Taxane's substituents at C3′ affect its regioselective metabolism: Different in vitro metabolism of cephalomannine and paclitaxel

Drug Metabolism and Disposition

Volumn 36, Issue 2, 2008, Pages 418-426

  Zhang, Jiang Wei ^a,d   Ge, Guang Bo ^a,d   Liu, Yong ^a   Wang, Li Ming ^b   Liu, Xing Bao ^a   Zhang, Yan Yan ^a,d   Li, Wei ^a,d   He, Yu Qi ^c   Wang, Zheng Tao ^c   Sun, Jie ^b   Xiao, Hong Bin ^a   Yang, Ling ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b DALIAN MEDICAL UNIVERSITY   (China)

^c SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

^d UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3' 4 HYDROXYPACLITAXEL; 4'' HYDROXYCEPHALOMANNINE; 6ALPHA HYDROXYCEPHALOMANNINE; 6ALPHA HYDROXYPACLITAXEL; CEPHALOMANNINE; CLOMETHIAZOLE; CYTOCHROME P450; CYTOCHROME P450 2C8; CYTOCHROME P450 3A4; DRUG METABOLITE; FURAFYLLINE; KETOCONAZOLE; MEPHENYTOIN; METHOXSALEN; PACLITAXEL; QUERCETIN; QUINIDINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SULFAPHENAZOLE; TAXANE DERIVATIVE; TROLEANDOMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG METABOLISM; DRUG STRUCTURE; HUMAN; HUMAN TISSUE; HYDROXYLATION; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MALE; MINIPIG; MOLECULAR DOCKING; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; TANDEM MASS SPECTROMETRY;

ADULT; ANIMALS; ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; BRIDGED COMPOUNDS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; HYDROXYLATION; MALE; MICROSOMES, LIVER; MIDDLE AGED; PACLITAXEL; RATS; RATS, SPRAGUE-DAWLEY; RECOMBINANT PROTEINS; SWINE; SWINE, MINIATURE; TAXOIDS;

RATTUS;

EID: 38749151892     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.018242     Document Type: Article

References (40)

1. Anderson CD, Wang J, Kumar GN, McMillan JM, Walle UK, and Walle T (1995) Dexamethasone induction of taxol metabolism in the rat. Drug Metab Dispos 23:1286-1290.
2. Anzenbacher P, Soucek P, Anzenbacherova E, Gut I, Hruby K, Svoboda Z, and Kvetina J (1998) Presence and activity of cytochrome P450 isoforms in minipig liver microsomes. Comparison with human liver samples. Drug Metab Dispos 26:56-59.
3. Barboni L, Ballini R, Giarlo G, Appendino G, Fontana G, and Bombardelli E (2005) Synthesis and biological evaluation of methoxylated analogs of the newer generation taxoids IDN5109 and IDN5390. Bioorg Med Chem Lett 15:5182-5186.
4. Bhalla KN, Kumar GN, Walle UK, Ibrado AM, Javed T, Stuart RK, Reed C, Arbuck SG, and Walle T (1999) Phase I and pharmacologic study of a 3-hour infusion of paclitaxel followed by cisplatinum and 5-fluorouracil in patients with advanced solid tumors. Clin Cancer Res 5:1723-1730.
5. Bjornsson TD, Callaghan JT, Einolf HJ, Fischer V, Gan L, Grimm S, Kao J, King SP, Miwa G, Ni L, et al. (2003) The conduct of in vitro and in vivo drug-drug interaction studies: a PhRMA perspective. J Clin Pharmacol 43:443-469.
6. Blanksby SJ and Ellison GB (2003) Bond dissociation energies of organic molecules. Acc Chem Res 36:255-263.
7. Broker LE, Veltkamp SA, Heath EI, Kuenen BC, Gall H, Astier L, Parker S, Kayitalire L, Lorusso PM, Schellens JH, et al. (2007) A phase I safety and pharmacologic study of a twice weekly dosing regimen of the oral taxane BMS-275183. Clin Cancer Res 13:3906-3912.
8. Chen TS, Li XH, Bollag D, Liu YC, and Chang CJ (2001) Biotransformation of taxol. Tetrahedron Lett 42:3787-3789.
9. Cresteil T, Monsarrat B, Dubois J, Sonnier M, Alvinerie P, and Gueritte F (2002) Regioselective metabolism of taxoids by human CYP3A4 and 2C8: structure-activity relationship. Drug Metab Dispos 30:438-445.
10. Desai PB, Duan JZ, Zhu YW, and Kouzi S (1998) Human liver microsomal metabolism of paclitaxel and drug interactions. Eur J Drug Metab Pharmacokinet 23:417-424.
11. Ekroos M and Sjogren T (2006) Structural basis for ligand promiscuity in cytochrome P450 3A4. Proc Natl Acad Sci U S A 103:13682-13687.
12. Ferlini C, Raspaglio G, Mozzetti S, Cicchillitti L, Filippetti F, Gallo D, Fattorusso C, Campiani G, and Scambia G (2005) The seco-taxane IDN5390 is able to target class III beta-tubulin and to overcome paclitaxel resistance. Cancer Res 65:2397-2405.
13. Frapolli R, Marangon E, Zaffaroni M, Colombo T, Falcioni C, Bagnati R, Simone M, D'Incalci M, Manzotti C, Fontana G, et al. (2006) Pharmacokinetics and metabolism in mice of IDN 5390 (13-(N-Boc-3-i-butylisoserinoyl)-C-7,8-seco-10- deacetylbaccatin III), a new oral c-secotaxane derivative with antiangiogenic property effective on paclitaxel-resistant tumors. Drug Metab Dispos 34:2028-2035.
14. Gut I, Ojima I, Vaclavikova R, Simek P, Horsky S, Linhart I, Soucek P, Kondrova E, Kuznetsova LV, and Chen J (2006) Metabolism of new-generation taxanes in human, pig, minipig and rat liver microsomes. Xenobiotica 36:772-792.
15. Harris JW, Rahman A, Kim BR, Guengerich FP, and Collins JM (1994) Metabolism of taxol by human hepatic microsomes and liver slices: participation of cytochrome P450 3A4 and an unknown P450 enzyme. Cancer Res 54:4026-4035.
16. Helson L and Ainsworth SK (1997) inventors; NaPro BioTherapeutics, Inc., assignee. Method for assessing sensitivity of tumor cells to cephalomannine and 10-deacetyltaxol. U.S. patent 5,688,517. 1997 Nov 18.
17. Huang SM, Temple R, Throckmorton DC, and Lesko LJ (2007) Drug interaction studies: study design, data analysis, and implications for dosing and labeling. Clin Pharmacol Ther 81:298-304.
18. Kobayashi K, Urashima K, Shimada N, and Chiba K (2003) Selectivities of human cytochrome P450 inhibitors toward rat P450 isoforms: study with cDNA-expressed systems of the rat. Drug Metab Dispos 31:833-836.
19. Li J, Liu Y, Zhang JW, Wei H, and Yang L (2006) Characterization of hepatic drug-metabolizing activities of Bama miniature pigs (Sus scrofa domestica): comparison with human enzyme analogs. Comp Med 56:286-290.
20. Lockhart AC, Bukowski R, Rothenberg ML, Wang KK, Cooper W, Grover J, Appleman L, Mayer PR, Shapiro M, and Zhu AX (2007) Phase I trial of oral MAC-321 in subjects with advanced malignant solid tumors. Cancer Chemother Pharmacol 60:203-209.
21. Lowry OH, Rosebrough NJ, Farr AL, and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
22. Mastalerz H, Cook D, Fairchild CR, Hansel S, Johnson W, Kadow JF, Long BH, Rose WC, Tarrant J, Wu MJ, et al. (2003) The discovery of BMS-275183: an orally efficacious novel taxane. Bioorg Med Chem 11:4315-4323.
23. Miller RW, Powell RG, Smith CR, Arnold E, and Clardy J (1981) Antileukemic alkaloids from Taxus wallichiana Zucc. J Org Chem. 46:1469-1474.
24. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, and Olson AJ (1998) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19:1639-1662.
25. Mroczek T, Glowniak K, and Hajnos M (2000) Screening for pharmaceutically important taxoids in Taxus baccata var. Aurea corr. with CC/SPE/HPLC-PDA procedure. Biomed Chromatogr 14:516-529.
26. Ojima I, Slater JC, Michaud E, Kuduk SD, Bounaud PY, Vrignaud P, Bissery MC, Veith JM, Pera P, and Bernacki RJ (1996) Syntheses and structure-activity relationships of the second-generation antitumor taxoids: exceptional activity against drug-resistant cancer cells. J Med Chem 39:3889-3896.
27. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2385.
28. Porter TD and Coon MJ (1991) Cytochrome P-450. Multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms. J Biol Chem 266:13469-13472.
29. Sanner MF (1999) Python: a programming language for software integration and development. J Mol Graph Model 17:57-61.
30. Sano D, Matsuda H, Ishiguro Y, Nishimura G, Kawakami M, and Tsukuda M (2006) Antitumor effects of IDN5109 on head and neck squamous cell carcinoma. Oncol Rep 15:329-334.
31. Shi Q, Wang HK, Bastow KF, Tachibana Y, Chen K, Lee FY, and Lee KH (2001) Antitumor agents 210. Synthesis and evaluation of taxoid-epipodophyllotoxin conjugates as novel cytotoxic agents. Bioorg Med Chem 9:2999-3004.
32. Singla AK, Garg A, and Aggarwal D (2002) Paclitaxel and its formulations. Int J Pharm 235:179-192.
33. Song L, Prey JD, Xue J, Kanter P, Manzotti C, Bombardelli E, Morazzoni P, and Pendyala L (2005) Pharmacokinetic measurements of IDN 5390 using electrospray ionization tandem mass spectrometry: structure characterization and quantification in dog plasma. Rapid Commun Mass Spectrom 19:3617-3625.
34. Sparreboom A, van Asperen J, Mayer U, Schinkel AH, Smit JW, Meijer DK, Borst P, Nooijen WJ, Beijnen JH, and van Tellingen O (1997) Limited oral bioavailability and active epithelial excretion of paclitaxel (Taxol) caused by P-glycoprotein in the intestine. Proc Natl Acad Sci U S A 94:2031-2035.
35. Spratlin J and Sawyer MB (2007) Pharmacogenetics of paclitaxel metabolism. Crit Rev Oncol Hematol 61:222-229.
36. Swindell CS, Krauss NE, Horwitz SB, and Ringel I (1991) Biologically active taxol analogues with deleted A-ring side chain substituents and variable C-2′ configurations. J Med Chem 34:1176-1184.
37. Taniguchi R, Kumai T, Matsumoto N, Watanabe M, Kamio K, Suzuki S, and Kobayashi S (2005) Utilization of human liver microsomes to explain individual differences in paclitaxel metabolism by CYP2C8 and CYP3A4. J Pharmacol Sci 97:83-90.
38. Vaclavikova R, Soucek P, Svobodova L, Anzenbacher P, Simek P, Guengerich FP, and Gut I (2004) Different in vitro metabolism of paclitaxel and docetaxel in humans, rats, pigs, and minipigs. Drug Metab Dispos 32:666-674.
39. Venkatakrishnan K, von Moltke LL, Obach RS, and Greenblatt DJ (2003) Drug metabolism and drug interactions: application and clinical value of in vitro models. Curr Drug Metab 4:423-459.
40. Vivekanandan K, Swamy MG, Prasad S, Mukherjee R, and Burman AC (2006) Identification of isocephalomannine in the presence of cephalomannine isomers and alkali metal ion adducts in a paclitaxel active pharmaceutical ingredient using electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom 20:1731-1735.