Role of hydrophilic interaction in binding of hydroxylated 3-deoxy C19 steroids to the active site of aromatase

Journal of Medicinal Chemistry

Volumn 44, Issue 24, 2001, Pages 4277-4283

  Numazawa, M ^a   Yamada, K ^a   Nitta, S ^a   Sasaki, C ^a   Kidokoro, K ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATASE; AROMATASE INHIBITOR; STEROID;

ACETYLATION; ARTICLE; COMPETITIVE INHIBITION; ENZYME ACTIVE SITE; ENZYME ACTIVITY; HYDROPHILICITY; NUCLEAR OVERHAUSER EFFECT; PROTEIN PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANDROSTENEDIOLS; AROMATASE; AROMATASE INHIBITORS; BINDING SITES; ENZYME INHIBITORS; FEMALE; HUMANS; HYDROXYLATION; MICROSOMES; PLACENTA; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035935681     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010282t     Document Type: Article

References (39)

1. The involvement of human placental microsomal cytochrome P-450 in aromatization
2. Purification and characterization of human placental aromatase cytochrome P-450
3. Purification of human placental aromatase cytochrome P-450 with monoclonal antibody and its characterization
4. Aromatase: New perspectives for breast cancer
5. Aromatase inhibitors: Their biochemistry and clinical studies
6. Recent developments in aromatase inhibition as a potential treatment of estrogen-dependent breast cancer
7. Inhibitors of P-450-dependent steroid biosynthesis: From research to medical treatment
8. Aromatase and its inhibitors in breast cancer treatment - Overview and perspective
9. Aromatase inhibitors
10. Synthesis and biochemical evolution of inhibitors of estrogen biosynthesis
11. 7α-substituted derivatives of androstenediones as inhibitors of estrogen biosynthesis
12. Synthesis, structure elucidation, and biochemical evaluation of 7α- and 7β-arylaliphatic-substituted androst-4-ene-3,17-diones as inhibitors of aromatase
13. Aromatase inhibition by 4-thiosubstituted 4-androstene-3,17-dione derivatives as potential aromatase inhibitors
14. Probing the hydrophobic pocket of the active site of aromatase with 4-phenoxy-7α-(phenylthio)-4-androstene-3,17-dione
15. Synthesis and evaluation of substituted-4-androstene-3,17-dione derivatives as aromatase inhibitors
16. 6-Alkyl- and 6-arylandrost-4-ene3,17-dione as aromatase inhibitors. Synthesis and structure-activity relationships
17. Further studies on 6-alkylandrost-4-ene-3,17-diones as aromatase inhibitors: Elongation of the 6-alkyl chain
18. 6-Phenylaliphatic-substituted androst-4-ene-3,17-diones as aromatase inhibitors: Structure-activity relationships
19. 6α,7α-cyclopropane derivatives of androst-4-ene: A novel class of competitive aromatase inhibitors
20. Detailed molecular model for human aromatase
21. A molecular model for the interaction between vorozole and other non-steroidal inhibitors and human cytochrome P-450 19 (P450 aromatase)
22. Three-dimensional quantitative structure-activity relationships of steroidal aromatase inhibitors
23. Binding characteristics of seven inhibitors of human aromatase: A site-directed mutagenesis study
24. A three-dimensional model of aromatase cytochrome P450
25. Review of the molecular modeling studies of the cytochrome P-450 estrogen synthase enzyme, aromatase
26. Probing the binding pocket of the active site of aromatase with 6-ether or 6-ester substituted androst-4-ene-3,17-diones and their diene and triene analogs
27. 19-Hydroxy-4-androsten-17-one: Potential competitive inhibitor of estrogen biosynthesis
28. Synthesis and biochemical studies of 16- or 19-substituted androst-4-enes as aromatase inhibitors
29. Synthesis of androst-5-en-7-ones and androsta-3,5-dien-7-ones and their related 7-deoxy analogs as conformational and catalytic probes for the active site of aromatase
30. Synthesis and structure-activity relationships of 6-substituted androst-4-ene analogs as aromatase inhibitors
31. 4-Oxygenated androst-5-en-17-ones and their 7-oxo derivatives as aromatase inhibitors
32. 1:3-Rearrangement of steroidal allylic acetoxy groups during epoxidation
33. Synthesis of 19-oxygenated derivatives of the competitive inhibitor of aromatase, 5-androstene-4,17-dione
34. Reaction of androst-5-en-17-one with hypobromous acid and its use for synthesis of 19-oxygenated 5-ene and 4-en-6-one steroids
35. Human Placental Aromatase
36. 19-Oxygenation of 3-deoxy androgens, potent competitive inhibitors of estrogen biosynthesis with human placental aromatase
37. Mechanism of human placental aromatase: A new active-site model
38. Anabolic agents. A-ring oxygenated androstane derivatives
39. Biological aromatization of steroids