Abstract
1, 8-(3, 6, 9-Trioxaundecane-1, 11-diyldioxy)xanthone (L), and its new Cu (II) complex [Cu·L·(CH3CN)2](ClO4)2 have been synthesized and characterized by 1H NMR, electrospray mass spectra (ESI-MS), elemental analyses, infrared spectra (IR) and X-ray single crystal diffraction. The crystal structure of complex shows that Cu (II) ion is encapsulated within the macrocycle of L. The geometry around copper is a distorted square bipyramid with two acetonitrile molecules at axial position, and four macrocyclic oxygens including the carbonyl oxygen on the equatorial positions. The interaction of Cu (II) complex with calf thymus DNA (ct DNA) has been investigated by spectrophotometric titrations, ethidium bromide (EB) displacement experiments, circular dichroism (CD) spectra and viscosity measurements. Rresults indicate that Cu (II) complex can intercalate into the DNA base pairs by the plane of xanthone ring. Furthermore, the Cu (II) complex was tested against tumor cell lines including ECA109, SGC7901and GLC-82 by MTT (microculture tetrazolium) method. The studies of DNA-binding agree with the effects on the inhibition of tumor cells in vitro.
Similar content being viewed by others
References
Liu CL, Wang M, Zhang T, Sun HZ (2004) DNA hydrolysis promoted by di- and multi-nuclear metal complexes. Coord Chem Rev 248:147–168. doi:10.1016/j.cct.2003.11.002
Metcalfe C, Thomas JA (2003) Kinetically inert transition metal complexes that reversibly bind to DNA. Chem Soc Rev 32:215–224. doi:10.1039/b201945k
Keenea FR, Smitha JA, Collins, JG (2009) Metal complexes as structure-selective binding agents for nucleic acids. Coord Chem Rev (in press). doi:10.1016/j.ccr.2009.01.004
Erkkila KE, Odom DT, Barton JK (1999) Recognition and reaction of metallointercalators with DNA. Chem Rev 99:2777–2796. doi:10.1021/cr9804341
Jiang Q, Xiao N, Shi PF, Zhua YG, Guo ZJ (2007) Design of artificial metallonucleases with oxidative mechanism. Coord Chem Rev 251:1951–1972. doi:10.1016/j.ccr.2007.02.013
Yang P, Guo ML (1999) Interactions of organometallic anticancer agents with nucleotides and DNA. Coord Chem Rev 185–186:189–211. doi:10.1016/S0010-8545(98)00268-9
Carter MT, Rodriguez M, Bard AJ (1989) Voltammetric studies of the interaction of metal chelates with DNA. 2. Tris-chelated complexes of cobalt(III) and iron(II) with 1,10-phenanthroline and 2,2′-bipyridine. J Am Chem Soc 111:8901–8911. doi:10.1021/ja00206a020
Reddy PR, Rao KS, Satyanarayana B (2006) Synthesis and DNA cleavage properties of ternary Cu(II) complexes containing histamine and amino acids. Tetrahedron Lett 47:7311–7315. doi:10.1016/j.tetlet.2006.08.033
Kumar RS, Arunachalam S, Periasamy VS, Preethy CP, Riyasdeen A, Akbarsha MA (2009) Surfactant–cobalt(III) complexes: Synthesis, critical micelle concentration (CMC) determination, DNA binding, antimicrobial and cytotoxicity studies. J Inorg Biochem 103:117–127. doi:10.1016/j.jinorgbio.2008.09.010
Ji LN, Zhou XH, Liu JG (2001) Shape- and enantioselective interaction of Ru(II)/Co(III) polypyridyl complexes with DNA. Coord Chem Rev 216:513–536. doi:10.1016/S0010-8545(01)00338-1
Li YP, Wu YB, Zhao J, Yang PJ (2007) DNA-binding and cleavage studies of novel binuclear copper(II) complex with 1, 1′-dimethyl-2, 2′-biimidazole ligand. Inorg Biochem 101:283–290. doi:10.1016/j.jinorgbio.2006.10.004
Zuber G Jr, Quada JC, Hecht SM (1998) Sequence Selective Cleavage of a DNA Octanucleotide by Chlorinated Bithiazoles and Bleomycins. J Am Chem Soc 120:9368–9369. doi:10.1021/ja981937r
Li VS, Choi D, Wang Z, Jimenez LS, Tang MS, Kohn H (1996) Role of the C-10 Substituent in Mitomycin C-1-DNA Bonding. J Am Chem Soc 118:2326–2331. doi:10.1021/ja953871v
Zhang H, Liu CS, Bu XH, Yang M (2005) Synthesis, crystal structure, cytotoxic activity and DNA-binding properties of the copper (II) and zinc (II) complexes with 1-[3-(2-pyridyl)pyrazol-1-ylmethyl]naphthalene. J Inorg Biochem 99:1119–1125. doi:10.1016/j.jinorgbio.2005.02.005
Zeng YB, Yang N, Liu WS, Tang N (2003) Synthesis, characterization and DNA-binding properties of La(III) complex of chrysin. J Inorg Biochem 97:258–264. doi:10.1016/S0162-0134(03)00313-1
Wang BD, Yang ZY, Wang Q, Cai TK, Crewdson P (2006) Synthesis, characterization, cytotoxic activities, and DNA-binding properties of the La(III) complex with Naringenin Schiff-base. Bioorg Med Chem 14:1880–1888. doi:10.1016/j.bmc.2005.10.031
Zhou J, Wang LF, Wang JY, Tang N (2001) Synthesis, characterization, antioxidative and antitumor activities of solid quercetin rare earth(III) complexes. J Inorg Biochem 83:41–48. doi:10.1016/S0162-0134(00)00128-8
Nakatani K, Nakahata N, Arakawa T, Yasuda H, Ohizumi Y (2002) Inhibition of cyclooxygenase and prostaglandin E2 synthesis by γ-mangostin, a xanthone derivative in mangosteen, in C6 rat glioma cells. Biochem Pharmacol 63:73–79. doi:10.1016/S0006-2952(01)00810-3
Wang LW, Kang JJ, Chen IJ, Teng CM, Lin CN (2002) Antihypertensive and vasorelaxing activities of synthetic xanthone derivatives. Bioorg Med Chem 10:567–572. doi:10.1016/S0968-0896(01)00315-7
Liu Y, Ma L, Chen WH, Wang B, Xu ZL (2007) Synthesis of xanthone derivatives with extended π-systems as α-glucosidase inhibitors: Insight into the probable binding mode. Bioorg Med Chem 15:2810–2814. doi:10.1016/j.bmc.2007.02.030
Jackson WT, Boyd RJ, Froelich LL, Gapinski DM, Mallett BE, Sawyer JS (1993) Design, synthesis, and pharmacological evaluation of potent xanthone dicarboxylic acid leukotriene B4 receptor antagonists. J Med Chem 36:1726–1734. doi:10.1021/jm00064a006
Mills OS, Mooney NJ, Robinson PM, Watt CF, Box BG (1995) Preparation and properties of some crown ethers incorporating stable carbocations. J Chem Soc Perkin Trans 2 697–706. doi:10.1039/p29950000697
CSJ (ed) (1986) Synthetical handbook for inorganic compounds II. Chemical Industry, Beijing
Michael TC, Marisol R, Allen JB (1989) Voltammetric studies of the interaction of metal chelates with DNA. 2. tris-chelated complexes of cobalt(III) and iron(II) with 1,10-phenanthroline and 2,2′-bipyridine. J Am Chem Soc 111:8901–8911. doi:10.1021/ja00206a020
Kumar CV, Asuncion EH (1993) DNA binding studies and site selective fluorescence sensitization of an anthryl probe. J Am Chem Soc 115:8547–8553. doi:10.1021/ja00072a004
Beddoes RS, Cox BG, Mills OS, Mooney NJ, Watt CF, Kirkland D, Martin D (1996) Structures and complexing properties of crown ethers incorporating 1,8-dioxyxanthones. J Chem Soc Perkin Trans 2 2091–2098. doi:10.1039/p29960002091
Nakamato K (1978) Infrared and raman spectra of inorganic and coordination compound, 3rd edn. Wiley-Interscience, New York
Bloomfield VA, Crothers DM, Tinoco I Jr (1974) Phsical chemistry of nucleic acids. Harper & Row, New York
Wolf A, Shimer GH Jr, Meehan T (1987) Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry 26:6392–6396. doi:10.1021/bi00394a013
Zhou CY, Zhao J, Wu YB, Yin CX, Yang P (2007) Synthesis, characterization and studies on DNA-binding of a new Cu(II) complex with N1, N8-bis(l-methyl-4-nitropyrrole-2-carbonyl)triethylenetetramine. J Inorg Biochem 101:10–18. doi:10.1016/j.jinorgbio.2006.07.011
Zhou QH, Yang P (2006) Crystal structure and DNA-binding studies of a new Cu(II) complex involving benzimidazole. Inorg Chim Acta 359:1200–1206. doi:10.1016/j.ica.2005.11.003
Boger DL, Fink BE, Brunette SR, Tse WC, Hedrick MP (2001) A Simple, high-resolution method for establishing DNA binding affinity and sequence selectivity. J Am Chem Soc 123:5878–5891. doi:10.1021/ja010041a
Satyanarayana S, Dabrowiak JC, Chaires JB (1992) Neither Δ- nor Λ-tris(phenanthroline)ruthenium(II) binds to DNA by classical intercalation. Biochemistry 31:9319–9324. doi:10.1021/bi00154a001
Lippard SJ (1978) Platinum complexes: probes of polynucleotide structure and antitumor drugs. Acc Chem Res 11:211–217. doi:10.1021/ar50125a006
Kumar CV, Barton JK, Turro NJ (1985) Photophysics of ruthenium complexes bound to double helical DNA. J Am Chem Soc 107:5518–5523. doi:10.1021/ja00305a032
Eftink MR, Ghiron CA (1981) Fluorescence quenching studies with proteins. Anal Biochem 114:199–227. doi:10.1016/0003-2697(81)90474-7
Ivanov VI, Minchenkova LE, Schyolkina AK, Poletayev AI (1973) Different conformations of double-stranded nucleic acid in solution as revealed by circular dichroism. Biopolymers 12:89–110. doi:10.1002/bip. 1973.360120109
Lincoln P, Tuite E, Nordén B (1997) Short-Circuiting the Molecular Wire: Cooperative Binding of Δ-[Ru(phen)2d ppz]2+ and Δ-[Rh(phi)2bipy]3+ to DNA. J Am Chem Soc 119:1454–1455. doi:10.1021/ja9631965
Nordén B, Tjerneld F (1982) Structure of methylene blue-DNA complexes studied by linear and circular dichroism spectroscopy. Biopolymers 21:1713–1734. doi:10.1002/bip. 360210904
Zou XH, Ye BH, Li H, Liu JG, Xiong Y, Ji LN (1999) Mono- and bi-nuclear ruthenium(II) complexes containing a new asymmetric ligand 3-(pyrazin-2-yl)-as-triazino [5,6-f ]1,10-phenanthroline: synthesis, characterization and DNA-binding properties. J Chem Soc Dalton Trans 1423–1428. doi:10.1039/a900064j
Sigman DS, Mazumder A, Perrin DM (1993) Chemical nucleases. Chem Rev 93:2295–2316. doi:10.1021/cr00022a011
Eriksson M, Leijon M, Hiort C, Norden B, Gradslund A (1994) Binding of Δ- and Λ-[Ru(phen)3]2+ to [d(CGCGATCGCG)]2 Studied by NMR. Biochemistry 33:5031–5040. doi:10.1021/bi00183a005
Xiong Y, He XF, Zou XH, Wu JZ, Chen XM, Ji LN, Li RH, Zhou JY, Yu KB (1999) Interaction of polypyridyl ruthenium(II) complexes containing non-planar ligands with DNA. J Chem Soc Dalton Trans 19–23. doi:10.1039/a806170j
Acknowledgement
We are grateful to the School of Pharmacy, Lanzhou University for their support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shen, R., Wang, P. & Tang, N. Synthesis, Crystal Structure, DNA-binding Properties and Cytotoxic Activity of the Copper (II) Complex Involving Xanthone. J Fluoresc 19, 1073–1082 (2009). https://doi.org/10.1007/s10895-009-0507-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-009-0507-6