfactant, sodium 4,4′-di(n-tetradecyl) diphenyl methane disulfonate, has been synthesized in four steps with high yield and only one isomer. The structures of intermediate products were analyzed by 1H-NMR spectrometry and elemental
- Xu, Kai,Wang, Danping,Xu, Hujun
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- Translation of Mycobacterium Survival Strategy to Develop a Lipo-peptide based Fusion Inhibitor**
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The entry of enveloped virus requires the fusion of viral and host cell membranes. An effective fusion inhibitor aiming at impeding such membrane fusion may emerge as a broad-spectrum antiviral agent against a wide range of viral infections. Mycobacterium survives inside the phagosome by inhibiting phagosome–lysosome fusion with the help of a coat protein coronin 1. Structural analysis of coronin 1 and other WD40-repeat protein suggest that the trp-asp (WD) sequence is placed at distorted β-meander motif (more exposed) in coronin 1. The unique structural feature of coronin 1 was explored to identify a simple lipo-peptide sequence (myr-WD), which effectively inhibits membrane fusion by modulating the interfacial order, water penetration, and surface potential. The mycobacterium inspired lipo-dipeptide was successfully tested to combat type 1 influenza virus (H1N1) and murine coronavirus infections as a potential broad-spectrum antiviral agent.
- Sardar, Avijit,Lahiri, Aritraa,Kamble, Mithila,Mallick, Amirul I.,Tarafdar, Pradip K.
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supporting information
p. 6101 - 6106
(2021/02/01)
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- ABUSE-RESISTANT LONG-ACTING RELEASE OPIOID PRODRUGS
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There are provided, prodrugs of opioid such as levorphanol or morphine, having enhanced physical and chemical stability to resist tampering and to make long- acting release formulations, and pharmaceutically accepted salts and solvates thereof. There are also provided methods of using the disclosed compounds as abuse deterrent products.
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Paragraph 93; 101
(2020/07/31)
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- Catalyst for synthesizing acyl chloride compounds and application thereof
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The invention relates to a catalyst for synthesizing an acyl chloride compound and application of the catalyst. The structural formula is as shown in the specification, and in the formula, R is alkali of which the carbon atom number is 1-12. The catalyst is capable of effectively increasing the product yield, improving the production efficiency and lowering the production cost of acyl chloride, and has wide application prospects. The invention further provides a method for synthesizing acyl chloride with the catalyst.
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Paragraph 0048-0052
(2020/10/20)
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- Novel fatty acid-thiadiazole derivatives as potential antimycobacterial agents
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The discovery of antibiotics around the middle twentieth century led to a decrease in the interest in antimycobacterial fatty acids. In order to re-establish the importance of naturally abundant fatty acid, a series of fatty acid-thiadiazole derivatives were designed and synthesized based on molecular hybridization approach. In vitro antimycobacterial potential was established by a screening of synthesized compounds against Mycobacterium tuberculosis H37Rv strain. Among them, compounds 5a, 5d, 5h, and 5j were the most active, with compound 5j exhibiting minimum inhibitory concentration of 2.34?μg/ml against M.tb H37Rv. Additionally, the compounds were docked to determine the probable binding interactions and understand the mechanism of action of most active molecules on enoyl-acyl carrier protein reductases (InhA), which is involved in the mycobacterium fatty acid biosynthetic pathway.
- Mali, Jaishree K.,Sutar, Yogesh B.,Pahelkar, Akshata R.,Verma, Preeti M.,Telvekar, Vikas N.
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p. 174 - 181
(2019/11/03)
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- Long-chain azobenzene compound, preparation method and applications thereof
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The invention discloses a long-chain azobenzene compound, a preparation method and applications thereof, wherein the structure of the compound is represented by a formula (I), and n is an integer of 10-14. According to the invention, the compound has cont
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Paragraph 0035; 0037; 0041; 0043; 0045; 0047; 0049; 0051
(2020/01/12)
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- The effect of vicinal di-halo substituents on the organogelling properties of aromatic supramolecular gelators and their application as soft templates
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A pronounced effect of vicinal dihalogen substituents on the gelling properties of aromatic low molecular weight organogelators is reported. A new family of N,N′-(4,5-dihalogen-1,2-phenylene)dialkylamides with fluorine, chlorine, bromine and iodine was designed and synthesized. A systematic investigation of their organogelling ability, thermic stability, mechanical properties and self-assembled structure was performed to elucidate the effect that the vicinal di-halo substituents have on the organogels. It was found that the presence of two halogen atoms (X) has a determinant effect as the brominated compounds are generally the most efficient organogelators. In hydrocarbons, the gelling ability increased from fluorine to iodine following the halogen bond donor ability trend. SAXS results were in agreement with a fibrillar self-assembly where the halogens are located at the surface of the fibers. Multiple cooperative interactions are involved in the self-assembly of the gels: π-π stacking, hydrogen bonds and X?X contacts. Thus, this work provides a new strategy for the design of new gelators or to improve the efficiency of known organogelators by introducing two vicinal halogen substituents into the aromatic rings. An ethanolic gel was also successfully used as a template to prepare silica and titania nanotubes. Hence, such organogels are promising materials for future research and development.
- Busch, Verónica M.,Di Chenna, Pablo H.,Di Salvo, Florencia,Giovanetti, Lisandro,Japas, M. Laura,MacCormack, Andrea S.
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supporting information
p. 8198 - 8208
(2020/06/09)
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- A dibenzocyclooctyne derivative and application thereof
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The invention relates to a dibenzocyclooctyne derivative and application thereof. The dibenzocyclooctyne derivative is especially used for carrying out click reaction with azide compounds to prepare stable 1,2,3-triazole compounds, and the latter have a wide range of uses in labeling glycans, proteins and lipids of living cells, glycoprotein enrichment of proteomics, protein and oligonucleotide modification, and tissue reconstruction engineering.
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Paragraph 0028
(2019/07/10)
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- Synthesis and anticancer evaluation of new lipophilic 1,2,4 and 1,3,4-oxadiazoles
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A series of1,2,4- and 1,3,4-oxadiazole derivatives were synthesized and evaluated for their anticancer activity. Halogenated 1,2,4-oxadiazoles were obtained from benzonitrile and coupled either lipophilic amines or with aminoalcohols. Lipophilic 1,3,4-oxadiazole derivatives were obtained through the Mannich reactions between 5-(aryl)-1,3,4-oxadiazole-2-thiol and alkylated or acylated amines. The in vitro cytotoxic effects were evaluated against 4T1– mammary carcinoma and CT26 – colon cancer cells. The best results were obtained for the 1,3,4-oxadiazole coupled to alkylated piperazine with 10–14 carbon chain moiety, with IC50 values ranging from 1.6 to 3.55μΜ for the 4T1 cell line, and from 1.6 to 3.9 μM for the CT26.WT cell line, and selectivity index up to 19. The most potent compounds were investigated with AnnexinV and PI staining as indicative of apoptosis induction.
- Caneschi, Wiliam,Enes, Karine Braga,Carvalho de Mendon?a, Camille,de Souza Fernandes, Fábio,Miguel, Fabio Balbino,da Silva Martins, Jefferson,Le Hyaric, Mireille,Pinho, Roberto Rosas,Duarte, Lucas Mattos,Leal de Oliveira, Marcone Augusto,Dos Santos, Hélio F.,Paz Lopes, Miriam Teresa,Dittz, Dalton,Silva, Heveline,Costa Couri, Mara Rubia
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- Cinnamyl alcohol fatty acid ester derivative and application and preparation method thereof
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The invention relates to a derivative and an application and a preparation method thereof, in particular to a cinnamyl alcohol fatty acid ester derivative and an application and a preparation method thereof. As application of a percutaneous absorption penetration enhancer, a percutaneous administration preparation is prepared, so that the percutaneous absorption of a drug is improved, and the cumulative penetration amount of the drug is increased. The cinnamyl alcohol fatty acid ester derivative is prepared into fatty acyl chloride, and the fatty acyl chloride reacts with cinnamyl alcohol to obtain the cinnamyl alcohol fatty acid ester derivative. The compound can be applied to the percutaneous administration preparation to enhance the drug permeability, can further be used as perfume to cover up the bad smell of the preparation, and has wide potential application prospects.
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Paragraph 0054; 0055
(2019/05/08)
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- Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters
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Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.
- Sun, Jun,Yoshiiwa, Toshiya,Iwata, Takayuki,Shindo, Mitsuru
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supporting information
p. 6585 - 6588
(2019/09/30)
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- Structure-Reactivity Relationships on Substrates and Inhibitors of the Lysine Deacylase Sirtuin 2 from Schistosoma mansoni (SmSirt2)
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The only drug currently available for treatment of the neglected disease Schistosomiasis is Praziquantel, and the possible emergence of resistance makes research on novel therapeutic agents necessary and urgent. To this end, the targeting of Schistosoma m
- Monaldi, Daria,Rotili, Dante,Lancelot, Julien,Marek, Martin,W?ssner, Nathalie,Lucidi, Alessia,Tomaselli, Daniela,Ramos-Morales, Elizabeth,Romier, Christophe,Pierce, Raymond J.,Mai, Antonello,Jung, Manfred
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p. 8733 - 8759
(2019/10/11)
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- Thiourea derivatives, preparation method and use thereof
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The present invention relates to thiourea derivatives having long chains, a preparation method thereof and a use thereof as urease inhibitors. The present invention provides a compound represented by chemical formula (1) or a pharmaceutically acceptable s
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Paragraph 0079; 0080
(2020/04/10)
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- NUCLEOSIDE-MODIFIED RNA FOR INDUCING AN ADAPTIVE IMMUNE RESPONSE
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The present invention generally relates to compositions and methods for inducing an adaptive immune response in a subject. In certain embodiments, the present invention provides a composition comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof. For example, in certain embodiments, the composition comprises a vaccine comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof.
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Page/Page column 115
(2018/05/24)
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- LIPID NANOPARTICLE FORMULATIONS
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Improved formulations of lipid nanoparticles are provided. Use of the lipid nanoparticles for delivery of a therapeutic agent and methods for their preparation are also provided.
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Page/Page column 142
(2018/05/24)
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- Discovery of long-chain salicylketoxime derivatives as monoacylglycerol lipase (MAGL) inhibitors
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Monoacylglycerol lipase (MAGL) is the enzyme hydrolyzing the endocannabinoid 2-arachidonoylglycerol (2-AG) to free arachidonic acid and glycerol. Therefore, MAGL is implicated in many physiological processes involving the regulation of the endocannabinoid system and eicosanoid network. MAGL inhibition represents a potential therapeutic target for many diseases, including cancer. Nowadays, most MAGL inhibitors inhibit this enzyme by an irreversible mechanism of action, potentially leading to unwanted side effects from chronic treatment. Herein, we report the discovery of long-chain salicylketoxime derivatives as potent and reversible MAGL inhibitors. The compounds herein described are characterized by a good target selectivity for MAGL and by antiproliferative activities against a series of cancer cell lines. Finally, modeling studies suggest a reasonable hypothetical binding mode for this class of compounds.
- Bononi, Giulia,Granchi, Carlotta,Lapillo, Margherita,Giannotti, Massimiliano,Nieri, Daniela,Fortunato, Serena,Boustani, Maguie El,Caligiuri, Isabella,Poli, Giulio,Carlson, Kathryn E.,Kim, Sung Hoon,Macchia, Marco,Martinelli, Adriano,Rizzolio, Flavio,Chicca, Andrea,Katzenellenbogen, John A.,Minutolo, Filippo,Tuccinardi, Tiziano
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p. 817 - 836
(2018/08/24)
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- Mesogenic 3,6-bis(4-hydroxyphenyl)-1,2,4,5-tetrazine alkanoate esters
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A novel series of 3,6-bis(4-hdroxyphenyl)-1,2,4,5-tetrazine alkanoate esters were synthesized and their mesogenic properties were studied using differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). The impact of changing the tail-core linkage from alkyl or alkoxy to ester is profound. Compared to the alkyl or alkoxy linkages, the ester linkage reduced mesogenic properties. Short-tailed compounds are non mesogenic (4a-4e), while long-tailed compounds (4f-4r) exhibit nematic phases. Unlike the alkyl or alkoxy tail series, none of the 18 presented esters in this series exhibits a smectic phase.
- Fouad, Farid,Khabouchi, Faycal,Nielsen, Alek,Twieg, Robert
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- Nitrogen mustard derivative N,N-di(2-chloroethyl)-N'-myristoyl-1,4-phenylenediamine and preparation method thereof
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The invention particularly discloses a structural formula of a nitrogen mustard derivative N,N-di(2-chloroethyl)-N'-myristoyl-1,4-phenylenediamine, and a preparation method thereof. The preparation method comprises the following steps: preparing N,N-di(2-chloroethyl)-1,4-phenylenediamine; putting the N,N-di(2-chloroethyl)-1,4-phenylenediamine, dichloromethane and triethylamine into a reactor, cooling in ice-water bath, stirring, dropwise adding a mixed solution of myristyl chloride and dichloromethane into the reactor, removing the ice-water bath after addition, reacting at room temperature for 10 to 14 hours, washing the reaction liquid after the reaction is conducted completely, drying with anhydrous cupric sulfate, performing normal-pressure distillation, and purifying the distilled filter cake to obtain the product. The nitrogen mustard derivative provided by the invention can effectively reduce the toxic and side effects of nitrogen mustard on the premise of enhancing the treatment index of the nitrogen mustard, and has sterilization and inflammation-diminishing curative effects to reduce the risk of complication caused by the fact that the immunity is reduced after a patient is subjected to chemical therapy.
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Paragraph 0045; 0057
(2017/07/04)
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- Structure-activity relationship study and optimisation of 2-aminopyrrole-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile as a broad spectrum metallo-β-lactamase inhibitor
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A SAR study on derivatives of 2-amino-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile 5a revealed that the 3-carbonitrile group, vicinal 4,5-diphenyl and N-benzyl side chains of the pyrrole are important for the inhibitory potencies of these compounds against members representing the three main subclasses of metallo-β-lactamases (MBLs), i.e. IMP-1 (representing the B1 subgroup), CphA (B2) and AIM-1 (B3). Coupling of 5a with a series of acyl chlorides and anhydrides led to the discovery of two N-acylamide derivatives, 10 and 11, as the two most potent IMP-1 inhibitors in this series. However, these compounds are less effective towards CphA and AIM-1. The N-benzoyl derivative of 5a retained potent in vitro activity against each of MBLs tested (with inhibition constants in the low μM range). Importantly, this compound also significantly enhanced the sensitivity of IMP-1, CphA- or AIM-1-producing cell cultures towards meropenem. This compound presents a promising starting point for the development of a universal MBL inhibitor, targeting members of each of the major subgroups of this family of enzymes.
- McGeary, Ross P.,Tan, Daniel T.C.,Selleck, Christopher,Monteiro Pedroso, Marcelo,Sidjabat, Hanna E.,Schenk, Gerhard
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p. 351 - 364
(2017/06/19)
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- Synthesis and biological evaluation of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thioglycosides
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In the present study, the synthesis of 1, 3, 4-thiadiazole-based thioglycosides were accomplished in good yields with employing a convergent synthetic route. The starting material 5-amino-1, 3, 4-thiadiazole-2-thiol and followed by a series of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thiols (4a–4j) were synthesized with different fatty acid chlorides. The glycosylation of compounds 4a–4j were achieved with trichloroacetimidate methodology. Antimicrobial and cytotoxicity activities of title compounds were evaluated. Among the entire compounds lauric acid and myristic acid derivatives showed good and moderate antimicrobial activity. In case of cytotoxicity results of compounds 8a–8j and 9a–9j, the acetate protected short chain (C6:0, C8:0, C10:0) compounds and the free hydroxyl long chain saturated (C16:0, C18:0) and unsaturated (C18:1, C22:1) compounds exhibited good activity against different cancer cell lines. Further, the free hydroxyl compounds 9a, 9c–9j did not show any toxicity towards normal CHO-K1 cell line whereas acylated compounds 8a–8j exhibited toxicity.
- Vudhgiri, Srikanth,Koude, Dhevendar,Veeragoni, Dileep Kumar,Misra, Sunil,Prasad,Jala, Ram Chandra Reddy
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supporting information
p. 3370 - 3373
(2017/07/07)
-
- Branched-chain and dendritic lipids for nanoparticles
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Lipid nanoparticles (LNPs) for drug-delivery applications are largely derived from natural lipids. Synthetic lipids, particularly those incorporating branched hydrocarbons and hyper-branched hydrocarbon architectures, may afford enhanced lipophilicity with enhanced fluidity and thereby lead to LNP stabilization. Hydrocarbon anchors based on serinol diesters were prepared from linear Cn (n = 14, 16, 18) and branched (n = 16) acids with Boc-protected serinol. These diesters were further dimerized on an iminodiacetamide backbone to provide eight branched-chain and dendritic lipid anchors. Derivatization of these core structures provided eight PEG-lipids and seven thiopurine linked lipid-drug conjugates. LNPs were prepared by microfluidic mixing from mixed lipids in ethanol diluted into aqueous media. The lipid-drug conjugates incorporated 5 mol% of a phosphocholine and 5 mol% of a commercial PEG-lipid to form LNPs with a thiopurine drug loading of 15 wt%. The PEG-lipids prepared were formulated at 1.5 mol% as a surface stabilizer to LNPs containing dsDNA lipoplexes. The stability of the LNPs was assessed under different storage conditions through monitoring of particle size. For both LNPs from lipid-Thiopurine conjugates and the PEG-lipid systems, there is strong preliminary evidence that hydrocarbon branching results in LNP stabilization. Four of the lipid-drug conjugate formulations were stable to cell culture conditions (10% serum, 37 °C) and the toxicity of these LNPs was assessed in two cell lines relative to the free thiopurines in the medium. The observed toxicity is consistent with cellular uptake of the LNPs and reductive release of the cargo thiopurine within the cell.
- Meanwell, Michael W.,O'Sullivan, Connor,Howard, Perry,Fyles, Thomas M.
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supporting information
p. 120 - 129
(2017/02/10)
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- Synthesis, antimicrobial activity and in silico studies on thymol esters
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Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.
- Lazarevi?, Jelena,Kolarevi?, Ana,Dordevi?, Aleksandra,Stojanovi?, Gordana,?melcerovi?, Andrija,Ciuffreda, Pierangela,Santaniello, Enzo
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p. 603 - 612
(2017/09/11)
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- d-menthol fatty acid ester derivative, application thereof and preparation method for d-menthol fatty acid ester derivative
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The invention belongs to the technical field of medicines and relates to a d-menthol fatty acid ester derivative, an application thereof and a preparation method for the d-menthol fatty acid ester derivative. The d-terpineol fatty acid ester is prepared through carrying out an esterification reaction on d-menthol and straight-chain fatty acid. The method comprises the steps of firstly, carrying out a reaction on fatty acid and thionyl chloride so as to prepare acyl chloride, and then, subjecting acyl chloride to a reaction with d-menthol, there by preparing the ester. The d-menthol ester is applied to external preparations such as plasters, cataplasm, ointment, gels, sprays and liniment as a penetration enhancer, so that the percutaneous absorption capacity of drugs, particularly, chiral drug enantiomers is increased; and the d-menthol ester is a very good percutaneous absorption penetration enhancer and has a broad application prospect.
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Paragraph 0032
(2017/08/29)
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- Citronellol fatty acid ester derivative and application and preparation method thereof
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The invention relates to a citronellol fatty acid ester derivative and an application and preparation method thereof. The citronellol fatty acid ester derivative is used as a transdermal absorption penetration enhancer for application and used for preparing a transdermal drug delivery preparation so that transdermal absorption of drugs can be improved, and the accumulative penetration amount of the drugs is increased. According to the citronellol fatty acid ester derivative, after reaction with thionyl chloride, fatty acyl chloride is prepared, then the fatty acyl chloride reacts with citronellol, and the citronellol fatty acid ester derivative is obtained. The citronellol fatty acid ester derivative can be applied to the transdermal drug delivery preparation, improves the penetration ability of the drugs, and can also be used as spice to mask the objectionable odor of the preparation.
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Paragraph 0055; 0056
(2017/12/09)
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- Nerol aliphatic ester derivative as well as application and preparation method thereof
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The invention belongs to the technical field of medicine, and relates to a nerol aliphatic ester derivative as well as application and a preparation method thereof. The nerol aliphatic ester is obtained by a esterification reaction between nerol and straight-chain fatty acid and is prepared from the following steps: preparing acyl chloride by reaction between fatty acid and sulfoxide chloride; preparing nerol aliphatic ester. by reaction between acyl chloride and nerol. The nerol aliphatic ester can be used as a penetration enhancer to be applied to external preparation, such as a patch, a cataplasm, an ointment, a gelling agent and a spraying agent, so that the percutaneous absorption of medicine is improved. The nerol aliphatic ester is a good percutaneous absorption enhancer and has a wide application prospect.
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Paragraph 0053; 0054
(2017/11/04)
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- Lavandulol fatty acid ester derivative, application and preparation method thereof
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The invention relates to a derivative, application and a preparation method of the derivative, in particular to a lavandulol fatty acid ester derivative, application and a preparation method thereof. The lavandulol fatty acid ester derivative is prepared by preparing fatty acyl chloride and then carrying out reaction with lavandulol. The lavandulol fatty acid ester derivative can be applied as a transdermal absorption penetration enhancer to prepare transdermal drug delivery preparations, and can improve transdermal absorption of drugs and increase the cumulative penetration amount of drugs. The compound provided by the invention can be applied to transdermal drug delivery preparations to strengthen the penetration performance of drugs, and also can be used as lavender alcohol fatty acid ester derivative, and its application and preparation method. Lavender fatty acid ester derivatives are prepared by preparing fatty acyl chloride and then reacting with lavender. As a percutaneous absorption and penetration enhancer, the transdermal drug preparation is prepared to improve the absorption of the drug and increase the cumulative permeation of the drug. The compounds described in the present invention can be used in the percutaneous drug delivery, enhance the permeation ability of the drug, and can also be used as a spice to cover up the objectionable odor of preparations.
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Paragraph 0006; 0007; 0054; 0055
(2017/12/27)
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- Eugenol fatty acid ester derivative as well as application and preparation method thereof
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The invention discloses a eugenol fatty acid ester derivative as well as application and a preparation method thereof. Eugenol fatty acid ester is obtained by an esterification reaction of eugenol and straight-chain fatty acid. The method comprises the following steps: firstly, preparing acyl chlorine by reacting fatty acid with thionyl chloride; mixing eugenol with an equal mole amount of pyridine or triethylamine; then, dropwise adding the prepared acyl chloride under the cooling action of an ice bath to generate the eugenol fatty acid ester. Eugenol ester can be applied to external preparations such as patches, cataplasm, ointments, gels and spray agents as a penetration enhancer in order to increase the transdermal absorption amount of medicaments, is a very good percutaneous absorption penetration enhancer, and has a wide application prospect.
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Paragraph 0056-0057
(2017/11/18)
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- Linalool fatty acid ester type derivative as well as application and preparation method thereof
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The invention belongs to the technical field of medicines and relates to a linalool fatty acid ester type derivative as well as application and a preparation method thereof. A fatty acid ester is obtained by carrying out esterification reaction on linalool and straight-chain fatty acid; the method comprises the following steps: firstly, taking fatty acid and sulfoxide chloride to react to prepare acyl chloride; taking the acyl chloride and the linalool to react to prepare ester. The linalool is used as a penetration enhancer and is applied to external preparations including patches, cataplasm, ointment, gel, spray, liniments and the like, so that the transdermal absorption amount of drugs, especially chiral drug enantiomers, is improved; the linalool fatty acid ester type derivative is a very good transdermal absorption penetration enhancer and has a wide application prospect.
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Paragraph 0051; 0052
(2018/01/03)
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- Method for preparing acyl chloride by catalyzing phosgene and acid
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The invention discloses a method for preparing acyl chloride by catalyzing phosgene and acid. The method includes the following steps that 1, with carboxylic acid as a raw material, a catalyst and a solvent are added, and under the condition that the temperature is maintained to range from 20 DEG C to 200 DEG C, phosgene is introduced into a reaction flask for a reaction; 2, after the molar ratio of carboxylic acid to phosgene reaches 1:1.0-1:10, phosgene introduction is stopped, reacted mixed liquor is obtained and filtered, obtained filter liquor is subjected to reduced pressure distillation at a high vacuum degree to obtain acyl chloride, and an obtained filter cake continues to serve as the catalyst in the step 1 to be recycled. Compared with an existing catalyst adopted for preparing acyl chloride according to a phosgene method, the catalyst used in the method is small in dosage, convenient to recycle, easy to separate from a product, better in product quality, safe, stable and environmentally friendly, generated solid waste is greatly reduced, the experience of operators is greatly improved, and safety risks are lowered.
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Paragraph 0082; 0083; 0084
(2016/10/20)
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- Synthesis of novel ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1,4-dihydro-4-oxoquinoline-3-carboxylate derivatives and their biological evaluation
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A series of novel ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1,4-dihydro-4-oxoquinoline-3-carboxylate derivatives were prepared through multistep synthesis. The key step in the synthesis was to obtain the C-7 fatty amide derivative. The azide was selectively formed at C-7 position using sodium azide at 60 °C. Subsequently, the azide was reduced under mild conditions using zinc and ammonium chloride to form the corresponding amine. The synthesized derivatives were further subjected to biological evaluation studies like cytotoxicity against a panel of cancer cell lines such as DU145, A549, SKOV3, MCF7 and normal lung cells, IMR-90 as well as with antimicrobial and antioxidant activities. It was observed that the carboxylated quinolone derivatives with hexanoic (8a), octanoic (8b), lauric (8d) and myristic (8e) moieties exhibited promising cytotoxicity against all the tested cancer cell lines. The results also suggested that hexanoic acid-based fatty amide carboxylated quinolone derivative (8a) exhibited promising activity against both bacterial and fungal strains and significant antibacterial activity was observed against Staphylococcus aureus MTCC 96 (MIC value of 3.9 μg/mL). The compound 8a also showed excellent anti-biofilm activity against Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 121 with MIC values of 2.1 and 4.6 μg/mL, respectively.
- Venepally, Vijayendar,Prasad,Poornachandra,Kumar, C. Ganesh,Jala, Ram Chandra Reddy
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supporting information
p. 613 - 617
(2016/01/09)
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- Structure, supramolecular organization and phase behavior of N-acyl-β-alanines: Structural homologues of mammalian brain constituents N-acylglycine and N-acyl-GABA
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N-Acyl-β-alanines (NABAs) are structural homologues of N-acylglycines (NAGs) and N-acyl-γ-aminobutyric acids (NAGABAs), and achiral isomers of N-acylalanines, which are all present in mammalian brain and other tissues and modulate activity of biological receptors with various functions. In the present study, we synthesized and characterized a homologous series of NABAs bearing saturated acyl chains (n = 8-20) and investigated their supramolecular organization and thermotropic phase behavior. In differential scanning calorimetric (DSC) studies, most of the NABAs gave one or two minor transitions before the main chain-melting phase transition in the dry state as well as upon hydration with water, but gave only a single transition when hydrated with buffer (pH 7.6). Transition enthalpies (ΔHt) and entropies (ΔSt), obtained from the DSC studies showed linear dependence on the chain length in the dry state and upon hydration with buffer, whereas odd-even alteration was observed when hydrated with water. The crystal structures of N-lauroyl-β-alanine (NLBA) and N-myristoyl-β-alanine (NMBA) were solved in monoclinic system in the P21/c space group. Both NLBA and NMBA were packed in tilted bilayers with head-to-head (and tail-to-tail) arrangement with tilt angles of 33.28° and 34.42°, respectively. Strong hydrogen bonding interactions between [sbnd]COOH groups of the molecules from opposite leaflets as well as N[sbnd]H?O hydrogen bonds between the amide groups from adjacent molecules in the same leaflet as well as dispersion interactions between the acyl chains stabilize the bilayer structure. The d-spacings calculated from powder X-ray diffraction studies showed odd-even alteration with odd-chain length compounds exhibiting higher values as compared to the even-chain length ones and the tilt angles calculated from the PXRD data are higher for the even chain NABAs. These observations are relevant to developing structure-activity relationships for these amphiphiles and understand how NABAs differ from their homologues and isomers, namely NAGs, NAGABAs, and N-acylalanines.
- Sivaramakrishna,Swamy, Musti J.
-
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- NUCLEOSIDE-MODIFIED RNA FOR INDUCING AN ADAPTIVE IMMUNE RESPONSE
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The present invention relates to compositions and methods for inducing adaptive immune response in a subject. In certain embodiments, the present invention provides a composition comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof. For example, in certain embodiments, the composition comprises a vaccine comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof.
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Page/Page column 143
(2016/11/17)
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- Α-terpineol fatty acid ester derivatives and use
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The invention belongs to the technical field of medicine and discloses alpha-terpineol aliphatic ester and a preparation with the compound. The alpha-terpineol aliphatic ester is formed by alpha-terpineol and fatty acid after esterification reaction. According to a method, first, fatty acid and thionyl chloride react to prepare acyl chloride, and then acyl chloride and alpha-terpineol react to prepare the alpha-terpineol aliphatic ester. The alpha-terpineol ester can be used as penetration enhancers to be used for external preparations of patching agents, Cataplasm, ointment agents, gel agents and the like, accordingly, the percutaneous absorptive amount of medicine is improved, and the alpha-terpineol aliphatic ester is good percutaneous absorptive penetration enhancers and has wide application prospect.
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Paragraph 0055; 0056
(2017/03/18)
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- Oil soluble molybdenum amine complex and preparation method thereof
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The invention discloses an oil soluble molybdenum amine complex and a preparation method of the oil soluble molybdenum amine complex. The method adopts long-chain saturated fatty acid as the starting material, acylchlorination reaction is carried out on the long-chain saturated fatty acid and thionyl chloride to obtain 1-chloro saturated fatty acid, then amidation reaction is carried out on the 1-chloro saturated fatty acid and diethanol amine to obtain saturated fatty acid amide, and finally complexation is carried out on the saturated fatty acid amide and a molybdenum trioxide solution so as to obtain the oil soluble molybdenum amine complex. The prepared molybdenum amine complex has good oil solubility, solves the poor oil solubility, corrosion resistance, wear resistance and friction reduction and other problems difficult to overcome in existing products, at the same time significantly reduces the adding amount of high sulfur and phosphorus components, and has enormous boosting effect on organic molybdenum series lubricating products currently under research in China, thus promoting nationalization of high-end lubricating oil and efficient utilization and high added value of molybdenum resources.
- -
-
Paragraph 0051
(2017/07/19)
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- Investigation of fatty acid conjugates of 3,5-bisarylmethylene-4-piperidone derivatives as antitumor agents and human topoisomerase-IIα inhibitors
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A series of five 3,5-bisarylidene-4-piperidones designed as analogs of curcumin and their twenty five fatty acid conjugates were synthesized as candidate anticancer agents. The fatty acid conjugates were designed for efficient delivery of these compounds at the targeted cancer sites. The cytostatic potential of these compounds was evaluated against three representative cancer cell lines namely murine leukemic L1210 cells, and human T-lymphocyte CEM cells and cervical HeLa cells. Most compounds were found to exhibit significant anti-cancer activity in vitro. QSAR studies indicated electrophilicity of these compounds towards cellular nucleophiles may have a key role to play in their cytostatic activity. Representative compounds were also tested for topoisomerase IIα inhibitory potential, which indicated strong catalytic inhibition of the enzyme in vitro. The data showed that the fatty acid conjugates also possessed robust antioxidant activity in multiple analyses. This study also indicated that these compounds prompted significantly lower cellular damage in human fibroblasts than a currently used cancer drug sorafenib in vitro. The wide spectrum of anticancer action, supplemented with antioxidant potential along with non-toxic manifestations, certainly augment the anticancer candidacy of the novel fatty acid conjugates.
- Potter, Elizabeth,Jha, Mamta,Bhullar, Khushwant S.,Rupasinghe, H.P. Vasantha,Balzarini, Jan,Jha, Amitabh
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p. 411 - 421
(2015/01/30)
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- Preparation and properties of a novel form-stable phase change material based on a gelator
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A series of gelators (Gm, m is the length of the alkyl tails, m = 2, 4, 6, 8, 10, 12, 14, 16 and 18) containing 4,4′-diaminodiphenylmethane moieties were synthesized. The chemical structures of Gm were confirmed by 1H NMR and MS. The form-stable phase change materials (FSPCMs) were prepared by introducing Gm into paraffin. The minimum gelation concentration (MGC) and gel-to-sol transition temperature (TGS) properties were tested by the "tube-testing method". It found that Gm (m = 2, 4, 6) was insoluble in paraffin, while the MGC and TGS of Gm (m = 8, 10, 12, 14, 16, 18) increased with the increase of alkyl chain. The structure and morphology of the PCMs were systematically investigated by FT-IR, POM, 1D WXAD and SEM. Experimental results revealed that paraffin was restricted because the gelators could self-assemble into three-dimensional netted structures, leading to form the shape-stable PCMs without leakage even above their melting point. The thermal properties were studied by DSC. The research showed that the G18/paraffin FSPCMs exhibited excellent thermal stability and high heat storage density. The shape stability of G18/paraffin was investigated by rheological measurements, indicating that solid hard gel soft gel liquid was observed with the increase of temperature. This work is useful in the comprehensive academic research and industrial application of PCMs.
- Wu, Dang,Wen, Wen,Chen, Sheng,Zhang, Hailiang
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supporting information
p. 2589 - 2600
(2015/02/19)
-
- Differential scanning calorimetric and powder X-ray diffraction studies on a homologous series of N-acyl-L-alanine esters with matched chains (n = 9-18)
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A homologous series of two chain derivatives of L-alanine, namely N-acyl L-alanine alkyl esters (NAAEs), bearing matched, saturated, acyl and alkyl chains (n= 9-18) have been synthesized. The thermotropic phase transitions and supramolecular structure of NAAEs were investigated by differential scanning calorimetry (DSC) and powder X-ray diffraction (PXRD). Results obtained from DSC studies indicate that the transition temperatures (T t), enthalpies (ΔH t) and entropies (ΔS t) exhibit odd-even alternation with compounds bearing odd acyl and alkyl chains showing higher values of T t, ΔH t and ΔS t as compared to NAAEs with even acyl and alkyl chains. However, the transition enthalpies and entropies of the odd- and even chain length series independently exhibit a linear dependence on the chain length. The d-spacings obtained from PXRD increase linearly with chain length with an increment of 1.76 ?/CH 2, suggesting that NAAEs adopt either a tilted bilayer structure or a bent structure. The present results provide a thermodynamic and structural basis for investigating the interaction of NAAEs with other membrane lipids, which in turn can shed light in understanding how they can enhance the transdermal permeability of stratum corneum.
- Sivaramakrishna,Swamy, Musti J.
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p. 1627 - 1635
(2015/12/01)
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- NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
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Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, R6, R7, R8, R9, L1, L2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.
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Page/Page column 71
(2016/05/02)
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- Synthesis, characterization and biological evaluation of novel diesters of 4,4'-dihydroxy azoxy benzene with long chain carboxylic acids
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Synthesis of novel symmetrical azoxy diesters have been prepared by the reaction of 4,4'-dihydroxyazoxy benzene with aliphatic acid halides of varying chain lengths. The synthesized compounds have been characterized by spectral and analytical data. These symmetrical azoxy diesters exhibit good antifungal activity against six fungal strains (Mucor species, Aspergillus niger, Aspergillus flavus, Alternaria solani, Fusarium solani and Aspergillus fumigatus) and antitumor activities while no significant antibacterial activity has been observed. These synthesized compounds are also potent free radical scavengers.
- Shehzadi, Sumaira,Siddiqi, Humaira Masood,Qasim, Malik Muhammed,Fawad, Musfirah,Manan, Abdul,Khan, Naeema,Saleem, Samreen,Bashir, Farah,Mirza, Bushra
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p. 462 - 472
(2014/08/05)
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- Comparative metabolomics and structural characterizations illuminate colibactin pathway-dependent small molecules
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The gene cluster responsible for synthesis of the unknown molecule colibactin has been identified in mutualistic and pathogenic Escherichia coli. The pathway endows its producer with a long-term persistence phenotype in the human bowel, a probiotic activity used in the treatment of ulcerative colitis, and a carcinogenic activity under host inflammatory conditions. To date, functional small molecules from this pathway have not been reported. Here we implemented a comparative metabolomics and targeted structural network analyses approach to identify a catalog of small molecules dependent on the colibactin pathway from the meningitis isolate E. coli IHE3034 and the probiotic E. coli Nissle 1917. The structures of 10 pathway-dependent small molecules are proposed based on structural characterizations and network relationships. The network will provide a roadmap for the structural and functional elucidation of a variety of other small molecules encoded by the pathway. From the characterized small molecule set, in vitro bacterial growth inhibitory and mammalian CNS receptor antagonist activities are presented.
- Vizcaino, Maria I.,Engel, Philipp,Trautman, Eric,Crawford, Jason M.
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supporting information
p. 9244 - 9247
(2014/07/21)
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- Fabrication of organogels achieved by prodrug-based organogelators of ketoprofen
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The treatment strategy of curing diseases using prodrugs of an anti-inflammatory drug is widespread. In the present study, we report on the synthesis of prodrugs of ketoprofen, consisting of a derivatization of ketoprofen and long hydrocarbon chain of fat
- Mahire, Rahul R.,Agrawal, Deepika S.,Patil, Devanand K.,More, Dhananjay H.
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p. 33286 - 33291
(2014/08/18)
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- Structure and thermotropic phase behavior of a homologous series of n -Acylglycines: Neuroactive and antinociceptive constituents of biomembranes
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N-Acylglycines (NAGs) with different acyl chains have been found in the mammalian brain and other tissues. They exhibit significant biological and pharmacological properties and appear to play important roles in communication and signaling pathways within and between cells. In view of this, a homologous series of NAGs have been synthesized and characterized in the present study. Differential scanning calorimetric (DSC) studies show that the transition enthalpies and entropies of dry as well as hydrated NAGs exhibit a linear dependence on the acyl chain length. Most of the NAGs show a minor transition below the chain-melting phase transition, suggesting the presence of polymorphism in the solid state. Structures of N-myristoylglycine (NMG) and N-palmitoylglycine (NPG) were solved in monoclinic system with C2/c and P21 space groups, respectively. Analysis of the crystal structures show that NAGs are organized in a bilayer fashion, with head-to-head (and tail-to-tail) arrangement of molecules. The acyl chains in both structures are essentially perpendicular to the bilayer plane, which is consistent with a lack of odd-even alternation in the thermodynamic properties. The bilayer is stabilized by strong hydrogen bonding interactions between COOH groups of the molecules from opposite leaflets as well as N-H···O hydrogen bonds between the amide groups of adjacent molecules in the same leaflet and dispersion interactions among the acyl chains. Powder X-ray diffraction data show that the d-spacings for the NAGs with different acyl chains (n = 8-20) exhibit a linear dependence on the chain length, suggesting that all the NAGs investigated here adopt a similar packing arrangement in the crystal lattice. These observations are relevant for understanding the role of N-acylglycines in biological membranes.
- Reddy, S. Thirupathi,Krovi, Krishna Prasad,Swamy, Musti J.
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p. 4944 - 4954
(2014/12/10)
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