Optimal pH 8.5 to 9 for the hydrolysis of vixotrigine and other basic substrates of carboxylesterase-1 in human liver microsomes

References

• Bergmann F, Rimon S. 1958. The effect of pH variations on the activities of Cesterase. Biochem J. 70(2):339–344.
   PubMed Web of Science ®Google Scholar
• Friedman JR, Voeltz GK. 2011. The ER in 3D: a multifunctional dynamic membrane network. Trends Cell Biol. 21(12):709–717.
   PubMed Web of Science ®Google Scholar
• Gleason NJ, Vostrikov VV, Greathouse DV, Koeppe RE. 2013. Buried lysine, but not arginine, titrates and alters transmembrane helix tilt. Proc Natl Acad Sci USA. 110(5):1692–1695.
   PubMed Web of Science ®Google Scholar
• Hinckley CA, Kuryshev Y, Sers A, Barre A, Buisson B, Naik H, Hajos M. 2021. Characterization of vixotrigine, a broad-spectrum voltage-gated sodium channel blocker. Mol Pharmacol. 99(1):49–59.
   PubMed Web of Science ®Google Scholar
• Imai T. 2006. Human carboxylesterase isozymes: catalytic properties and rational drug design. Drug Metab Pharmacokinet. 21(3):173–185.
   PubMed Web of Science ®Google Scholar
• Isom DG, Castañeda CA, Cannon BR, García-Moreno EB. 2011. Large shifts in pKa values of lysine residues buried inside a protein. Proc Natl Acad Sci USA. 108(13):5260–5265.
   PubMed Web of Science ®Google Scholar
• Kamei A. 1996. Properties of partially purified esterase in human crystalline lens and variation in its enzyme activity during aging and with advance of senile cataract. Biol Pharm Bull. 19(9):1223–1226.
   PubMed Web of Science ®Google Scholar
• Kotecha M, Cheshire WP, Finnigan H, Giblin K, Naik H, Palmer J, Tate S, Zakrzewska JM. 2020. Design of phase 3 studies evaluating vixotrigine for treatment of trigeminal neuralgia. J Pain Res. 13:1601–1609.
   PubMed Web of Science ®Google Scholar
• Laizure SC, Herring V, Hu Z, Witbrodt K, Parker RB. 2013. The role of human carboxylesterases in drug metabolism: have we overlooked their importance? Pharmacotherapy. 33(2):210–222.
   PubMed Web of Science ®Google Scholar
• Lombardo D, Deprez P, Guy O. 1980. Esterification of cholesterol and lipid-soluble vitamins by human pancreatic carboxyl ester hydrolase. Biochimie. 62(7):427–432.
   PubMed Web of Science ®Google Scholar
• Milletti F, Storchi L, Sforna G, Cruciani G. 2007. New and original pKa prediction method using grid molecular interaction fields. J Chem Inf Model. 47(6):2172–2181.
   PubMed Web of Science ®Google Scholar
• Miyakawa K, Albee R, Letzig LG, Lehner AF, Scott MA, Buchweitz JP, James LP, Ganey PE, Roth RA. 2015. A cytochrome P450–independent mechanism of acetaminophen-induced injury in cultured mouse hepatocytes. J Pharmacol Exp Ther. 354(2):230–237.
   PubMed Web of Science ®Google Scholar
• Peng T, Fu S, Liu H, Lucia LA. 2016. Accurately determining esterase activity via the isosbestic point of p-nitrophenol. BioResources. 11(4):10099–10111.
   Web of Science ®Google Scholar
• Rougee LRA, Mohutsky MA, Bedwell DW, Ruterbories KJ, Hall SD. 2016. The impact of the hepatocyte-to-plasma pH gradient on the prediction of hepatic clearance and drug-drug interactions for CYP2D6 substrates. Drug Metab Dispos. 44(11):1819–1827.
   PubMed Web of Science ®Google Scholar
• Rougee LRA, Mohutsky MA, Bedwell DW, Ruterbories KJ, Hall SD. 2017. The impact of the hepatocyte-to-plasma pH gradient on the prediction of hepatic clearance and drug-drug interactions for CYP2C9 and CYP3A4 substrates. Drug Metab Dispos. 45(9):1008–1018.
   PubMed Web of Science ®Google Scholar
• Schindler R, Mentlein R, Feldheim W. 1998. Purification and characterization of retinyl ester hydrolase as a member of the non-specific carboxylesterase supergene family. Eur J Biochem. 251(3):863–873.
   PubMedGoogle Scholar
• Shimizu M, Fukami T, Nakajima M, Yokoi T. 2014. Screening of specific inhibitors for human carboxylesterases or arylacetamide deacetylase. Drug Metab Dispos. 42(7):1103–1109.
   PubMed Web of Science ®Google Scholar
• Tabata T, Katoh M, Tokudome S, Nakajima M, Yokoi T. 2004. Identification of the cytosolic carboxylesterase catalyzing the 59-deoxy-5-fluorocytidine formation from capecitabine in human liver. Drug Metab Dispos. 32(10):1103–1110.
   PubMed Web of Science ®Google Scholar
• Umehara K-I, Zollinger M, Kigondu E, Witschi M, Juif C, Huth F, Schiller H, Chibale K, Camenisch G. 2016. Esterase phenotyping in human liver in vitro: specificity of carboxylesterase inhibitors. Xenobiotica. 46(10):862–867.
   PubMed Web of Science ®Google Scholar
• Vistoli G, Pedretti A, Mazzolari A, Testa B. 2010. In silico prediction of human carboxylesterase-1 (hCES1) metabolism combining docking analyses and MD simulations. Bioorg Med Chem. 18(1):320–329.
   PubMed Web of Science ®Google Scholar
• Wang D, Zou L, Jin Q, Hou J, Ge G, Yang L. 2018. Human carboxylesterases: a comprehensive review. Acta Pharm Sin B. 8(5):699–712.
   PubMed Web of Science ®Google Scholar
• Watanabe A, Fukami T, Takahashi S, Kobayashi Y, Nakagawa N, Nakajima M, Yokoi T. 2010. Arylacetamide deacetylase is a determinant enzyme for the difference in hydrolase activities of phenacetin and acetaminophen. Drug Metab Dispos. 38(9):1532–1537.
   PubMed Web of Science ®Google Scholar
• Witty DR, Alvaro G, Derjean D, Giblin GMP, Gunn K, Large C, Macpherson DT, Morisset V, Owen D, Palmer J, et al. 2020. Discovery of vixotrigine: a novel use-dependent sodium channel blocker for the treatment of trigeminal neuralgia. ACS Med Chem Lett. 11(9):1678–1687.
   PubMed Web of Science ®Google Scholar
• Woodward C, Naik H, Versavel M, Xu L, Miao X, Sun H, Gohdes M, Dunbar J. 2017. Phase 1 study to evaluate the absorption, metabolism, and excretion of the Nav1.7-selective sodium channel blocker BIIB074. 21st North American Meeting of the International Society for the Study of Xenobiotics; Sep 24–28, Providence, RI.
   Google Scholar