Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents

Molecules

Volumn 19, Issue 10, 2014, Pages 16058-16081

  Leong, Sze Wei ^a   Mohd Faudzi, Siti Munirah ^a   Abas, Faridah ^a   Mohd Aluwi, Mohd Fadhlizil Fasihi ^b   Rullah, Kamal ^b   Wai, Lam Kok ^b   Abdul Bahari, Mohd Nazri ^a   Ahmad, Syahida ^a   Tham, Chau Ling ^a   Shaari, Khozirah ^a   Lajis, Nordin H ^c  

^a UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^b UNIVERSITI KEBANGSAAN MALAYSIA   (Malaysia)

^c TAIBAH UNIVERSITY   (Saudi Arabia)

Author keywords

Anti inflammatory; Curcumin; Diarylpentanoid; Pharmacophore; RAW 264.7; SAR

Indexed keywords

ANTIINFLAMMATORY AGENT; CURCUMIN; GAMMA INTERFERON; LIPOPOLYSACCHARIDE; NITRIC OXIDE;

ANIMAL; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECTS; DRUG STABILITY; HYDROGEN BOND; IC50; IMMUNOLOGY; MACROPHAGE; METABOLISM; MOUSE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CELL LINE; CURCUMIN; DRUG STABILITY; HYDROGEN BONDING; INHIBITORY CONCENTRATION 50; INTERFERON-GAMMA; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITRIC OXIDE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84911922324     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules191016058     Document Type: Article

References (36)

1. Masuda, T.; Jitoe, A.; Isobe, J.; Nakatani, N.; Yonemoria, S. Anti-oxidative and anti-inflammatory curcumin-related phenolics from rhizomes of Curcuma domestica. Phytochemistry 1993, 32, 1157-1160.
2. Lee, K.H.; Ab Aziz, F.H.; Syahida, A.; Abas, F.; Shaari, K.; Israf, D.A.; Lajis, N.H. Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities. Eur. J. Med. Chem. 2009, 44, 3195-3200.
3. Lam, K.W.; Tham, C.L.; Liew, C.Y.; Syahida, A.; Rahman, M.B.A.; Israf, D.A.; Lajis, N.H. Synthesis and evaluation of DPPH and anti-inflammatory activities of 2, 6-bisbenzylidenecyclohexanone and pyrazoline derivatives. Med. Chem. Res. 2012, 21, 333-344.
4. Tham, C.L.; Liew, C.Y.; Lam, K.W.; Mohamad, A.S.; Kim, M.K.; Cheah, Y.K.; Zakaria, Z.A.; Sulaiman, M.R.; Lajis, N.H.; Israf, D. A synthetic curcuminoid derivative inhibits nitric oxide and proinflammatory cytokine synthesis. Eur. J. Pharmacol. 2010, 628, 247-254.
5. Tham, C.L.; Lam, K.W.; Rajajendram, R.; Cheah, Y.K.; Sulaiman, M.R.; Lajis, N.H.; Kim, M.K.; Israf, D.A. The effects of a synthetic curcuminoid analogue, 2, 6-bis-(4-hydroxyl-3-methoxybenzylidine)cyclohexanone on proinflammatory signaling pathways and CLP-induced lethal sepsis in mice. Eur. J. Pharmacol. 2011, 652, 136-144.
6. Ming-Tatt, L.; Khalivulla, S.I.; Akhtar, M.N.; Mohamad, A.S.; Perimal, E.K.; Khalid, M.H.; Akira, A.; Lajis, N.; Israf, D.A.; Sulaiman, M.R. Antinociceptive activity of a synthetic curcuminoid analogue, 2, 6-bis-(4-hydroxy-3-methoxybenzylidene)cyclohexanone, on nociception-induced models in mice. Basic Clin. Pharmacol. Toxicol. 2012, 110, 275-282.
7. Katsori, A.M.; Chatzopoulou, M.; Dimas, K.; Kontogiorgis, C.; Patsilinakos, A.; Trangas, T.; Hadjipavlou-Litina, D. Curcumin analogues as possible anti-proliferative & anti-inflammatory agents. Eur. J. Med. Chem. 2011, 46, 2722-2735.
8. Adams, B.K.; Ferstl, E.M.; Davis, M.C.; Herold, M.; Kurtkaya, S.; Camalier, R.F.; Hollingshead, M.G.; Kaur, G.; Sausville, E.A.; Rickles, F.R.; et al. Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents. Bioorg. Med. Chem. 2004, 12, 3871-3883.
9. Hosoya, T.; Nakata, A.; Yamasaki, F.; Abas, F.; Shaari, K.; Lajis, N.H.; Morita, H. Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors. J. Nat. Med. 2012, 66, 166-176.
10. Lee, K.H.; Abas, F.; Alitheen, N.B.; Shaari, K.; Lajis, N.H.; Ahmad, S. A curcumin derivative, 2, 6-bis(2, 5-dimethoxybenzylidene)-cyclohexanone (BDMC33) attenuates prostaglandin E2 synthesis via selective suppression of cyclooxygenase-2 in IFN-gamma/LPS-stimulated macrophages. Molecules 2011, 16, 9728-9738.
11. Lee, Y.Z.; Ming-Tatt, L.; Lajis, N.H.; Sulaiman, M.R.; Israf, D.A.; Tham, C.L. Development and validation of a bioanalytical method for quantification of 2, 6-bis-(4-hydroxy-3-methoxybenzylidene)-cyclohexanone (BHMC) in rat plasma. Molecules 2012, 17, 14555-14564.
12. Korhonen, R.; Lahti, A.; Kankaanranta, H.; Moilanen, E. Nitric oxide production and signaling in inflammation. Curr. Drug Targets Inflamm. Allergy 2005, 4, 471-479.
13. Scheller, J.; Chalaris, A.; Schmidt-Arras, D.; Rose-John, S. The pro-and anti-inflammatory properties of the cytokine interleukin-6. Biochim. Biophys. Acta 2011, 1813, 878-888.
14. Miller, S.B. Prostaglandins in health and disease: An overview. Semin. Arthritis Rheum. 2006, 36, 37-49.
15. Rouhani, F.N.; Meitin, C.A.; Kaler, M.; Miskinis-Hilligoss, D.; Stylianou, M.; Levine, S.J. Effect of tumor necrosis factor antagonism on allergen-mediated asthmatic airway inflammation. Respir. Med. 2005, 99, 1175-1182.
16. Galley, H.F.; Webster, N.R. The immuno-inflammatory cascade. Br. J. Anaesth. 1996, 77, 11-16.
17. Birkedal-Hansen, H. Role of cytokines and inflammatory mediators in tissue destruction. J. Periodontal Res. 1993, 28, 500-510.
18. Ridnour, L.A.; Thomas, D.D.; Switzer, C.; Flores-Santana, W.; Isenberg, J.S.; Ambs, S.; Roberts, D.D.; Wink, D.A. Molecular mechanisms for discrete nitric oxide levels in cancer. Nitric Oxide 2008, 19, 73-76.
19. Naseem, K.M. The role of nitric oxide in cardiovascular diseases. Mol. Asp. Med. 2005, 26, 33-65.
20. Fitzpatrick, A.M.; Brown, L.A.; Holguin, F.; Teague, W.G. Levels of nitric oxide oxidation products are increased in the epithelial lining fluid of children with persistent asthma. J. Allergy Clin. Immun. 2009, 124, 990-996.
21. Hensley, K.; Tabatabaie, T.; Stewart, C.A.; Pye, Q.; Floyd, R.A. Nitric oxide and derived species as toxic agents in stroke, AIDS dementia, and chronic neurodegenerative disorders. Chem. Res. Toxicol. 1997, 10, 527-532.
22. Sellebjerg, F.; Giovannoni, G.; Hand, A.; Madsen, H.O.; Jensen, C.V.; Garred, P. Cerebrospinal fluid levels of nitric oxide metabolites predict response to methylprednisolone treatment in multiple sclerosis and optic neuritis. J. Neuroimmunol. 2002, 125, 198-203.
23. Marnett, L.J. Inflammation and cancer: Chemical approaches to mechanisms, imaging and treatment. J. Org. Chem. 2012, 77, 5224-5238.
24. Simpson, C.J.; Fitzhenry, M.J.; Stamford, N.P.J. Preparation of vinylphenols from 2-and 4-hydroxybenzaldehydes. Tetrahedron Lett. 2005, 46, 6893-6896.
25. Gomes, A.; Neuwirth, O.; Freitas, M.; Couto, D.; Ribeiro, D.; Figueiredo, A.G.; Silva, A.M.; Seixas, R.S.; Pinto, D.C.; Tome, A.C.; et al. Synthesis and antioxidant properties of new chromone derivatives. Bioorg. Med. Chem. 2009, 17, 7218-7226.
26. Khatib, S.; Nerya, O.; Musa, R.; Shmuel, M.; Tamir, S.; Vaya, J. Chalcones as potent tyrosinase inhibitors: The importance of a 2, 4-substituted resorcinol moiety. Bioorg. Med. Chem. 2005, 13, 433-441.
27. Wu, J.H.; Tung, Y.T.; Chien, S.C.; Wang, S.Y.; Kuo, Y.H.; Shyur, L.F.; Chang, S.T. Effect of phytocompounds from the heartwood of Acacia confusa on inflammatory mediator production. J. Agric. Food Chem. 2008, 56, 1567-1573.
28. Li, J.; Liao, C.R.; Wei, J.Q.; Chen, L.X.; Zhao, F.; Qiu, F. Diarylheptanoids from Curcuma kwangsiensis and their inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages. Bioorg. Med. Chem. Lett. 2011, 21, 5363-5369.
29. Shin, S.Y.; Shin, M.C.; Shin, J.S.; Lee, K.T.; Lee, Y.S. Synthesis of aurones and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells. Bioorg. Med. Chem. Lett. 2011, 21, 4520-4523.
30. Wang, L.; Tu, Y.C.; Lian, T.W.; Hung, J.T.; Yen, J.H.; Wu, M.J. Distinctive antioxidant and antiinflammatory effects of flavonols. J. Agric. Food Chem. 2006, 54, 9798-9804.
31. Chiang, Y.M.; Lo, C.P.; Chen, Y.P.; Wang, S.Y.; Yang, N.S.; Kuo, Y.H.; Shyur, L.F. Ethyl caffeate suppresses NF-kappaB activation and its downstream inflammatory mediators, iNOS, COX-2 and PGE2 in vitro or in mouse skin. Br. J. Pharmacol. 2005, 146, 352-363.
32. Sivakumar, P.M.; Geetha Babu, S.K.; Mukesh, D. QSAR studies on chalcones and flavonoids as anti-tuberculosis agents using genetic function approximation (GFA) method. Chem. Pharm. Bull. 2007, 55, 44-49.
33. Wallach, I. Pharmacophore inference and its application to computational drug discovery. Drug Dev. Res. 2011, 72, 17-25.
34. Zhu, Y.; Li, H.F.; Lu, S.; Zheng, Y.X.; Wu, Z.; Tang, W.F.; Zhou, X.; Lu, T. Investigation on the isoform selectivity of histone deacetylase inhibitors using chemical feature based pharmacophore and docking approaches. Eur. J. Med. Chem. 2010, 45, 1777-1791.
35. Vyas, V.K.; Ghate, M.; Goel, A. Pharmacophore modeling, virtual screening, docking and in silico ADMET analysis of protein kinase B (PKB beta) inhibitors. J. Mol. Graph. Model. 2013, 42, 17-25.
36. Dong, X.; Zhou, X.; Jing, H.; Chen, J.; Liu, T.; Yang, B.; He, Q.; Hu, Y. Pharmacophore identification, virtual screening and biological evaluation of prenylated flavonoids derivatives as PKB/Akt1 inhibitors. Eur. J. Med. Chem. 2011, 46, 5949-5458.