Metabolic map of the antiviral drug podophyllotoxin provides insights into hepatotoxicity

References

• Ardalani H, Avan A, Ghayour-Mobarhan M. 2017. Podophyllotoxin: a novel potential natural anticancer agent. Avicenna J Phytomed. 7(4):285–294.
   PubMed Web of Science ®Google Scholar
• Borsche W, Niemann J. 1932a. Über Podophyllin. Justus Liebigs Ann Chem. 494(1):126–142.
   Google Scholar
• Borsche W, Niemann J. 1932b. Zur Konstitution des Podophyllotoxins und Pikro‐podophyllins. Ber Dtsch Chem Ges A/B. 65(11):1846–1846.
   Google Scholar
• Canel C, Moraes RM, Dayan FE, Ferreira D. 2000. Podophyllotoxin. Phytochemistry. 54(2):115–120.
   PubMed Web of Science ®Google Scholar
• Damayanthi Y, Lown JW. 1998. Podophyllotoxins: current status and recent developments. Curr Med Chem. 5(3):205–252.
   PubMed Web of Science ®Google Scholar
• Dobb GJ, Edis RH. 1984. Coma and neuropathy after ingestion of herbal laxative containing podophyllin. Med J Aust. 140(8):495–496.
   PubMed Web of Science ®Google Scholar
• Fan Y, Schreiber EM, Giorgianni A, Yalowich JC, Day BW. 2006. Myeloperoxidase-catalyzed metabolism of etoposide to its quinone and glutathione adduct forms in HL60 cells. Chem Res Toxicol. 19(7):937–943.
   PubMed Web of Science ®Google Scholar
• Fang ZZ, Krausz KW, Li F, Cheng J, Tanaka N, Gonzalez FJ. 2012. Metabolic map and bioactivation of the anti-tumour drug noscapine. Br J Pharmacol. 167(6):1271–1286.
   PubMed Web of Science ®Google Scholar
• Filley CM, Graff-Richard NR, Lacy JR, Heitner MA, Earnest MP. 1982. Neurologic manifestations of podophyllin toxicity. Neurology. 32(3):308–311.
   PubMed Web of Science ®Google Scholar
• Gan J, Ruan Q, He B, Zhu M, Shyu WC, Humphreys WG. 2009. In vitro screening of 50 highly prescribed drugs for thiol adduct formation-comparison of potential for drug-induced toxicity and extent of adduct formation. Chem Res Toxicol. 22(4):690–698.
   PubMed Web of Science ®Google Scholar
• Gantchev TG, Hunting DJ. 1998. The ortho-quinone metabolite of the anticancer drug etoposide (VP-16) is a potent inhibitor of the topoisomerase II/DNA cleavable complex. Mol Pharmacol. 53(3):422–428.
   PubMed Web of Science ®Google Scholar
• Gensler WJ, Gatsonis CD. 1962. Synthesis of podophyllotoxin. J Am Chem Soc. 84(9):1748–1749.
   Web of Science ®Google Scholar
• Gensler WJ, Gatsonis CD. 1966. Synthesis of Podophyllotoxin1, 2. J Org Chem. 31(12):4004–4008.
   PubMed Web of Science ®Google Scholar
• Giri A, Narasu ML. 2000. Production of podophyllotoxin from Podophyllum hexandrum: a potential natural product for clinically useful anticancer drugs. Cytotechnology. 34(1–2):17–26.
   PubMed Web of Science ®Google Scholar
• Haim N, Nemec J, Roman J, Sinha BK. 1987. Peroxidase-catalyzed metabolism of etoposide (VP-16-213) and covalent binding of reactive intermediates to cellular macromolecules. Cancer Res. 47(22):5835–5840.
   PubMed Web of Science ®Google Scholar
• Haim N, Roman J, Nemec J, Sinha BK. 1986. Peroxidative free radical formation and O-demethylation of etoposide(VP-16) and teniposide(VM-26). Biochem Biophys Res Commun. 135(1):215–220.
   PubMed Web of Science ®Google Scholar
• Hartwell J, Shear M. 1947. Chemotherapy of cancer-classes of compounds under investigation and active components of podophyllin. Cancer Res. 7:716–717.
   Web of Science ®Google Scholar
• Hartwell JL, Schrecker AW. 1951. Components of podophyllin. V. the constitution of podophyllotoxin1. J Am Chem Soc. 73(6):2909–2916.
   Web of Science ®Google Scholar
• Hornberg JJ, Mow T. 2014. How can we discover safer drugs? Future Med Chem. 6(5):481–483.
   PubMed Web of Science ®Google Scholar
• Huang L, Li Y, Pan H, Lu Y, Zhou X, Shi F. 2020. Cortex dictamni-induced liver injury in mice: the role of P450-mediated metabolic activation of furanoids. Toxicol Lett. 330:41–52.
   PubMed Web of Science ®Google Scholar
• Jobin C, Sartor RB. 2000. The I kappa B/NF-kappa B system: a key determinant of mucosal inflammation and protection. Am J Physiol Cell Physiol. 278(3):C451–C62.
   PubMed Web of Science ®Google Scholar
• Kao WF, Hung DZ, Tsai WJ, Lin KP, Deng JF. 1992. Podophyllotoxin intoxication: toxic effect of Bajiaolian in herbal therapeutics. Hum Exp Toxicol. 11(6):480–487.
   PubMed Web of Science ®Google Scholar
• Kaplan I. 1942. Condylomata acuminate. New Orleans Med Surg J. 94:388–390.
   Google Scholar
• Kelly M, Hartwell JL. 1954. The biological effects and the chemical composition of podophyllin: a review. J Natl Cancer Inst. 14(4):967–1010.
   PubMedGoogle Scholar
• Kilkenny C, Browne W, Cuthill IC, Emerson M, Altman DG, NC3Rs Reporting Guidelines Working Group. 2010. Animal research: reporting in vivo experiments: the ARRIVE guidelines. Br J Pharmacol. 160(7):1577–1579.
   PubMed Web of Science ®Google Scholar
• Li J, Dai C-X, Sun H, Jin L, Guo C-Y, Cao W, Wu J, Tian H-Y, Luo C, Ye W-C, et al. 2012. Protective effects and mechanisms of curcumin on podophyllotoxin toxicity in vitro and in vivo. Toxicol Appl Pharmacol. 265(2):190–199.
   PubMed Web of Science ®Google Scholar
• Lin JH, Lu AY. 1997. Role of pharmacokinetics and metabolism in drug discovery and development. Pharmacol Rev. 49(4):403–449.
   PubMed Web of Science ®Google Scholar
• Longstaff E, Von Krogh G. 2001. Condyloma eradication: self-therapy with 0.15–0.5% podophyllotoxin versus 20–25% podophyllin preparations—an integrated safety assessment. Regul Toxicol Pharm. 33(2):117–137.
   PubMed Web of Science ®Google Scholar
• McGrath J, Drummond G, McLachlan E, Kilkenny C, Wainwright C. 2010. Guidelines for reporting experiments involving animals: the ARRIVE guidelines. Br J Pharmacol. 160(7):1573–1576.
   PubMed Web of Science ®Google Scholar
• Meschter CL, Mico BA, Mortillo M, Feldman D, Garland WA, Riley JA, Kaufman LS. 1994. A 13-week toxicologic and pathologic evaluation of prolonged cytochromes P450 inhibition by 1-aminobenzotriazole in male rats. Fundam Appl Toxicol. 22(3):369–381.
   PubMedGoogle Scholar
• Murray M. 2000. Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation. Curr Drug Metab. 1(1):67–84.
   PubMed Web of Science ®Google Scholar
• Naik SR, Thakare VN, Patil SR. 2011. Protective effect of curcumin on experimentally induced inflammation, hepatotoxicity and cardiotoxicity in rats: evidence of its antioxidant property. Exp Toxicol Pathol. 63(5):419–431.
   PubMedGoogle Scholar
• Neurath MF, Fuss I, SchÜrmann G, Pettersson S, Arnold K, Müller‐Lobeck H, Strober W, Herfarth C, Zum Büschenfelde KHM. 1998. Cytokine gene transcription by NF-kappa B family members in patients with inflammatory bowel disease . Ann N Y Acad Sci. 859:149–159.
   PubMed Web of Science ®Google Scholar
• Pandey SK, Nakka H, Ambhore SR, Londhe S, Goyal VK, Nirogi R. 2020. Short-term toxicity study of 1-aminobenzotraizole, a CYP inhibitor, in Wistar rats. Drug Chem Toxicol. 1–9. DOI: 10.1080/01480545.2020.1850755
   PubMed Web of Science ®Google Scholar
• Podwissotzki V. 1882. On the active constituents of Podophyllin. American Journal of Pharmacy (1835–1907). .12:102–105.
   Google Scholar
• Podwyssotzki V. 1880. Pharmakologische studien über Podophyllum peltatum. Archiv f Experiment Pathol u Pharmakol. 13(1–2):29–52.
   Google Scholar
• Schrecker A, Hartwell J. 1956. Communications-components of podophyllin. XX. the absolute configuration of podophyllotoxin and related lignans. J Org Chem. 21(3):381–382.
   Web of Science ®Google Scholar
• Shah Z, Gohar UF, Jamshed I, Mushtaq A, Mukhtar H, Zia-Ui-Haq M, Toma SI, Manea R, Moga M, Popovici B. 2021. Podophyllotoxin: history, recent advances and future prospects. Biomolecules. 11(4):603–629.
   PubMed Web of Science ®Google Scholar
• Smith NA, Byl JA, Mercer SL, Deweese JE, Osheroff N. 2014. Etoposide quinone is a covalent poison of human topoisomerase IIβ. Biochemistry. 53(19):3229–3236.
   PubMed Web of Science ®Google Scholar
• Song JH, Sun DX, Chen B, Ji DH, Pu J, Xu J, Tian FD, Guo L. 2011. Inhibition of CYP3A4 and CYP2C9 by podophyllotoxin: Implication for clinical drug-drug interactions. J Biosci. 36(5):879–885.
   PubMed Web of Science ®Google Scholar
• Späth E, Wessely F, Kornfeld L. 1932. Über die konstitution von podophyllotoxin und pikro‐podophyllin. Ber Dtsch Chem Ges A/B. 65(8):1536–1549.
   Google Scholar
• Sullivan M, King LS. 1947. Effects of resin of podophyllum on normal skin, condylomata acuminata and verrucae vulgares. Arch Derm Syphilol. 56(1):30–47.
   PubMedGoogle Scholar
• Tian X, Yang L, Liu YQ. 2007. Podophyllotoxin: current perspectives. CBC. 3(1):37–66.
   Google Scholar
• Walsh JS, Miwa GT. 2011. Bioactivation of drugs: risk and drug design. Annu Rev Pharmacol Toxicol. 51:145–167.
   PubMed Web of Science ®Google Scholar
• Yang C, Deng J, Chen C, Chang L. 1994. Experimental podophyllotoxin (bajiaolian) poisoning: III. biochemical bases for toxic effects. Biomed Environ Sci: BES. 7:259–265.
   PubMedGoogle Scholar
• Zhao SX, Dalvie DK, Kelly JM, Soglia JR, Frederick KS, Smith EB, Obach RS, Kalgutkar AS. 2007. NADPH-dependent covalent binding of [3H]paroxetine to human liver microsomes and S-9 fractions: identification of an electrophilic quinone metabolite of paroxetine. Chem Res Toxicol. 20(11):1649–1657.
   PubMed Web of Science ®Google Scholar
• Zong C, Garner CE, Huang C, Zhang X, Zhang L, Chang J, Toyokuni S, Ito H, Kato M, Sakurai T, et al. 2016. Preliminary characterization of a murine model for 1-bromopropane neurotoxicity: Role of cytochrome P450. Toxicol Lett. 258:249–258.
   PubMed Web of Science ®Google Scholar