112-64-1Relevant academic research and scientific papers
Fatty acid-indole fluorescent derivatives as probes to measure the polarity of interfaces containing gangliosides
Bagatolli, Luis A.,Montich, Guillermo G.,Ravera, Mario,Perez, Jorge D.,Fidelio, Gerardo D.
, p. 193 - 202 (1995)
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.
Synthesis and biological evaluation of fatty acyl ester derivatives of 2′,3′-didehydro-2′,3′-dideoxythymidine
Agarwal, Hitesh K.,Loethan, Kelly,Mandal, Deendayal,Doncel, Gustavo F.,Parang, Keykavous
, p. 1917 - 1921 (2011)
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.
Pyridinium based amphiphilic hydrogelators as potential antibacterial agents
Brahmachari, Sayanti,Debnath, Sisir,Dutta, Sounak,Das, Prasanta Kumar
, p. 859 - 868 (2010)
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.
Synthesis of the enantiomers of 13-methylheptacosane, the sex pheromone of pear psylla, Cacopsylla pyricola
Yuan, Gucheng,Yang, Yuxiong,Liu, Jiawei,Bian, Qinghua,Wang, Min,Zhong, Jiangchun
, p. 274 - 280 (2021)
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.
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
Zhao, Donghong,Luo, Haofan,Chen, Binhui,Chen, Wenteng,Zhang, Guolin,Yu, Yongping
, p. 7860 - 7866 (2018)
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.
Temperature Control of Sequential Nucleation–Growth Mechanisms in Hierarchical Supramolecular Polymers
Osypenko, Artem,Moulin, Emilie,Gavat, Odile,Fuks, Gad,Maaloum, Mounir,Koenis, Mark A. J.,Buma, Wybren Jan,Giuseppone, Nicolas
, p. 13008 - 13016 (2019)
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.
Homologous, long-chain alkyl dendrons form homologous thin films on silver oxide surfaces
Williams, Andre A.,Day, B. Scott,Kite, Brett L.,McPherson, Melinda K.,Slebodnick, Carla,Morris, John R.,Gandour, Richard D.
, p. 5053 - 5055 (2005)
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.
Synthesis and In Vitro Evaluation of Inherent Properties of L-Glutamic Acid Based Dendritic Lipopeptide Oligomers
Hegde, Namita,Juvale, Kapil,Prabhakar, Bala
, p. 228 - 236 (2022)
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.
Synthesis, characterization and mixed micellization study of benzene sulphonate based gemini surfactant with sodium dodecyl sulphate
Wani, Farooq Ahmad,Khan, Abbul Bashar,Alshehri, Abdulmohsen Ali,Malik, Maqsood Ahmad,Ahmad, Rabia,Patel, Rajan
, p. 270 - 278 (2019)
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.
Synthesis of New Lipophilic Cyclopentafullerenes from Long-Chain Alka-2,3-dienoates
Biglova, Yu. N.,Mukhametyanova, A. F.,Nugumanov, T. R.,Sakhautdinov, I. M.
, p. 1191 - 1195 (2020)
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.
