Molecular modelling insights into a physiologically favourable approach to eicosanoid biosynthesis inhibition through novel thieno[2,3-b]pyridine derivatives

References

• Dennis EA, Norris PC. Eicosanoid storm in infection and inflammation. Nat Rev Immunol 2015;15:511–23.
   PubMed Web of Science ®Google Scholar
• Elliott JA, Smith HS. Handbook of acute pain management. Boca Raton (FL): CRC Press; 2016.
   Google Scholar
• Funk CD. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001;294:1871–5.
   PubMed Web of Science ®Google Scholar
• Harizi H, Corcuff J-B, Gualde N. Arachidonic-acid-derived eicosanoids: roles in biology and immunopathology. Trends Mol Med 2008;14:461–9.
   PubMed Web of Science ®Google Scholar
• Smith WL, Urade Y, Jakobsson P-J. Enzymes of the cyclooxygenase pathways of prostanoid biosynthesis. Chem Rev 2011;111:5821–65.
   PubMed Web of Science ®Google Scholar
• FitzGerald GA, Patrono C. The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med 2001;345:433–42.
   PubMed Web of Science ®Google Scholar
• Melnikova I. Future of COX2 inhibitors. Nat Rev Drug Discov 2005;4:453–4.
   PubMed Web of Science ®Google Scholar
• Khanna D, Khanna PP, Furst DE. COX-2 controversy: where are we and where do we go from here? Inflammopharma-cology 2005;13:395–402.
   PubMedGoogle Scholar
• Bello AE, Holt RJ. Cardiovascular risk with non-steroidal anti-inflammatory drugs: clinical implications. Drug Saf 2014;37:897–902.
   PubMed Web of Science ®Google Scholar
• Scifinder (Scifinder.cas.org) for “COX-1 Housekeeping” returned 161 references that used this term to date (6 Dec 2017).
   Google Scholar
• Prochazkova M, Dolezal T, Sliva J, Krsiak M. Different Patterns of Spinal cyclooxygenase-1 and cyclooxygenase-2 mRNA expression in inflammatory and postoperative pain. Basic Clin Pharmacol Toxicol 2006;99:173–7.
   PubMed Web of Science ®Google Scholar
• Wallace JL, Chapman K, McKnight W. Limited anti-inflammatory efficacy of cyclo-oxygenase-2 inhibition in carrageenan-airpouch inflammation. Br J Pharmacol 1999;126:1200–4.
   PubMed Web of Science ®Google Scholar
• Martinez-Gonzalez J, Badimon L. Mechanisms underlying the cardiovascular effects of COX-inhibition: benefits and risks. Curr Pharm Des 2007;13:2215–27.
   PubMed Web of Science ®Google Scholar
• Suleyman H, Demircan B, Karagoz Y. Anti-inflammatory and side effects of cyclooxygenase inhibitors. Pharmacol Rep 2007;59:247.
   PubMed Web of Science ®Google Scholar
• Marcouiller P, Pelletier J-P, Guévremont M, et al. Leukotriene and prostaglandin synthesis pathways in osteoarthritic synovial membranes: regulating factors for interleukin 1beta synthesis. J Rheumatol 2005;32:704–12.
   PubMed Web of Science ®Google Scholar
• Rainsford K. Leukotrienes in the pathogenesis of NSAID-induced gastric and intestinal mucosal damage. Inflamm Res 1993;39:C24–26.
   Google Scholar
• Funk CD. Role of leukotrienes revealed by targeted disruption of the 5-lipoxygenase gene. Nature 1994;372:10.
   Web of Science ®Google Scholar
• Luo M, Lee S, Brock T. Leukotriene synthesis by epithelial cells. Histol Histopathol 2003;18:587–95.
   PubMed Web of Science ®Google Scholar
• Bouchette D, Pellegrini MV, Zileuton. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2018.
   Google Scholar
• Weinblatt M, Kremer J, Coblyn J, et al. Zileuton, a 5-lipoxygenase inhibitor in rheumatoid arthritis. J Rheumatol 1992;19:1537–41.
   PubMed Web of Science ®Google Scholar
• Samuelsson B, Dahlen S-E, Lindgren JA, et al. Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science 1987;237:1171–6.
   PubMed Web of Science ®Google Scholar
• Wittenberg RH, Willburger RE, Kleemeyer KS, Peskar BA. In vitro release of prostaglandins and leukotrienes from synovial tissue, cartilage, and bone in degenerative joint diseases. Arthrit Rheumatol 1993;36:1444–50.
   PubMed Web of Science ®Google Scholar
• Sharma RN, Xavier FP, Vasu KK, et al. Synthesis of 4-benzyl-1, 3-thiazole derivatives as potential anti-inflammatory agents: an analogue-based drug design approach. J Enzyme Inhibit Med Chem 2009;24:890–7.
   PubMed Web of Science ®Google Scholar
• Martel-Pelletier J, Lajeunesse D, Reboul P, Pelletier JP. Therapeutic role of dual inhibitors of 5-LOX and COX, selective and non-selective non-steroidal anti-inflammatory drugs. Ann Rheum Dis 2003;62:501–9.
   PubMed Web of Science ®Google Scholar
• Deshmukh R, Goyal A, Sharma P. Licofelone: A dual COX/5-LOX inhibitor attenuates intracerebroventricular streptozotocin-induced cognitive deficit, oxidative stress and neuro-inflammatory cytokines in rats. Alzheimer's Dement 2013;9:P302.
   PubMed Web of Science ®Google Scholar
• Sharma B, Pilania P, Singh P. Modeling of cyclooxygenase-2 and 5-lipooxygenase inhibitory activity of apoptosis-inducing agents potentially useful in prostate cancer chemotherapy: derivatives of diarylpyrazole. J Enzyme Inhibit Med Chem 2009;24:607–15.
   PubMed Web of Science ®Google Scholar
• Kumar G, Patlolla JMR, Madka V, et al. Simultaneous targeting of 5-LOX-COX and ODC block NNK-induced lung adenoma progression to adenocarcinoma in A/J mice. Am J Cancer Res 2016;6:894.
   PubMed Web of Science ®Google Scholar
• Ammar YA, Fayed EA, Bayoumi AH, et al. Design and synthesis of pyridine-amide based compounds appended naproxen moiety as anti-microbial and anti-inflammatory agents. Am J PharmTech Res 2015;5:245–73.
   Google Scholar
• Abouzid KA, Khalil NA, Ahmed EM, et al. Structure-based molecular design, synthesis, and in vivo anti-inflammatory activity of pyridazinone derivatives as nonclassic COX-2 inhibitors. Med Chem Res 2010;19:629–42.
   Web of Science ®Google Scholar
• El-Araby M, Omar A, Hassanein HH, et al. Design, synthesis and in vivo anti-inflammatory activities of 2,4-diaryl-5-4H-imidazolone derivatives. Molecules 2012;17:12262–75.
   PubMed Web of Science ®Google Scholar
• Zeng X-X, Zheng R-L, Zhou T, et al. Novel thienopyridine derivatives as specific anti-hepatocellular carcinoma (HCC) agents: synthesis, preliminary structure–activity relationships, and in vitro biological evaluation. Bioorg Med Chem Lett 2010;20:6282–5.
   PubMed Web of Science ®Google Scholar
• Morwick T, Berry A, Brickwood J, et al. Evolution of the thienopyridine class of inhibitors of IkappaB kinase-beta: part I: hit-to-lead strategies. J Med Chem 2006;49:2898–908.
   PubMed Web of Science ®Google Scholar
• Liu H, Li Y, Wang X-Y, et al. Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation of 6-aryl-3-amino-thieno [2, 3-b] pyridine derivatives as potential anti-inflammatory agents. Bioorg Med Chem Lett 2013;23:2349–52.
   PubMed Web of Science ®Google Scholar
• Zafar A, Pilkington LI, Haverkate NA, et al. Investigation into improving the aqueous solubility of the thieno[2,3-b]pyridine anti-proliferative agents. Molecules 2018;23:E145.
   PubMed Web of Science ®Google Scholar
• Zafar A, Sari S, Leung E, et al. GPCR modulation of thieno[2,3-b]pyridine anti-proliferative agents. Molecules 2017;22:E2254.
   PubMed Web of Science ®Google Scholar
• El-Miligy MM, Hazzaa AA, El-Messmary H, et al. New benzothiophene derivatives as dual COX-1/2 and 5-LOX inhibitors: synthesis, biological evaluation and docking study. Future Med Chem 2017;9:443–68.
   PubMed Web of Science ®Google Scholar
• Yassin F. Synthesis, reactions and biological activity of 2-substituted 3-cyano-4, 6-dimethylpyridine derivatives. Chem Heterocyclic Comp 2009;45:35–41.
   Web of Science ®Google Scholar
• Selinsky BS, Gupta K, Sharkey CT, Loll PJ. Structural analysis of NSAID binding by prostaglandin H2 synthase: time-dependent and time-independent inhibitors elicit identical enzyme conformations. Biochemistry 2001;40:5172–80.
   PubMed Web of Science ®Google Scholar
• El-Sayed M-IK, Amin HA-KA. Mechanism of endothelial cyto-protective and thrombo-resistance effects of sildenafil, vardenafil and tadalafil in male rabbit. Arch Med Sci 2015;11:190.
   PubMed Web of Science ®Google Scholar
• Wisniewski-Rebecca ES, Rocha BA, Wiirzler LA, et al. Synergistic effects of anethole and ibuprofen in acute inflammatory response. Chem Biol Interact. 2015;242:247–53.
   PubMed Web of Science ®Google Scholar
• ACD/Labs, ChemSketch version 12.01, Advanced Chemistry Development, Inc., Toronto, On, Canada, www.acdlabs.com, 2015.
   Google Scholar
• Pilkington LI, Haverkate NA, Van Rensburg M, et al. Synthesis of 3-Amino-2-carboxamide tetrahydropyrrolo [2, 3-b] quinolines. Synlett 2016;27:2811–4.
   Web of Science ®Google Scholar
• Khalifa NM, Abdel-Rahman AA, El Gwaad AAA, Al-Omar MA. Synthesis and characterization of some novel substituted thiazolo [3, 2-a] pyridine and thioxopyrimido [4, 5-d] pyrimidine derivatives. Asian J Chem 2014;26:8202.
   Google Scholar
• Elneairy MA, Gad-Elkareem MA, Abdel-Fattah AM. Thieno [2, 3-b] pyridine-2-carbohydrazide in polyheterocyclic synthesis: the synthesis of pyrido [3′, 2′: 4, 5] thieno [3, 2-d] pyrimidine, pyrido [3′, 2′: 4, 5] thieno [3, 2-d][1, 2, 3] triazine, and pyrazolyl, oxadiazolylthieno [2, 3-b] pyridine derivatives. Phosphorus Sulfur Silicon 2006;181:1451–66.
   Web of Science ®Google Scholar
• Rainsford KD. Ibuprofen: a critical bibliographic review. Boca Raton (FL): CRC Press; 2003.
   Google Scholar
• Borchardt R, Kerns E, Hageman M, et al. Optimizing the” drug-like” properties of leads in drug discovery. Berlin: Springer; 2007.
   Google Scholar
• Gilbert NC, Bartlett SG, Waight MT, et al. The structure of human 5-lipoxygenase. Science 2011;331:217–9.
   PubMed Web of Science ®Google Scholar
• Orlando BJ, Lucido MJ, Malkowski MG. The structure of ibuprofen bound to cyclooxygenase-2. J Struct Biol 2015;189:62–6.
   PubMed Web of Science ®Google Scholar
• Gilbert NC, Rui Z, Neau DB, et al. Conversion of human 5-lipoxygenase to a 15-lipoxygenase by a point mutation to mimic phosphorylation at Serine-663. FASEB J 2012;26:3222–9.
   PubMed Web of Science ®Google Scholar
• Neau DB, Gilbert NC, Bartlett SG, et al. The 1.85 A structure of an 8R-lipoxygenase suggests a general model for lipoxygenase product specificity. Biochemistry 2009;48:7906–15.
   PubMed Web of Science ®Google Scholar
• Jain AN. Surflex: fully automatic flexible molecular docking using a molecular similarity-based search engine. J Med Chem 2003;46:499–511.
   PubMed Web of Science ®Google Scholar
• Kurumbail RG, Stevens AM, Gierse JK, et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 1996;384:644–8.
   PubMed Web of Science ®Google Scholar
• Vecchio AJ, Malkowski MG. The structural basis of endocannabinoid oxygenation by cyclooxygenase-2. J Biol Chem 2011;286:20736–45.
   PubMed Web of Science ®Google Scholar
• Kalgutkar AS, Crews BC, Rowlinson SW, et al. Aspirin-like molecules that covalently inactivate cyclooxygenase-2. Science 1998;280:1268–70.
   PubMed Web of Science ®Google Scholar
• Luong C, Miller A, Barnett J, et al. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat Struct Biol 1996;3:927–33.
   PubMedGoogle Scholar