Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 49, 2019 - Issue 12
237
Views
8
CrossRef citations to date
0
Altmetric
Molecular Toxicology

Cytotoxicity of safrole in HepaRG cells: studies on the role of CYP1A2-mediated ortho-quinone metabolic activation

, , , , &
Pages 1504-1515 | Received 14 Jan 2019, Accepted 03 Mar 2019, Published online: 19 Jun 2019

References

  • Alegria AE, Sanchez-Cruz P. (2008). Ortho-quinone-enhanced ascorbate oxidation. Combined roles of lipid charge and the magnesium cation. Toxicol Environ Chem 90:327–40.
  • Allen EE, Zhu C, Panek JS, et al. (2017). Multicomponent condensation reactions via ortho-quinone methides. Org Lett 19:1878–81.
  • Andersson TB, Kanebratt KP, Kenna JG. (2012). The HepaRG cell line: a unique in vitro tool for understanding drug metabolism and toxicology in human. Expert Opin Drug Metab Toxicol 8:909–20.
  • Aninat C, Piton A, Glaise D, et al. (2006). Expression of cytochromes P450, conjugating enzymes and nuclear receptors in human hepatoma HepaRG cells. Drug Metab Dispos 34:75–83.
  • Attwa MW, Kadi AA, Darwish HW, et al. (2018). LC-MS/MS reveals the formation of reactive ortho-quinone and iminium intermediates in saracatinib metabolism: phase I metabolic profiling. Clin Chim Acta 482:84–94.
  • Benedetti MS, Malnoe A, Broillet AL. (1977). Absorption, metabolism and excretion of safrole in the rat and man. Toxicology 7:69–83.
  • Bolton JL, Acay NM, Vukomanovic V. (1994). Evidence that 4-allyl-o-quinones spontaneously rearrange to their more electrophilic quinone methides: potential bioactivation mechanism for the hepatocarcinogen safrole. Chem Res Toxicol 7:443–50.
  • Borchert P, Miller JA, Miller EC, et al. (1973). 1'-Hydroxysafrole, a proximate carcinogenic metabolite of safrole in the rat and mouse. Cancer Res 33:590–600.
  • Chen XW, Serag ES, Sneed KB, et al. (2011). Herbal bioactivation, molecular targets and the toxicity relevance. Chem Biol Interact 192:161–76.
  • Chien KJ, Yang ML, Tsai PK, et al. (2018). Safrole induced cytotoxicity, DNA damage, and apoptosis in macrophages via reactive oxygen species generation and Akt phosphorylation. Environ Toxicol Pharmacol 64:94–100.
  • Chung YT, Chen CL, Wu CC, et al. (2008). Safrole-DNA adduct in hepatocellular carcinoma associated with betel quid chewing. Toxicol Lett 183:21–7.
  • Costa PR, Torres LB, Rabi JA. (1980). Synthesis of quinolines from safrole. An Acad Bras Cienc 52:483–8.
  • Crampton RF, Gray TJ, Grasso P, et al. (1977). Long-term studies on chemically induced liver enlargement in the rat. II. Transient induction of microsomal enzymes leading to liver damage and nodular hyperplasia produced by safrole and Ponceau MX. Toxicology 7:307–26.
  • Farag SE, Abo-Zeid M. (1997). Degradation of the natural mutagenic compound safrole in spices by cooking and irradiation. Nahrung 41:359–61.
  • Fontana E, Dansette PM, Poli SM. (2005). Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metab 6:413–54.
  • Gripon P, Rumin S, Urban S, et al. (2002). Infection of a human hepatoma cell line by hepatitis B virus. Proc Natl Acad Sci USA 99:15655–60.
  • Guillouzo A, Corlu A, Aninat C, et al. (2007). The human hepatoma HepaRG cells: a highly differentiated model for studies of liver metabolism and toxicity of xenobiotics. Chem Biol Interact 168:66–73.
  • Hecht SS, Mcintee EJ, Wang M. (2001). New DNA adducts of crotonaldehyde and acetaldehyde. Toxicology 166:31–6.
  • Kalgutkar AS, Soglia JR. (2005). Minimising the potential for metabolic activation in drug discovery. Expert Opin Drug Metab Toxicol 1:91–142.
  • Kanebratt KP, Andersson TB. (2008a). Evaluation of HepaRG cells as an in vitro model for human drug metabolism studies. Drug Metab Dispos 36:1444–52.
  • Kanebratt KP, Andersson TB. (2008b). HepaRG cells as an in vitro model for evaluation of cytochrome P450 induction in humans. Drug Metab Dispos 36:137–45.
  • Klungsoyr J, Scheline RR. (1983). Metabolism of safrole in the rat. Acta Pharmacol Toxicol (Copenh) 52:211–6.
  • Liu TY, Chung YT, Wang PF, et al. (2004). Safrole-DNA adducts in human peripheral blood-an association with areca quid chewing and CYP2E1 polymorphisms. Mutat Res 559:59–66.
  • Martati E, Boersma MG, Spenkelink A, et al. (2012). Physiologically based biokinetic (PBBK) modeling of safrole bioactivation and detoxification in humans as compared with rats. Toxicol Sci 128:301–16.
  • Mcgill MR, Yan HM, Ramachandran A, et al. (2011). HepaRG cells: a human model to study mechanisms of acetaminophen hepatotoxicity. Hepatology 53:974–82.
  • Mcmahon BK, Gunnlaugsson T. (2012). Selective detection of the reduced form of glutathione (GSH) over the oxidized (GSSG) form using a combination of glutathione reductase and a Tb(III)-cyclen maleimide based lanthanide luminescent ‘switch on’ assay. J Am Chem Soc 134:10725–8.
  • Monks TJ, Jones DC. (2002). The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers. Curr Drug Metab 3:425–38.
  • Murray M. (2000). Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation. Curr Drug Metab 1:67–84.
  • Ogasawara A, Kato N, Torimoto N, et al. (2018). Cytochrome P450 1A2 messenger RNA is a more reliable marker than cytochrome P450 1A2 activity, phenacetin O-Deethylation, for assessment of induction potential of drug-metabolizing enzymes using HepaRG cells. Drug Metab Lett 12:14–23.
  • Park BK, Kitteringham NR, Maggs JL, et al. (2005). The role of metabolic activation in drug-induced hepatotoxicity. Annu Rev Pharmacol Toxicol 45:177–202.
  • Phillips DH, Reddy MV, Randerath K. (1984). 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. II. Newborn male B6C3F1 mice. Carcinogenesis 5:1623–8.
  • Rodrigues AD. (1999). Integrated cytochrome P450 reaction phenotyping: attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes. Biochem Pharmacol 57:465–80.
  • Shi F, Zhao P, Li X, et al. (2015). Cytotoxicity of luteolin in primary rat hepatocytes: the role of CYP3A-mediated ortho-benzoquinone metabolite formation and glutathione depletion. J Appl Toxicol 35:1372–80.
  • Sun M, Tang Y, Ding T, et al. (2014). Inhibitory effects of celastrol on rat liver cytochrome P450 1A2, 2C11, 2D6, 2E1 and 3A2 activity. Fitoterapia 92:1–8.
  • Ueng YF, Hsieh CH, Don MJ, et al. (2004). Identification of the main human cytochrome P450 enzymes involved in safrole 1'-hydroxylation. Chem Res Toxicol 17:1151–6.
  • Wu Y, Geng XC, Wang JF, et al. (2016). The HepaRG cell line, a superior in vitro model to L-02, HepG2 and hiHeps cell lines for assessing drug-induced liver injury. Cell Biol Toxicol 32:37–59.
  • Yang AH, Zhang L, Zhi DX, et al. (2018). Identification and analysis of the reactive metabolites related to the hepatotoxicity of safrole. Xenobiotica 48:1164–72.
  • Zhang D, Ogan M, Gedamke R, et al. (2003). Protein covalent binding of maxipost through a cytochrome P450-mediated ortho-quinone methide intermediate in rats. Drug Metab Dispos 31:837–45.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.