Synthesis, characterization, and antitumor activity of binuclear curcumin-metal(II) hydroxo complexes

Medicinal Chemistry Research

Volumn 23, Issue 4, 2014, Pages 1683-1689

  Khalil, Mutasim I ^a   Al Zahem, Aisha M ^a   Qunaibit, Maha M ^a  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Antitumor; Binuclear curcumin metal(II) complexes; Cadmium(II); Copper; Curcumin; Oxolating precursors; Zinc

Indexed keywords

ANTINEOPLASTIC METAL COMPLEX; CADMIUM DERIVATIVE; COPPER COMPLEX; CURCUMIN; NITRATE; ZINC COMPLEX;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CELL STRAIN HCT116; CELL STRAIN HEPG2; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; FEMALE; HELA CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; ULTRAVIOLET SPECTROSCOPY;

EID: 84899449018     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0727-9     Document Type: Article

References (31)

1. Adams BK, Ferstl EM, Davis MC, Herlod M, Kurtkaya S, Camalier RF, Hollingshead MG, Kaur G, Sausville EA, Rickles FR (2004) Synthesis and biological evaluation of novel curcumin analogs anticancer and anti-angiogenesis agents. Bioorg Med Chem 12:3871-3883 (Pubitemid 38798249)
2. Barclay LRC, Cross C, Vinqvist MR, Mukai K, Goto H, Hashimoto NB (2000) On the antioxidant mechanism of curcumin: classical methods are needed to determine antioxidant mechanism and activity. Can Org Lett 2:2841-2843
3. Barik A, Mishra B, Kunwar A, Kadam RM, Shen L, Dutta S, Padhye S, Satpati AK, ZangH Yu, Priydarsini KI (2007) Comparative study of copper(II) -curcumin complexes as superoxide dismutase mimics and free radical scavengers. Euro J. Med. Chem. 42:431-439 (Pubitemid 46517793)
4. Bong PH (2000) Development of curcuminoids loaded poly(butyl) cyanoacrylate nanoparticles: physiochemical and stability study. Bull Korean Chem Soc 21:81-86
5. Cerivello JV, Bulut U (2006) Indian tumeric and its use in Cationic phtopolymerization. Macromol Symp 240:1-11
6. Diaz A, Pogni R, Cao R, Basosi R (1998) EPR Characterization of a series of mono- and bis-thiosemicarbazone copper(II) complexes. Inorg Chim Acta 275-276:552-556 (Pubitemid 128351384)
7. Dutta S, Murugkar A, Gandhe N, Padhye S (2001) Enhanced antioxidant activities of curcumin metal conjugates. Met-Based Drugs 8(4):183-188 (Pubitemid 34168348)
8. Eybl V, Kotyzova D, Leseticky L, Bludovska M, Koutensky J (2006) The influence of curcumin and manganese complex of curcumin on cadmium-induced oxidative damage and trace elements status in tissues of mice. J App Toxicol 26:207-212 (Pubitemid 43773881)
9. Gafner S, Lee SK, Cuendent M, Barthelemy S, Vergens L, Labidalle S, Mehta RG, Boone CW, Pezzuto JMM (2004) Biologic evaluation of curcumin and structural derivatives in cancer chemoprevention model system. Phytochem 65:2849-2859 (Pubitemid 40292116)
10. Hahm ER, Gho YS, Park S, Park C, Kim KW, Yang CH (2004) Synthetic curcumin analogs inhibit activator protein-1 transcription and tumor-induced angiogenesis. Biochem Biophys Res Comm 321:337-344 (Pubitemid 39055751)
11. Ishida J, Ohtsu H, Tchibana Y, Nakanishi Y, Bastow KF, Nagai M, Wang HK, Itokawa H, Lee KH (2002) Antitumor agents part 214: synthesis and evaluation of curcumin analogues as cytotoxic agents. Bioorg Med Chem 10:3481-3487
12. Javanovic SV, Steenken S, Boone CW, Trinoga M, Kaskey RB (2001) How curcumin works preferentially with water soluble antioxidants. J Am Chem Soc 123:3064-3068 (Pubitemid 32879574)
13. Krishnankutty K, John VD (2003) Synthesi, charactrization, and antitumour studies of metal chelates of some synthetic curcuminoids. Synth React Inorg Metr-Org Chem. 33:343-358 (Pubitemid 36315018)
14. Kunchandy E, Rao MNA (1989) Effect of curcumin on hydroxyl radicalgeneration through Fenton reaction. Int J Pharm 57:173-176 (Pubitemid 20011842)
15. Kunchandy E, Rao MNA (1990) Oxygen radical scavenging activity of curcumin. Int J Pharm 58:237-240 (Pubitemid 20079739)
16. Liu RH (2004) Potential synergy of phytochemicals in cancer prevention: mechanism of action. J Nutr 134:3479S-3485S
17. Masauda T, Hidaka K, Shinohara A, Mackawa T, Takeda Y, Yamaguchi H (1999) Chemical studies on antioxidant mechanism of curcuminoid: analysis of radical reaction products from curcumin. J Agric Food Chem 47:71-77 (Pubitemid 29179626)
18. Mingxiong T, Jinchan Z, Yingming P, Zhenfeng C, Hong L, Huagang L, Hengshan W (2009) Synthesis, cytotoxic activity, and DNA binding properties of copper (II) complexes with hesperetin, naringenin, and apigenin. Bioinorg Chem Appl 2009:1-9
19. Mutasim IK, Aisha MA, Maha HA (2013) Synthesis, characterization, mossbauer parameters, and antitumor activity of Fe(II) curcumin complex. Bioinorg Chem Appl 2013:982423
20. Sharma KK, Chandra S, Basu DK (1987) Synthesis and antiarithmatic study of a new orally active diferuloyl methane (curcumin) gold complex. Inorg Chim Acta 135(1):47-48
21. Sheng X, Lu XM, Chen YT et al (2007) "Synthesis, DNA-binding, cleavage, and cytotoxic activityof new 1,7-dioxo-4,10-diazacyclododecane artificial receptors containing bis-guanidinoethyl or diaminoethyl double side arms. Chemistry 13:9703-9712 (Pubitemid 350197530)
22. Tajbakhsh S, Mohammadi K, Deilami I, Zandi K, Failadvand M, Ramadani E, Asayesh G (2008) Antibacterial activity of indium curcumin and indium diacetylcurcumin. Afr J Biotech 7(21):3822-3835
23. Thompson KH, Orvig C (2003) Boon and bane of metal ions in medicine. Science 300:936-939 (Pubitemid 36548871)
24. Thompson KH, Böhmerle K, Polishchuck E, Martins C, Toleikis P, Tse J, Yuen V, McNeill JH, Orvig C (2004) Complementary inhibition of synoviocyte, smooth muscle cell or mouse lymphoma cell profileration by a vandyl curcumin complex compared curcumin alone. J Inorg Biochem 98:2063-2070 (Pubitemid 39489898)
25. Tonnesen HH (1989) Studies on curcumin and curcumonoids. XIII: catalytic effect of curcumin on the preoxidation of linoleic acid by 15-lipoxygenese. Int J Pharm 50:67-69
26. Tonnesen HH, Greenhill JV (1992) Study on curcumin and curcuminoids XXII: curcumin as a reducing agent and radical scavenger. Int J Pharm 87:79-87
27. Vajragupta O, Boonchoong P, Watanabe H, Tohda M, Kummasud N, Somanont Y (2003) Manganese complexes of curcumin and its derivatives: evaluation for the radical scavenging ability and neuroprotective activity. Free Radical Biol Med 35:1632-1644 (Pubitemid 37532914)
28. Valentini A, Conforti F, Crispini A, De Martino R, Cardello R, Stellitano C, Rotilio G, Ghedini M, Federici G, Bernadini S, Pucci D (2009) Synthesis, oxidant properties, and antitumoral effects of a heteroleptic palladium(II) complex of curcumin on human prostate cancer cells. J Med Chem 52:484-491
29. Weijun N, Edward HW, Gary RW, Kin-Chung L, Arnold LR (1999) Two novel zinc(II) complexes of the 1,8-cross-bridged cyclam ligand and their structures. Inorg Chem Comm 2:358-360
30. Xiao Z, Xiao YD, Feng J, Golbraikh A, Tropsha A, Lee KHJ (2002) Antitumor agents. 213. Modeling of epipodophyllotoxin derivatives using variable selection k nearest neighbor QSAR method. J Med Chem 45:2294
31. Zhang S, Tu C, Wang X et al (2004) Novel cytotoxic copper(II) complexes of 8 aminoquinoline derivatives: crystal structure and different reactivity towards glutathione. Inorg Euro J Chem 98:4028-4035