Enzyme-assisted synthesis and structure characterization of glucuronic acid conjugates of losartan, candesartan, and zolarsartan

Bioorganic Chemistry

Volumn 36, Issue 3, 2008, Pages 148-155

  Alonen, Anna ^a   Jansson, Johanna ^a   Kallonen, Sirkku ^a   Kiriazis, Alexandros ^a   Aitio, Olli ^b   Finel, Moshe ^a   Kostiainen, Risto ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Biosynthesis; Candesartan; Glucuronide; GR117289; Losartan; Regioisomer; Zolarsartan

Indexed keywords

AGLYCONE; ANGIOTENSIN 2 RECEPTOR ANTAGONIST; CANDESARTAN; DRUG METABOLITE; GLUCURONIC ACID; GLUCURONIDE; GLUCURONOSYLTRANSFERASE; LOSARTAN; ZOLASARTAN;

ANIMAL CELL; ARTICLE; CATALYST; CONTROLLED STUDY; DRUG CONJUGATION; DRUG GLUCURONIDATION; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; LIVER MICROSOME; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKERS; ANIMALS; BENZIMIDAZOLES; CATTLE; DEER; GLUCURONIC ACID; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; LOSARTAN; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROSOMES, LIVER; RATS; RECEPTORS, ANGIOTENSIN; SWINE; TETRAZOLES;

BOVINAE; RATTUS; SUIDAE;

EID: 43249113309     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2008.02.004     Document Type: Article

References (36)

1. Radominska-Pandya A., Czernik P.J., Little J.M., Battaglia E., and Mackenzie P.I. Drug Metab. Rev. 31 (1999) 817-899
2. King C.D., Rios G.R., Green M.D., and Tephly T.R. Curr. Drug Metab. 1 (2000) 143-161
3. Tukey R.H., and Strassburg C.P. Annu. Rev. Pharmacol. Toxicol. 40 (2000) 581-616
4. Mackenzie P.I., Walter Bock K., Burchell B., Guillemette C., Ikushiro S., Iyanagi T., Miners J.O., Owens I.S., and Nebert D.W. Pharmacogenet. Genomics 15 (2005) 677-685
5. Robertson M.J., Barnes J.C., Drew G.M., Clark K.L., Marshall F.H., Michel A., Middlemiss D., Ross B.C., Scopes D., and Dowle M.D. Br. J. Pharmacol. 107 (1992) 1173-1180
6. Hilditch A., Hunt A.A., Gardner C.J., Twissell D.J., Polley J., Travers A., Drew G.M., Middlemiss D., Ross B.C., and Robertson M.J. Br. J. Pharmacol. 111 (1994) 137-144
7. Huskey S.W., Miller R.R., and Chiu S.H.L. Drug Metab. Dispos. 21 (1993) 792-799
8. Stearns R.A., Doss G.A., Miller R.R., and Chiu S.H. Drug Metab. Dispos. 19 (1991) 1160-1162
9. Stearns R.A., Miller R.R., Doss G.A., Chakravarty P.K., Rosegay A., Gatto G.J., and Chiu S.H. Drug Metab. Dispos. 20 (1992) 281-287
10. Bowers G.D., Eddershaw P.J., Hughes S.Y., Manchee G.R., and Oxford J. Rapid Commun. Mass Spectrom. 8 (1994) 217-221
11. Kondo T., Yoshida K., Yoshimura Y., Motohashi M., and Tanayama S. J. Mass Spectrom. 31 (1996) 873-878
12. Kondo T., Yoshida K., Yoshimura Y., Motohashi M., and Tanayama S. Arzneimittelforschung 46 (1996) 594-600
13. Sallustio B.C., Sabordo L., Evans A.M., and Nation R.L. Curr. Drug Metab. 1 (2000) 163-180
14. Shipkova M., Armstrong V.W., Oellerich M., and Wieland E. Ther. Drug Monit. 25 (2003) 1-16
15. Bailey M.J., and Dickinson R.G. Chem. Biol. Interact 145 (2003) 117-137
16. Stachulski A.V., Harding J.R., Lindon J.C., Maggs J.L., Park B.K., and Wilson I.D. J. Med. Chem. 49 (2006) 6931-6945
17. Kaspersen F.M., and Van Boeckel C.A. Xenobiotica 17 (1987) 1451-1471
18. Stachulski A.V., and Jenkins G.N. Nat. Prod. Rep. 15 (1998) 173-186
19. Reiss P., Burnett D.A., and Zaks A. Bioorg. Med. Chem. 7 (1999) 2199-2202
20. Luukkanen L., Kilpelainen I., Kangas H., Ottoila P., Elovaara E., and Taskinen J. Bioconjug. Chem. 10 (1999) 150-154
21. Stevenson D.E., and Hubl U. Enzyme Microb. Technol. 24 (1999) 388-396
22. Soars M.G., Mattiuz E.L., Jackson D.A., Kulanthaivel P., Ehlhardt W.J., and Wrighton S.A. J. Pharmacol. Toxicol. Methods 47 (2002) 161-168
23. Kuuranne T., Aitio O., Vahermo M., Elovaara E., and Kostiainen R. Bioconjug. Chem. 13 (2002) 194-199
24. Alonen A., Aitio O., Hakala K., Luukkanen L., Finel M., and Kostiainen R. Drug Metab. Dispos. 33 (2005) 657-663
25. Jantti S.E., Kiriazis A., Reinila R.R., Kostiainen R.K., and Ketola R.A. Steroids 72 (2007) 287-296
26. Hintikka L., Kuuranne T., Aitio O., Thevis M., Schanzer W., and Kostiainen R. Steroids 73 (2008) 257-265
27. Zhu B., Bush D., Doss G.A., Vincent S., Franklin R.B., and Xu S. Drug Metab. Dispos. 36 (2008) 331-338
28. Luukkanen L., Elovaara E., Lautala P., Taskinen J., and Vainio H. Pharmacol. Toxicol. 80 (1997) 152-158
29. Kurkela M., Garcia-Horsman J.A., Luukkanen L., Morsky S., Taskinen J., Baumann M., Kostiainen R., Hirvonen J., and Finel M. J. Biol. Chem. 278 (2003) 3536-3544
30. Kuuranne T., Kurkela M., Thevis M., Schanzer W., Finel M., and Kostiainen R. Drug Metab. Dispos. 31 (2003) 1117-1124
31. Chando T.J., Everett D.W., Kahle A.D., Starrett A.M., Vachharajani N., Shyu W.C., Kripalani K.J., and Barbhaiya R.H. Drug Metab. Dispos. 26 (1998) 408-417
32. Perrier L., Bourrie M., Marti E., Tronquet C., Masse D., Berger Y., Magdalou J., and Fabre G. J. Pharmacol. Exp. Ther. 271 (1994) 91-99
33. Huskey S.W., Doss G.A., Miller R.R., Schoen W.R., and Chiu S.H. Drug Metab. Dispos. 22 (1994) 651-658
34. Huskey S.W., Magdalou J., Ouzzine M., Siest G., and Chiu S.H. Drug Metab. Dispos. 22 (1994) 659-662
35. Stevens J.C., Fayer J.L., and Cassidy K.C. Drug Metab. Dispos. 29 (2001) 289-295
36. Cannell R.J., Knaggs A.R., Dawson M.J., Manchee G.R., Eddershaw P.J., Waterhouse I., Sutherland D.R., Bowers G.D., and Sidebottom P.J. Drug Metab. Dispos. 23 (1995) 724-729