Xenobiotic/medium chain fatty acid: CoA ligase – a critical review on its role in fatty acid metabolism and the detoxification of benzoic acid and aspirin

References

• Watkins PA. Fatty acid activation. Prog Lipid Res. 1997 Mar;36:55–83.
   PubMed Web of Science ®Google Scholar
• Watkins PA, Maiguel D, Jia Z, et al. Evidence for 26 distinct acyl-coenzyme A synthetase genes in the human genome. J Lipid Res. 2007;48:2736–2750.
   PubMed Web of Science ®Google Scholar
• Grafflin AL, Green DE. Studies on the cyclophorase system; the complete oxidation of fatty acids. J Biol Chem. 1948 Oct;176:95–115.
   PubMed Web of Science ®Google Scholar
• Knox WE, Noyce BN, Auerbach VH. Studies on the cyclophorase system; obligatory sparking of fatty acid oxidation. J Biol Chem. 1948 Oct;176:117–122.
   PubMed Web of Science ®Google Scholar
• Mahler HR, Wakil SJ, Bock RM. Studies on fatty acid oxidation. I. Enzymatic activation of fatty acids. J Biol Chem. 1953 Sep;204:453–468.
   PubMed Web of Science ®Google Scholar
• Groot PH, Scholte HR, Hulsmann WC. Fatty acid activation: specificity, localization, and function. Adv Lipid Res. 1976;14:75–126.
   PubMedGoogle Scholar
• Waku K. Origins and fates of fatty acyl-CoA esters. Biochim Biophys Acta. 1992 Mar 4;1124:101–111.
   PubMed Web of Science ®Google Scholar
• Ellis JM, Frahm JL, Li LO, et al. Acyl-coenzyme A synthetases in metabolic control. Curr Opin Lipidol. 2010;21:212–217.
   PubMed Web of Science ®Google Scholar
• Vessey DA, Kelley M, Warren RS. Characterization of the CoA ligases of human liver mitochondria catalyzing the activation of short- and medium-chain fatty acids and xenobiotic carboxylic acids. Biochim Biophys Acta. 1999;1428:455–462.
   PubMed Web of Science ®Google Scholar
• Lopaschuk GD, Ussher JR, Folmes CD, et al. Myocardial fatty acid metabolism in health and disease. Physiol Rev. 2010;90:207–258.
   PubMed Web of Science ®Google Scholar
• Webster LT Jr. Studies of the acetyl coenzyme A synthetase reaction. II. Crystalline acetyl coenzyme A synthetase. J Biol Chem. 1965 Nov;240:4158–4163.
   PubMed Web of Science ®Google Scholar
• Webster LT Jr, Gerowin LD, Rakita L. Purification and characteristics of a butyryl coenzyme a synthetase from bovine heart mitochondria. J Biol Chem. 1965 Jan;240:29–33.
   PubMed Web of Science ®Google Scholar
• Kornberg A, Pricer WE Jr. Enzymatic synthesis of the coenzyme A derivatives of long chain fatty acids. J Biol Chem. 1953 Sep;204:329–343.
   PubMed Web of Science ®Google Scholar
• Tanaka T, Hosaka K, Hoshimaru M, et al. Purification and properties of long-chain acyl-coenzyme-A synthetase from rat liver. Eur J Biochem/FEBS. 1979;98:165–172.
   PubMedGoogle Scholar
• Knights KM. Role of hepatic fatty acid: coenzymeA ligases in the metabolism of xenobiotic carboxylic acids. Clininal Exp Pharmacol Physiol. 1998;25:776–782.
   PubMed Web of Science ®Google Scholar
• Fears R. Lipophilic xenobiotic conjugates: the pharmacological and toxicological consequences of the participation of drugs and other foreign compounds as substrates in lipid biosynthesis. Prog Lipid Res. 1985;24:177–195.
   PubMed Web of Science ®Google Scholar
• Gregus Z, Fekete T, Varga F, et al. Availability of glycine and coenzyme A limits glycine conjugation in vivo. Drug Metab Dispos. 1992;20:234–240.
   PubMed Web of Science ®Google Scholar
• Daugherty M, Polanuyer B, Farrell M, et al. Complete reconstitution of the human coenzyme A biosynthetic pathway via comparative genomics. J Biol Chem. 2002 Jun 14;277:21431–21439.
   PubMed Web of Science ®Google Scholar
• Depeint F, Bruce WR, Shangari N, et al. Mitochondrial function and toxicity: role of the B vitamin family on mitochondrial energy metabolism. Chem Biol Interact. 2006 Oct 27;163:94–112.
   PubMed Web of Science ®Google Scholar
• Kelly GS. Pantethine: A review of its biochemistry and therapeutic applications. Altern Med RevJ Clin Ther. 1997;2:365–376.
   Google Scholar
• Stipanuk MH, Dominy Jr JE, Lee J-I, et al. Mammalian cysteine metabolism: new insights into regulation of cysteine metabolism. J Nutr. 2006;136(6):1652S–1659S.
   Google Scholar
• Fiermonte G, Paradies E, Todisco S, et al. A novel member of solute carrier family 25 (SLC25A42) is a transporter of coenzyme A and adenosine 3ʹ,5ʹ-diphosphate in human mitochondria. J Biol Chem. 2009 Jul 3;284:18152–18159.
   PubMed Web of Science ®Google Scholar
• Houten SM, Wanders RJ. A general introduction to the biochemistry of mitochondrial fatty acid beta-oxidation. J Inherit Metab Dis. 2010 Oct;33:469–477.
   PubMed Web of Science ®Google Scholar
• Darnell M, Weidolf L. Metabolism of xenobiotic carboxylic acids: focus on coenzyme A conjugation, reactivity, and interference with lipid metabolism. Chem Res Toxicol. 2013 Aug 19;26:1139–1155.
   PubMed Web of Science ®Google Scholar
• Kirkby B, Roman N, Kobe B, et al. Functional and structural properties of mammalian acyl-coenzyme A thioesterases. Prog Lipid Res. 2010;49:366–377.
   PubMed Web of Science ®Google Scholar
• Weimar JD, DiRusso CC, Delio R, et al. Functional role of fatty acyl-coenzyme A synthetase in the transmembrane movement and activation of exogenous long-chain fatty acids. Amino acid residues within the ATP/AMP signature motif of Escherichia coli FadD are required for enzyme activity and fatty acid transport. J Biol Chem. 2002 Aug 16;277:29369–29376.
   PubMed Web of Science ®Google Scholar
• Li LO, Klett EL, Coleman RA. Acyl-CoA synthesis, lipid metabolism and lipotoxicity. Biochim Biophys Acta. 2010 Mar;1801:246–251.
   PubMed Web of Science ®Google Scholar
• Brass EP. Overview of coenzyme A metabolism and its role in cellular toxicity. Chem Biol Interact. 1994 Mar;90:203–214.
   PubMed Web of Science ®Google Scholar
• Mitchell GA, Gauthier N, Lesimple A, et al. Hereditary and acquired diseases of acyl-coenzyme A metabolism. Mol Genet Metab. 2008;94:4–15.
   PubMed Web of Science ®Google Scholar
• Ellis JM, Bowman CE, Wolfgang MJ. Metabolic and tissue-specific regulation of acyl-CoA metabolism. Plos One. 2015;10:e0116587.
   PubMed Web of Science ®Google Scholar
• Coleman RA, Lewin TM, Van Horn CG, et al. Do long-chain acyl-CoA synthetases regulate fatty acid entry into synthetic versus degradative pathways? J Nutr. 2002;132:2123–2126.
   PubMed Web of Science ®Google Scholar
• Knights KM, Drogemiller CJ. Xenobiotic-CoA ligases: kinetic and molecular characterization. Curr Drug Metab. 2000;1:49–66.
   PubMed Web of Science ®Google Scholar
• Kasuya F, Igarashi K, Fukui M. Inhibition of a medium chain acyl-CoA synthetase involved in glycine conjugation by carboxylic acids. Biochem Pharmacol. 1996 Nov 22;52:1643–1646.
   PubMed Web of Science ®Google Scholar
• Killenberg PG, Davidson ED, Webster LT Jr. Evidence for a medium-chain fatty acid: coenzyme A ligase (adenosine monophosphate) that activates salicylate. Mol Pharmacol. 1971 May;7:260–268.
   PubMed Web of Science ®Google Scholar
• Schachter D, Taggart JV. Benzoyl coenzyme A and hippurate synthesis. J Biol Chem. 1953;203:925–934.
   PubMed Web of Science ®Google Scholar
• Fujino T, Takei YA, Sone H, et al. Molecular identification and characterization of two medium-chain acyl-CoA synthetases, MACS1 and the Sa gene product. J Biol Chem. 2001 Sep 21;276:35961–35966.
   PubMed Web of Science ®Google Scholar
• Vessey DA, Lau E, Kelley M, et al. Isolation, sequencing, and expression of a cDNA for the HXM-A form of xenobiotic/medium-chain fatty acid: CoAligase from human liver mitochondria. J Biochem Mol Toxicol. 2003;17:1–6.
   PubMed Web of Science ®Google Scholar
• Boomgaarden I, Vock C, Klapper M, et al. Comparative analyses of disease risk genes belonging to the acyl-CoA synthetase medium-chain (ACSM) family in human liver and cell lines. Biochem Genet. 2009;47:739–748.
   PubMed Web of Science ®Google Scholar
• Celis JE, Gromov P, Cabezon T, et al. 15-prostaglandin dehydrogenase expression alone or in combination with ACSM1 defines a subgroup of the apocrine molecular subtype of breast carcinoma. Mol Cell Proteomics MCP. 2008;7:1795–1809.
   PubMed Web of Science ®Google Scholar
• Haketa A, Soma M, Nakayama T, et al. Two medium-chain acyl-coenzyme A synthetase genes, SAH and MACS1, are associated with plasma high-density lipoprotein cholesterol levels, but they are not associated with essential hypertension. J Hypertens. 2004;22:1903–1907.
   PubMed Web of Science ®Google Scholar
• Athanasiu L, Mattingsdal M, Kahler AK, et al. Gene variants associated with schizophrenia in a Norwegian genome-wide study are replicated in a large European cohort. J Psychiatr Res. 2010;44:748–753.
   PubMed Web of Science ®Google Scholar
• Li W, Ji W, Li Z, et al. Genetic association of ACSM1 variation with schizophrenia and major depressive disorder in the Han Chinese population. Am J Med Genet Part B. 2015;168B:144–149.
   PubMed Web of Science ®Google Scholar
• Martin J, Han C, Gordon LA, et al. The sequence and analysis of duplication-rich human chromosome 16. Nature. 2004 Dec 23;432:988–994.
   PubMed Web of Science ®Google Scholar
• Loftus BJ, Kim UJ, Sneddon VP, et al. Genome duplications and other features in 12 Mb of DNA sequence from human chromosome 16p and 16q. Genomics. 1999 Sep 15;60:295–308.
   PubMed Web of Science ®Google Scholar
• Kochan G, Pilka ES, Von Delft F, et al. Structural snapshots for the conformation-dependent catalysis by human medium-chain acyl-coenzyme A synthetase ACSM2A. J Mol Biol. 2009 May 22;388:997–1008.
   PubMed Web of Science ®Google Scholar
• Samani NJ, Whitmore SA, Kaiser MA, et al. Chromosomal assignment of the human SA gene to 16p13.11 and demonstration of its expression in the kidney. Biochem Biophys Res Commun. 1994 Mar 15;199:862–868.
   PubMed Web of Science ®Google Scholar
• Telgmann R, Brand E, Nicaud V, et al. SAH gene variants are associated with obesity-related hypertension in Caucasians: the PEGASE Study. J Hypertens. 2007;25:557–564.
   PubMed Web of Science ®Google Scholar
• Iwai N, Katsuya T, Mannami T, et al. Association between SAH, an acyl-CoA synthetase gene, and hypertriglyceridemia, obesity, and hypertension. Circulation. 2002 Jan 1;105:41–47.
   PubMed Web of Science ®Google Scholar
• Lin MW, Hwu CM, Liou TL, et al. Human SA gene polymorphisms are associated with non-high-density lipoprotein cholesterol in postmenopausal women: a pilot study. Maturitas. 2009 Jan 20;62:66–71.
   PubMed Web of Science ®Google Scholar
• Yates A, Akanni W, Amode MR, et al. Ensembl 2016. Nucleic Acids Res. 2016 Jan 4;44:D710–6.
   PubMed Web of Science ®Google Scholar
• Guzman-Fulgencio M, Jimenez JL, Jimenez-Sousa MA, et al. ACSM4 polymorphisms are associated with rapid AIDS progression in HIV-infected patients. J Acquir Immune Defic Syndr. 2014 Jan 1;65:27–32.
   PubMed Web of Science ®Google Scholar
• Hendrickson SL, Lautenberger JA, Chinn LW, et al. Genetic variants in nuclear-encoded mitochondrial genes influence AIDS progression. Plos One. 2010;5:e12862.
   PubMed Web of Science ®Google Scholar
• Iwai N, Mannami T, Tomoike H, et al. An acyl-CoA synthetase gene family in chromosome 16p12 may contribute to multiple risk factors. Hypertension. 2003;41:1041–1046.
   PubMed Web of Science ®Google Scholar
• Grupe A, Li Y, Rowland C, et al. A scan of chromosome 10 identifies a novel locus showing strong association with late-onset Alzheimer disease. Am J Hum Genet. 2006;78:78–88.
   PubMed Web of Science ®Google Scholar
• Irjala K. Synthesis of p-aminohippuric, hippuric, and salicyluric acids in experimental animals and man. Annales Academiae Scientiarum Fennicae Ser A5, Medica. 1972;154:1–40.
   PubMedGoogle Scholar
• Furst DE, Gupta N, Paulus HE. Salicylate metabolism in twins. Evidence suggesting a generic influence and induction of salicylurate formation. J Clin Invest. 1977;60:32–42.
   PubMed Web of Science ®Google Scholar
• Nandi DL, Lucas SV, Webster LT Jr. Benzoyl-coenzyme A: glycineN-acyltransferase and phenylacetyl-coenzyme A: glycineN-acyltransferase from bovine liver mitochondria. Purification and characterization. JBiolChem. 1979;254:7230–7237.
   PubMed Web of Science ®Google Scholar
• Schachter D, Taggart JV. Glycine N-acylase: purification and properties. JBiolChem. 1954;208:263–275.
   PubMed Web of Science ®Google Scholar
• Tanaka K, Isselbacher KJ. The isolation and identification of N-isovalerylglycine from urine of patients with isovaleric acidemia. JBiolChem. 1967;242:2966–2972.
   PubMed Web of Science ®Google Scholar
• Bartlett K, Gompertz D. The specificity of glycine-N-acylase and acylglycine excretion in the organicacidaemias. BiochemMed. 1974;10:15–23.
   Google Scholar
• Campbell L, Wilson HK, Samuel AM, et al. Interactions of m-xylene and aspirin metabolism in man. Br J Ind Med. 1988;45:127–132.
   PubMedGoogle Scholar
• Cheng TO. The history of aspirin. Tex Heart Inst J. 2007;34:392–393.
   PubMed Web of Science ®Google Scholar
• Levine M, Wong D, Brown DF, et al. Chest pain and arthritis. J Emerg Med. 2005;29:91–95.
   PubMed Web of Science ®Google Scholar
• Lewis HD Jr, Davis JW, Archibald DG, et al. Protective effects of aspirin against acute myocardial infarction and death in men with unstable angina. Results of a veterans administration cooperative study. N Engl J Med. 1983 Aug 18;309:396–403.
   PubMed Web of Science ®Google Scholar
• Singh G, Triadafilopoulos G. Epidemiology of NSAID induced gastrointestinal complications. J Rheumatology Suppl. 1999 Apr;56:18–24.
   PubMedGoogle Scholar
• Bloom BS. Direct medical costs of disease and gastrointestinal side effects during treatment for arthritis. Am J Med. 1988 Feb 22;84:20–24.
   PubMedGoogle Scholar
• Pirmohamed M, James S, Meakin S, et al. Adverse drug reactions as cause of admission to hospital: prospective analysis of 18 820 patients. BMJ (Clin Res Ed). 2004 Jul 3;329:15–19.
   PubMed Web of Science ®Google Scholar
• Ali B, Kaur S. Mammalian tissue acetylsalicylic acid esterase(s): identification, distribution and discrimination from other esterases. J Pharmacol Exp Ther. 1983 Aug;226:589–594.
   PubMed Web of Science ®Google Scholar
• Levy G, Procknal JA. Drug biotransformation interactions in man. I. Mutual inhibition in glucuronide formation of salicylic acid and salicylamide in man. J Pharm Sci. 1968 Aug;57:1330–1335.
   PubMed Web of Science ®Google Scholar
• Lares-Asseff I, Juarez-Olguin H, Flores-Perez J, et al. Pharmacokinetics and metabolic rates of acetyl salicylic acid and its metabolites in an Otomi ethnic group of Mexico. Biol Pharm Bull. 2004;27:706–709.
   PubMed Web of Science ®Google Scholar
• Hutt AJ, Caldwell J, Smith RL. The metabolism of aspirin in man: a population study. Xenobiotica. 1986 Mar;16:239–249.
   PubMed Web of Science ®Google Scholar
• Bigler J, Whitton J, Lampe JW, et al. CYP2C9 and UGT1A6 genotypes modulate the protective effect of aspirin on colon adenoma risk. Cancer Res. 2001 May 1;61:3566–3569.
   PubMed Web of Science ®Google Scholar
• MacDonald CJ, Ciolino HP, Yeh GC. The drug salicylamide is an antagonist of the aryl hydrocarbon receptor that inhibits signal transduction induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Cancer Res. 2004 Jan 1;64:429–434.
   PubMed Web of Science ®Google Scholar
• Patel DK, Notarianni LJ, Bennett PN. Comparative metabolism of high doses of aspirin in man and rat. Xenobiotica. 1990 Aug;20:847–854.
   PubMed Web of Science ®Google Scholar
• Temellini A, Mogavero S, Giulianotti PC, et al. Conjugation of benzoic acid with glycine in human liver and kidney: a study on the interindividual variability. Xenobiotica. 1993;23:1427–1433.
   PubMed Web of Science ®Google Scholar
• Knights KM, Sykes MJ, Miners JO. Amino acid conjugation: contribution to the metabolism and toxicity of xenobiotic carboxylic acids. Expert Opin Drug Metab Toxicol. 2007;3:159–168.
   PubMed Web of Science ®Google Scholar
• Levy G. Pharmacokinetics of salicylate elimination in man. J Pharm Sci. 1965 Jul;54:959–967.
   PubMed Web of Science ®Google Scholar
• Quick AJ. The conjugation of benzoic acid in man. J Biol Chem. 1931;92:65–85.
   Google Scholar
• Nelson E, Hanano M, Levy G. Comparative pharmacokinetics of salicylate elimination in man and rats. J Pharmacol Exp Ther. 1966 Jul;153:159–166.
   PubMed Web of Science ®Google Scholar
• Amsel LP, Levy G. Drug biotransformation interactions in man II: A pharmacokinetic study of the simultaneous conjugation of benzoic and salicylic acids with glycine. J Pharm Sci. 1969;58:321–326.
   PubMed Web of Science ®Google Scholar
• Levy G, Amsel LP. Kinetics of competitive inhibition of salicylic acid conjugation with glycine in man. Biochem Pharmacol. 1966 Aug;15:1033–1038.
   PubMed Web of Science ®Google Scholar
• Levy G, Yaffe SJ. Clinical implications of salicylate-induced liver damage. Am J Dis Child. 1975 Dec;129:1385–1386.
   PubMedGoogle Scholar
• Zimmerman HJ. Effects of aspirin and acetaminophen on the liver. Arch Intern Med. 1981 Feb 23;141:333–342.
   PubMed Web of Science ®Google Scholar
• Beyoglu D, Idle JR. The glycine deportation system and its pharmacological consequences. Pharmacol Ther. 2012 Aug;135:151–167.
   PubMed Web of Science ®Google Scholar
• Miners JO, Grgurinovich N, Whitehead AG, et al. Influence of gender and oral contraceptive steroids on the metabolism of salicylic acid and acetylsalicylic acid. Br J Clin Pharmacol. 1986;22:135–142.
   PubMed Web of Science ®Google Scholar
• Ho PC, Triggs EJ, Bourne DW, et al. The effects of age and sex on the disposition of acetylsalicylic acid and its metabolites. Br J Clin Pharmacol. 1985;19:675–684.
   PubMed Web of Science ®Google Scholar
• Steinberg SJ, Wang SJ, Kim DG, et al. Human very-long-chain acyl-CoA synthetase: cloning, topography, and relevance to branched-chain fatty acid metabolism. Biochem Biophys Res Commun. 1999 Apr 13;257:615–621.
   PubMed Web of Science ®Google Scholar
• Black PN, Zhang Q, Weimar JD, et al. Mutational analysis of a fatty acyl-coenzyme A synthetase signature motif identifies seven amino acid residues that modulate fatty acid substrate specificity. J Biol Chem. 1997 Feb 21;272:4896–4903.
   PubMed Web of Science ®Google Scholar
• Wei X, Walia V, Lin JC, et al. Exome sequencing identifies GRIN2A as frequently mutated in melanoma. Nat Genet. 2011;43:442–446.
   PubMed Web of Science ®Google Scholar
• Agundez JA, Martinez C, Perez-Sala D, et al. Pharmacogenomics in aspirin intolerance. Curr Drug Metab. 2009;10:998–1008.
   PubMed Web of Science ®Google Scholar
• Lindner I, Rubin D, Helwig U, et al. The L513S polymorphism in medium-chain acyl-CoA synthetase 2 (MACS2) is associated with risk factors of the metabolic syndrome in a Caucasian study population. Mol Nutr Food Res. 2006;50:270–274.
   PubMed Web of Science ®Google Scholar
• Badenhorst CP, Erasmus E, Van Der Sluis R, et al. A new perspective on the importance of glycine conjugation in the metabolism of aromatic acids. Drug Metab Rev. 2014;46(3):343–361.
   PubMed Web of Science ®Google Scholar
• Menguy R, Desbaillets L, Masters YF, et al. Evidence for a sex-linked difference in aspirin metabolism. Nature. 1972 Sep 8;239:102–103.
   PubMed Web of Science ®Google Scholar
• Kalow W. Interethnic variation of drug metabolism. Trends Pharmacol Sci. 1991 Mar;12:102–107.
   PubMed Web of Science ®Google Scholar
• Garcia-Martin E, Martinez C, Ladero JM, et al. Interethnic and intraethnic variability of CYP2C8 and CYP2C9 polymorphisms in healthy individuals. Mol Diagn Ther. 2006;10:29–40.
   PubMed Web of Science ®Google Scholar
• Garcia-Martin E. Interethnic and intraethnic variability of NAT2 single nucleotide polymorphisms. Curr Drug Metab. 2008 Jul;9:487–497.
   PubMed Web of Science ®Google Scholar
• Van Der Sluis R, Badenhorst CPS, Van Der Westhuizen FH, et al. Characterisation of the influence of genetic variations on the enzyme activity of a recombinant human glycine N-acyltransferase. Gene. 2013;515:447–453.
   PubMed Web of Science ®Google Scholar