2,516
Views
3
CrossRef citations to date
0
Altmetric
Research Papers

Comparative chemical and biological hydrolytic stability of homologous esters and isosteres

, , , , , , & show all
Pages 718-727 | Received 21 Sep 2021, Accepted 06 Jan 2022, Published online: 13 Feb 2022

References

  • Beaumont K, Webster R, Gardner I, et al. Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: challenges to the discovery scientist. Curr Drug Metab 2003;4:461–85.
  • Lavis LD. Ester bonds in prodrugs. ACS Chem Biol 2008;3:203–6.
  • Larsen EM, Johnson RJ. Microbial esterases and ester prodrugs: an unlikely marriage for combating antibiotic resistance. Drug Dev Res 2019;80:33–47.
  • Karaman R. Prodrugs design based on inter- and intramolecular chemical processes. Chem Biol Drug Des 2013;82:643–68.
  • Buchwald P. Soft drugs: design principles, success stories, and future perspectives. Expert Opin Drug Metabol Toxicol 2020;16:645–50.
  • Hung DY, Mellick GD, Anissimov YG, et al. Hepatic disposition and metabolite kinetics of a homologous series of diflunisal esters. J Pharma Sci 1998;87:943–51.
  • Lukka PB, Paxton JW, Kestell P, et al. Comparison of a homologous series of benzonaphthyridine anti-cancer agents in mice: divergence between tumour and plasma pharmacokinetics. Cancer Chemother Pharmacol 2012;70:151–60.
  • Dagher Z, Borgie M, Magdalou J, et al. p-Hydroxybenzoate esters metabolism in MCF7 breast cancer cells. Food Chem Toxicol 2012;50:4109–14.
  • Jordan CGM. How an increase in the carbon chain length of the ester moiety affects the stability of a homologous series of oxprenolol esters in the presence of biological enzymes. J Pharma Sci 1998;87:880–5.
  • Hung DY, Mellick GD, Anissimov YG, et al. Hepatic structure-pharmacokinetic relationships: The hepatic disposition and metabolite kinetics of a homologous series of O-acyl derivatives of salicylic acid: Hepatic disposition and metabolite kinetics of aspirin analogues. Br J Pharmacol 1998;124:1475–83.
  • Graffner-Nordberg M, Sjodin K, Tunek A, et al. Synthesis and enzymatic hydrolysis of esters, constituting simple models of soft drugs. Chem Pharm Bull 1998;46:591–601.
  • Lima LM, Alves MA, do Amaral DN. Homologation: a versatile molecular modification strategy to drug discovery. Curr Top Med Chem 2019;19:1734–50.
  • Lima L, Barreiro E. Bioisosterism: a useful strategy for molecular modification and drug design. Curr Med Chem 2005;12:23–49.
  • Chackalamannil S, Rotella D, Ward SE, et al. Comprehensive medicinal chemistry III. 1st ed. Elsevier; 2017.
  • Fife TH, Singh R, Bembi R. Intramolecular general base catalyzed ester hydrolysis. the hydrolysis of 2-aminobenzoate esters. J Org Chem 2002;67:3179–83.
  • Venkatakrishnan K, von Moltke L, Obach R, et al. Drug metabolism and drug interactions: application and clinical value of in vitro models. Curr Drug Metab 2003;4:423–59.
  • Cabrera M, Lavaggi ML, Hernández P, et al. Cytotoxic, mutagenic and genotoxic effects of new anti-T. cruzi 5-phenylethenylbenzofuroxans. Contribution of phase I metabolites on the mutagenicity induction. Toxicol Lett 2009;190:140–9.
  • Smith PK, Krohn RI, Hermanson GT, et al. Measurement of protein using bicinchoninic acid. Analyt Biochem 1985;150:76–85.
  • Büch H, Buzello W, Heymann E, et al. Inhibition of phenacetin- and acetanilide-induced methemoglobinemia in the rat by the carboxylesterase inhibitor bis-[p-nitrophenyl] phosphate. Biochem Pharmacol 1969;18:801–811.
  • Kim M-J, Jeong ES, Park J-S, et al. Multiple cytochrome P450 isoforms are involved in the generation of a pharmacologically active thiol metabolite, whereas paraoxonase 1 and carboxylesterase 1 catalyze the formation of a thiol metabolite isomer from ticlopidine. Drug Metab Dispos 2014;42:141–52.
  • RESOLUÇÃO - RDC N° 27, DE 17 DE MAIO DE 2012 online [internet]. Brazil: ANVISA-Ministério da Saúde; 2012-2021[cited 2021 Sep 15]. Available from: https://bvsms.saude.gov.br/bvs/saudelegis/anvisa/2012/rdc0027_17_05_2012.html
  • Bioanalytical Method Validation Guidance for Industry online [internet]. Silver Spring (US): Food and Drug Administration; 2018-2021 [cited 2021 Sep 2015]. Available from: https://www.fda.gov/files/drugs/published/Bioanalytical-Method-Validation-Guidance-for-Industry.pdf
  • Stewart JJP. Optimization of parameters for semiempirical methods VI: more modifications to the NDDO approximations and re-optimization of parameters. J Mol Model 2013;19:1–32.
  • Hansch C, Sammes PG, Taylor JB, Comprehensive medicinal chemistry. The rational design, mechanistic study and therapeutic application of chemical compounds. 4th Ed. Oxford: Pergamon Press; 1991.
  • Hansch C, Leo A, Hoekman DH, Exploring QSAR: hydrophobic, electronic, and steric constants. 2nd Ed. Washington: American Chemical Society; 1995.
  • Fleming CD, Bencharit S, Edwards CC, et al. Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by Benzil. Journal of Molecular Biology 2005;352:165–77.
  • Korb O, Stützle T, Exner TE. Empirical scoring functions for advanced protein-ligand docking with plants. J Chem Inf Model 2009;49:84–96.
  • Jones G, Willett P, Glen RC, et al. Development and validation of a genetic algorithm for flexible docking. J Mol Biol. 1997;267:727–748.
  • Eldridge MD, Murray CW, Auton TR, et al. Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes. J Comput Aided Mol Des. 1997;11:425–445.
  • Mooij WTM, Verdonk ML. General and targeted statistical potentials for protein-ligand interactions. Proteins 2005;61:272–87.
  • Satoh T, Hosokawa M. The mammalian carboxylesterases: from molecules to functions. Annu Rev Pharmacol Toxicol 1998;38:257–88.
  • Frey P, Whitt S, Tobin J. A low-barrier hydrogen bond in the catalytic triad of serine proteases. Science 1994;264:1927–30.
  • Korth M, Pitoňák M, Řezáč J, et al. A Transferable H-bonding correction for semiempirical quantum-chemical methods. J Chem Theory Comput 2010;6:344–52.
  • Klamt A, Schüürmann G. COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J Chem Soc Perkin Trans 2 1993;(5):799–805.
  • Stewart JJP. An investigation into the applicability of the semiempirical method PM7 for modeling the catalytic mechanism in the enzyme chymotrypsin. J Mol Model 2017;23:154.
  • Baker J. An algorithm for the location of transition states. J Comput Chem 1986;7:385–95.
  • Sant'Anna CMR, De Souza VP, Santos De Andrade D. Semiempirical simulation of a theta-class glutathione S-transferase-catalyzed glutathione attack to the allelochemical DIMBOA. Int J Quantum Chem 2002;87:311–21.
  • Gómez-Bombarelli R, Calle E, Casado J. Mechanisms of lactone hydrolysis in neutral and alkaline conditions. J Org Chem 2013;78:6868–79.
  • Wang H. An accurate theoretical study of energy barriers of alkaline hydrolysis of carboxylic esters. Res Chem Intermed 2012;38:2175–90.
  • Bender ML. Mechanisms of catalysis of nucleophilic reactions of carboxylic acid derivatives. Chem Rev 1960;60:53–113.
  • Jencks WP, Carriuolo J. General base catalysis of ester hydrolysis 1. J Am Chem Soc 1961;83:1743–50.
  • Yu X, Sigler SC, Hossain D, et al. Global and local molecular dynamics of a bacterial carboxylesterase provide insight into its catalytic mechanism. J Mol Model 2012;18:2869–83.