Aspirin metabolites are GPR35 agonists

Naunyn-Schmiedeberg's Archives of Pharmacology

Volumn 385, Issue 7, 2012, Pages 729-737

  Deng, Huayun ^a   Fang, Ye ^a  

^a Corning Inc ^*  (United States)

Author keywords

arrestin translocation; 2,3,5 Trihydroxybenzoic acid; Aspirin; Aspirin metabolite; Dynamic mass redistribution; GPR35; Salicyluric acid

Indexed keywords

2,3 DIHYDROXYBENZOIC ACID; 3,5 DIIDOSALICYLIC ACID; 5 BROMOSALICYLURIC ACID; ACETYLSALICYLIC ACID; DRUG METABOLITE; G PROTEIN COUPLED RECEPTOR; G PROTEIN COUPLED RECEPTOR 35; GALLIC ACID; GENTISIC ACID; GENTISURIC ACID; HIPPURIC ACID; SALICYLACYL GLUCURONIDE; SALICYLPHENOL GLUCURONIDE; SALICYLURIC ACID; TRIHYDROXYBENZOIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC 50;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIPYRETICS; ASPIRIN; FIBRINOLYTIC AGENTS; GALLIC ACID; GENTISATES; HIPPURATES; HT29 CELLS; HUMANS; RECEPTORS, G-PROTEIN-COUPLED;

EID: 84862860856     PISSN: 00281298     EISSN: 14321912     Source Type: Journal    
DOI: 10.1007/s00210-012-0752-0     Document Type: Article

References (36)

1. Barth MC, Ahluwalia N, Anderson TJ, Hardy GJ, Sinha S, AlvarezCardona JA, Pruitt IE, Rhee EP, Colvin RA, Gerszten RE (2009) Kynurenic acid triggers firm arrest of leukocytes to vascular endothelium under flow conditions. J Biol Chem 284:19189-19195
2. Chan AT, Arber N, Burn J, Whay-Kuang Chia J, Elwood P, Hull MA, Logan RF, Rothwell PM, Schror K, Baron JA (2012) Aspirin in the chemoprevention of colorectal neoplasia: an overview. Cancer Prev Res 5:164-178
3. Deng H, Fang Y (2012) Anti-inflammatory gallic acid and wedelolactone are G protein-coupled receptor-35 agonists. Pharmacology 89:211-219
4. Deng H, Hu H, Fang Y (2011a) Tyrphostin analogs are GPR35 agonists. FEBS Lett 585:1957-1962
5. Deng H, Hu H, He M, Hu J, Niu W, Ferrie AM, Fang Y (2011b) Discovery of 2-(4-methylfuran-2(5H)-ylidene)malononitrile and thieno[3,2-b]thiophene-2- carboxylic acid derivatives as G protein-coupled receptor-35 (GPR35) agonists. J Med Chem 54:7385-7396
6. Fang Y, Ferrie AM, Fontaine NH, Mauro J, Balakrishnan J (2006) Resonant waveguide grating biosensor for living cell sensing. Biophys J 91:1925-1940 (Pubitemid 44352454)
7. 2-adrenergic receptor drugs. Sci Rep 1:e33
8. Fuster V, Sweeny JM (2011) Aspirin: a historical and contemporary therapeutic overview. Circulation 123:768-778
9. Grootveld M, Halliwell B (1988) 2,3-dihydroxybenzoic acid is a product of human aspirin metabolism. Biochem Pharmacol 37:271-280 (Pubitemid 18039708)
10. Grzelewska-Rzymowska I, Szmidt M, Rozniecki J, Grzegorczyk J (1994) Aspirin-induced neutrophil chemotactic activity (NCA) in patients with aspirin-sensitive urticaria after desensitization to the drug. J Investig Allergol Clin Immunol 4:28-31 (Pubitemid 24123098)
11. Haynes DR, Wright PFA, Gadd SJ, Whitehouse MW, Vernon-Roberts B (1993) Is aspirin a prodrug for antioxidant and cytokinemodulating oxymetabolites? Agents Actions 39:49-58 (Pubitemid 23286456)
12. Heynen-Genel S, Dahl R, Shi S, Sauer M, Hariharan S, Sergienko E, Dad S, Chung TDY, Stonich D, Su Y, Caron M, Zhao P, Abood ME, Barak LS (2010) Antagonists for the orphan receptor GPR35. Probe Reports from the Molecular Libraries Program 2010, NBK5070
13. Hutt AJ, Caldwell J, Smith RL (1986) The metabolism of aspirin in man: a population study. Xenobiotica 16:239-249 (Pubitemid 16164017)
14. Kenakin T, Miller LJ (2010) Seven transmembrane receptors as shapeshifting proteins: the impact of allosteric modulation and functional selectivity on new drug discovery. Pharmacol Rev 62:265-304
15. Kim SH, Jun CD, Suk K, Choi BJ, Lim H, Park S, Lee SH, Shin HY, Kim DK, Shin TY (2006) Gallic acid inhibits histamine release and pro-inflammatory cytokine production in mast cells. Toxicol Sci 91:123-131
16. Kopp E, Ghosh S (1994) Inhibition of NF-κB by sodium salicylate and aspirin. Science 265:956-959
17. Lattin JE, Schroder K, Su AI, Walker JR, Zhang J, Wiltshire T, Saijo K, Glass CK, Hume DA, Kellie S, Sweet MJ (2008) Expression analysis of G protein-coupled receptors in mouse macrophages. Immunome Res 4:5
18. Lorico A, Masturzo P, Villa S, Salmona M, Semeraro N, de Gaetano G (1986) Gentisic acid: an aspirin metabolite with multiple effects on human blood polymorphonuclear leukocytes. Biochem Pharmacol 35:2443-2445 (Pubitemid 16041966)
19. MacKenzie AE, Lappin JE, Taylor DL, Nicklin SA, Milligan G (2011) GPR35 as a novel therapeutic target. Front Endocrin 2:e68
20. Mailman RB (2007) GPCR functional selectivity has therapeutic impact. Trends Pharmacol Sci 8:390-396 (Pubitemid 47087963)
21. Marimuthu S, Chivukula RSV, Alfonso LF, Moridani LF, Moridani M, Hagen FK, Bhat GJ (2011) Aspirin acetylates multiple cellular proteins in HCT-116 colon cancer cells: identification of novel targets. Int J Onco 29:1273-1283
22. Moon H-G, Kim Y-S, Choi J-P, Choi D-S, Yoon CM, Jeon SG, Gho YS, Kim Y-K (2010) Aspirin attenuates the anti-inflammatory effects of theophylline via inhibition of cAMP production in mice with non-eosinophilic asthma. Exp Mol Med 42:47-60
23. Morris T, Stables M, Gilroy DW (2006) New perspectives on aspirin and the endogenous control of acute inflammatory resolution. Sci World J 6:1045-1068
24. Musumba C, Pritchard DM, Pirmohamed M (2009) Cellular and molecular mechanisms of NSAID-induced peptic ulcers. Aliment Pharmacol Ther 30:517-531
25. Parent MA, Bellaire BH, Murphy EA, Roop RM 2nd, Elzer PH, Baldwin CL (2002) Brucella abortus siderophore 2,3-dihydroxybenzoic acid (DHBA) facilitates intracellular survival of the bacteria. Microb Pathog 32:239-48 (Pubitemid 34729218)
26. Pillinger MH, Capodici C, Rosenthal P, Kheterpal N, Hanft S, Philips MR, Weissmann G (1998) Modes of action of aspirin-like drugs: salicylates inhibit Erk activation and integrin-dependent neutrophil adhesion. Proc Natl Acad Sci USA 95:14540-14545 (Pubitemid 28549403)
27. Schaefer LE, Rashkoff IA, Megibow RS (1950) Sodium gentisate in the treatment of acute rheumatic fever. Circulation 11:265-270
28. Schröder R, Janssen N, Schmidt J, Kebig A, Merten N, Hennen S, Müller A, Blättermann S, Mohr-Andrä M, Zahn S, Wenzel J, Smith NJ, Gomeza J, Drewke C, Milligan G, Mohr K, Kostenis E (2010) Deconvolution of complex G protein-coupled receptor signaling in live cells using dynamic mass redistribution measurements. Nat Biotechnol 28:943-949
29. Sweeny JM, Gorog DA, Fuster V (2009) Antiplatelet drug "resistance", Part 1: mechanisms and clinical measurements. Nat Rev Cardiol 6:273-282
30. Szczeklik A, Stevenson DD (2003) Aspirin-induced asthma: advances in pathogenesis, diagnosis, and management. J Allergy Clin Immunol 111:913-21 (Pubitemid 36570845)
31. Vane JR (1971) Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol 231: 232-235
32. Wang J, Simonavicius N, Wu X, Swaminath G, Reagan J, Tian H, Ling L (2006) Kynurenic acid as a ligand for orphan G protein-coupled receptor GPR35. J Biol Chem 281:22021-22028 (Pubitemid 44181906)
33. Xu X-M, Sansores-Garcia L, Chen X-M, Matijevic-Aleksic N, Du M, Wu KK (1999) Suppression of inducible cyclooxygenases-2 gene transcription by aspirin and sodium salicylate. Proc Natl Acad Sci USA 96:5292-5297 (Pubitemid 29214576)
34. Yang Y, Lu JYL, Wu X, Summer S, Whoriskey J, Saris C, Reagan JD (2010) G-protein-coupled receptor 35 is a target of the asthma drugs cromolyn disodium and nedocromil sodium. Pharmacology 86:1-5
35. Yeomans ND (2010) Aspirin: old drug, new uses and challenges. J Gastroenterol Hepatol 26:426-431
36. Yoshida S, Amayasu H, Sakamoto H, Onuma K, Shoji T, Nakagawa T, Tajima T (1998) Cromolyn sodium prevents bronchoconstriction and urinary LTE4 excretion in aspirin-induced asthma. Ann Allergy Asthma Immunol 80:171-176 (Pubitemid 28103151)