- Functionalization of poly(amidoamine) dendrimers with hydrophobic chains for improved gene delivery in mesenchymal stem cells
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A new family of gene delivery vectors is synthesized consisting of a medium-size generation PAMAM dendrimer (generation 5, with amine termini) core randomly linked at the periphery to hydrophobic chains that vary in length (12 to 16 carbon alkyl chains) and number (from 4.2 to 9.7 in average). The idea subjacent to the present work is to join the advantages of the cationic nature of the dendrimer with the capacity of lipids to interact with biological membranes. Unlike other amphiphilic systems designed for the same purpose, where the hydrophobic and hydrophilic moieties coexist in opposite sides, the present vectors have a hydrophilic interior and a hydrophobic corona. The vectors are characterized in respect to their ability to neutralize, bind and compact plasmid DNA (pDNA). The complexes formed between the vectors and pDNA are analyzed concerning their size, ζ-potential, resistance to serum nucleases, capacity of being internalized by cells and transfection efficiency. These new vectors show a remarkable capacity for mediating the internalization of pDNA with minimum cytotoxicity, being this effect positively correlated with the -CH2- content present in the hydrophobic corona. Gene expression in MSCs, a cell type with relevancy in the regenerative medicine clinical context, is also enhanced using the new vectors but, in this case, the higher efficiency is shown by the vectors containing the smallest hydrophobic chains.
- Santos, José L.,Oliveira, Hugo,Pandita, Deepti,Rodrigues, Jo?o,Pêgo, Ana P.,Granja, Pedro L.,Tomás, Helena
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- Luliberin analogues exhibiting a cytotoxic effect on tumor cells in vitro
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Luliberin analogues modified at the N-terminus were synthesized to search for drugs exerting a cytotoxic effect on cells of hormone-dependent tumors. A synthetic scheme effective in the preparation of analogues containing fatty acid residues was proposed. The cytotoxic effect of the peptides was studied on a number of cell lines of human tumors in vitro. The dependence of the antitumor effect on the length of peptide chain, amino acid sequence, and structure of the N-terminal group was demonstrated. Modification with palmitic acid was found to result in highly active compounds in the case of analogues containing more than ten aa, whereas modifications with lauric, caproic, or trimethylacetic acid led to compounds with significantly lower activities. Analogues of luliberin containing a palmitic acid residue and effectively inhibiting the growth of tumor cells in vitro were synthesized. Pleiades Publishing, Inc., 2006.
- Burov,Yablokova,Dorosh,Shkarubskaya,Blank,Epstein,Fridkin
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- Chemical modification of recombinant hirudin with palmitic acid in mixed aqueous-organic solutions
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In this study, chemical modification of recombinant hirudin variant-2 (HV2) with palmitic acid (PAL) was proposed as an alternative approach to circumvent the limitations of PEGylation. To facilitate a sufficient contact of the hydrophilic HV2 to the hydrophobic PAL, thereby improving the reaction specificity to achieve the desired mono-PAL-HV2 with high retained bioactivity, the reaction was developed in mixed aqueous-organic solutions. Compared with HV2 conjugation with PAL-benzotriazole (PAL-BTA) in mixed aqueous-NMP solution, the conjugation of HV2 with PAL-N-hydroxysuccinimide (PAL-NHS) in mixed aqueous-DMSO solution could improve the site-specific conjugation of one PAL molecule to a particular lysine residue. Furthermore, the reaction mixture of the latter was further purified by preparative liquid chromatography. Three mono-PAL-HV2 isomers were obtained and retained 36%, 4% and 89% of the in vitro anticoagulant activity of unmodified HV2, respectively. One of the mono-PAL-HV2 isomers, namely, mono-PAL-HV2-3, was isolated with the highest selectivity and exhibited the highest in vitro anticoagulant bioactivity. Modification site analysis of mono-PAL-HV2-3 revealed that a single PAL molecule was conjugated at Lys27 of HV2. This study presented a successful PAL modification in which site-specific reaction was improved to achieve the desired mono-PAL-HV2 with highly retained bioactivity in mixed aqueous-organic solutions.
- Wang, Shu-Chang,Wang, Xu-Dong,Teng, Xin-Nan,Xiu, Zhi-Long
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- Chemoselective acylation of fully deprotected hydrazino acetyl peptides. Application to the synthesis of lipopeptides
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Fully deprotected N-terminal α-hydrazino acetyl peptides were synthesized and chemoselectively acylated on the hydrazine moiety with various fatty acid succinimidyl esters or N-(cholesterylcarbonyloxy) succinimide to give lipopeptides of high purity. The buffer and pH were adjusted in order to minimize the oxidation of the hydrazine moiety and to achieve the best conversion and selectivity. The acylation was performed in a citrate - Phosphate buffer/2-methylpropan-2-ol mixture of pH 5.1. The pKa of the α-hydrazino acetyl group on our model peptide was found to be 6.45, i.e., about 2 units lower than the pKa of a glycyl residue. The reaction was subsequently applied to the synthesis of a 38AA peptide derivatized by a palmitoyl group.
- Bonnet,Ollivier,Gras-Masse,Melnyk
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- Systematic exploration of lipophilic tags that allow efficient anchoring of aptamers to live cell surfaces
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We carried out a systematic exploration of lipophilic tag molecules that allow efficient anchoring of aptamers to live cell surfaces. Among the lipids tested, the C16 dialkyl (dipalmitoylphosphatidylethanolamine) tag showed a good performance: a high anchoring yield and long retention on live cells. The 3'-C16 dialkyl tag-labeled fluorescent aptamer sensor, targeting thrombin, was prepared. The aptamer sensor was anchored successfully to live cells, allowing fluorescence detection of thrombin on the cell surface.
- Tokunaga, Takeshi,Kuwahata, Kohei,Sando, Shinsuke
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- Innovative chemical synthesis and conformational hints on the lipopeptide liraglutide
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Liraglutide is a new generation lipopeptide drug used for the treatment of type II diabetes. In this work, we describe new approaches for its preparation fully by chemical methods. The key step of these strategies is the synthesis in solution of the Lys/γ-Glu building block, Fmoc-Lys-(Pal-γ-Glu-OtBu)-OH, in which Lys and Glu residues are linked through their side chains and γ-Glu is Nα-palmitoylated. This dipeptide derivative is then inserted into the peptide sequence on solid phase. As liraglutide is obtained with great purity and high yield, our approach can be particularly attractive for an industrial production. We also report here the results of a circular dichroism conformational analysis in a membrane mimetic environment that offers new insights into the mechanism of action of liraglutide. Copyright
- Guryanov, Ivan,Bondesan, Alex,Visentini, Dario,Orlandin, Andrea,Biondi, Barbara,Toniolo, Claudio,Formaggio, Fernando,Ricci, Antonio,Zanon, Jacopo,Cabri, Walter
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- Palmitoyl derivatives of interferon α: Potential for cutaneous delivery
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Palmitoyl derivatives of interferon α2b (p-IFNα) were prepared by covalent attachment of the fatty acid to lysine residues in the protein through a reaction with N-hydroxysuccinimide palmitate ester. The p-IFNα was characterized by capillary electrophoresis (CE), mass spectrometry (MS), SDS- PAGE, and antiviral assay. Flow-through diffusion cells and human breast skins were used to measure cutaneous and percutaneous absorption. Formation of p-IFNα derivatives was demonstrated by CE to be dependent on reaction time and reagent: protein ratio. Electrospray MS of the crude p-IFNα mixture indicated three populations of IFNα derivatives with 10, 11, and 12 palmitoyl substitutions. The addition of palmitoyl residues to IFNα under the conditions described reduced the antiviral specific activity by 50%. However, the cutaneous absorption of p-IFNα was about 5-6 times greater than the parent protein. The amount of p-IFNα and IFN α in whole skin after 24 h of treatment was 2.106 ± 1.216 μg/cm2 and 0.407 ± 0.108μg/cm2, respectively. Approximately two times higher flux was detected for p-IFNα compared to the nonfatty acylated IFNα. The total amount of drug diffused in 24 h was also approximately two times higher for the p-IFNα. The results indicate a potential for using fatty acylated derivatives of IFN α for dermal and transdermal delivery.
- Foldvari, Marianna,Attah-Poku, Samuel,Hu, Jiaping,Li, Qimin,Hughes, Huw,Babiuk, Lorne A.,Kruger, Sandra
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- Blended polar/nonpolar peptide conjugate interferes with human insulin amyloid-mediated cytotoxicity
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Insulin, a peptide hormone and a key regulator of blood glucose level, is routinely administered to type-I diabetic patients to achieve the required glycemic control. Insulin aggregation and ensuing amyloidosis has been observed at repeated insulin injection sites and in injectable formulations. The latter occurs due to insulin agglomeration during shipping and storage. Such insulin amyloid leads to enhanced immunogenicity and allow potential attachment to cell membranes leading to cell permeability and apoptosis. Small molecule inhibitors provide useful interruption of this process and inhibit protein misfolding as well as amyloid formation. In this context, we report the propensity of a palmitoylated peptide conjugate to inhibit insulin aggregation and amyloid-mediated cytotoxicity, via designed interference with polypeptide interfacial interactions.
- Sen, Shantanu,Singh, Prerana,Mishra, Narendra Kumar,Ganesh, Subramaniam,Sivakumar, Sri,Verma, Sandeep
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- Synthesis and Antitumor Activity of Conjugates Based on the Phe-D-Trp-Lys-Thr Peptide Fragment of Somatostatin
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Abstract: New somatostatin analogs containing the fragments of adamantane, coumarin, tetrahydrocarbazole, and palmitic acid of the general formula R-Phe-D-Trp-Lys(Boc)-Thr-OMe have been synthesized. The structure of the conjugates combines a peptide fragm
- Avdeev,Sidorova,Ovchinnikov,Moiseeva,Osipov,Balaev,Khachatryan
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- COMPOUNDS AND METHODS FOR THE TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY
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Disclosed herein are compounds including a single-stranded oligonucleotide (A) having a nucleobase sequence complementary to a portion of the dystrophin pre-mRNA, their preparation, and uses thereof for the treatment of Duchenne muscular dystrophy.
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Paragraph 0439; 0443; 0495
(2021/06/04)
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- COMPOUND COMPRISING A NUCLEIC ACID AND A HALF-LIFE EXTENSION MOTIF
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Disclosed herein are compounds including a nucleic acid (A), their preparation, and their use.
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Paragraph 0750; 0763; 0806
(2021/06/04)
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- AN IMPROVED PROCESS FOR PREPARATION OF LIRAGLUTIDE
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The present invention relates to an improved process for the preparation of Liraglutide. The present invention further related an improved process for the preparation of substantially pure material having a purity of greater than or equal to 99.5% by HPLC.
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(2021/07/02)
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- PALMITOYLETHANOLAMIDE COMPOUNDS
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The present application provides palmitoylethanolamide compounds useful for treating a disease or disorder in a subject in need thereof. Pharmaceutical compositions comprising the compounds and methods of treating diseases or disorders are also provided.
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(2021/10/02)
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- Method for preparing high-purity fatty acid derivative
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The invention provides a method for preparing a fatty acid derivative. The preparation method comprises the following specific steps: firstly, reacting long-chain fatty acid with Nhydroxysuccinimide to obtain long-chain fatty acid succinimide ester; then
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Paragraph 0063-0067
(2020/11/23)
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- Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis
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Lipid metabolism in Mycobacterium tuberculosis (Mtb) relies on 34 fatty acid adenylating enzymes (FadDs) that can be grouped into two classes: fatty acyl-CoA ligases (FACLs) involved in lipid and cholesterol catabolism and long chain fatty acyl-AMP ligases (FAALs) involved in biosynthesis of the numerous essential and virulence-conferring lipids found in Mtb. The precise biochemical roles of many FACLs remain poorly characterized while the functionally non-redundant FAALs are much better understood. Here we describe the systematic investigation of 5′-O-[N-(alkanoyl)sulfamoyl]adenosine (alkanoyl adenosine monosulfamate, alkanoyl-AMS) analogs as potential multitarget FadD inhibitors for their antitubercular activity and biochemical selectivity towards representative FAAL and FACL enzymes. We identified several potent compounds including 12-azidododecanoyl-AMS 28, 11-phenoxyundecanoyl-AMS 32, and nonyloxyacetyl-AMS 36 with minimum inhibitory concentrations (MICs) against M. tuberculosis ranging from 0.098 to 3.13 μM. Compound 32 was notable for its impressive biochemical selectivity against FAAL28 (apparent Ki = 0.7 μM) versus FACL19 (Ki > 100 μM), and uniform activity against a panel of multidrug and extensively drug-resistant TB strains with MICs ranging from 3.13 to 12.5 μM in minimal (GAST) and rich (7H9) media. The SAR analysis provided valuable insights for further optimization of 32 and also identified limitations to overcome.
- Aldrich, Courtney C.,Baran, Marzena,Boshoff, Helena I. M.,Fu, Peng,Grimes, Kimberly D.,Sibbald, Paul A.,Wilson, Daniel J.
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- Preparation method of high-purity liraglutide side chain
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The invention discloses a preparation method of a high-purity liraglutide side chain, palmitic acid, N-hydroxysuccinimide and N, N'-diisopropylcarbodiimide are used as starting materials to react to obtain Palmitoyl-OSu, Palmitoyl-Glu-OtBu, Liraglutide side chain crude product Palmitoyl-Glu (OSu)-OtBu in sequence; the reaction solution is filtered, the obtained filtrate is washed with an acidic aqueous solution, and an organic phase is concentrated the until being dry; the organic phase is recrystallized by using an alkane and a fatty alcohol or a mixed solvent of the alkane and the fatty alcohol to obtain the high-purity liraglutide side chain. The method for preparing the high-purity liraglutide side chain is simple to operate, the synthesis period is short, the cost is low, the after-treatment is easy, the product purity can reach 99.41%, and the method can effectively remove HOSU, DIU, tetradecanoic acid impurities, L5-S2 and octadecanoic acid impurities and other unknown impurities, and is beneficial to large-scale production.
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Paragraph 0046-0047
(2019/07/04)
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- LIPID-MODIFIED NUCLEIC ACID COMPOUNDS AND METHODS
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Disclosed herein, inter alia, are lipid-modified nucleic acid compounds of the following structure, their preparation, and their use: (I).
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Paragraph 0548; 0561; 0605
(2019/12/25)
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- Synthesis and Characterization of Fatty Acid Grafted Chitosan Polymer and Their Nanomicelles for Nonviral Gene Delivery Applications
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The aim of this study was to synthesize and characterize fatty acid-grafted-chitosan (fatty acid-g-CS) polymer and their nanomicelles for use as carriers for gene delivery. CS was hydrophobically modified using saturated fatty acids of increasing fatty acyl chain length. Carbodiimide along with N-hydroxysuccinimide was used for coupling carboxyl group of fatty acids with amine groups of CS. Proton nuclear magnetic resonance and Fourier transform infrared spectroscopy were used to quantify fatty acyl substitution onto CS backbone. The molecular weight distribution of the synthesized polymers was determined using size exclusion high performance liquid chromatography and was found to be in range of the parent CS polymer (~50 kDa). The critical micelle concentration (cmc) of the polymers was determined using pyrene as a fluorescent probe. The cmc was found to decrease with an increase in fatty acyl chain length. The amphiphilic fatty acid-g-CS polymers self-assembled in an aqueous environment to form nanomicelles of ~200 nm particle size and slightly positive net charge due to the cationic nature of free primary amino groups on CS molecule. These polymeric nanomicelles exhibited excellent hemo- and cytocompatibility, as evaluated by in vitro hemolysis and MTT cell viability assay, respectively, and showed superior transfection efficiency compared to unmodified chitosan and naked DNA. The surface of these nanomicelles can be further modified with ligands allowing for selective targeting, enhanced cell binding, and internalization. These nanomicelles can thus be exploited as potential nonviral gene delivery vectors for safe and efficient gene therapy.
- Sharma, Divya,Singh, Jagdish
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p. 2772 - 2783
(2017/11/20)
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- Single-stranded nucleic acid molecule for regulating expression of gene having delivering function
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The invention provides a single-stranded nucleic acid capable of inhibiting expression of a target gene having a delivery function. The nucleic acid contains, from the 5′-side to the 3′-side, a 5′-side region (Xc), a linker region (Lx), an inner region (Z), a linker region (Ly) and a 3′-side region (Yc) in this order, wherein the inner region (Z) is constituted by linkage of the inner 5′-side region (X) and the inner 3′-side region (Y), the 5′-side region (Xc) is complementary to the inner 5′-side region (X), the 3′-side region (Yc) is complementary to the inner 3′-side region (Y), at least one of the inner region (Z), the 5′-side region (Xc) and the 3′-side region (Yc) comprises an expression inhibitory sequence that inhibits expression of a target gene, and at least one of the 5′-terminus, the 3′-terminus, the linker region (Lx) and the linker region (Ly) is bound to a bio-related substance.
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Page/Page column 41; 42
(2017/06/19)
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- Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs
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Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide-alkyn
- Berthelot, Nathan,Brossay, Antoine,Gasciolli, Virginie,Bono, Jean-Jacques,Baron, Aurélie,Beau, Jean-Marie,Urban, Dominique,Boyer, Fran?ois-Didier,Vauzeilles, Boris
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supporting information
p. 7802 - 7812
(2017/10/06)
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- Lipid dipeptide and gel
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A gelator that includes a lipid peptide of Formula (1) wherein R1 is a C9-23 aliphatic group, R2 is a hydrogen atom or a C1-4 alkyl group optionally having a C1-2 branched chain, R3 is a —(CH2)n—X group, n is a number from 1 to 4, and X is an amino group, a guanidino group, a —CONH2 group, or a 5-membered ring optionally having 1 to 3 nitrogen atoms, a 6-membered ring optionally having 1 to 3 nitrogen atoms, or a fused heterocycle including a 5-membered ring and a 6-membered ring that optionally has 1 to 3 nitrogen atoms; or a pharmaceutically usable salt of the lipid peptide.
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Page/Page column 25
(2016/05/19)
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- Amphiphilic peptide molecule and its preparation method and use
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The invention relates to an amphiphilic peptide molecule and its preparation method. The amphiphilic peptide molecule comprises a glutamic acid peptide molecule with palmitic acid as an end group and methoxypolyethylene glycol as a side chain. The amphiphilic peptide molecule has hydrophobicity of a palmitic acid molecule hydrocarbon chain at the middle of the peptide molecule and hydrophily of a glutamic acid side group methoxypolyethylene glycol chain segment. The amphiphilic peptide molecule has a wide application prospect in preparation of a polypeptide drug carrier or reagent, a drug loading and temperature control release reagent and a temperature-responsive polypeptide or construction of a polypeptide hydrogel system.
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Paragraph 0030; 0031; 0032
(2017/01/17)
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- A systematic understanding of gelation self-assembly: solvophobically assisted supramolecular gelation via conformational reorientation across amide functionality on a hydrophobically modulated dipeptide based ambidextrous gelator, N-n-acyl-(l)Val-X(OBn), (X = 1,ω-amino acid)
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A systematic investigation on gelation self-assembly has been performed on a hydrophobically modulated dipeptide based ambidextrous gelator, N-n-acyl-(l)Val-X(OBn), (X = 1,ω-amino acid). To elucidate the effect of hydrophobic tuning on gelator architecture towards its gelation self-assembly, three sets of gelators with a common formula: CmH2m+1C(=O)NH(l)Val(C=O)NH-(CH2)n-(C=O)OBn, were synthesized, Set-I includes gelators with n = 2, m = 9, 11, 13, 15, 17, for Set-II it is n = 2, 3, 5, m = 13 and Set-III comprises of two isomeric gelators (n = 2, m = 15; n = 10, m = 7). Gelation has been critically analyzed in various apolar (aromatic and aliphatic) and polar (protic and aprotic) solvents using FESEM, CD, IR, WAXRD and rheological studies. Obtained results reveal that π-π type interaction dictates the primary molecular alignment and positioning of amide functionality across the aliphatic chain which influences the peptidic orientation in parallel (when m > n) or antiparallel (when m gel and yield stress of gel systems increases with m, but for a given m, the trend goes apparently inverse with the increasing n. Circular dichroism (CD) studies suggest an intriguing evidence of non-planarity of amide plane during self-assembly, highlighting the involvement of conformational change taking place during molecular organization towards its gelation. Despite complex nature of solvent-gelator interaction, the effect of H-bonding component of solubility parameters was found to have a significant role on self-assembly. Overall, supramolecular forces acting at specific functionalities encrypted in gelator backbone must overcome the solvation energy with synergic assistance of solvophobic effect towards stabilization of gel-network with optimum gelator backbone conformation for achieving required enthalpic contribution for self-assembly.
- Haldar, Saubhik,Karmakar, Koninika
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p. 66339 - 66354
(2015/08/18)
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- POLYNUCLEOTIDE CONSTRUCTS HAVING DISULFIDE GROUPS
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The invention features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components is attached to an internudeotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains one or more bulky groups proximal to the disulfide group. The invention also features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components (i) is attached to an internudeotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains at least 4 atoms in a chain between the disulfide linkage and the phosphorus atom of the internudeotide bridging group or the terminal group; and where the chain does not contain a phosphate, an amide, an ester, or an alkenylene. The invention also features methods of delivering a polynucleotide to a cell using the polynucleotide constructs of the invention.
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Page/Page column 174
(2015/05/26)
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- POLYNUCLEOTIDE CONSTRUCTS HAVING BIOREVERSIBLE AND NON-BIOREVERSIBLE GROUPS
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The invention features a hybridized polynucleotide construct containing a passenger strand, a guide strand loadable into a RISC complex, and (i) a 3'-terminal or an internucleotide non-bioreversible group in the guide strand; or (ii) a 5'-terminal, a 3'-terminal, or an internucleotide non-bioreversible group in the passenger strand, and a 5'-terminal, a 3'-terminal, or an internucleotide disulfide bioreversible group in the guide strand or the passenger strand. The invention also features methods of delivering a polynucleotide to a cell using the hybridized polynucleotide construct. The invention further features methods of reducing the expression of a polypeptide in a cell using the hybridized polynucleotide construct.
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Page/Page column 180
(2016/02/19)
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- Co-liposomes comprising a lipidated multivalent RGD-peptide and a cationic gemini cholesterol induce selective gene transfection in αvβ3 and αvβ5 integrin receptor-rich cancer cells
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The αvβ3 and αvβ5 integrins, transmembrane glycoprotein receptors, are over-expressed in numerous tumors and in endothelial cells that constitute tumor blood vessels. As this protein selectively binds to the Arg-Gly-Asp (RGD) sequence containing peptides, it is an attractive way to target tumors. Herein we have developed novel formulations for integrin mediated selective gene delivery. These formulations are composed of a novel palmitoylated tetrameric RGD containing scaffold (named RAFT-RGD), cationic gemini cholesterol (GL5) and a natural helper lipid 1,2-dioleoyl-l-α- glycero-3-phosphatidylethanolamine (DOPE). We have optimized a co-liposomal formulation to introduce the multivalent RGD-containing macromolecule in GL5: DOPE (GL5D) mixture to produce GL5D-RGD. We have unambiguously shown the selectivity of these formulations towards cancer cells that over express αvβ3 and αvβ5 integrins. Two reporter plasmids, pEGFP-C3 and PGL-3, were employed for the transfection experiments and it was shown that GL5D-RGD liposomes increased exclusively the transfection in αvβ3 and αvβ5-overexpressing HeLa cells. This journal is the Partner Organisations 2014.
- Misra, Santosh K.,Kondaiah, Paturu,Bhattacharya, Santanu,Boturyn, Didier,Dumy, Pascal
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supporting information
p. 5758 - 5767
(2014/11/08)
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- Multifunctional core-shell silica nanoparticles for highly sensitive 19F magnetic resonance imaging
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19F magnetic resonance imaging (19F MRI) is useful for monitoring particular signals from biological samples, cells, and target tissues, because background signals are missing in animal bodies. Therefore, highly sensitive 19/su
- Matsushita, Hisashi,Mizukami, Shin,Sugihara, Fuminori,Nakanishi, Yosuke,Yoshioka, Yoshichika,Kikuchi, Kazuya
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supporting information
p. 1008 - 1011
(2014/03/21)
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- Synthesis and physicochemical properties of new tripodal amphiphiles bearing fatty acids as a hydrophobic group
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Saturated fatty acids (FA) were grafted using tyrosine as a spacer group to the cyclotriphosphazene ring along with equimolar hydrophilic methoxy poly(ethylene glycol) (MPEG) in cis-nongeminal way. Seven new cyclotriphosphazene amphiphiles were prepared from combinations of hydrophilic MPEGs with different molecular weights of 350, 550, 750 and 1000 and four different fatty acids of different hydrophobicity including lauric, myristic, palmitic and stearic acids. These steric amphiphiles bearing fatty acids as a hydrophobic group were found to form more stable micelles with very low critical micelle concentrations (CMC) (2.95-7.80 mg/L) compared with oligopeptide analogues, and their highly hydrophobic core environment is unique and potentially useful for various biomedical applications.
- Avaji, Prakash G.,Jadhav, Vithal B.,Cui, Jin Xin,Jun, Yong Joo,Lee, Hwa Jeong,Sohn, Youn Soo
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supporting information
p. 1763 - 1767
(2013/04/10)
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- SPRAY BASE MATERIAL INCLUDING LOW-MOLECULAR GELATOR
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There is provided a spray base material that can be safely used with a sense of security, that prevents leakage of liquid from a spray container, that is sprayable under any condition (when inverted, for example), that is sprayable to achieve uniform coat
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Page/Page column 9
(2012/02/15)
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- Synthesis and characterization of maltose-based amphiphiles as supramolecular hydrogelators
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Low molecular mass amphiphilic glycolipids have been prepared by linking a maltose polar head and a hydrophobic linear chain either by amidation or copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. The liquid crystalline properties of these amphiphilic materials have been characterized. The influence of the chemical structure of these glycolipids on the gelation properties in water has also been studied. Glycolipids obtained by the click coupling of the two components give rise to stable hydrogels at room temperature. The fibrillar structure of supramolecular hydrogels obtained by the self-assembly of these gelators have been characterized by electron microscopy. Fibers showed some torsion, which could be related with a chiral supramolecular arrangement of amphiphiles, as confirmed by circular dichroism (CD). The sol-gel transition temperature was also determined by differential scanning calorimetry (DSC) and NMR.
- Clemente, Maria J.,Fitremann, Juliette,Mauzac, Monique,Serrano, Jose L.,Oriol, Luis
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experimental part
p. 15236 - 15247
(2012/05/20)
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- Cell adhesion through clustered ligand on fluid supported lipid bilayers
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The quartz crystal microbalance technique with dissipation monitoring and the complementary optical microscopy technique were used for monitoring cell adhesion on an RGD-functionalized supported lipid bilayer. A critical interligand RGD spacing of nearly 80 nm was estimated for cell adhesion when an RGD spacing of 10 nm was necessary to observe flattened cells on a fluid surface.
- Sandrin, Ludivine,Coche-Guerente, Liliane,Bernstein, Amandine,Basit, Hajra,Labbe, Pierre,Dumy, Pascal,Boturyn, Didier
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supporting information; experimental part
p. 1531 - 1534
(2010/07/04)
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- Synthesis of lipoamino acids and their activity against cerebral ischemic injury
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A series of lipoamino acids were synthesized and their neuroprotective effect against brain ischemia induced by oxygen-glucose deprivation (OGD) on rat cerebral slices was evaluated. Among these compounds, N-stearoyl-L-tyrosine (4), N-stearoyl-L-serine (5) and N-stearoyl-L-threonine (6) exhibited good neuroprotective activity. We found that the neuroprotective activity of lipoamino acids depended on the acyl group, the presence of a free carboxylic function and a free hydroxyl group at the branched chain of the amino acids. The results also showed that 5 was the most active compound, protecting rat brain slices against OGD as well as hydrogen peroxide (H2O2) insult at the range of 1-10 M.
- Yao, Li-Yun,Lin, Qi,Niu, Yin-Yao,Deng, Ke-Min,Zhang, Jian-Hua,Lu, Yang
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experimental part
p. 4051 - 4064
(2009/12/26)
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- COMPOUNDS AND METHODS OF TREATING OBESITY
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The present invention relates to novel fatty acid derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds and compositions, especially as agents for the treatment of obesity and related disorders, and for improving cognition.
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Page/Page column 64-65
(2009/10/22)
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- Synthetic libraries of tyrosine-derived bacterial metabolites
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The preparation of a collection of 131 small molecules, reminiscent of families of long chain N-acyl tyrosines, enamides and enol esters that have been isolated from heterologous expression of environmental DNA (eDNA) in Escherichia coli, is reported. The synthetic libraries of N-acyl tyrosines and their 3-keto counterparts were prepared via solid-phase routes, whereas the enamides and enol esters were synthesized in solution-phase.
- Georgiades, Savvas N.,Clardy, Jon
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supporting information; experimental part
p. 3117 - 3121
(2009/04/03)
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- Determination of N-terminal myristoylation of proteins using a combined gas chromatographic/mass spectrometric assay of derived myristoylglycine: Electron impact-induced fragmentation of acylglycine derivatives
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A method based on gas chromatography/mass spectrometry is described for the detection of N-terminal myristoylation of proteins. Myristoylglycine, derivatized as its trimethylsily (TMS) ester, gave an electron impact mass spectrum containing abundant molecular and [M - CH3]+ ions, together with several ions diagnostic of the acyl glycine moiety, namely at m/z 145, 158, 172 and 189. The compositions of these ions and the mechanism that produced them were investigated by high-resolution mass measurements, deuterium labelling and the preparation of analogons compounds. As these ions were present in the spectra of all acylglycines examined, they could be used as markers for these compounds. A selected-ion monitoring method for the detection of myristoylglycine was set up using the above ions and was used to confirm the presence of N-terminal myristoylation in three referenee peptides. A series of ions produced by radical-induced cleavage of the alkyl chain following TMS group migration and elimination of carbon dioxide gave information on the structure of the chain and could be used to determine the structure of other potential acylglycines such as those with unsaturated acyl chains. Thus the derivatives could be used not only to detect myristoylation of protein, but also to detect and determine the structures of other acyl substituents.
- McIlhinney,Harvey
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p. 900 - 910
(2007/10/02)
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- SYNTHESIS AND BIOLOGICAL ACTIVITIES OF SOME PEPTIDOGLYCAN MONOMER DERIVATIVES
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N-acyl derivatives and N-acetyl-glucosaminyl-β-(1->4)-N-acetyl-muramoyl-L-alanyl-D-isoglutaminyl-L-meso-diaminopimelyl-(D-amide)-(L)-D-alanyl-D-alanine (peptidoglycan monomer, PGM) complexes with some bivalent metals were prepared and their immunomodulatory activities examined.
- Suskovic, B.,Vajtner, Z.,Naumski, R.
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p. 8407 - 8416
(2007/10/02)
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- Synthesis and Biological Activities of N-Acetylglucosaminyl-&β(1->4)-N-Acetylmuramyl Tri- and Tetrapeptide Derivatives
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The acylated, amidated and esterified derivatives of N-acetylglucosaminyl-β(1->4)-N-acetylmuramyl tri- and tetrapeptide were synthesized and examined as to their protective effect on pseudomonal infection in the mouse and pyrogenicity in the rabbit.Modifications of the terminal end function of the peptide moieties in their molecules caused enhancement of resistance to pseudomonal infection and reduction of pyrogenicity.Among the compounds tested, sodium N-acetylglucosaminyl-β(1->4)-N-acetylmuramyl-L-alanyl-D-isoglutaminyl-(L)-stearoyl-(D)-meso-2,6-diaminopimelic acid-(D)-amide and sodium N-acetylglucosaminyl-β(1->4)-N-acetylmuramyl-L-alanyl-D-isoglutaminyl-(L)-stearoyl-(D)-meso-2,6-diaminopimelic acid-(D)-amide-(L)-D-alanine were found to be advantageous and conceivably worthwhile for further investigation as immunobiologically active compounds.
- Furuta, Rhyuji,Kawata, Shigeo,Naruto, Shunsuke,Minami, Akira,Kotani, Shozo
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p. 2561 - 2572
(2007/10/02)
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- Kasugamycin derivatives, pharmaceutical compositions and method of use
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This invention relates to new aminoglycoside derivatives and pharmaceutically acceptable salts thereof. More particularly it relates to new aminoglycoside derivatives and pharmaceutically acceptable salts thereof which have anti-viral activity, and immuno-stimulating activity and pharmaceutical compositions comprising the same. In addition, this invention also relates to methods of preparing the aminoglycoside derivatives and salts thereof.
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- Use of esters of N-hydroxysuccinimide in the synthesis of N-acylamino acids.
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Several crystalline N-hydroxysuccinimide esters of short- and long-chain fatty acids have been synthesized. These compounds react with free amino acids to form preferentially N-acylamino acids. The reaction of the N-hydroxysuccinimide esters with hydroxylamine and the behavior of the N-acylamino acids on thin-layer chromatography are described.
- Lapidot,Rappoport,Wolman
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p. 142 - 145
(2007/10/08)
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