Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents

Medicinal Chemistry Research

Volumn 22, Issue 3, 2013, Pages 1147-1162

  Bayomi, Said M ^a   El Kashef, Hassan A ^a   El Ashmawy, Mahmoud B ^a   Nasr, Magda N A ^b   El Sherbeny, Magda A ^a   Badria, Farid A ^a   Abou Zeid, Laila A ^b   Ghaly, Mariam A ^a   Abdel Aziz, Naglaa I ^a  

^a MANSOURA UNIVERSITY   (Egypt)

^b University of Mansoura   (Egypt)

Author keywords

Antihaemolytic effect; Antitumor effect; Curcumin; Free radical scavenging; Molecular modelling studies; Synthesis

Indexed keywords

2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); ANTINEOPLASTIC AGENT; ANTIOXIDANT; CURCUMIN; FLUOROURACIL; FREE RADICAL; SCAVENGER;

ALDOL REACTION; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL VIABILITY; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ERYTHROCYTE; HEMOLYSIS; HUMAN; HUMAN CELL; LIPID PEROXIDATION; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION;

EID: 84874106438     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0116-9     Document Type: Article

References (32)

1. Aggarwal BB, Kumar A, Bharti AC (2003) Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res 23:363-398
2. Al-Omary FAM, Abou-zeid LA, Nagi MN, Habib EE, Abdel-Aziz AA-M, El-Azab AS, Abdel-Hamide SG, Al-Omar MA, Al-Obaid AM, El-Subbagh HI (2010) Non-classical antifolates. Part 2. Synthesis, biological evaluation, and molecular modeling study of some new 2,6-substituted quinazolin-4-ones. Bioorg Med Chem 18:2849-2863
3. Anand P, Kunnumakkara AB, Newman RB, Aggarwal BB (2007) Bioavailability of curcumin: problems and promises. Mol Pharm 4:807-818
4. .+ scavenging activity of polypyrrole, polyaniline and poly(3,4-ethylenedioxythiophene). Polym Int 60:69-77
5. Dinkova-Kostova AT, Talalay P (2008) Direct and indirect antioxidant properties of inducers of cytoprotective proteins. Mol Nutr Food Res 52:5128-5138
6. Djordjevic VB (2004) Free radical in cell biology. Int Rev Cytol 237:57-89
7. Du Z, Liu R, Shao W, Mao X, Ma L, Gu L, Huang Z, Cham ASC (2006) α-Glucosidase inhibition of natural curcuminoids and curcumin analogs. Eur J Med Chem 41:213-218
8. El-Sherbeny MA, Abdel-Aziz AA-M, Ahmed MA (2010) Synthesis and antitumor evaluation of novel diarylsulfonylurea derivatives: molecular modeling applications. Eur J Med Chem 45:689-697
9. Fadda AA, Badria FA, El-Attar KM (2010) Synthesis and evaluation of curcumin analogues as cytotoxic agents. Med Chem Res 19:413-430
10. Geol A, Kunnumakkara AB, Aggarwal BB (2008) Curcumin as "curecumin": from kitchen to clinic. Biochem Pharm 75:787-809
11. Guthrie N, Carroll KK (1998) Inhibition of mammary cancer by citrus flavonoids. In: Manthey JA, Buslig BS (eds) Flavonoids in the living system. Plenum, New York, p 227
12. Halgren TAJ (1996) Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J Comput Chem 17:490-519
13. Kálai T, Kuppusamy ML, Balog M, Selvendiran K, Rivera BK, Kuppusamy P, Hideg K (2011) Synthesis of N-substituted 3,5-bis(arylidene)-4- piperidones with high antitumor and antioxidant activity. J Med Chem 54:5414-5421
14. Kuang ZH, Wang PF, Zheng RL, Liu Z, Liu Y (1994) Making vitamin C liposoluble enhances its protective effect against radical induced hemolysis of erythrocytes. Chem Phys Lipids 91:95-97
15. Labute P, Williams C, Feher M, Sourial E, Schmidt JM (2001) Flexible alignment of small molecules. J Med Chem 44:1483-1490
16. Lee K, Ab Aziz FH, Syahida A, Abas F, Shaari K, Israf DA, Lajis NH (2009) Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and antityrosinase activities. Eur J Med Chem 44:3195-3200
17. Liang G, Shao L, Wang Y, Zhao C, Chu Y, Xiao J, Zhao Y, Li X, Yang S (2009) Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents. Bioorg Med Chem 17:2623-2631
18. Ligeret H, Barthelemy S, Zini R, Tillement J, Labidalle S, Morin D (2004) Effects of curcumin and curcumin derivatives on mitochondrial permeability transition pore. Free Radic Biol Med 36:919-929
19. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Del Rev 23:3-25
20. Lissi E, Modak B, Torres R, Escobar J, Urzua A (1999) Total antioxidant potential of resinous exudates from Heliotropium species, and a comparison of ABTS and DPPH methods. Free Radic Res 30:471-477
21. Memon VP, Sudheer AR (2007) Antioxidant and anti-inflammatory properties of curcumin. In: Aggarwal BB, Surh Y, Shishodia S (eds) The molecular targets and therapeutic uses of curcumin in health and disease. Springer, New York, pp 106-107
22. MOE 2007.9 of Chemical Computing Group. Inc.
23. Oprea TI, Davis AM, Teague SJ, Leeson PD (2001) Is there a difference between leads and drugs? A historical perspective. J Chem Inf Comput Sci 41:1308-1315
24. Roughley PJ, Whiting DA (1973) Experiments in the biosynthesis of curcumin. J Chem Soc Perkin Trans 1(20):2379-2388
25. Shang Y, Jin X, Shang X, Tang J, Liu G, Dai F, Qian Y, Fan G, Liu Q, Zhou B (2010) Antioxidant capacity of curcumin-directed analogues: structure-activity relationship and influence of microenvironment. Food Chem 119:1435-1442
26. Sharma RA, Gescher AJ, Verma WP (2005) Curcumin: the story so far. Eur J Cancer 41:1958-1968
27. Singh N, Pandey J, Yadav A, Chaturvedi V, Bhatnagar S, Gaikwad AN, Sinha SK, Kumar A, Shukla PK, Tripathi RT (2009) A facile synthesis of α,α'-(EE)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations. Eur J Med Chem 44:1705-1709
28. Venkatesan P, Rao MN (2000) Structure-activity relationships for the inhibition of lipid peroxidation and the scavenging of free radicals by synthetic symmetrical curcumin analogues. J Pharm Pharmacol 52:1123-1128
29. Wang L, Sheng J, Tian H, Han J, Fan Z, Qian C (2004) A convenient synthesis of α,α'-bis(substituted benzylidene)cycloalkanones catalyzed by Yb(OTf)3 under solvent-free conditions. Synthesis 18:3060-3064
30. Weber WM, Hunsaker LA, Abcouwer SF, Deck LM, Vander Jagt DL (2005) Anti-oxidant activities of curcumin and related enones. Bioorg Med Chem 13:3811-3820
31. Weber WM, Hunsaker LA, Gonzales AM, Heynekamp JJ, Orlando RA, Deck LM, Vander Jagt DL (2006) TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin. Biochem Pharmacol 72:928-940
32. Zhou J (2003) One-step synthesis of pyridine and 4H-pyran derivatives from bisarylidenecyclohexanone and malononitrile under microwave irradiation. Syn Commun 33:99-103