Metallkomplexe von Farbstoffen. VIII Übergangsmetallkomplexe des Curcumins und seiner Derivate

Abstract

Die zweizähnigen Monoanionen von Curcumin[CU, (1,7‐bis(4‐hydroxy‐3‐methoxyphenyl)‐hepta‐1,6‐dien‐3,5‐dion)], Diacetylcurcumin[DACU, (1,7‐bis(4‐acetyl‐3‐methoxyphenyl)‐hepta‐1,6‐dien‐3,5‐dion)], Dihydroxycurcumin[DHCU, (1,7‐bis(4‐hydroxiphenyl)‐hepta‐1,6‐dien‐3,5‐dion)], Dimethylcurcumin[DMCU, (1,7‐bis(3,4‐dimethoxyphenyl)‐hepta‐1,6‐dien‐3,5‐dion)] und Trimethylcurcumin[TMCU, (1,7‐bis(3,4‐dimethoxyphenyl)‐4‐methylhepta‐1,6‐dien‐3,5‐dion] bilden mit den chloroverbrückten Komplexen [(R3P)MCl2]2 (MPd, Pt; RPhenyl, n‐Butyl, Ethyl, Tolyl), [η5‐C5Me5MCl2]2, MRh, Ir, [(η6‐p‐Cymol)RuCl2]2, [(η3‐C3H5)PdCl]2, Di‐μ‐chlorobis[N‐(diphenylmethylen)‐glycinethylester‐(C, N)]‐dipalladium(II) sowie [(η5‐C5Me5)Co(CO)I2] Monochelat‐Komplexe. Die Struktur von [(η6‐p‐Cymol)(Cl)Ru(DMCU)] wurde röntgenographisch bestimmt. Die Bischelate der Form (DMCU)2M mit MCu, Ni, (CU)2Pd sowie ein Trischelat (CU)3Fe konnten erhalten werden. Kationische Bipyridinkupfer(II)‐Komplexe mit CU, CHCU und DMCU bilden sich durch Umsetzung der Farbstoffliganden mit Kupfer(II)‐acetat, 2,2′‐Bipyridin und Ammoniumtetrafluoroborat. Eine Rotverschiebung der längstwelligen Absorptionsbande im UV/VIS Spektrum der Komplexe gegenüber den freien 1,3‐Diketonen wird beobachtet.

Syntheses, characterization and biological activities of rare earth metal complexes with curcumin and 1,10-phenanthroline-5,6-dione

“…Orvig et al have reported vanadyl, gallium and indium complexes of curcumin for medicinal applications [7], corroborating the importance of curcumin's free phenolic OH groups for scavenging oxidants and correlated with reduced cytotoxic potential. And curcumin with other transition metals ions Ni 2+ , Zn 2+ , Pd 2+ , Fe 3+ can form strong chelates [8][9][10]. However, studies on Biological activities of the rare earth metal complexes with Curcumin and 1,10-phenanthroline-5,6-dione have been rarely reported.…”

Synthesis and Characterization of some Ternary Metal Complexes of Curcumin with 1,10-phenanthroline and their Anticancer Applications

“…[16,17]. Also, curcumin with other transition metals ions Ni(II), Zn(II), Pd(II), Fe(III), Cr(III), Mn(II), can form strong chelates [10,[18][19][20]. Curcumin complexes with Zn(II), Cu(II), Mg(II) and Se(II) are synthesized by mechanical mixture, without any conventional organic solvents and found to form complexes with 1:1 for Zn(II), Cu(II) and Mg(II) complexes and 1:2 for Se(II) complex [21].…”

Curcumin and cyclopalladated complexes: A recipe for bifunctional biomaterials

“…Recently the study of the mechanism of their chemiopreventive activity has attracted increasing attention [13][14][15][16][17]. Although b-diketones are known to form complexes with almost every metal, few metal complexes of curcumin and its derivatives have been reported [18], most of which are based on bis M(curc) 2 , M@VO, Cu(II), Ni(II) and Co(II) or tris M(curc) 3 M@Ga(III) and In(III), for evaluation as anticancer agents in vitro and in vivo [19][20][21][22][23].…”