Electrospray ionisation (ESI) mass spectra obtained for solutions containing curcumin, copper cation and other metal cations, namely Co2+, Ni2+, Mn2+ and Zn2+, have shown an abundant curcumin molecular ion at m/z 368. This ion was not formed for solutions containing curcumin and copper cations or for those containing curcumin and other metal cations. To the best of our knowledge, it is the first example of a system in which copper cations and other metal cations promote formation of organic radical cation under ESI conditions.
GuptaS.C.PrasadS.KimJ.H.PatchvaS.WebbL.J.PriyadarsinicI.K.AggarwalB.B., “Multitargeting by curcumin as revealed by molecular interaction studies”, Nat. Prod. Rep.28, 1937 (2011). doi: https://dx-doi-org.web.bisu.edu.cn/10.1039/C1NP00051A
2.
PadhyeS.ChavanD.PandeyS.DeshpandeJ.SwamyK.V.SarkarF.H., “Perspectives on chemopreventive and therapeutic potential of curcumin analogs in medicinal chemistry”, Mini Rev. Med. Chem.10, 372 (2010). doi: https://dx-doi-org.web.bisu.edu.cn/10.2174/138955710791330891
DarveshA.S.CarrollR.T.BishayeeA.NovotnyN.A.GeldenhuysW.J.Van Der SchyfC.J., “Curcumin and neurodegenerative diseases: A perspective”, Expert Opinion on Investigational Drugs21, 1123 (2012). doi: https://dx-doi-org.web.bisu.edu.cn/10.1517/13543784.2012.693479
7.
ZhangC.BrowneA.ChildD.TanzilR.E., “Curcumin decreases amyloid-peptide levels by attenuating the maturation of amyloid-precursor protein”, J. Biol. Chem.285, 28472 (2010). doi: https://dx-doi-org.web.bisu.edu.cn/10.1074/jbc.M110.133520
ChenS.-Y.ChenY.LiY.P.ChenS.-H.TanJ.-H.OuT.-M.GuL.-Q.HuangZ.-S., “Design, synthesis, and biological evaluation of curcumin analogues as multifunctional agents for the treatment of Alzheimer's disease”, Bioorg. Med. Chem.19, 5596 (2011). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.bmc.2011.07.033
ZebibB.MoulounguiZ.NoirotV., “Stabilization of curcumin by complexation with divalent cations in glycerol/water system”, Bioinorg. Chem. Appl.2010, 1 (2010). doi: https://dx-doi-org.web.bisu.edu.cn/10.1155/2010/292760
14.
DanielS.LimsonJ.-L.DairamA.WatkinsG.M.DayaS., “Through metal binding, curcumin protects against lead- and cadmium-induced lipid peroxidation in rat brain homogenates and against lead-induced tissue damage in rat brain”, J. Inorg. Biochem.98, 266 (2004). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.jinorgbio.2003.10.014
JiangT.WangL.ZhangS.SunP.-C.DingC.F. Chuan-FanChuY.Q.ZhouP., “Interaction of curcumin with Al(III) and its complex structures based on experiments and theoretical calculations”, J. Mol. Struct.1004, 163 (2011). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.molstruc.2011.07.059
ChenZ.ZhuL.SongT.ChenJ.GuoZ., “A novel curcumin assay with the metal ion Cu (II) as a simple probe by resonance light scattering technique”, Spectrochim. Acta A72, 518 (2009). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.saa.2008.10.034
20.
SongY.-M.XuJ.-P.DingL.HouQ.LiuJ.-W.ZhuZ.-L., “Syntheses, characterization and biological activities of rare earth metal complexes with curcumin and 1,10-phenanthroline-5,6-dione”, J. Inorg. Biochem.103, 396 (2009). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.jinorgbio.2008.12.001
MeiX.XuD.XuS.ZhengY.XuS., “Gastroprotective and antidepressant effects of a new zinc(II)–curcumin complex in rodent models of gastric ulcer and depression induced by stresses”, Pharmacol. Biochem. Behav.99, 66 (2011). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.pbb.2011.04.002
23.
ValentiniA.ConfortiF.CrispiniA.De MartinoA.CondelloR.StellitanoC.RotilioG.GhediniM.FedericiG.BernardiniS.PucciD., “Synthesis, oxidant properties, and antitumoral effects of a heteroleptic palladium(II) complex of curcumin on human prostate cancer cells”, J. Med. Chem.52, 484 (2009). doi: https://dx-doi-org.web.bisu.edu.cn/10.1021/jm801276a
24.
BaumL.NgA., “Curcumin interaction with copper and iron suggests one possible mechanism of action in Alzheimer's disease animal models”, J. Alzh. Dis.6, 367 (2004).
25.
ShenL.ZhangH.-Y.JiH.-F., “A theoretical study on Cu(II)-chelating properties of curcumin and its implications for curcumin as a multipotent agent to combat Alzheimer's disease”, J. Mol. Struct. Theochem.757, 199 (2005). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.theochem.2005.05.016
RimolaA.Rodriguez-SantiagoL.SodupeM., “Cation-n interactions and oxidative effects on Cu+ and Cu2+ binding to Phe, Tyr, Trp, and His amino acids in the gas phase. Insights from first-principles calculations”, J. Phys. Chem. B110, 24189 (2006). doi: https://dx-doi-org.web.bisu.edu.cn/10.1021/jp064957l
28.
BarlowC.K.McFadyenW.D.O'HairR.A.J., “Formation of cationic peptide radicals by gas-phase redox reactions with trivalent chromium, manganese, iron, and cobalt complexes”, J. Am. Chem. Soc.127, 6109 (2005). doi: https://dx-doi-org.web.bisu.edu.cn/10.1021/ja043088f
ChuI.K.LaskinJ., “Formation of peptide radical ions through dissociative electron transfer in ternary metal–ligand–peptide complexes”, Eur. J. Mass Spectrom.17, 543 (2011). doi: https://dx-doi-org.web.bisu.edu.cn/10.1255/ejms.1156
32.
BarlowC.K.MoranD.RadomL.McFadyenW.D.O'HairR.A.J., “Metal-mediated formation of gas-phase amino acid radical cations”, J. Phys. Chem. A110, 8304 (2006). doi: https://dx-doi-org.web.bisu.edu.cn/10.1021/jp056471v
33.
ChuI.K.RodriguezC.F.HopkinsonA.C.SiuK.W.M.LauT.-C., “Formation of molecular radical cations of enkephalin derivatives via collision-induced dissociation of electrospray-generated copper(II) complex ions of amines and peptides”, J. Am. Soc. Mass Spectrom.12, 1114 (2001). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/S1044-0305(01)00297-5
34.
WeeS.O'HairR.A.J.McFadyenW.D., “Can radical cations of the constituents of nucleic acids be formed in the gas phase using ternary transition metal complexes?”, Rapid Commun. Mass Spectrom.19, 1797 (2005). doi: https://dx-doi-org.web.bisu.edu.cn/10.1002/rcm.1988
35.
FrańskiR.GierczykB.SchroederG., “Anion p interactions – interactions between benzo-crown ether metal cation complexes and counter ion”, J. Am. Chem. Soc. Mass Spectrom.20, 257 (2009). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.jasms.2008.09.027
36.
OstrowskiW.LinkoK.FrańskiR., “Formation of diclofenac molecular ions as the effect of Cu2+-π interaction under electrospray ionization mass spectrometry conditions”, Eur. J. Mass Spectrom.18, 43 (2012). doi: https://dx-doi-org.web.bisu.edu.cn/10.1255/ejms.1166
37.
SchäferM.DrayßM.SpringerA.ZachariasP.MeerholzK., “Radical cations in electrospray mass spectrometry: Formation of open-shell species, examination of the fragmentation behaviour in ESI-MSn and reaction mechanism studies by detection of transient radical cations”, Eur. J. Org. Chem.5162 (2007). doi: https://dx-doi-org.web.bisu.edu.cn/10.1002/ejoc.200700199
38.
VessecchiR.CrottiA.E. M.GuaratiniT.ColepicoloP.GalembeckS.E.LopesN.P., “Radical ion generation processes of organic compounds in electrospray ionization mass spectrometry”, Mini-Rev. Org. Chem.4, 75 (2007). doi: https://dx-doi-org.web.bisu.edu.cn/10.2174/157019307779815910
39.
HuangM.-T.MaN.LuY.-P.ChangR.L.FisherC.ManchandP.S.NewmarkH.L.ConneyA.H., “Effects of curcumin, demethoxycurcumin, bisdemethoxycurcumin and tetrahydrocurcumin on 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion”, Carcinogenesis16, 2493 (1995).
