The aminosalicylate - folate connection

References

• Allgayer H. 2003. Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 18 Suppl 2(s2):10–14. doi:10.1046/j.1365-2036.18.s2.1.x.
   PubMedGoogle Scholar
• Allgayer H, Sonnenbichler J, Kruis W, Paumgartner G. 1985. Determination of the pK values of 5-aminosalicylic acid and N-acetylaminosalicylic acid and comparison of the pH dependent lipid-water partition coefficients of sulphasalazine and its metabolites. Arzneimittelforschung. 35:1457–1459.
   PubMed Web of Science ®Google Scholar
• Andersen T, Hvid M, Johansen C, Stengaard-Pedersen K, Hetland ML, Hørslev-Petersen K, Junker P, Østergaard M, Deleuran B. 2015. Interleukin-23 in early disease development in rheumatoid arthritis. Scand J Rheumatol. 44(6):438–442. doi:10.3109/03009742.2015.1033007.
   PubMed Web of Science ®Google Scholar
• Ariens EJ, Simonis AM. 1955. The biosynthesis of folic-acid homologues from amino-carboxy-pyridine and other para-aminobenzoic-acid substitutes by E. coli. Schweiz Z Pathol Bakteriol. 18(1):71–80. doi:10.1159/000160761.
   PubMedGoogle Scholar
• Auletta AE, Gery AM, Parmar A, Davis J, Mishra L, Mead JA. 1974. The effect of folate and folate analogs upon dihydrofolate reductase and DNA synthesis in kidneys of normal mice. Life Sci. 14(8):1541–1553. doi:10.1016/0024-3205(74)90165-9.
   PubMed Web of Science ®Google Scholar
• Bailey SW, Ayling JE. 2009. The extremely slow and variable activity of dihydrofolate reductase in human liver and its implications for high folic acid intake. Proc Natl Acad Sci U S A. 106(36):15424–15429. doi:10.1073/pnas.0902072106.
   PubMed Web of Science ®Google Scholar
• Beeken W, Howard D, Bigelow J, Trainer T, Roy M, Thayer W, Wild G. 1997. Controlled trial of 4-ASA in ulcerative colitis. Dig Dis Sci. 42(2):354–358. doi:10.1023/a:1018874120749.
   PubMed Web of Science ®Google Scholar
• Bergman R, Parkes M. 2006. Systematic review: the use of mesalazine in inflammatory bowel disease. Aliment Pharmacol Ther. 23(7):841–855. doi:10.1111/j.1365-2036.2006.02846.x.
   PubMed Web of Science ®Google Scholar
• Bock L, Miller GH, Schaper KJ, Seydel JK. 1974. Sulfonamide structure-activity relationships in a cell-free system. 2. Proof for the formation of a sulfonamide-containing folate analog. J Med Chem. 17(1):23–28. doi:10.1021/jm00247a006.
   PubMed Web of Science ®Google Scholar
• Bryskier A, Grosset J. 2005. Antituberculosis Agents. in A. Bryskier (ed.), Antimicrobial Agents: antibacterials and Antifungals (ASM Press American Society of Microbiology: washington, D.C.), Chapter 43, pp. 1088–1123.
   Google Scholar
• Campieri M, Lanfranchi GA, Bertoni F, Brignola C, Bazzocchi G, Minguzzi MR, Labò G. 1984. A double-blind clinical trial to compare the effects of 4-aminosalicylic acid to 5-aminosalicylic acid in topical treatment of ulcerative colitis. Digestion. 29(4):204–208. doi:10.1159/000199034.
   PubMed Web of Science ®Google Scholar
• Cao H, Gao M, Zhou H, Skolnick J. 2018. The crystal structure of a tetrahydrofolate-bound dihydrofolate reductase reveals the origin of slow product release. Commun Biol. 1(1):226. doi:10.1038/s42003-018-0236-y.
   PubMedGoogle Scholar
• Chakraborty S, Gruber T, Barry CE, 3rd, Boshoff HI, Rhee KY. 2013. Para-aminosalicylic acid acts as an alternative substrate of folate metabolism in Mycobacterium tuberculosis. Science. 339(6115):88–91. doi:10.1126/science.1228980.
   PubMed Web of Science ®Google Scholar
• Cheng YS, Sacchettini JC. 2016. Structural Insights into Mycobacterium tuberculosis Rv2671 Protein as a Dihydrofolate Reductase Functional Analogue Contributing to para-Aminosalicylic Acid Resistance. Biochemistry. 55(7):1107–1119. doi:10.1021/acs.biochem.5b00993.
   PubMed Web of Science ®Google Scholar
• Chitnumsub P, Jaruwat A, Talawanich Y, Noytanom K, Liwnaree B, Poen S, Yuthavong Y. 2020. The structure of Plasmodium falciparum hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase reveals the basis of sulfa resistance. Febs J. 287(15):3273–3297. doi:10.1111/febs.15196.
   PubMed Web of Science ®Google Scholar
• Collins EN, Hewlett JS. 1946. Succinyl sulfathiazole (sulfasuxidine) in the treatment of chronic ulcerative colitis; a report of 55 cases followed two years; its value by retention enema in early cases. Gastroenterology. 7(5):549–554.
   PubMed Web of Science ®Google Scholar
• Czekster CM, Vandemeulebroucke A, Blanchard JS. 2011. Two parallel pathways in the kinetic sequence of the dihydrofolate reductase from Mycobacterium tuberculosis. Biochemistry. 50(32):7045–7056. doi:10.1021/bi200608n.
   PubMed Web of Science ®Google Scholar
• Dahl JU, Gray MJ, Bazopoulou D, Beaufay F, Lempart J, Koenigsknecht MJ, Wang Y, Baker JR, Hasler WL, Young VB, et al. 2017. The anti-inflammatory drug mesalamine targets bacterial polyphosphate accumulation. Nat Microbiol. 2(4):16267. doi:10.1038/nmicrobiol.2016.267.
   PubMed Web of Science ®Google Scholar
• Dai L, Tang Y, Zhou W, Dang Y, Sun Q, Tang Z, Zhu M, Ji G. 2021a. Gut Microbiota and Related Metabolites Were Disturbed in Ulcerative Colitis and Partly Restored After Mesalamine Treatment. Front Pharmacol. 11:620724. doi:10.3389/fphar.2020.620724.
   PubMed Web of Science ®Google Scholar
• Dai ZF, Ma XY, Yang RL, Wang HC, Xu DD, Yang JN, Guo XB, Meng SS, Xu R, Li YX, et al. 2021b. Intestinal flora alterations in patients with ulcerative colitis and their association with inflammation. Exp Ther Med. 22(5):1322. doi:10.3892/etm.2021.10757.
   PubMed Web of Science ®Google Scholar
• Das KM, Dubin R. 1976. Clinical pharmacokinetics of sulphasalazine. Clin Pharmacokinet. 1(6):406–425. doi:10.2165/00003088-197601060-00002.
   PubMedGoogle Scholar
• Das KM, Eastwood MA, McManus JP, Sircus W. 1973. Adverse reactions during salicylazosulfapyridine therapy and the relation with drug metabolism and acetylator phenotype. N Engl J Med. 289(10):491–495. doi:10.1056/NEJM197309062891001.
   PubMed Web of Science ®Google Scholar
• Dawadi S, Kordus SL, Baughn AD, Aldrich CC. 2017. Synthesis and Analysis of Bacterial Folate Metabolism Intermediates and Antifolates. Org Lett. 19(19):5220–5223. doi:10.1021/acs.orglett.7b02487.
   PubMed Web of Science ®Google Scholar
• Deloménie C, Fouix S, Longuemaux S, Brahimi N, Bizet C, Picard B, Denamur E, Dupret JM. 2001. Identification and functional characterization of arylamine N-acetyltransferases in eubacteria: evidence for highly selective acetylation of 5-aminosalicylic acid. J Bacteriol. 183(11):3417–3427. doi:10.1128/JB.183.11.3417-3427.2001.
   PubMed Web of Science ®Google Scholar
• Dennis ML, Lee MD, Harjani JR, Ahmed M, DeBono AJ, Pitcher NP, Wang ZC, Chhabra S, Barlow N, Rahmani R, et al. 2018. 8-Mercaptoguanine Derivatives as Inhibitors of Dihydropteroate Synthase. Chemistry. 24(8):1922–1930. doi:10.1002/chem.201704730.
   PubMed Web of Science ®Google Scholar
• Desai U, Joshi JM. 2018. Utility of para-aminosalicylic acid in drug-resistant tuberculosis: should it be classified as Group D3 or Group C? Lung India. 35(6):488–493. doi:10.4103/lungindia.lungindia_141_18.
   PubMed Web of Science ®Google Scholar
• Dhaneshwar SS. 2014. Colon-specific prodrugs of 4-aminosalicylic acid for inflammatory bowel disease. World J Gastroenterol. 20(13):3564–3571. doi:10.3748/wjg.v20.i13.3564.
   PubMed Web of Science ®Google Scholar
• Dick AP, Grayson MJ, Carpenter RG, Petrie A. 1964. Controlled Trial of Sulphasalazine in the Treatment of Ulcerative Colitis. Gut. 5(5):437–442. doi:10.1136/gut.5.5.437.
   PubMed Web of Science ®Google Scholar
• Dilger K, Trenk D, Rössle M, Cap M, Zähringer A, Wacheck V, Remmler C, Cascorbi I, Kreisel W, Novacek G. 2007. A clinical trial on absorption and N-acetylation of oral and rectal mesalazine. Eur J Clin Invest. 37(7):558–565. doi:10.1111/j.1365-2362.2007.01809.x.
   PubMed Web of Science ®Google Scholar
• Donald PR, Diacon AH. 2015. Para-aminosalicylic acid: the return of an old friend. Lancet Infect Dis. 15(9):1091–1099. doi:10.1016/S1473-3099(15)00263-7.
   PubMed Web of Science ®Google Scholar
• Dubuquoy L, Rousseaux C, Thuru X, Peyrin-Biroulet L, Romano O, Chavatte P, Chamaillard M, Desreumaux P. 2006. PPARgamma as a new therapeutic target in inflammatory bowel diseases. Gut. 55(9):1341–1349. doi:10.1136/gut.2006.093484.
   PubMed Web of Science ®Google Scholar
• Duff MR, Jr., Gabel SA, Pedersen LC, DeRose EF, Krahn JM, Howell EE, London RE. 2020. The Structural Basis for Nonsteroidal Anti-Inflammatory Drug Inhibition of Human Dihydrofolate Reductase. J Med Chem. 63(15):8314–8324. doi:10.1021/acs.jmedchem.0c00546.
   PubMed Web of Science ®Google Scholar
• Efimov AV, Brazhnikov EV. 2003. Relationship between intramolecular hydrogen bonding and solvent accessibility of side-chain donors and acceptors in proteins. FEBS Lett. 554(3):389–393. doi:10.1016/s0014-5793(03)01189-x.
   PubMed Web of Science ®Google Scholar
• Fabre I, Fabre G, Goldman ID. 1984. Polyglutamylation, an important element in methotrexate cytotoxicity and selectivity in tumor versus murine granulocytic progenitor cells in vitro. Cancer Res. 44(8):3190–3195.
   PubMed Web of Science ®Google Scholar
• Fierke CA, Johnson KA, Benkovic SJ. 1987. Construction and evaluation of the kinetic scheme associated with dihydrofolate reductase from Escherichia coli. Biochemistry. 26(13):4085–4092. doi:10.1021/bi00387a052.
   PubMed Web of Science ®Google Scholar
• French DL, Mauger JW. 1993. Evaluation of the physicochemical properties and dissolution characteristics of mesalamine: relevance to controlled intestinal drug delivery. Pharm Res. 10(9):1285–1290. doi:10.1023/a:1018909527659.
   PubMed Web of Science ®Google Scholar
• Ginsberg AL, Davis ND, Nochomovitz LE. 1992. Placebo-controlled trial of ulcerative colitis with oral 4-aminosalicylic acid. Gastroenterology. 102(2):448–452. doi:10.1016/0016-5085(92)90089-h.
   PubMed Web of Science ®Google Scholar
• Green JR, Lobo AJ, Holdsworth CD, Leicester RJ, Gibson JA, Kerr GD, Hodgson HJ, Parkins KJ, Taylor MD. 1998. Balsalazide is more effective and better tolerated than mesalamine in the treatment of acute ulcerative colitis. The Abacus Investigator Group. Gastroenterology. 114(1):15–22. doi:10.1016/s0016-5085(98)70627-4.
   PubMed Web of Science ®Google Scholar
• Hajian B, Scocchera E, Shoen C, Krucinska J, Viswanathan K, G-Dayanandan N, Erlandsen H, Estrada A, Mikušová K, Korduláková J, et al. 2019. Drugging the Folate Pathway in Mycobacterium tuberculosis: the Role of Multi-targeting Agents. Cell Chem Biol. 26(6):781–791 e6. doi:10.1016/j.chembiol.2019.02.013.
   PubMed Web of Science ®Google Scholar
• Ham M, Moss AC. 2012. Mesalamine in the treatment and maintenance of remission of ulcerative colitis. Expert Rev Clin Pharmacol. 5(2):113–123. doi:10.1586/ecp.12.2.
   PubMed Web of Science ®Google Scholar
• Hammerum AM, Sandvang D, Andersen SR, Seyfarth AM, Porsbo LJ, Frimodt-Møller N, Heuer OE. 2006. Detection of sul1, sul2 and sul3 in sulphonamide resistant Escherichia coli isolates obtained from healthy humans, pork and pigs in Denmark. Int J Food Microbiol. 106(2):235–237. doi:10.1016/j.ijfoodmicro.2005.06.023.
   PubMed Web of Science ®Google Scholar
• Hanauer SB, Sandborn WJ, Dallaire C, Archambault A, Yacyshyn B, Yeh C, Smith-Hall N. 2007. Delayed-release oral mesalamine 4.8 g/day (800 mg tablets) compared to 2.4 g/day (400 mg tablets) for the treatment of mildly to moderately active ulcerative colitis: the ASCEND I trial. Can J Gastroenterol. 21(12):827–834. doi:10.1155/2007/862917.
   PubMed Web of Science ®Google Scholar
• Haruki H, Pedersen MG, Gorska KI, Pojer F, Johnsson K. 2013. Tetrahydrobiopterin biosynthesis as an off-target of sulfa drugs. Science. 340(6135):987–991. doi:10.1126/science.1232972.
   PubMed Web of Science ®Google Scholar
• Hotchkiss RD, Evans AH. 1960. Fine Structure of a Genetically Modified Enzyme as Revealed by Relative Affinities for Modified Substrate. Federation Proceedings. 19:912–925.
   PubMedGoogle Scholar
• Iacucci M, de Silva S, Ghosh S. 2010. Mesalazine in inflammatory bowel disease: a trendy topic once again? Can J Gastroenterol. 24(2):127–133. doi:10.1155/2010/586092.
   PubMed Web of Science ®Google Scholar
• Jobanputra P, Amarasena R, Maggs F, Homer D, Bowman S, Rankin E, Filer A, Raza K, Jubb R. 2008. Hepatotoxicity associated with sulfasalazine in inflammatory arthritis: a case series from a local surveillance of serious adverse events. BMC Musculoskelet Disord. 9(1):48. doi:10.1186/1471-2474-9-48.
   PubMedGoogle Scholar
• Kashkooli SB, Rouhani M, Saibil F. 2014. Ultra-high dose of mesalamine to treat steroid-dependent ulcerative colitis. J Crohns Colitis. 8(12):1745–1746. doi:10.1016/j.crohns.2014.08.007.
   PubMed Web of Science ®Google Scholar
• Krishnaswamy K, Madhavan Nair K. 2001. Importance of folate in human nutrition. Br J Nutr. 85 Suppl 2(S2):S115–S24. doi:10.1079/bjn2000303.
   PubMedGoogle Scholar
• Kwon YK, Lu W, Melamud E, Khanam N, Bognar A, Rabinowitz JD. 2008. A domino effect in antifolate drug action in Escherichia coli. Nat Chem Biol. 4(10):602–608. doi:10.1038/nchembio.108.
   PubMed Web of Science ®Google Scholar
• Lee H, Reyes VM, Kraut J. 1996. Crystal structures of Escherichia coli dihydrofolate reductase complexed with 5-formyltetrahydrofolate (folinic acid) in two space groups: evidence for enolization of pteridine O4. Biochemistry. 35(22):7012–7020. doi:10.1021/bi960028g.
   PubMed Web of Science ®Google Scholar
• Lehmann J. 1946. Para-aminosalicylic acid in the treatment of tuberculosis. Lancet. 1(6384):15. doi:10.1016/s0140-6736(46)91185-3.
   PubMedGoogle Scholar
• Lei J, Zhou Y, Xie D, Zhang Y. 2015. Mechanistic insights into a classic wonder drug–aspirin. J Am Chem Soc. 137(1):70–73. doi:10.1021/ja5112964.
   PubMed Web of Science ®Google Scholar
• Li Y, Jiang L, Zhang S, Yin L, Ma L, He D, Shen J. 2012. Methotrexate attenuates the Th17/IL-17 levels in peripheral blood mononuclear cells from healthy individuals and RA patients. Rheumatol Int. 32(8):2415–2422. doi:10.1007/s00296-011-1867-1.
   PubMed Web of Science ®Google Scholar
• Lidin-Janson G. 1977. Sulphonamides in the treatment of acute Escherichia coli infection of the urinary tract in women. Clinical and ecological effects of sulphasomidine and sulphalene. Scand J Infect Dis. 9(3):211–217. doi:10.3109/inf.1977.9.issue-3.11.
   PubMed Web of Science ®Google Scholar
• Liu Y, Grimm M, Dai WT, Hou MC, Xiao ZX, Cao Y. 2020. CB-Dock: a web server for cavity detection-guided protein-ligand blind docking. Acta Pharmacol Sin. 41(1):138–144. doi:10.1038/s41401-019-0228-6.
   PubMed Web of Science ®Google Scholar
• Loveridge EJ, Hroch L, Hughes RL, Williams T, Davies RL, Angelastro A, Luk LY, Maglia G, Allemann RK. 2017. Reduction of Folate by Dihydrofolate Reductase from Thermotoga maritima. Biochemistry. 56(13):1879–1886. doi:10.1021/acs.biochem.6b01268.
   PubMed Web of Science ®Google Scholar
• Marteau P, Halphen M. 1995. [Comparative randomized open study of the efficacy and tolerance of enemas with 2 gr of 4-amino-salicylic acid (4-ASA) and 1 gr of 5-amino-salicylic acid (5-ASA) in distal forms of hemorrhagic rectocolitis]. Gastroenterol Clin Biol. 19:31–35.
   PubMedGoogle Scholar
• Meier FMP, Frerix M, Hermann W, Müller-Ladner U. 2013. Current immunotherapy in rheumatoid arthritis. Immunotherapy. 5(9):955–974. doi:10.2217/imt.13.94.
   PubMed Web of Science ®Google Scholar
• Naganuma M. 2020. Solving the questions regarding 5-aminosalitylate formulation in the treatment of ulcerative colitis. J Gastroenterol. 55(11):1013–1022. doi:10.1007/s00535-020-01713-8.
   PubMed Web of Science ®Google Scholar
• Patanwala I, King MJ, Barrett DA, Rose J, Jackson R, Hudson M, Philo M, Dainty JR, Wright AJ, Finglas PM, et al. 2014. Folic acid handling by the human gut: implications for food fortification and supplementation. Am J Clin Nutr. 100(2):593–599. doi:10.3945/ajcn.113.080507.
   PubMed Web of Science ®Google Scholar
• Perrotta C, Pellegrino P, Moroni E, De Palma C, Cervia D, Danelli P, Clementi E. 2015. Five-aminosalicylic Acid: an update for the reappraisal of an old drug. Gastroenterol Res Pract. 2015:456895–456899. doi:10.1155/2015/456895.
   PubMed Web of Science ®Google Scholar
• Posner BA, Li L, Bethell R, Tsuji T, Benkovic SJ. 1996. Engineering specificity for folate into dihydrofolate reductase from Escherichia coli. Biochemistry. 35(5):1653–1663. doi:10.1021/bi9518095.
   PubMed Web of Science ®Google Scholar
• Poth EJ, Knotts FL. 1941. Succinyl sulfathiazole, a new bacteriostatic agent locally active in the gastrointestinal tract’, Proceedings of the Society for. Exp Biol Med. 48(1):129–130. doi:10.3181/00379727-48-13244P.
   Google Scholar
• Poth EJ, Knotts FL. 1942. Clinical Use of Succinylsulfathiazole. Arch Surg. 44(2):208–222. doi:10.1001/archsurg.1942.01210200024002.
   Google Scholar
• Potshangbam AM, Rathore RS, Nongdam P. 2020. Discovery of sulfone-resistant dihydropteroate synthase (DHPS) as a target enzyme for kaempferol, a natural flavanoid. Heliyon. 6(2):e03378. doi:10.1016/j.heliyon.2020.e03378.
   PubMed Web of Science ®Google Scholar
• Qi J, Virga KG, Das S, Zhao Y, Yun MK, White SW, Lee RE. 2011. Synthesis of bi-substrate state mimics of dihydropteroate synthase as potential inhibitors and molecular probes. Bioorg Med Chem. 19(3):1298–1305. doi:10.1016/j.bmc.2010.12.003.
   PubMed Web of Science ®Google Scholar
• Ragunath K, Williams JG. 2001. Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 15(10):1549–1554. doi:10.1046/j.1365-2036.2001.01062.x.
   PubMed Web of Science ®Google Scholar
• Rengarajan J, Sassetti CM, Naroditskaya V, Sloutsky A, Bloom BR, Rubin EJ. 2004. The folate pathway is a target for resistance to the drug para-aminosalicylic acid (PAS) in mycobacteria. Mol Microbiol. 53(1):275–282. doi:10.1111/j.1365-2958.2004.04120.x.
   PubMed Web of Science ®Google Scholar
• Roland S, Ferone R, Harvey RJ, Styles VL, Morrison RW. 1979. The characteristics and significance of sulfonamides as substrates for Escherichia coli dihydropteroate synthase. J Biol Chem. 254(20):10337–10345. doi:10.1016/S0021-9258(19)86714-5.
   PubMed Web of Science ®Google Scholar
• Rousseaux C, Lefebvre B, Dubuquoy L, Lefebvre P, Romano O, Auwerx J, Metzger D, Wahli W, Desvergne B, Naccari GC, et al. 2005. Intestinal antiinflammatory effect of 5-aminosalicylic acid is dependent on peroxisome proliferator-activated receptor-gamma. J Exp Med. 201(8):1205–1215. doi:10.1084/jem.20041948.
   PubMed Web of Science ®Google Scholar
• Sawaya MR, Kraut J. 1997. Loop and subdomain movements in the mechanism of Escherichia coli dihydrofolate reductase: crystallographic evidence. Biochemistry. 36(3):586–603. doi:10.1021/bi962337c.
   PubMed Web of Science ®Google Scholar
• Schreiber S, Howaldt S, Raedler A. 1994. Oral 4-aminosalicylic acid versus 5-aminosalicylic acid slow release tablets. Double blind, controlled pilot study in the maintenance treatment of Crohn’s ileocolitis. Gut. 35(8):1081–1085. doi:10.1136/gut.35.8.1081.
   PubMed Web of Science ®Google Scholar
• Seydel JK, Butte W. 1977. P-Aminobenzoic acid derivatives. Mode of action and structure-activity relationships in a cell-free system (Escherichia coli). J Med Chem. 20(3):439–447. doi:10.1021/jm00213a023.
   PubMed Web of Science ®Google Scholar
• Seydel JK, Richter M, Wempe E. 1980. Mechanism of action of the folate blocker diaminodiphenylsulfone (dapsone, DDS) studied in E. coli cell-free enzyme extracts in comparison to sulfonamides (SA). Int J Lepr Other Mycobact Dis. 48:18–29.
   PubMedGoogle Scholar
• Staerk Laursen L, Stokholm M, Bukhave K, Rask-Madsen J, Lauritsen K. 1990. Disposition of 5-aminosalicylic acid by olsalazine and three mesalazine preparations in patients with ulcerative colitis: comparison of intraluminal colonic concentrations, serum values, and urinary excretion. Gut. 31(11):1271–1276. doi:10.1136/gut.31.11.1271.
   PubMed Web of Science ®Google Scholar
• Strober W, Fuss I, Mannon P. 2007. The fundamental basis of inflammatory bowel disease. J Clin Invest. 117(3):514–521. doi:10.1172/JCI30587.
   PubMed Web of Science ®Google Scholar
• Tabas I, Glass CK. 2013. Anti-inflammatory therapy in chronic disease: challenges and opportunities. Science. 339(6116):166–172. doi:10.1126/science.1230720.
   PubMed Web of Science ®Google Scholar
• Taffet SL, Das KM. 1983. Sulfasalazine. Adverse effects and desensitization. Dig Dis Sci. 28(9):833–842. doi:10.1007/BF01296907.
   PubMed Web of Science ®Google Scholar
• Van de Graaf B, Hoefnagel AJ, Wepster BM. 1981. Substituent Effects.7. Microscopic Dissociation-Constants of 4-Amino-Benzoic Acid and 4-(Dimethylamino)Benzoic Acid. J Org Chem. 46(4):653–657. doi:10.1021/jo00317a002.
   Web of Science ®Google Scholar
• Vane JR. 1971. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 231(25):232–235. doi:10.1038/newbio231232a0.
   PubMedGoogle Scholar
• Venkitakrishnan RP, Zaborowski E, McElheny D, Benkovic SJ, Dyson HJ, Wright PE. 2004. Conformational changes in the active site loops of dihydrofolate reductase during the catalytic cycle. Biochemistry. 43(51):16046–16055. doi:10.1021/bi048119y.
   PubMed Web of Science ®Google Scholar
• Visentin M, Zhao R, Goldman ID. 2012. The antifolates. Hematol Oncol Clin North Am. 26(3):629–648, ix. doi:10.1016/j.hoc.2012.02.002.
   PubMed Web of Science ®Google Scholar
• Wacker A, Kolm H, Ebert M. 1958. Uber Den Stoffwechsel Der Para-Aminosalicylsaure Und Salicylsaure Bei Enterococcus. Zeitschrift Fur Naturforschung Part B-Chemie Biochemie Biophysik Biologie Und Verwandten Gebiete. 13(3):147–150. doi:10.1515/znb-1958-0302.
   Google Scholar
• Wadworth AN, Fitton A. 1991. Olsalazine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in inflammatory bowel disease. Drugs. 41(4):647–664. doi:10.2165/00003495-199141040-00009.
   PubMed Web of Science ®Google Scholar
• Woods DD. 1940. The relation of p-aminobenzoic acid to the mechanism of the action of sulphanilamide. British Journal of Experimental Pathology. 21:74–90.
   Google Scholar
• Yogavel M, Nettleship JE, Sharma A, Harlos K, Jamwal A, Chaturvedi R, Sharma M, Jain V, Chhibber-Goel J, Sharma A. 2018. Structure of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase-dihydropteroate synthase from Plasmodium vivax sheds light on drug resistance. J Biol Chem. 293(39):14962–14972. doi:10.1074/jbc.RA118.004558.
   PubMed Web of Science ®Google Scholar
• Yun MK, Wu Y, Li Z, Zhao Y, Waddell MB, Ferreira AM, Lee RE, Bashford D, White SW. 2012. Catalysis and sulfa drug resistance in dihydropteroate synthase. Science. 335(6072):1110–1114. doi:10.1126/science.1214641.
   PubMed Web of Science ®Google Scholar
• Zhang Z, Tang H, Chen P, Xie H, Tao Y. 2019. Demystifying the manipulation of host immunity, metabolism, and extraintestinal tumors by the gut microbiome. Signal Transduct Target Ther. 4:41.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Shadrick WR, Wallace MJ, Wu Y, Griffith EC, Qi J, Yun MK, White SW, Lee RE. 2016. Pterin-sulfa conjugates as dihydropteroate synthase inhibitors and antibacterial agents. Bioorg Med Chem Lett. 26(16):3950–3954. doi:10.1016/j.bmcl.2016.07.006.
   PubMed Web of Science ®Google Scholar
• Zheng J, Rubin EJ, Bifani P, Mathys V, Lim V, Au M, Jang J, Nam J, Dick T, Walker JR, et al. 2013. para-Aminosalicylic acid is a prodrug targeting dihydrofolate reductase in Mycobacterium tuberculosis. J Biol Chem. 288(32):23447–23456. doi:10.1074/jbc.M113.475798.
   PubMed Web of Science ®Google Scholar