14565-47-0

Usage

Biochem/physiol Actions

Lauric acid N-hydroxysuccinimide ester may be used for the synthesis of N-acylamino acids and lipidization of polypeptides or other applications that use N-hydroxysuccinimide ester conjugation chemistry.

InChI:InChI=1/C16H27NO4/c1-2-3-4-5-6-7-8-9-10-11-16(20)21-17-14(18)12-13-15(17)19/h2-13H2,1H3

Upstream product

• 143-07-7 lauric acid 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 74124-79-1 di(succinimido) carbonate 
• 112-16-3 n-dodecanoyl chloride 
• 123-56-8 Succinimide 

Downstream Products

• 14379-28-3 N-Lauroyl-L-valine 
• 83048-76-4 (S)-methyl 2-(dodecanamido)-3-(4-hydroxyphenyl)propanoate 
• 123725-51-9 N-<(2S,2'S)-2-<2-(dodecanoylamino)-5-hydroxypentyloxy>propanoyl>-L-alanyl-D-isoglutamine benzyl ester 
• 14379-56-7 N-Lauroylserine 
• 58725-39-6 N-dodecanoyl-L-proline 
• 66653-99-4 2-<2-(Dodecanoylamino)ethoxy>acetic acid 
• 1080673-18-2 C₂₆H₄₄O₃Si 
• 1039560-21-8 C₂₆H₄₄O₃Si 
• 1069128-45-5 C₆₉H₁₀₂N₁₂O₁₇S 
• 1426701-67-8 C₂₃H₃₆NO₄^(1-)*Na⁽¹⁺⁾ 
• 113535-14-1 C₂₃H₃₇NO₄ 
• 1352209-30-3 1-(4-fluorophenyl)-1-dodecanone 
• 1428743-62-7 1-(4-[1-(tert-butyl)-1,1-dimethylsilyl]oxyphenyl)-1-dodecanone 

Relevant academic research and scientific papers

L-serine and glycine based ceramide analogues as transdermal permeation enhancers: Polar head size and hydrogen bonding

Novel transdermal permeation enhancers related to stratum corneum ceramides were investigated. The synthesis of a series of simple compounds based on two selected amino acids, L-serine and glycine, and their enhancement activities are reported. Glycine derivative 3 enhanced the permeation of theophylline through human skin in vitro 12.5±0.5 times. The relationships between properties of the polar head of the compounds and their activity are discussed.

The Study of Stability of Proline-Containing Derivatives of Dopamine and Serotonin in the Biological Media in Vitro Experiments

Abstract—: The peptides Boc-Gly-Pro-DP, Z-Gly-Pro-DP, LA-Gly-Pro-DP, Boc-Gly-Pro-Srt, Z-Gly-Pro-Srt have been synthesized for the first time. The study of their stability in the presence of leucine aminopeptidase, carboxypeptidase Y, carboxypeptidase B, and proline endopeptidase (PEP) has shown that the synthesized peptides are stable in the presence of aminopeptidases and carboxypeptidases. In the presence of PEP, dopamine (DP) and serotonin (Srt) have been cleaved from these substances. Thus, the originally synthesized proline derivatives of Srt and DP may be considered as the resources, from which Srt and DP can be gradually released. This creates the possibility of a prolonged action of these biologically active compounds on cells and, consequently, on the whole body.

Glucosamine anchored cancer targeted nano-vesicular drug delivery system of doxorubicin

Background: Efficacy of an anticancer drug is challenged by severe adverse effects persuaded by the drug itself; hence designing a tumour targeted delivery system is chosen as an objective of this research work.Purpose: We propose, glucose transporter targeting ligand, i.e. synthesised N-lauryl glucosamine (NLG) anchored doxorubicin (DOX) in niosomal formulation.Methods: Synthesised NLG was incorporated into niosomal formulation of DOX using Span 60 as surfactant, cholesterol as membrane stabilizer and dicetyl phosphate (DCP) as stabilizer.Results: The formulation was stable with particle size of 110 ± 5 nm, zeta potential -30 ± 5 mV and entrapment efficiency approximately 95%. DSC and XRD pattern of freeze-dried formulation demonstrated encapsulation of DOX in niosomal formulation. Cytotoxicity of targeted niosomal formulation (IC50 = 0.830 ppm) was higher than non-targeted niosomal formulation (IC50 = 1.369 ppm) against B6F10 melanoma cell lines. In vitro cellular internalization revealed that targeted niosomal formulation was internalised more efficiently with higher cellular retention by cancer cells compared to the non-targeted niosomal formulation and free DOX. In vitro receptor binding and docking study of targeted niosomal formulation had shown the comparative association potential with glucose receptor.Conclusion: NLG anchored niosomal formulation of DOX with enhanced cytotoxicity, internalization and receptor binding potential has implication in targeted cancer therapy.

Dendrimeric pyridoxamine enzyme mimics

PAMAM dendrimers from generations 1-6 were synthesized with pyridoxamine in their core. They transaminated pyruvic and phenylpyruvic acids in water to alanine and phenylalanine, respectively, with Michaelis-Menten kinetics and high effectiveness compared with simple pyridoxamine. The largest dendrimerssimilar in size to some globular proteinswere comparable in effectiveness to a previous polyethylenimine (PEI)-pyridoxamine catalyst, and to a protein-pyridoxamine catalyst, but not as effective as a previous PEI-pyridoxamine carrying lauryl hydrophobic groups. The new catalysts showed both general acid/base catalysis by their amino groups and hydrophobic binding of the phenylpyruvate substrate. Copyright

Encapsulation of paclitaxel into lauric acid-O-carboxymethyl chitosan-transferrin micelles for hydrophobic drug delivery and site-specific targeted delivery

Transferrin/PEG/O-carboxymethyl chitosan/fatty acid/paclitaxel (TPOCFP) micelles were tested for suitability as a drug carrier characterized by low cytotoxicity, sustained release, high cellular uptake, and site-specific targeted delivery of hydrophobic drugs. Characterization, drug content, encapsulation efficiency, and in vitro drug release were investigated. When the feeding amount of paclitaxel (PTX) was increased, the drug content increased, but loading efficiency decreased. TPOCFP micelles had a spherical shape, with a particle size of approximately 140-649 nm. In vitro cell cytotoxicity and hemolysis assays were conducted to confirm the safety of the micelles. Anticancer activity and confocal laser scanning microscopy (CLSM) were used to confirm the targeting efficiency of target ligand-modified TPOCFP micelles. Anticancer activity and CLSM results clearly demonstrated that transferrin-modified TPOCFP micelles were quickly taken up by the cell. The endocytic pathway of TPOCFP micelles was analyzed by flow cytometry, revealing transfection via receptor-mediated endocytosis. These results suggest that PTX-encapsulated TPOCFP micelles may be used as an effective cancer-targeting drug delivery system for chemotherapy.

Convenient synthesis of N-hydroxysuccinimide esters from carboxylic acids using triphosgene

A simple and convenient method for the synthesis of N-hydroxysuccinimide ester is developed using triphosgene as an acid activator. Several aromatic and aliphatic N-hydroxysuccinimide esters are prepared from their corresponding carboxylic acids at room temperature in good yields in a rapid process using triphosgene. Some of the major advantages are mild conditions, good yields, and easy operation.

Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis

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.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATORY SKIN DISEASES AND CANCER

The invention relates to the compounds or its pharmaceutical acceptable polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, formula II formula III, formula IV, formula V, formula VI, formula VII, and formula VIII and the methods for the treatment of inflammatory skin diseases and cancer may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, lozenge, spray, intravenous, oral solution, nasal spray, oral solution, suspension, oral spray, buccal mucosal layer tablet, parenteral administration, syrup, or injection. Such compositions may be used to treatment of facial hirsutism, GI Polyps, rosacea, acne, melanoma, psoriasis, dermatitis and cancer including gliomas, gastrointestinal polyps, anaplastic astrocytoma and metastatic cancers.

A reagent for analysis of blood and preparation method therof

The present invention relates to a compound for hemanalysis, capable of lysing blood cells except leukocytes without globulolysis of leukocytes. The present invention further relates to a production method thereof. According to various embodiments of the present invention, the compound can lyse every blood cell except the leukocyte without globulolysis of leukocyte, thereby being selectively applicable to various fields. In addition, a kit or a composition for globulolysis using the compound and a kit or a composition for hemanalysis exhibit excellent efficiency compared to conventional counterparts. To this end, the compound is represented by chemical formula 14 or 15.COPYRIGHT KIPO 2018

Synthesis and Characterization of Fatty Acid Grafted Chitosan Polymer and Their Nanomicelles for Nonviral Gene Delivery Applications

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.