On how the conformation of biliverdins influences their reduction to bilirubins: A biological and molecular modeling study

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 21, 2003, Pages 4661-4672

  Mora, María E ^a   Bari, Sara E ^a   Awruch, Josefina ^a   Delfino, José M ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

BILIRUBIN; BILIVERDIN; BILIVERDIN REDUCTASE; CYCLIC 2,18 BRIDGED BILIVERDIN; ENZYME; UNCLASSIFIED DRUG;

ARTICLE; BILE SECRETION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; ENZYME ACTIVITY; HYDROGEN BOND; MALE; MONTE CARLO METHOD; NONHUMAN; RAT; REDUCTION; STOCHASTIC MODEL; STRUCTURE ANALYSIS;

EID: 0141838887     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00479-6     Document Type: Article

References (43)

1. Schmid, R.; McDonagh, A. F. In The Porphyrins; Dolphin D., Ed.; Academic: New York, 1979; Vol. VI, p 257.
2. Frydman R.B., Frydman B. Acc. Chem. Res. 20:1987;250.
3. Blumenthal S.G., Taggart D.B., Ikeda R.M., Ruebner B.H., Bergstrom D.E. Biochem. J. 167:1977;535.
4. Heirwegh K.P.M., Van Hees G.P., Leroy P., Van Roy F.P., Jansen F.H. Biochem. J. 120:1970;877.
5. Gordon E.R., Chan T.H., Samodai K., Goresky C.A. Biochem. J. 167:1977;1.
6. Yamaguchi T., Nakajima H. Eur. J. Biochem. 233:1995;467.
7. Awruch J., Mora M.E., Lemberg A., Coll C.T., Frydman R.B. Biol. Chem. Hoppe-Seyler. 375:1994;617.
8. Hirota K., Yamamoto S., Itano H.A. Biochem. J. 229:1985;477.
9. Hirota K. Biol. Pharm. Bull. 18:1995;481.
10. Frydman R.B., Tomaro M.L., Rosenfeld J., Awruch J., Sambrotta L., Valasinas A., Frydman B. Biochim. Biophys. Acta. 916:1987;500.
11. Mora M.E., Bari S.E., Awruch J. Bioorg. Med. Chem. Lett. 7:1997;1249.
12. Frydman R.B., Bari S.E., Tomaro M.L., Frydman B. Biochem. Biophys. Res. Commun. 171:1990;465.
13. Kogan M.J., Mora M.E., Bari S.E., Iturraspe J., Awruch J., Delfino J.M. Bioorg. Med. Chem. 7:1999;1309.
14. Bari S., Frydman R.B., Grosman C., Frydman B. Biochem. Biophys. Res. Commun. 188:1992;48.
15. Bonnett R., McDonagh A.F. J. Chem. Soc., Perkin Trans. 1. 1973;881.
16. Tomaro M.L., Frydman R.B., Awruch J., Valasinas A., Frydman B., Pandey R.K., Smith K.M. Biochim. Biophys. Acta. 791:1984;350.
17. Krois D., Lehner H. J. Chem. Soc., Perkin Trans. 1. 1989;2179.
18. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. J. Comp. Chem. 11:1990;440.
19. Chang G., Guida W.C., Still W.C. J. Am. Chem. Soc. 111:1989;4379.
20. Sheldrick W.S. J. Chem. Soc., Perkin Trans. 2. 1976;1457. Coordinates entry BILVER, Cambridge Structural Database System, Version 5.24, Cambridge Crystallographic Data Centre, Cambridge, UK, April 2003.
21. Sturrock E.D., Bull J.R., Kirsch R.E., Pandey R.K., Senge M.O., Smith K.M. J. Chem. Soc. Chem. Commun. 1993;872. Coordinates entry YAMVIR, Cambridge Structural Database System, Version 5.24, Cambridge Crystallographic Data Centre, Cambridge, UK, April 2003.
22. Wagner U., Kratky C., Falk H., Woss H. Monatsch. Chem. 122:1991;749. Coordinates entry SUBGOL, Cambridge Structural Database System, Version 5.24, Cambridge Crystallographic Data Centre, Cambridge, UK, April 2003.
23. Guarnieri F., Still W.C. J. Comp. Chem. 15:1994;1302.
24. Kogan M.J., Mora M.E., Awruch J., Delfino J.M. Bioorg. Med. Chem. 6:1998;151.
25. Senderowitz H., Guarnieri F., Still W.C. J. Am. Chem. Soc. 117:1995;8211.
26. Gorb L., Korkin A., Leszczynski J., Varnek A., Mark F., Schaffner K. THEOCHEM. 425:1998;137.
27. Person R.V., Peterson B.R., Lightner D.A. J. Am. Chem. Soc. 116:1994;42. and references cited therein.
28. Falk H. The Chemistry of Linear Oligopyrroles and Bile Pigments. 1989;Springer, Wien.
29. Hwang K.-O., Lightner D.A. Heterocycles. 37:1994;807.
30. Kikuchi A., Park S.-Y., Miyatake H., Sun D., Sato M., Yoshida T., Shiro Y. Nature Struct. Biol. 8:2001;221.
31. Barbosa Pereira P.J., Macedo-Ribeiro S., Párraga A., Pérez-Luque R., Cunningham O., Darcy K., Mantle T.J., Coll M. Nature Struct. Biol. 8:2001;215.
32. Awruch J., Lemberg A., Frydman R.B., Frydman B. Biochim. Biophys. Acta. 714:1982;209.
33. Awruch J., Tomaro M.L., Frydman R.B., Frydman B. Biochim. Biophys. Acta. 787:1984;146.
34. Cunningham O., Dunne A., Sabido P., Lightner D., Mantle T.J. J. Biol. Chem. 275:2000;19009.
35. Heirwegh K.P.M., Blanckaert N., Van Hees G. Anal. Biochem. 195:1991;273.
36. McDonagh A.F., Palma L.A. Biochem. J. 189:1980;193.
37. Sieg A., Stiehl A., Heirwegh K.P.M., Fevery J., Raedsch R., Kommerell B. Hepatology. 10:1989;14.
38. Blanckaert N., Fevery J., Heirwegh K.P.M., Compernolle F. Biochem. J. 164:1977;237.
39. Crawford J.M., Ransil B.J., Potter C.S., Westmoreland S.V., Gollan J.L. J. Clin. Invest. 79:1987;1172.
40. MacroModel, A Primer, Version 5.5.; Department of Chemistry: Columbia University, New York, NY 10027, USA, 1996.
41. Weiner S.J., Kollman P.A., Case D.A., Singh U.C., Ghio C., Alagona G., Profeta S. Jr., Weiner P. J. Am. Chem. Soc. 106:1984;765.
42. Ferguson D.M., Kollman P.A. J. Comp. Chem. 12:1990;620.
43. Still W.C., Tempczyk A., Hawley R.C., Hendrickson T. J. Am. Chem. Soc. 112:1990;6127.