Inhibition of UDP-glucuronosyltransferase by 5'-O-amino acid and oligopeptide derivatives of uridine: Structure-activity relationships

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 53, Issue 3-4, 1998, Pages 173-181

  Naydenova, Zlatina G ^a   Grancharov, Konstantin C ^a   Alargov, Dimitar K ^a   Golovinsky, Evgeny V ^a   Stanoeva, Ivanka M ^b   Shalamanova, Liliana D ^b   Pajeva, Ilza K ^b  

^a INSTITUTE OF MOLECULAR BIOLOGY   (Bulgaria)

^b BULGARIAN ACADEMY OF SCIENCES   (Bulgaria)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENOL; ENZYME INHIBITION; GLUCURONIDATION; GLUCURONOSYLTRANSFERASE; ISOPROPYLIDENEURIDINE; PHENOLPHTHALEIN; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP;

EID: 0032031994     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-1998-3-406     Document Type: Article

References (21)

1. Alargov D. K., Naydenova Z., Grancharov K., Denkova P. S. and Golovinsky. E. V. (1997), Synthesis of some 5′-O-amino acid derivatives of uridine as potential inhibitors of UDP-glucuronosyltransferase. Monatsh. Chem. 128, 725-732.
2. Battaglia E., Elass A., Drake R. R., Paul P., Treat S., Magdalou J., Fournel-Gigleux S., Siest G., Vergoten G., Lester R. and Radominska A. (1995), Characterization of a new class of inhibitors of the recombinant human liver UDP-glucuronosyltransferase. UGT*6. Biochim. Biophys. Acta 1243, 9-14.
3. Bock K. W., Bock-Hennig B. S., Fischer, G. and Lilienblum W. (1986), UDP-glucuronosyltransferases and their toxicological significance. Adv. Exp. Med. Biol. 197, 171-176.
4. Bock K. W. and Lilienblum W (1994), Roles of uridine diphosphate glucuronosyltransferases in chemical carcinogenesis. Handb. Exper. Pharmacol. 112, 391-428.
5. Clarke D. J. and Burchell B. (1994), The uridine diphosphate glucuronosyltransferase multigene family: function and regulation. Handb. Exper. Pharmacol. 112, 3-43.
6. Fournel S., Gregoire B., Magdalou J., Carre M-Ch., Lafourie Ch., Siest G. and Coubere P. (1986), Inhibition of bilirubin UDP-glucuronosyltransferase activity by triphenylacetic acid and related compounds. Biochim. Biophys. Acta 883, 190-196.
7. Fournel-Gigleux S., Shepherd S. R. P., Carre M-Ch., Burchell B., Siest G. and Coubere P. (1989), Novel inhibitors and substrates of bilirubin-UDP-glucuronosyltransferase. Arylalkylcarboxylic acids. Eur. J. Biochem. 183, 653-659.
8. Hochman J. and Zakim D. (1983), A comparison of the kinetic properties of two different forms of microsomal UDP-glucuronyltransferase. J. Biol. Chem. 258, 4143-4146.
9. Lowry O. H., Rosebrough N. J., Farr A. L. and Randall R. J. (1951), Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275.
10. Matsui M. and Watanabe H. K. (1982), Developmental alteration of hepatic UDP-glucuronosyltransferase and sulfotransferase towards androsterone and 4-nitrophenol in Wistar rats. Biochem. J. 204, 441-447.
11. Miners J. and Mackenzie P. (1991), Drug glucuronidation in humans. Pharmacol. Ther. 51, 347-369.
12. Naydenova Z., Alargov D., Grancharov K. and Golovinsky E. (1996), Inhibitory effects of 5′-O-amino acid derivatives of uridine on UDP-glucuronosyltransferase in rat liver microsomes. Exp. Toxicol. Pathol. 48 Suppl II, 295-298.
13. Naydenova Z., Grancharov K., Shopova M. and Golovinsky E. (1995), Inhibition of UDP-glucuronyltransferase activity in rat liver microsomes by pyrimidine derivatives. Comp. Biochem. Physiol. 112C, 321-325.
14. Noort D., Coughtrie M. W. H., Burchell B., van der Marel G. A., van Boom J. H., van der Gen A. and Mulder G. J. (1990), Inhibition of UDP-glucuronosyltransferase activity by possible transition-state analogues in rat liver microsomes. Eur. J. Biochem. 188, 309-312.
15. Paul P., Lutz T. M., Osborn C., Kyosseva S., Elbein A. D., Towbin H., Radominska A. and Drake R. R. (1993), Synthesis and characterization of a new class of inhibitors of membrane-associated UDP-glucosyltransferase. J. Biol. Chem. 268, 12933-12938.
16. Radominska A., Paul P., Treat S., Towbin H., Pratt G., Little J., Magdalou J., Lester R. and Drake R. (1994), Photoaffinity labeling for evaluation of uridinyl analogs as specific inhibitors of rat liver microsomal UDP-glucuronosyltransferases. Biochim. Biophys. Acta 1205, 336-345.
17. Rekker R. F. and Mannhold R. (1992), Calculation of Drug Lipophilicity. The Hydrophobic Fragmental Constant Approach. VCH, Weinheim, N. Y., Basel, Cambridge.
18. Said M., Noort D., Magdalou J., Ziegler J. C., van der Marel G. A., van Boom J. H., Mulder G. J. and Siest G. (1992), Selective and potent inhibition of different hepatic UDP-glucuronosyltransferase activities by ω, ω, ω-triphenylalcohols and UDP derivatives. Biochem. Biophvs. Res. Commun. 187, 140-145.
19. Seydel J. K. and Schaper K.-J. (1979), Chemische Struktur und biologische Aktivität von Wirkstoffen (Methoden der quantitativen Struktur-Wirkung-Analyse) Verlag Chemie, Weinheim, New York, pp. 137-147.
20. Tephly T. R. and Burchell B. (1990), UDP-glucuronosyltransferases: a family of detoxifying enzymes. Trends Pharmacol. Sci. 11, 276-279.
21. Wishart G. J. (1978), Functional heterogeneity of UDP-glucuronosyltransferase as indicated by its differential development and inducibility by glucocorticoids. Demonstration of two groups within the enzyme's activity towards twelve substrates. Biochem. J. 174, 485-489.