Metabolic map and bioactivation of the anti-tumour drug noscapine

British Journal of Pharmacology

Volumn 167, Issue 6, 2012, Pages 1271-1286

  Fang, Zhong Ze ^a   Krausz, Kristopher W ^a   Li, Fei ^a   Cheng, Jie ^a   Tanaka, Naoki ^a   Gonzalez, Frank J ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

bioactivation; metabolic map; noscapine

Indexed keywords

CATECHOL; CYTOCHROME P450; DIMETHYLANILINE MONOOXYGENASE; DRUG METABOLITE; GLUCURONIDE; GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A3; GLUCURONOSYLTRANSFERASE 1A9; GLUCURONOSYLTRANSFERASE 2B7; GLUTATHIONE; NOSCAPINE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BLOOD CHEMISTRY; CONTROLLED STUDY; DRUG ACTIVATION; DRUG BIOACTIVATION; DRUG DETERMINATION; DRUG FECES LEVEL; DRUG METABOLISM; DRUG STRUCTURE; DRUG URINE LEVEL; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ASSAY; FECES ANALYSIS; FEEDING; IN VITRO STUDY; IN VIVO STUDY; LIVER LEVEL; MALE; METABOLITE; METABOLOMICS; MOUSE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; QUADRUPOLE MASS SPECTROMETRY; TANDEM MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; URINALYSIS;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; GLUCURONOSYLTRANSFERASE; GLUTATHIONE; HUMANS; LIVER; MALE; METABOLOMICS; MICE; MICE, INBRED C57BL; MICROSOMES, LIVER; NOSCAPINE;

EID: 84867824844     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2012.02067.x     Document Type: Article

References (43)

1. Aneja R, Katyal A, Chandra R, (2004). Modulatory influence of noscapine on the ethanol-altered hepatic biotransformation system enzymes, glutathione content and lipid peroxidation in vivo in rats. Eur J Drug Metab Pharmacokinet 29: 157-162.
2. Aneja R, Dhiman N, Idnani J, Awasthi A, Arora SK, Chandra R, et al,. (2007). Preclinical pharmacokinetics and bioavailability of noscapine, a tubulin-binding anticancer agent. Cancer Chemother Pharmacol 60: 831-839.
3. Antolino-Lobo I, Meulenbelt J, Nijmeijer SM, Scherpenisse P, van den Berg M, van Duursen MBM, (2010). Differential roles of phase I and phase II enzymes in 3,4-methylendioxymethamphetamine-induced cytotoxicity. Drug Metab Dispos 38: 1105-1112.
4. Baillie TA, (2006). Future of toxicology-metabolic activation and drug design: challenges and opportunities in chemical toxicology. Chem Res Toxicol 19: 889-893.
5. Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ, (2000). Roles of quinines in toxicity. Chem Res Toxicol 13: 135-160.
6. Buckley DB, Klaassen CD, (2007). Tissue- and Gender-specific mRNA expression of UDP-glucuronosyltransferases (UGTs) in mice. Drug Metab Dispos 35: 121-127.
7. Cheng Z, Rios GR, King CD, Coffman BL, Green MD, Mojarrabi B, et al,. (1998). Glucuronidation of catechol estrogens by expressed human UDP-glucuronosyltransferases (UGTs) 1A1, 1A3, and 2B7. Toxicol Sci 45: 52-57.
8. Choi JS, Piao YJ, Kang KW, (2011). Effects of quercetin on the bioavailability of doxorubicin in rats: role of CYP3A4 and P-gp inhibition by quercetin. Arch Pharm Res 34: 607-613.
9. Chougule M, Patel AR, Jackson T, Singh M, (2011a). Antitumor activity of noscapine in combination with doxorubicin in triple negative breast cancer. PLoS ONE 6: e17733.
10. Chougule M, Patel AR, Sachdeva P, Jackson T, Singh M, (2011b). Anticancer activity of noscapine, an opioid alkaloid in combination with cisplatin in human non-small cell lung cancer. Lung Cancer 71: 271-282.
11. Cresteil T, Monsarrat B, Alvinerie P, Treluyer JM, Vieira I, Wright M, (1994). Taxol metabolism by human liver microsomes: identification of cytochrome P450 isozymes involved in its biotransformation. Cancer Res 54: 386-392.
12. Empey DW, Laitinen LA, Young GA, Bye CE, Hughes DTD, (1979). Comparison of the antitussive effects of codeine phosphate 20 mg, dextromethorphan 30 mg and noscapine 30 mg using citric acid-induced cough in normal subjects. Eur J Clin Pharmacol 16: 393-397.
13. Fang ZZ, Zhang YY, Ge GB, Huo H, Liang SC, Yang L, (2010). Time-dependent inhibition (TDI) of CYP3A4 and CYP2C9 by noscapine potentially explains clinical noscapine-warfarin interaction. Br J Clin Pharmacol 69: 193-199.
14. Fang ZZ, Zhang YY, Wang XL, Cao YF, Huo H, Yang L, (2011). Bioactivation of herbal constituents: simple alerts in the complex system. Expert Opin Drug Metab Toxicol 7: 989-1007.
15. Giri S, Idle JR, Chen C, Zabriskie TM, Krausz KW, Gonzalez FJ, (2006). A metabolomic approach to the metabolism of the areca nut alkaloids arecoline and arecaidine in the mouse. Chem Res Toxicol 19: 818-827.
16. Jackson T, Chougule MB, Ichite N, Patlolla RR, Singh M, (2008). Antitumor activity of noscapine in human non-small cell lung cancer xenograft model. Cancer Chemother Pharmacol 63: 117-126.
17. Jian W, Yao M, Zhang D, Zhu M, (2009). Rapid detection and characterization of in vitro and urinary N-acetyl-L-cysteine conjugates using quadrupole-linear ion trap mass spectrometry and polarity switching. Chem Res Toxicol 22: 1246-1255.
18. Kalgutkar AS, Solia JR, (2005). Minimising the potential for metabolic activation in drug discovery. Expert Opin Drug Metab Toxicol 1: 91-142.
19. Ke Y, Ye K, Grossniklaus HE, Archer DR, Joshi HC, Kapp JA, (2000). Noscapine inhibits tumor growth with little toxicity to normal tissues or inhibition of immune responses. Cancer Immunol Immunother 49: 217-225.
20. Kilkenny C, Browne W, Cuthill IC, Emerson M, Altman DG, (2010). NC3Rs Reporting Guidelines Working Group. Br J Pharmacol 160: 1577-1579.
21. Landen JW, Lang R, McMahon SJ, Rusan NM, Yvon AM, Adams AW, et al,. (2002). Noscapine alters microtubule dynamics in living cells and inhibits the progression of melanoma. Cancer Res 62: 4109-4114.
22. Landen JW, Hau V, Wang M, Davis T, Ciliax B, Wainer BH, et al,. (2004). Noscapine crosses the blood-brain barrier and inhibits glioblastoma growth. Clin Cancer Res 10: 5187-5201.
23. Li F, Lu J, Ma X, (2011a). Profiling the reactive metabolites of xenobiotics using metabolomic technologies. Chem Res Toxicol 24: 744-751.
24. Li F, Patterson AD, Hofer CC, Krausz KW, Gonzalez FJ, Idle JR, (2011b). A comprehensive understanding of thioTEPA metabolism in the mouse using UPLC-ESI-QTOFMS-based metabolomics. Biochem Pharmacol 81: 1043-1053.
25. Lin JH, Lu AYH, (1997). Role of pharmacokinetics and metabolism in drug discovery and development. Pharmacol Rev 49: 403-449.
26. Liu M, Luo XJ, Liao F, Lei XF, Dong WG, (2011). Noscapine induces mitochondria-mediated apoptosis in gastric cancer cells in vitro and in vivo. Cancer Chemother Pharmacol 67: 605-612.
27. Mahmoudian M, Rahimi-Moghaddam P, (2009). The anti-cancer activity of noscapine: a review. Recent Pat Anticancer Drug Discov 4: 92-97.
28. McGrath J, Drummond G, McLachlan E, Kilkenny C, Wainwright C, (2010). Guidelines for reporting experiments involving animals: the ARRIVE guidelines. Br J Pharmacol 160: 1573-1576.
29. Monks TJ, Jones DC, (2002). The metabolism and toxicity of quinines, quinonimines, quinine methides, and quinine-thioethers. Curr Drug Metab 3: 425-438.
30. Monks TJ, Hanzlik RP, Cohen GM, Ross D, Graham DG, (1992). Quinone chemistry and toxicity. Toxicol Appl Pharmacol 112: 2-16.
31. Naik PK, Chatterji BP, Vangapandu SN, Aneja R, Chandra R, Kanteveri S, et al,. (2011). Rational design, synthesis and biological evaluations of amino-noscapine: a high affinity tubulin-binding noscapinoid. J Comput Aided Mol Des 25: 443-454.
32. Pang XY, Cheng J, Kim JH, Matsubara T, Krausz KW, Gonzalez FJ, (2012). Expression and regulation of human fetal-specific CYP3A7 in mice. Endocrinology 153: 1453-1463.
33. Porter R, Parry EM, Parry JM, (1992). Morphological transformation of an established-hamster dermal cell with the anti-tussive agent noscapine. Mutagenesis 7: 205-209.
34. Sandanaraj E, Lal S, Selvarajan V, Ooi LL, Wong ZW, Wong NS, et al,. (2008). PXR pharmacogenetics: association of haplotypes with hepatic CYP3A4 and ABCB1 messenger RNA expression and doxorubicin clearance in asian breast cancer patients. Clin Cancer Res 14: 7116-7126.
35. Santoshi S, Naik PK, Joshi HC, (2011). Rational design of novel anti-microtubule agent (9-azido-noscapine) from quantitative structure activity relationship (QSAR) evaluation of noscapinoids. J Biomol Screen 16: 1047-1058.
36. Scandlyn MJ, Stuart EC, Rosengren RJ, (2008). Sex-specific differences in CYP450 isoforms in humans. Expert Opin Drug Metab Toxicol 4: 413-424.
37. Schuler M, Muehlbauer P, Guzzie P, Eastmond DA, (1999). Noscapine hydrochloride disrupts the mitotic spindle in mammalian cells and induces aneuploidy as well as polyploidy in cultured human lymphocytes. Mutagenesis 14: 51-56.
38. Tsunoda N, Yoshimura H, (1981). Metabolic fate of noscapine. III. Further studies on identification and determination of the metabolites. Xenobiotica 11: 23-32.
39. Tucker GT, Lennard MS, Ellis SW, Woods HF, Cho AK, Lin LY, et al,. (1994). The demethylenation of methylenedioxymethamphetamine ('ecstasy') by debrisoquine hydroxylase (CYP2D6). Biochem Pharmacol 47: 1151-1156.
40. Walsh JS, Miwa GT, (2011). Bioactivation of drugs: risk and drug design. Annu Rev Pharmacol Toxicol 51: 145-167.
41. Yan Z, Caldwell GW, (2003). Metabolic assessment in liver microsomes by co-activating cytochrome P450s and UDP-glucuronosyltransferases. Eur J Drug Metab Pharmacokinet 28: 223-232.
42. Ye KQ, Ke Y, Keshava N, Shanks J, Kapp JA, Tekmal RR, et al,. (1998). Opium alkaloid noscapine is an antitumor agent that arrests metaphase and induces apoptosis in dividing cells. Proc Natl Acad Sci U S A 95: 1601-1606.
43. 3H]paroxetine to human liver microsomes and S-9 fractions: identification of an electrophilic quinine metabolite of paroxetine. Chem Res Toxicol 20: 1649-1657.