Application of homology modeling to generate CYP1A1 mutants with enhanced activation of the cancer chemotherapeutic prodrug dacarbazine

Molecular Pharmacology

Volumn 80, Issue 5, 2011, Pages 879-888

  Lewis, Benjamin C ^a   Mackenzie, Peter I ^a   Miners, John O ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 1A1; DACARBAZINE; HEME; IMIDAZOLE; IRON;

ARTICLE; AUTOMATION; CATALYSIS; COMPUTER MODEL; DEMETHYLATION; DRUG ACTIVATION; DRUG METABOLISM; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME ENGINEERING; ESCHERICHIA COLI; HYDROGEN BOND; MICHAELIS MENTEN KINETICS; MUTATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; SITE DIRECTED MUTAGENESIS; STRUCTURE ACTIVITY RELATION; SUBSTITUTION LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; BASE SEQUENCE; BIOTRANSFORMATION; CYTOCHROME P-450 CYP1A1; DACARBAZINE; DNA PRIMERS; HYDROGEN BONDING; MUTAGENESIS, SITE-DIRECTED; PRODRUGS; RATS;

EID: 80054776251     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.111.072124     Document Type: Article

References (34)

1. Aghi M, Hochberg F, and Breakefield XO (2000) Prodrug activation enzymes in cancer gene therapy. J Gene Med 2:148-164.
2. Baldwin A, Huang ZQ, Jounaidi Y, Waxman DJ (2003) Identification of novel enzyme-prodrug combinations for use in cytochrome P450-based gene therapy for cancer. Arch Biochem Biophys 409:197-206. (Pubitemid 36042916)
3. Daly AK (2003) Pharmacogenetics of the major polymorphic metabolizing enzymes. Fundam Clin Pharmacol 17:27-41.
4. Denny WA (2003) Prodrugs for Gene-Directed Enzyme-Prodrug Therapy (Suicide Gene Therapy). J Biomed Biotechnol 2003:48-70.
5. Erdmann MK (2010) Immunity unleashed in melanoma. Lancet Oncology 11:108-109.
6. Ericksen SS and Szklarz GD (2005) Regiospecificity of human cytochrome P450 1A1-mediated oxidations: the role of steric effects. J Biomol Struct Dyn 23:243-256. (Pubitemid 41642429)
7. Ferguson MJ, Ahmed FY, and Cassidy J (2001) The role of pro-drug therapy in the treatment of cancer. Drug Resist Updat 4:225-232. (Pubitemid 34456376)
8. Gillam EM, Baba T, Kim BR, Ohmori S, and Guengerich FP (1993) Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Arch Biochem Biophys 305:123-131. (Pubitemid 23242002)
9. Haines DC, Tomchick DR, Machius M, and Peterson JA (2001) Pivotal role of water in the mechanism of P450BM-3. Biochemistry 40:13456-13465. (Pubitemid 33130773)
10. Houston JB and Galetin A (2005) Modelling atypical CYP3A4 kinetics: principles and pragmatism. Arch Biochem Biophys 433:351-360. (Pubitemid 39610415)
11. Kan O, Griffiths L, Baban D, Iqball S, Uden M, Spearman H, Slingsby J, Price T, Esapa M, Kingsman S, et al. (2001) Direct retroviral delivery of human cytochrome P450 2B6 for gene-directed enzyme prodrug therapy of cancer. Cancer Gene Therapy 8:473-482. (Pubitemid 32737833)
12. Lewis BC, Mackenzie PI, and Miners JO (2007) Comparative homology modeling of human cytochrome P4501A1 (CYP1A1) and confirmation of residues involved in 7-ethoxyresorufin O-deethylation by site-directed mutagenesis and enzyme kinetic analysis. Arch Biochem Biophys 468:58-69. (Pubitemid 350087843)
13. Lewis DF (2003) Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. Arch Biochem Biophys 409:32-44.
14. Lewis DF, Modi S, and Dickins M (2002) Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev 34:69-82. (Pubitemid 34311089)
15. Lewis DF, Lake BG, and Dickins M (2004) Quantitative structure-activity relationships within a homologous series of 7-alkoxyresorufins exhibiting activity towards CYP1A and CYP2B enzymes: molecular modelling studies on key members of the resorufin series with CYP2C5-derived models of human CYP1A1, CYP1A2, CYP2B6 and CYP3A4. Xenobiotica 34:501-513. (Pubitemid 38981366)
16. Liu J, Ericksen SS, Sivaneri M, Besspiata D, Fisher CW, and Szklarz GD (2004) The effect of reciprocal active site mutations in human cytochromes P450 1A1 and 1A2 on alkoxyresorufin metabolism. Arch Biochem Biophys 424:33-43. (Pubitemid 38326852)
17. Löhr M, Hoffmeyer A, Kröger J, Freund M, Hain J, Holle A, Karle P, Knöfel WT, Liebe S, Müller P, et al. (2001) Microencapsulated cell-mediated treatment of inoperable pancreatic carcinoma. Lancet 357:1591-1592. (Pubitemid 32488821)
18. Lowry OH, Rosenbrough NJ, Farr L, and Randall RJ (1951) Protein measurement with the folin phenol reagent. J Biol Chem 193:267-275.
19. Luce JK, Thurman WG, Isaacs BL, and Talley RW (1970) Clinical trials with the antitumor agent 5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide(NSC- 45388). Cancer Chemother Rep 54:119-124.
20. Meer L, Janzer RC, Kleihues P, and Kolar GF (1986) In vivo metabolism and reaction with DNA of the cytostatic agent, 5-(3,3-dimethyl-1-triazeno) imidazole-4-carboxamide (DTIC). Biochem Pharmacol 35:3243-3247. (Pubitemid 16001430)
21. Miles CS, Ost TW, Noble MA, Munro AW, and Chapman SK (2000) Protein engineering of cytochromes P-450. Biochim Biophys Acta 1543:383-407. (Pubitemid 32057100)
22. Omura T and Sato R (1964a) The carbon monoxide-binding pigment of liver microsomes: Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
23. Omura T and Sato R (1964b) The carbon monoxide-binding pigmentof liver microsomes. J Biol Chem 239:2379-2385.
24. Parikh A, Josephy PD, and Guengerich FP (1999) Selection and characterization of human cytochrome P450 1A2 mutants with altered catalytic properties. Biochemistry 38:5283-5289. (Pubitemid 29211211)
25. Reid JM, Kuffel MJ, Miller JK, Rios R, and Ames MM (1999) Metabolic activation of dacarbazine by human cytochromes P450: the role of CYP1A1, CYP1A2, and CYP2E1. Clin Cancer Res 5:2192-2197. (Pubitemid 29399277)
26. Ridderström M, Zamora I, Fjellström O, and Andersson TB (2001) Analysis of selective regions in the active sites of human cytochromes P450, 2C8, 2C9, 2C18, and 2C19 homology models using GRID/CPCA. J Med Chem 44:4072-4081. (Pubitemid 33095316)
27. Rooseboom M, Commandeur JN, and Vermeulen NP (2004) Enzyme-catalyzed activation of anticancer prodrugs. Pharmacol Rev 56:53-102. (Pubitemid 38314580)
28. Sanada M, Takagi Y, Ito R, and Sekiguchi M (2004) Killing and mutagenic actions of dacarbazine, a chemotherapeutic alkylating agent, on human and mouse cells: effects of Mgmt and Mlh1 mutations. DNA Repair 3:413-420. (Pubitemid 38316848)
29. Schwarz D, Kisselev P, Ericksen SS, Szklarz GD, Chernogolov A, Honeck H, Schunck WH, and Roots I (2004) Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: highly stereoselective formation of 17(R),18(S)- epoxyeicosatetraenoic acid. Biochem Pharmacol 67:1445-1457. (Pubitemid 38388207)
30. Shen AL, Porter TD, Wilson TE, and Kasper CB (1989) Structural analysis of the FMN binding domain of NADPH-cytochrome P-450 oxidoreductase by site-directed mutagenesis. J Biol Chem 264:7584-7589. (Pubitemid 19119176)
31. Stevens MF, Hickman JA, Langdon SP, Chubb D, Vickers L, Stone R, Baig G, Goddard C, Gibson NW, and Slack JA (1987) Antitumor activity and pharmacokinetics in mice of 8-carbamoyl-3-methyl-imidazo[5,1-d]-1,2,3,5- tetrazin-4(3H)-one (CCRG 81045; M & B 39831), a novel drug with potential as an alternative to dacarbazine. Cancer Res 47:5846-5852. (Pubitemid 18018717)
32. Xu G and McLeod HL (2001) Strategies for enzyme/prodrug cancer therapy. Clin Cancer Res 7:3314-3324. (Pubitemid 33069960)
33. Yasukochi Y and Masters BS (1976) Some properties of a detergent-solubilized NADPH-cytochrome c(cytochrome P-450) reductase purified by biospecific affinity chromatography. J Biol Chem 251:5337-5344.
34. Zheng L, Baumann U, and Reymond JL (2004) An efficient one-step site-directed and site-saturation mutagenesis protocol. Nucleic Acids Res 32:e115.