Structure-toxicity relationship and structure-activity relationship study of 2-phenylaminophenylacetic acid derived compounds

Food and Chemical Toxicology

Volumn 71, Issue , 2014, Pages 207-216

  Pang, Yi Yun ^a   Yeo, Wee Kiang ^a   Loh, Kep Yong ^b   Go, Mei Lin ^a   Ho, Han Kiat ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b DIVISION OF MEDICAL ONCOLOGY   (Singapore)

Author keywords

Diclofenac; Liver; Lumiracoxib; Structure activity relationship; Structure toxicity relationship

Indexed keywords

2 PHENYLAMINOPHENYLACETIC ACID DERIVATIVE; CYCLOOXYGENASE 2; DICLOFENAC; DICLOFENAC DERIVATIVE; LUMIRACOXIB; PHENYLACETIC ACID DERIVATIVE; PROSTAGLANDIN SYNTHASE; UNCLASSIFIED DRUG; ANILINE DERIVATIVE; GLYCINE; 1 (2,6 DISUBSTITUTED PHENYL) 5 ETHYLINDOLINE 2,3 DIONE DERIVATIVE; 1 (2,6 DISUBSTITUTED) 5 METHYLINDOLIN 2 ONE DERIVATIVE; 2 IODOPHENYL N,N DIMETHYLACETAMIDE; 2 [(2,6 DISUBSTITUTED PHENYL)AMINO]PHENYL N,N DIETHYLACETAMIDE DERIVATIVE; 2 [2 (2,6 DISUBSTITUTEDPHENYL)AMINO] 5 DERIVATIVE; 2,6 DISUBSTITUTED N (PARA ALKYL)ANILINE DERIVATIVE; 2,6 DISUBSTITUTED N (PARA TOLYL)ANILINE DERIVATIVE; N ACETYLATED 2,6 DISUBSTITUTED N (PTOLYL)ANILINE DERIVATIVE; PROSTAGLANDIN SYNTHASE INHIBITOR; [2 [2 (2,6 DISUBSTITUTEDPHENYL)AMINO] 5 ALKYLPHENYL]ACETIC ACID DERIVATIVE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LIPOPHILICITY; LIVER CELL; MOUSE; NONHUMAN; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; STRUCTURE TOXICITY RELATION; TOXICITY; ANALOGS AND DERIVATIVES; ANIMAL; CELL LINE; CHEMISTRY; TOXICITY TESTING; BIOACTIVATION; CASE REPORT; CYTOTOXICITY TEST; DRUG SAFETY; IC50; LIVER TOXICITY; MALE; METABOLIC ACTIVATION; STRUCTURE TOXICITY RELATIONSHIP;

ANILINE COMPOUNDS; ANIMALS; CELL LINE; GLYCINE; MICE; STRUCTURE-ACTIVITY RELATIONSHIP; TOXICITY TESTS;

EID: 84904105298     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2014.06.013     Document Type: Article

References (48)

1. Acemoglu M., Allmendinger T., Calienni J., Cercus J., Loiseleur O., Sedelmeier G.H., Xu D. Synthesis of new N-aryl oxindoles as intermediates for pharmacologically active compounds. Tetrahedron 2004, 60:11571-11586.
2. Agundez J.A., Lucena M.I., Martinez C., Andrade R.J., Blanca M., Ayuso P., Garcia-Martin E. Assessment of nonsteroidal anti-inflammatory drug-induced hepatotoxicity. Exp. Opin. Drug Metab. Toxicol. 2011, 7:817-828.
3. Bannwarth B., Berenbaum F. Lumiracoxib in the management of osteoarthritis and acute pain. Expert Opin. Pharmacother. 2007, 8:1551-1564.
4. Berg J., Christoph T., Widerna M., Bodenteich A. Isoenzyme-specific cyclooxygenase inhibitors: a whole cell assay system using the human erythroleukemic cell line HEL and the human monocytic cell line Mono Mac 6. J. Pharmacol. Toxicol. Methods 1997, 37:179-186.
5. Bessems J.G.M., Gaisser H.D., Koppele J.M.T., VanBennekom W.P., Commandeur J.N.M., Vermeulen N.P.E. 3,5-disubstituted analogues of paracetamol. Synthesis, analgesic activity and cytotoxicity. Chem. Biol. Interact. 1995, 98:237-250.
6. Bessone F. Non-steroidal anti-inflammatory drugs: what is the actual risk of liver damage?. World J. Gastroenterol. 2010, 16:5651-5661.
7. Blobaum A.L., Marnett L.J. Molecular determinants for the selective inhibition of cyclooxygenase-2 by lumiracoxib. J. Biol. Chem. 2007, 282:16379-16390.
8. Bruggemann R., Bartel H.G. A theoretical concept to rank environmentally significant chemicals. J. Chem. Inf. Comput. Sci. 1999, 39:211-217.
9. Bruggemann R., Bucherl C., Pudenz S., Steinberg C.E.W. Application of the concept of partial order on comparative evaluation of environmental chemicals. Acta Hydrochim. Hydrobiol. 1999, 27:170-178.
10. Carlsen L. Assessment of chemicals ppplying partial order ranking techniques. Comb. Chem. High Throughput Screening 2008, 11:794-805.
11. Castell J.V., Gomez-Lechon M.J., Ponsod A.X., Bort R. The use of cultured hepatocytes to investigate the mechanisms of drug hepatotoxicity. Cell Biol. Toxicol. 1997, 13:331-338.
12. Chan K., Jensen N.S., Silber P.A., O'Brien P.J. Structure-activity relationships for halobenzene induced cytotoxicity in rat and human hepatoctyes. Chem. Biol. Interact. 2007, 165:165-174.
13. Coe K.J., Jia Y., Ho H.K., Rademacher P., Bammler T.K., Beyer R.P., Farin F.M., Woodke L., Plymate S.R., Fausto N., Nelson S.D. Comparison of the cytotoxicity of the nitroaromatic drug flutamide to its cyano analogue in the hepatocyte cell line TAMH: evidence for complex I inhibition and mitochondrial dysfunction using toxicogenomic screening. Chem. Res. Toxicol. 2007, 20:1277-1290.
14. Cronin M.T.D., Schultz T.W. Structure-toxicity relationships for phenols to Tetrahymena pyriformis. Chemosphere 1996, 32:1453-1468.
15. Fratello G., Marchini S., Zucco F., Sapora O., Stammati A. Cytotoxicity of halogenated benzenes and its relationship with logP. Toxicol. In Vitro 1997, 11:673-677.
16. Gan T.J. Diclofenac: an update on its mechanism of action and safety profile. Curr. Med. Res. Opin. 2010, 26:1715-1731.
17. Guo L., Dial S., Shi L.M., Branham W., Liu J., Fang J.L., Green B., Deng H., Kaput J., Ning B.T. Similarities and differences in the expression of drug-metabolizing enzymes between human hepatic cell Lines and primary human hepatocytes. Drug Metab. Dispos. 2011, 39:528-538.
18. Halfon E., Reggiani M.G. On ranking chemicals for enviromental-hazard. Environ. Sci. Technol. 1986, 20:1173-1179.
19. Hernandes M.Z., Cavalcanti S.M.T., Moreira D.R.M., de Azevedo W.F., Leite A.C.L. Halogen atoms in the modern medicinal chemistry: hints for the drug design. Curr. Drug Targets 2010, 11:303-314.
20. Kang P., Dalvie D., Smith E., Renner M. Bioactivation of lumiracoxib by peroxidases and human liver microsomes: identification of multiple quinone imine intermediates and GSH adducts. Chem. Res. Toxicol. 2009, 22:106-117.
21. Kenny J.R., Maggs J.L., Meng X.L., Sinnott D., Clarke S.E., Park B.K., Stachulski A.V. Syntheses and characterization of the acyl glucuronide and hydroxy metabolites of diclofenac. J. Med. Chem. 2004, 47:2816-2825.
22. Kretzrommel A., Boelsterli U.A. Diclofenac covalent protein-binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes. Toxicol. Appl. Pharmacol. 1993, 120:155-161.
23. Kretzrommel A., Boelsterli U.A. Mechanism of covalent adduct fomation of diclofenac to rat hepatic-microsomal proteins - retention of the glucuronic-acid moiety in the adduct. Drug Metab. Dispos. 1994, 22:956-961.
24. Leemann T., Transon C., Dayer P. Cytochrome-P450TB (CYP2C) - a major monooxygenase catalyzing diclofenac 4'-hydroxylation in human liver. Life Sci. 1993, 52:29-34.
25. Lerche D., Bruggemann R., Sorensen P., Carlsen L., Nielsen O.J. A comparison of partial order technique with three methods of multi-criteria analysis for ranking of chemical substances. J. Chem. Inf. Comput. Sci. 2002, 42:1086-1098.
26. Li Y., Slatter J.G., Zhang Z.P., Doss G.A., Braun M.P., Stearns R.A., Dean D.C., Baillie T.A., Tang W. In vitro metabolic activation of lumiracoxib in rat and human liver preparations. Drug Metab. Dispos. 2008, 36:469-473.
27. Mangold J.B., Gu H., Rodriguez L.C., Bonner J., Dickson J., Rordorf C. Pharmacokinetics and metabolism of lumiracoxib in healthy male subjects. Drug Metab. Dispos. 2004, 32:566-571.
28. McDonald M.G., Rettie A.E. Sequential metabolism and bioactivation of the hepatotoxin benzbromarone: formation of glutathione adducts from a catechol intermediate. Chem. Res. Toxicol. 2007, 20:1833-1842.
29. Monks T.J., Hinson J.A., Gillette J.R. Bromobenzene and para-bromophenol toxicity and covalent binding in vivo. Life Sci. 1982, 30:841-848.
30. Moser P., Sallmann A., Wiesenberg I. Synthesis and quantitative structure-activity-relationships of diclofenac analogs. J. Med. Chem. 1990, 33:2358-2368.
31. Nelson S.D. Structure toxicity relationships - how useful are they in predicting toxicities of new drugs?. Biol. React. Intermed. Vi: Chem. Biol. Mech. Suscept. Prev. Environ. Diseases 2001, 500:33-43.
32. Park B.K., Kitteringham N.R., O'Neill P.M. Metabolism of fluorine-containing drugs. Annu. Rev. Pharmacol. Toxicol. 2001, 41:443-470.
33. Pierce R.H., Franklin C.C., Campbell J.S., Tonge R.P., Chen W.C., Fausto N., Nelson S.D., Bruschi S.A. Cell culture model for acetaminophen-induced hepatocyte death in vivo. Biochem. Pharmacol. 2002, 64:413-424.
34. Plumb J.A., Milroy R., Kaye S.B. Effects of the pH dependence of 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide-formazan absorption on chemosensitivity determined by a novel tetrazolium-based assay. Cancer Res. 1989, 49:4435-4440.
35. Poon G.K., Chen Q., Teffera Y., Ngui J.S., Griffin P.R., Braun M.P., Doss G.A., Freeden C., Stearns R.A., Evans D.C., Baillie T.A., Tang W. Bioactivation of diclofenac via benzoquinone imine intermediates-identification of urinary mercapturic acid derivatives in rats and humans. Drug Metab. Dispos. 2001, 29:1608-1613.
36. Prins B., Dartee W.P., Verboom W., Reinhoudt D.N., Koster A.S. Quantitative structure-activity relationship for the acute cytotoxicity of 13(bis)aziridinyl-benzoquinones - relation to cellular ATP depletion. Arch. Toxicol. 1994, 68:255-260.
37. Schultz T.W., Cajinaquezada M., Wesley S.K. Structure toxicity relationships for mono alkyl-substituted or halogen-substituted anilines. Bull. Environ. Contam. Toxicol. 1989, 43:564-569.
38. Selassie C.D. History of quantitative structure-activity relationship. Burger's Medicinal Chemistry and Drug Discovery 2003, 1-48. John Wiley & Sons Inc., New York. D.J. Abraham (Ed.).
39. Shen S.J., Marchick M.R., Davis M.R., Doss G.A., Pohl L.R. Metabolic activation of diclofenac by human cytochrome P450 3A4: role of 5-hydroxydiclofenac. Chem. Res. Toxicol. 1999, 12:214-222.
40. Sivertsson L., Ek M., Darnell M., Edebert I., Ingelman-Sundberg M., Neve E.P.A. CYP3A4 catalytic activity is induced in confluent Huh7 hepatoma cells. Drug Metab. Dispos. 2010, 38:995-1002.
41. Tang W., Stearns R.A., Bandiera S.M., Zhang Y., Raab C., Braun M.P., Dean D.C., Pang J.M., Leung K.H., Doss G.A., Strauss J.R., Kwei G.Y., Rushmore T.H., Chiu S.H.L., Baillie T.A. Studies on cytochrome P-450-mediated bioactivation of diclofenac in rats and in human hepatocytes: identification of glutathione conjugated metabolites. Drug Metab. Dispos. 1999, 27:365-372.
42. United-Nations, 2005a. Consolidated List of products whose consumption and/or sale have been banned, withdrawn, severly restricted or not approved by governments. In: Nations, U. (Ed.), Pharmaceuticals: Restrictions in Use and Availability. United Nations Publications, New York.
43. United-Nations, 2005b. Consolidated List of products whose consumption and/or sale have been banned, withdrawn, severly restricted or not approved by governments. In: Nations, U. (Ed.), Pharmaceuticals: Restrictions in Use and Availability. United Nations Publication, New York.
44. United-Nations, 2009. Consolidated list of products whose consumption and/or sale have been banned, withdrawn, severly restricted or not approved by governments. In: Nations, U. (Ed.), Pharmaceuticals: Restrictions in Use and Availability. United Nations Publications, New York.
45. Vogel A.I. A Textbook of Practical Organic Chemistry 1989, Longman Scientific & Technical, London.
46. Warne M.A., Osborn D., Lindon J.C., Nicholson J.K. Quantitative structure-toxicity relationships for halogenated substituted-benzenes to Vibrio fischeri, using atom-based semi-empirical molecular-orbital descriptors. Chemosphere 1999, 38:3357-3382.
47. Wolfe J.P., Buchwald S.L. Scope and limitations of the Pd/BINAP-catalyzed amination of aryl bromides. J. Org. Chem. 2000, 65:1144-1157.
48. Wu J.C., Merlino G., Cveklova K., Mosinger B., Fausto N. Autonomous growth in serum-free medium and production of hepatocellular carcinomas by differentiated hepatocyte lines that overexpress transforming growth-factor-alpha. Cancer Res. 1994, 54:5964-5973.