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Chemical Compound Review

Phenylbutyrate     4-phenylbutanoic acid

Synonyms: SureCN1716, NSC-295, AGN-PC-006I8K, AG-C-45091, ACMC-209eip, ...
 
 
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Disease relevance of NSC 295

  • 1-Aryl-3-(2-chloroethyl) ureas and 1-aryl-3-nitroso-3-(2-chloroethyl) ureas, derived from 4-phenylbutyric acid and alkylanilines, were synthesized and their cytotoxicity was evaluated on human adenocarcinoma cells in vitro [1].
 

High impact information on NSC 295

 

Biological context of NSC 295

  • In contrast, its enantiomer PD 140548 ((benzenebutanoic acid, beta-[[3-(1H-indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3.3.1.1(3,7] dec-2-yloxy)carbonyl]amino]propyl] amino],-[S-(R*,S*)) displayed the reverse selectivity (CCKA IC50 = 2.8 nM, CCKB IC50 = 260 nM) [5].
 

Anatomical context of NSC 295

 

Associations of NSC 295 with other chemical compounds

  • The structural analysis of the isolated product by (1)H, (13)C NMR, mass spectroscopy and FT-IR revealed it to be a 4-phenyl butanoic acid derivative (CL) of lisinopril [6].
  • HPLC stability studies at pH 5.0 with the related model compounds 5, 7, 8, and 9, in which chlorambucil was substituted by 4-phenylbutyric acid, demonstrated that the carboxylic hydrazone derivatives have acid-sensitive properties; the acid lability of 7 was particular prominent with a half-life of only a few hours [7].
 

Gene context of NSC 295

 

Analytical, diagnostic and therapeutic context of NSC 295

References

  1. 1-Aryl-3-(2-chloroethyl) ureas: synthesis and in vitro assay as potential anticancer agents. Gaudreault, R.C., Lacroix, J., Pagé, M., Joly, L.P. Journal of pharmaceutical sciences. (1988) [Pubmed]
  2. Chemical chaperones protect from effects of apoptosis-inducing mutation in carbonic anhydrase IV identified in retinitis pigmentosa 17. Bonapace, G., Waheed, A., Shah, G.N., Sly, W.S. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  3. Inhibition of Histone Deacetylation Does Not Block Resilencing of p16 after 5-Aza-2'-Deoxycytidine Treatment. Egger, G., Aparicio, A.M., Escobar, S.G., Jones, P.A. Cancer Res. (2007) [Pubmed]
  4. The peroxisome proliferator phenylbutyric acid (PBA) protects astrocytes from ts1 MoMuLV-induced oxidative cell death. Liu, N., Qiang, W., Kuang, X., Thuillier, P., Lynn, W.S., Wong, P.K. J. Neurovirol. (2002) [Pubmed]
  5. Peptoid CCK receptor antagonists: pharmacological evaluation of CCKA, CCKB and mixed CCKA/B receptor antagonists. Singh, L., Field, M.J., Hill, D.R., Horwell, D.C., McKnight, A.T., Roberts, E., Tang, K.W., Woodruff, G.N. Eur. J. Pharmacol. (1995) [Pubmed]
  6. Identification of a new impurity in lisinopril. Shinde, V., Trivedi, A., Upadhayay, P.R., Gupta, N.L., Kanase, D.G., Chikate, R. Journal of pharmaceutical and biomedical analysis (2007) [Pubmed]
  7. Albumin conjugates of the anticancer drug chlorambucil: synthesis, characterization, and in vitro efficacy. Kratz, F., Beyer, U., Roth, T., Schütte, M.T., Unold, A., Fiebig, H.H., Unger, C. Arch. Pharm. (Weinheim) (1998) [Pubmed]
  8. Antitumor drug-protein interactions. Binding of 1-beta-D-arabinofuranosyl cytosine to albumin and chemically modified albumin. Szekerke, M., Horváth, M., Hudecz, F. Arzneimittel-Forschung. (1979) [Pubmed]
  9. Chemical chaperones mediate increased secretion of mutant alpha 1-antitrypsin (alpha 1-AT) Z: A potential pharmacological strategy for prevention of liver injury and emphysema in alpha 1-AT deficiency. Burrows, J.A., Willis, L.K., Perlmutter, D.H. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
 
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