The CYP2W1 enzyme: regulation, properties and activation of prodrugs

References

• Bandala C, Floriano-Sanchez E, Cardenas-Rodriguez N, et al. (2012). RNA expression of cytochrome P450 in Mexican women with breast cancer. Asian Pac J Cancer Prev 13:2647–2653.
   PubMedGoogle Scholar
• Choong E, Guo J, Persson A, et al. (2015). Developmental regulation and induction of cytochrome P450 2W1, an enzyme expressed in colon tumors. PLoS One 10:e0122820.
   Google Scholar
• Choudhary D, Jansson I, Stoilov I, et al. (2005). Expression patterns of mouse and human CYP orthologs (families 1–4) during development and in different adult tissues. Arch Biochem Biophys 436:50–61.
   PubMed Web of Science ®Google Scholar
• Du L, Neis MM, Ladd PA, Keeney DS. (2006a). Differentiation-specific factors modulate epidermal CYP1–4 gene expression in human skin in response to retinoic acid and classic aryl hydrocarbon receptor ligands. J Pharmacol Exp Ther 319:1162–1171.
   PubMed Web of Science ®Google Scholar
• Du L, Neis MM, Ladd PA, et al. (2006b). Effects of the differentiated keratinocyte phenotype on expression levels of CYP1–4 family genes in human skin cells. Toxicol Appl Pharmacol 213:135–144.
   PubMed Web of Science ®Google Scholar
• Edler D, Stenstedt K, Ohrling K, et al. (2009). The expression of the novel CYP2W1 enzyme is an independent prognostic factor in colorectal cancer – A pilot study. Eur J Cancer 45:705–712.
   PubMed Web of Science ®Google Scholar
• Eun CY, Han S, Lim YR, et al. (2010). Bioactivation of aromatic amines by human CYP2W1, an orphan cytochrome P450 enzyme. Toxicol Res 26:171–175.
   PubMedGoogle Scholar
• Fei-Lei Chung F, Wai Mai C, Yuen NGP, Leong CO. (2015). Cytochrome P450 2W1 (CYP2W1) in colorectal cancers. Curr Cancer Drug Targets 16:71–78.
   Web of Science ®Google Scholar
• Fujikura K, Ingelman-Sundberg M, Lauschke VM. (2015). Genetic variation in the human cytochrome P450 supergene family. Pharmacogenet Genomics 25:584–594.
   PubMed Web of Science ®Google Scholar
• Gervasini G, DE Murillo SG, Ladero JM, Agundez JA. (2010). CYP2W1 variant alleles in Caucasians and association of the CYP2W1 G541A (Ala181Thr) polymorphism with increased colorectal cancer risk. Pharmacogenomics 11:919–925.
   PubMed Web of Science ®Google Scholar
• Gomez A, Karlgren M, Edler D, et al. (2007). Expression of CYP2W1 in colon tumors: Regulation by gene methylation. Pharmacogenomics 8:1315–1325.
   PubMed Web of Science ®Google Scholar
• Gomez A, Nekvindova J, Travica S, et al. (2010). Colorectal cancer-specific cytochrome P450 2W1: Intracellular localization, glycosylation, and catalytic activity. Mol Pharmacol 78:1004–1011.
   PubMed Web of Science ®Google Scholar
• Guo J, Thiess S, Johansson I, et al. (2016). Membrane topology and search for potential redox partners of colon cancer-specific cytochrome P450 2W1. FEBS Lett 590:330–339.
   PubMed Web of Science ®Google Scholar
• Hanzawa Y, Sasaki T, Mizugaki M, et al. (2008). Genetic polymorphisms and haplotype structures of the human CYP2W1 gene in a Japanese population. Drug Metab Dispos 36:349–352.
   PubMed Web of Science ®Google Scholar
• Hartanto FK, Karen-Ng LP, Vincent-Chong VK, et al. (2015). KRT13, FAIM2 and CYP2W1 mRNA expression in oral squamous cell carcinoma patients with risk habits. Asian Pac J Cancer Prev 16:953–958.
   PubMedGoogle Scholar
• Karlgren M, Gomez A, Stark K, et al. (2006). Tumor-specific expression of the novel cytochrome P450 enzyme, CYP2W1. Biochem Biophys Res Commun 341:451–458.
   PubMed Web of Science ®Google Scholar
• Molina-Ortiz D, Camacho-Carranza R, Gonzalez-Zamora JF, et al. (2014). Differential expression of cytochrome P450 enzymes in normal and tumor tissues from childhood rhabdomyosarcoma. PLoS One 9:e93261.
   PubMed Web of Science ®Google Scholar
• Neve EP, Ingelman-Sundberg M. (2000). Molecular basis for the transport of cytochrome P450 2E1 to the plasma membrane. J Biol Chem 275:17130–17135.
   PubMed Web of Science ®Google Scholar
• Neve EP, Ingelman-Sundberg M. (2010). Cytochrome P450 proteins: Retention and distribution from the endoplasmic reticulum. Curr Opin Drug Discov Devel 13:78–85.
   PubMed Web of Science ®Google Scholar
• Nishida CR, Lee M, DE Montellano PR. (2010). Efficient hypoxic activation of the anticancer agent AQ4N by CYP2S1 and CYP2W1. Mol Pharmacol 78:497–502.
   PubMed Web of Science ®Google Scholar
• Qi GZ, Wang X, Miao XJ, et al. (2015). Novel single nucleotide polymorphisms (SNPs) of CYP2W1 gene in Chinese Uygur and Han populations. Drug Metab Pharmacokinet 30:449–452.
   PubMed Web of Science ®Google Scholar
• Ronchi CL, Sbiera S, Volante M, et al. (2014). CYP2W1 is highly expressed in adrenal glands and is positively associated with the response to mitotane in adrenocortical carcinoma. PLoS One 9:e105855.
   PubMed Web of Science ®Google Scholar
• Sheldrake HM, Travica S, Johansson I, et al. (2013). Re-engineering of the duocarmycin structural architecture enables bioprecursor development targeting CYP1A1 and CYP2W1 for biological activity. J Med Chem 56:6273–6277.
   PubMed Web of Science ®Google Scholar
• Stenstedt K, Hallstrom M, Johansson I, et al. (2012). The expression of CYP2W1: A prognostic marker in colon cancer. Anticancer Res 32:3869–3874.
   PubMed Web of Science ®Google Scholar
• Stenstedt K, Hallstrom M, Ledel F, et al. (2014). The expression of CYP2W1 in colorectal primary tumors, corresponding lymph node metastases and liver metastases. Acta Oncol 53:885–891.
   PubMed Web of Science ®Google Scholar
• Stenstedt K, Travica S, Guo J, et al. (2013). CYP2W1 polymorphism: Functional aspects and relation to risk for colorectal cancer. Pharmacogenomics 14:1615–1622.
   PubMed Web of Science ®Google Scholar
• Sutherland M, Gill JH, Loadman PM, et al. (2013). Antitumor activity of a duocarmycin analogue rationalized to be metabolically activated by cytochrome P450 1A1 in human transitional cell carcinoma of the bladder. Mol Cancer Ther 12:27–37.
   PubMed Web of Science ®Google Scholar
• Tan BS, Tiong KH, Muruhadas A, et al. (2011). CYP2S1 and CYP2W1 mediate 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (GW-610, NSC 721648) sensitivity in breast and colorectal cancer cells. Mol Cancer Ther 10:1982–1992.
   PubMed Web of Science ®Google Scholar
• Travica S, Pors K, Loadman PM, et al. (2013). Colon cancer-specific cytochrome P450 2W1 converts duocarmycin analogues into potent tumor cytotoxins. Clin Cancer Res 19:2952–2961.
   PubMed Web of Science ®Google Scholar
• Wang K, Guengerich FP. (2012). Bioactivation of fluorinated 2-aryl-benzothiazole antitumor molecules by human cytochrome P450s 1A1 and 2W1 and deactivation by cytochrome P450 2S1. Chem Res Toxicol 25:1740–1751.
   PubMed Web of Science ®Google Scholar
• Wu ZL, Sohl CD, Shimada T, Guengerich FP. (2006). Recombinant enzymes overexpressed in bacteria show broad catalytic specificity of human cytochrome P450 2W1 and limited activity of human cytochrome P450 2S1. Mol Pharmacol 69:2007–2014.
   PubMed Web of Science ®Google Scholar
• Xiao Y, Guengerich FP. (2012). Metabolomic analysis and identification of a role for the orphan human cytochrome P450 2W1 in selective oxidation of lysophospholipids. J Lipid Res 53:1610–1617.
   PubMed Web of Science ®Google Scholar
• Yoshioka H, Kasai N, Ikushiro S, et al. (2006). Enzymatic properties of human CYP2W1 expressed in Escherichia coli. Biochem Biophys Res Commun 345:169–174.
   PubMed Web of Science ®Google Scholar
• Zhang K, Jiang L, He R, et al. (2014). Prognostic value of CYP2W1 expression in patients with human hepatocellular carcinoma. Tumour Biol 35:7669–7673.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Wan D, Yang J, et al. (2016). Catalytic activities of tumor-specific human cytochrome P450 CYP2W1 towards endogenous substrates. Drug Metab Dispos 44:771–780.
   Google Scholar