114134-57-5Relevant articles and documents
SYNTHESIS OF ENZYME-INHIBITORY PHOSPHOLIPID ANALOGS II. PREPARATION OF CHIRAL 1-ACYL-2-ACYLAMIDO-2-DEOXYGLYCEROPHOSPHORYLCHOLINES FROM SERINE
Chandrakumar, Nizal S.,Hajdu, Joseph
, p. 2949 - 2952 (1981)
A facile and efficient stereospecific route to the enzyme-inhibitory 2-amide analogs of phosphatidylcholine is reported.
N-acyl-O-phosphocholineserines: Structures of a novel class of lipids that are biomarkers for Niemann-Pick C1 disease
Sidhu, Rohini,Mondjinou, Yawo,Qian, Mingxing,Song, Haowei,Kumar, Arun Babu,Hong, Xinying,Hsu, Fong-Fu,Dietzen, Dennis J.,Yanjanin, Nicole M.,Porter, Forbes D.,Berry-Kravis, Elizabeth,Vite, Charles H.,Gelb, Michael H.,Schaffer, Jean E.,Ory, Daniel S.,Jiang, Xuntian
, p. 1410 - 1424 (2019)
Niemann-Pick disease type C1 (NPC1) is a fatal, neurodegenerative, cholesterol storage disorder. With new therapeutics in clinical trials, there is an urgency to improve diagnostics and monitor therapeutic efficacy with biomarkers. In this study, we sought to define the structure of an unknown lipid biomarker for NPC1 with [M + H]+ ion at m/z 509.3351, previously designated as lysoSM-509. The structure of N-palmitoyl-O-phosphocholineserine (PPCS) was proposed for the lipid biomarker based on the results from mass spectrometric analyses and chemical derivatizations. As no commercial standard is available, authentic PPCS was chemically synthesized, and the structure was confirmed by comparison of endogenous and synthetic compounds as well as their derivatives using liquid chromatographytandem mass spectrometry (LC-MS/MS). PPCS is the most abundant species among N-acyl-O-phosphocholineserines (APCS), a class of lipids that have not been previously detected in biological samples. Further analysis demonstrated that all APCS species with acyl groups ranging from C14 to C24 were elevated in NPC1 plasma. PPCS is also elevated in both central and peripheral tissues of the NPC1 cat model. Identification of APCS structures provide an opportunity for broader exploration of the roles of these novel lipids in NPC1 disease pathology and diagnosis.-Sidhu, R., Y. Mondjinou, M. Qian, H. Song, A. B. Kumar, X. Hong, F-F. Hsu, D. J. Dietzen, N. M. Yanjanin, F. D. Porter, E. Berry- Kravis, C. H. Vite, M. H. Gelb, J. E. Schaffer, D. S. Ory, and X. Jiang. N-acyl-O-phosphocholineserines: structures of a novel class of lipids that are biomarkers for Niemann-Pick C1 disease. J. Lipid Res. 2019. 60: 1410-1424.
In situ formation of AuNPs using fatty N-acylamino hydrazide organogelators as templates
Ongaratto, Renata,Conte, Naiane,Montes D'Oca, Caroline R.,Brinkerhoff, Rafael C.,Ruas, Caroline Pires,Gelesky, Marcos Alexandre,Montes D'Oca, Marcelo G.
, p. 295 - 303 (2019/01/04)
This work reports, for the first time, the synthesis of new fatty N-acylamino hydrazides and demonstrates the activity of these compounds as low-molecular-weight organic gelators and templates for preparation of gold nanoparticles (AuNPs). Initially, we evaluated the gelation properties of fatty N-acylamino hydrazides in various nonpolar and polar solvents (n-hexane, toluene, benzene, cyclohexane, and ethanol). Fatty N-acylamino hydrazide derived of the glycine and stearic acid (C18:0) did not form gels in any of the tested solvents. All other hydrazides did form gels in at least two of the organic solvents tested. The morphology of each gel was observed via scanning electron microscopy. The organogels derived from alanine, valine, and phenylalanine had translucid properties, while the serine organogels were opaque. Afterwards, the synthesis of AuNPs in the presence of the organogelator using microwave irradiation was realized. Organogelator agents reduced HAuCl4 showing plasmon band peaks between 530 and 543 nm. In addition, the method does not require a reducing agent, which is typically a potential source of contamination and toxicity. Therefore, this work confirms the importance of the hydrazide group of the new fatty N-acylamino hydrazides in gel formation and as organogelator agents for preparation of AuNPs.
COMPOSITIONS AND METHODS FOR THE MODULATION OF SPECIFIC AMIDASES FOR N-ACYLETHANOLAMINES FOR USE IN THE THERAPY OF INFLAMMATORY DISEASES
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Paragraph 0055; 0056, (2015/03/04)
The present invention regards compositions and methods for the modulation of amidases capable of hydrolysing N-acylethanolamines useable in the therapy of inflammatory diseases. In particular, the present invention regards a compound of general formula (I): enantiomers, diastereoisomers, racemes and mixtures, polymorphs, salts, solvates thereof, wherein: (a) R is a linear alkyl radical having 13 to 19 carbon atoms or alkenyl radical having 13 to 19 carbon atoms carrying a double bond; (b) X is 0 or S; (c) Y is a 2 or 3 carbon atom alkylene residue, optionally substituted with one or two groups equal or different from each other and selected from among the group consisting of: —CH3, —CH2OH, —COOCH3, —COOH. Y may preferably be: —CH2—CH2—, —CH2—CH2—CH2—, CH(CH3)—CH2—, —CH2—CH(CH3)—, —CH2—C(CH3)2—, —CH2—CH(CH2OH)—, —CH2—C((CH2OH)2)—, —CH═CH—, —CH2—CH(COOCH3)—, —CH2—CH(COOH)—, for use as a medicine.
