19097-15-5Relevant academic research and scientific papers
Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis
Aldrich, Courtney C.,Baran, Marzena,Boshoff, Helena I. M.,Fu, Peng,Grimes, Kimberly D.,Sibbald, Paul A.,Wilson, Daniel J.
, (2020/06/29)
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.
11-Phenoxyundecyl phosphate as a 2-acetamido-2-deoxy-α-d- glucopyranosyl phosphate acceptor in O-antigen repeating unit assembly of Salmonella arizonae O:59
Druzhinina, Tatyana N.,Danilov, Leonid L.,Torgov, Vladimir I.,Utkina, Natalya S.,Balagurova, Nadezhda M.,Veselovsky, Vladimir V.,Chizhov, Alexander O.
experimental part, p. 2636 - 2640 (2011/01/12)
A synthesis of 11-phenoxyundecyl phosphate and its biochemical transformation (using GlcNAc-P transferase from Salmonella arizonae O:59 membranes catalysing transfer of GlcNc-phosphate from UDP-GlcNAc on lipid-phosphate) into P1-11-phenoxyundec
4-DIMETHYLAMINOBUTYRIC ACID DERIVATIVES
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Page/Page column 15, (2009/10/31)
This invention relates to novel 4-dimethylaminobutyric acid derivatives of the formula wherein A1, A2, R1, m and n are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds inhibit carnitine palmitoyl transferase (CPT) activity, in particular CPT2 activity, and can be used as medicaments in methods for the treatment of diseases modulated by CPT2 inhibitors.
The influence of phenyl and phenoxy modification in the hydrophobic tails of di-n-alkyl phosphate amphiphiles on aggregate morphology
Visscher, Inge,Stuart, Marc C. A.,Engberts, Jan B. F. N.
, p. 707 - 712 (2007/10/03)
A series of di-n-alkyl phosphate amphiphiles containing phenyl and phenoxy groups in the hydrophobic tails were synthesised, and their aggregation behaviour was investigated using fluorescence spectroscopy, differential scanning calorimetry, and cryo-electron microscopy. The aggregates displayed a wide variety of aggregate morphologies. The incorporation of a phenyl group into the end or in the middle of the alkyl chain lowered the main phase transition temperature, resulting in closed vesicles only above the phase transition temperature. Introducing a phenoxy group at the end of the alkyl chain resulted in open bilayer structures and bicelles. The Royal Society of Chemistry.
Identification of a UDP-Gal: GlcNAc-R galactosyltransferase activity in Escherichia coli VW187
Montoya-Peleaz, Pedro J.,Riley, John G.,Szarek, Walter A.,Valvano, Miguel A.,Schutzbach, John S.,Brockhausen, Inka
, p. 1205 - 1211 (2007/10/03)
A novel acceptor substrate for galactosyltransferase was synthesized containing GlcNAcα-pyrophosphate, covalently bound to a hydrophobic phenoxyundecyl moiety (GlcNAc α-O-PO3-PO3-(CH 2)11-O-Phenyl). The new subs
Method of treating lipidemia with aryloxyalkylaminobenzoic acids and esters
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, (2008/06/13)
Aryloxyalkylaminobenzoic acids and esters as hypolipemic compounds.
