A hydroxyl-bridged dinuclear copper complex having planar structure shows efficient DNA cleavage activity in aqueous solution

Journal of Solution Chemistry

Volumn 38, Issue 10, 2009, Pages 1357-1367

  Shao, Ying ^a   Chen, Jingwen ^b  

^a SHAOXING UNIVERSITY   (China)

^b YANCHENG INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Copper complex; DNA cleavage; Polypyridylamine ligand; Synergistic effect

Indexed keywords

EID: 70349847559     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-009-9457-5     Document Type: Article

References (50)

1. M. Oivanen S. Kuusela H. Lonnberg 1998 Kinetics and mechanisms for the cleavage and isomerization of the phosphodiester bonds of RNA by Brønsted acids and bases Chem. Rev. 98 961 990 10.1021/cr960425x 10.1021/cr960425x 1:CAS:528:DyaK1cXis1yqu7s%3D
2. G. Pratviel J. Bernadou B. Meunier 1995 Carbon-hydrogen bonds of DNA sugar units as targets for chemical nucleases and drugs Angew. Chem. Int. Ed. Engl. 34 746 769 10.1002/anie.199507461 10.1002/anie.199507461 1:CAS:528:DyaK2MXlt1Wqurk%3D
3. P. Molenveld J.F.J. Engbersen D.N. Reinhoudt 2000 Dinuclear metallo-phosphodiesterase models: application of calix[4]arenes as molecular scaffolds Chem. Soc. Rev. 29 75 86 10.1039/a804295k 10.1039/a804295k 1:CAS:528:DC%2BD3cXhsV2jsbY%3D
4. G. Parkin 2004 Synthetic analogues relevant to the structure and function of zinc enzymes Chem. Rev. 104 699 767 10.1021/cr0206263 10.1021/cr0206263 1:CAS:528:DC%2BD2cXmtFalsw%3D%3D
5. Sigman, D.S.: In: Meunier, B. (ed.) DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases, p. 119. Kluwer, Dordrecht (1996)
6. C.-L. Liu M. Wang T.-L. Zhang H.-Z. Sun 2004 DNA hydrolysis promoted by di- and multi-nuclear metal complexes Coord. Chem. Rev. 248 147 168 10.1016/j.cct.2003.11.002 10.1016/j.cct.2003.11.002 1:CAS:528: DC%2BD2cXht1yhtrY%3D
7. Pyle, A.M., Barton, J.K.: In: Lippard, S.J. (ed.) Progress in Inorganic Chemistry, vol. 38, p. 413. Wiley, New York (1990)
8. C.B. Klein K. Frenkel M. Costa 1991 The role of oxidative processes in metal carcinogenesis Chem. Res. Toxicol. 4 592 604 10.1021/tx00024a001 10.1021/tx00024a001 1:CAS:528:DyaK3MXmt1Gms7s%3D
9. J.A. Cowan 2001 Chemical nucleases Curr. Opin. Chem. Biol. 5 634 642 10.1016/S1367-5931(01)00259-9 10.1016/S1367-5931(01)00259-9 1:CAS:528: DC%2BD3MXovVCnsbw%3D (Pubitemid 33153159)
10. Mancin, F., Scrimin, P., Tecilla, P., Tonellato, U.: Artificial metallonucleases. Chem. Commun. (Camb.), 2540-2548 (2005). doi: 10.1039/b418164f
11. 2 species J. Am. Chem. Soc. 128 7003 7008 10.1021/ja061014t 10.1021/ja061014t 1:CAS:528: DC%2BD28Xkt12nt7o%3D (Pubitemid 43830585)
12. 2/sodium ascorbate Inorg. Chem. 42 2992 2998 10.1021/ic020611n 10.1021/ic020611n 1:CAS:528: DC%2BD3sXisVOru7w%3D
13. K.J. Humphreys A.E. Johnson K.D. Karlin S.E. Rokita 2002 Oxidative strand scission of nucleic acids by a multinuclear copper(II) complex J. Biol. Inorg. Chem. 7 835 842 10.1007/s00775-002-0369-8 10.1007/s00775-002-0369-8 1:CAS:528:DC%2BD38Xotlajtr4%3D (Pubitemid 36061237)
14. W.K. Pogozelski T.D. Tullius 1998 Oxidative strand scission of nucleic acids: routes initiated by hydrogen abstraction from the sugar moiety Chem. Rev. 98 1089 1108 10.1021/cr960437i 10.1021/cr960437i 1:CAS:528:DyaK1cXis12gtL8%3D
15. C.J. Burrows J.G. Muller 1998 Oxidative nucleobase modifications leading to strand scission Chem. Rev. 98 1109 1152 10.1021/cr960421s 10.1021/cr960421s 1:CAS:528:DyaK1cXis12htrY%3D
16. An, Y., Tong, M.-L., Ji, L.-N., Mao, Z.-W.: Double-strand DNA cleavage by copper complexes of 2,2′-dipyridyl with electropositive pendants. Dalton Trans. 2066-2071 (2006). doi: 10.1039/b516132k (Pubitemid 43797516)
17. Y.M. Zhao J.H. Zhu W.J. He Z. Yang Y.G. Zhu Y.Z. Li J.F. Zhang Z.J. Guo 2006 Oxidative DNA cleavage promoted by multinuclear copper complexes: Activity dependence on the complex structure Chem. Eur. J. 12 6621 6629 10.1002/chem.200600044 10.1002/chem.200600044 1:CAS:528:DC%2BD28XptlKnsLg%3D (Pubitemid 44375689)
18. K. Selmeczi M. Giorgi G. Speier E. Farkas M. Réglier 2006 Mono-versus binuclear copper(II) complexes in phosphodiester hydrolysis Eur. J. Inorg. Chem. 5 1022 1031 10.1002/ejic.200500595 10.1002/ejic.200500595
19. L.J. Childs J. Malina B.E. Rolfsnes M. Pascu M.L. Prieto M.L. Broome P.M. Rodger E. Sletten V. Moreno A. Rodger M.J. Hannon 2006 A DNA-binding copper(I) metallosupramolecular cylinder that acts as an artificial nuclease Chem. Eur. J. 12 4919 4927 10.1002/chem.200600060 10.1002/chem.200600060 1:CAS:528: DC%2BD28Xmtlyjt7Y%3D (Pubitemid 43954721)
20. Y. Jin M.A. Lewis N.H. Gokhale E.C. Long J.A. Cowan 2007 Influence of stereochemistry and redox potentials on the single- and double-strand DNA cleavage efficiency of Cu(II) center dot and Ni(II) center dot Lys-Gly-His-derived ATCUN metallopeptides J. Am. Chem. Soc. 129 8353 8361 10.1021/ja0705083 10.1021/ja0705083 1:CAS:528:DC%2BD2sXmtFCns7w%3D (Pubitemid 47035146)
21. V.C. da Silveira J.S. Luz C.C. Oliveira I. Graziani M.R. Ciriolo A.M. da Costa Ferreira 2008 Double-strand DNA cleavage induced by oxindole-Schiff base copper(II) complexes with potential antitumor activity J. Inorg. Biochem. 102 1090 1103 10.1016/j.jinorgbio.2007.12.033 10.1016/j.jinorgbio.2007.12.033
22. Z.L. Lu T. Liu A.A. Neverov R.S. Brown 2007 Rapid three-step cleavage of RNA and DNA model systems promoted by a dinuclear Cu(II) complex in methanol. Energetic origins of the catalytic efficacy J. Am. Chem. Soc. 129 11642 11652 10.1021/ja073780l 10.1021/ja073780l 1:CAS:528:DC%2BD2sXpsVekurg%3D (Pubitemid 47555581)
23. J.L. García-Giménez G. Alzuet M. González- Álvarez A. Castiñeiras M. Liu-González J. Borrás 2007 A dinuclear copper(II) complex with adeninate bridge ligands and prominent DNA cleavage activity. Structural and spectroscopic characterization and magnetic properties Inorg. Chem. 46 7178 7188 10.1021/ic700751j 10.1021/ic700751j
24. 2 Inorg. Chem. 47 3719 3727 10.1021/ic702306f 10.1021/ic702306f 1:CAS:528:DC%2BD1cXksFars7c%3D
25. K.J. Humphreys K.D. Karlin S.E. Rokita 2002 Efficient and specific strand scission of DNA by a dinuclear copper complex: Comparative reactivity of complexes with linked tris(2-pyridylmethyl)amine moieties J. Am. Chem. Soc. 124 6009 6019 10.1021/ja020039z 10.1021/ja020039z 1:CAS:528:DC%2BD38Xjt12mtrw%3D (Pubitemid 34552845)
26. K.J. Humphreys K.D. Karlin S.E. Rokita 2002 Targeted strand scission of DNA substrates by a tricopper(II) coordination complex J. Am. Chem. Soc. 124 8055 8066 10.1021/ja012539i 10.1021/ja012539i 1:CAS:528:DC%2BD38XksVKnsLw%3D (Pubitemid 34755522)
27. Kirin, S.I., Happel, C.M., Hrubanova, S., Weyhermüller, T., Klein, C., Metzler-Nolte, N.: Synthesis, structure and comparison of the DNA cleavage ability of metal complexes M(II)L with the N-(2-ethoxyethanol)-bis(2-picolyl) amine ligand L (M = Co, Ni, Cu and Zn). Dalton Trans. 1201-1207 (2004). doi: 10.1039/b313634e
28. C. Tu Y. Shao N. Gan Q. Xu Z. Guo 2004 Oxidative DNA strand scission induced by a trinuclear copper(II) complex Inorg. Chem. 43 4761 4766 10.1021/ic049731g 10.1021/ic049731g 1:CAS:528:DC%2BD2cXlt1eitr4%3D
29. J.W. Chen X.Y. Wang Y. Shao J.H. Zhu Y.G. Zhu Y.Z. Li Q. Xu Z.J. Guo 2007 A trinuclear copper(II) complex of 2,4,6-tris(di-2-pyridylamine)-1,3,5-triazine shows prominent DNA cleavage activity Inorg. Chem. 46 3306 3312 10.1021/ic0614162 10.1021/ic0614162 1:CAS:528:DC%2BD2sXislens7g%3D
30. J. Marmur 1961 A procedure for the isolation of deoxyribonucleic acids from microorganisms J. Mol. Biol. 3 208 218 1:CAS:528:DyaF3MXosl2kuw%3D%3D
31. M.E. Reichmann S.A. Rice C.A. Thomas P. Doty 1954 A further examination of the molecular weight and size of sesoxypentose nucleic acid J. Am. Chem. Soc. 76 3047 3053 10.1021/ja01640a067 10.1021/ja01640a067 1:CAS:528: DyaG2cXmtVKmsg%3D%3D
32. J.A. Yergey 1983 A general approach to calculating isotopic distributions for mass spectrometry Int. J. Mass Spectrom. Ion Phys. 52 337 349 10.1016/0020-7381(83)85053-0 10.1016/0020-7381(83)85053-0 1:CAS:528: DyaL3sXlsFags74%3D
33. Sheldrick, G.M.: SHELXTL, v5 Reference Manual, Siemens Analytical X-Ray Systems. Madison, WI (1996)
34. Wilson, A.J.: International Table for X-Ray Crystallography, Vol. C. Kluwer, Dordrecht (1992). Tables 6.1.1.4 (p. 500) and 4.2.6.8 (p. 219), respectively
35. 5, as an efficient reagent for the oxidative cleavage of DNA Biochemistry 28 7268 7275 10.1021/bi00444a019 10.1021/bi00444a019 1:CAS:528:DyaL1MXltFWktLs%3D
36. L.P. Wu M.E. Keniry B.J. Hathaway 1992 Copper(I) reoxygenation products: the structures of di-μ-hydroxy-bis(di-2-pyridylamine)bis(tetrafluoroborato) dicopper(II) and μ-aqua-di-μ-hydroxy-bis(di-2-pyridylamine)dicopper(II) dichloride dehydrate Acta Crystallogr. C 48 35 40 10.1107/S0108270191008703
37. S. Youngme W. Somjitsripunya K. Chinnakali S. Chantrapromma H.K. Fun 1999 The crystal and molecular structures of di-μ-hydroxy-bis(di-2-pyridylamine) dinitratodicopper(II) and aqua-μ-formato-triformato-bis(di-2-pyridylamine) dicopper(II) monohydrate Polyhedron 18 857 862 10.1016/S0277-5387(98)00370-2 10.1016/S0277-5387(98)00370-2 1:CAS:528:DyaK1MXjt12mtLs%3D
38. S. Youngme G.A. van Albada O. Roubeau C. Pakawatchai N. Chaichit J. Reedijk 2003 Synthesis, crystal structures and magnetism of planar and roof-shaped hydroxo-bridged dinuclear copper(II) compounds with di-2-pyridylamine as a ligand Inorg. Chim. Acta 342 48 58 10.1016/S0020-1693(02) 01069-1 10.1016/S0020-1693(02)01069-1 1:CAS:528:DC%2BD38XpslGiur0%3D
39. M.J. Waring 1965 Complex formation between ethidium bromide and nucleic acids. J. Mol. Biol. J. Mol. Biol. 13 269 282 10.1016/S0022-2836(65)80096-1 1:CAS:528:DyaF2MXks1Cmuro%3D
40. B.C. Baguley M. Le Bret 1984 Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: a possible electron-transfer effect Biochemistry 23 937 943 10.1021/bi00300a022 10.1021/bi00300a022 1:CAS:528:DyaL2cXotFelsA%3D%3D (Pubitemid 14168073)
41. B. Selvakumar V. Rajendiran P. Uma Maheswari H. Stoeckli-Evans M. Palaniandavar 2006 Structures, spectra, and DNA-binding properties of mixed ligand copper(II) complexes of iminodiacetic acid: The novel role of diimine co-ligands on DNA conformation and hydrolytic and oxidative double strand DNA cleavage J. Inorg. Biochem. 100 316 330 10.1016/j.jinorgbio.2005.11.018 10.1016/j.jinorgbio.2005.11.018 1:CAS:528:DC%2BD28XhvVWht7Y%3D (Pubitemid 43276083)
42. C.V. Kumar J.K. Barton N.J. Turro 1985 Photophysics of ruthenium complexes bound to double helical DNA J. Am. Chem. Soc. 107 5518 5523 10.1021/ja00305a032 10.1021/ja00305a032 1:CAS:528:DyaL2MXltF2hsLw%3D
43. A. Mazumder C.L. Sutton D.S. Sigman 1993 1,10-Phenanthroline-linked Escherichia coli Trp repressor as a site-specific scission reagent. Metal ion requirement Inorg. Chem. 32 3516 3520 10.1021/ic00068a022 10.1021/ic00068a022 1:CAS:528:DyaK3sXks1KhurY%3D
44. D.S. Sigman T.W. Bruice A. Mazumder C.L. Sutton 1993 Targeted chemical nucleases Acc. Chem. Res. 26 98 104 10.1021/ar00027a004 10.1021/ar00027a004 1:CAS:528:DyaK3sXht1Sisr4%3D
45. M. Suzuki H. Furutachi H. Ohkawa 2000 Bimetallic dioxygen complexes derived from 'end-off' compartmental ligands Coord. Chem. Rev. 200-202 105 129 10.1016/S0010-8545(00)00323-4 10.1016/S0010-8545(00)00323-4
46. J.R. Morrow O. Iranzo 2004 Synthetic metallonucleases for RNA cleavage Curr. Opin. Chem. Biol. 8 192 200 10.1016/j.cbpa.2004.02.006 10.1016/j.cbpa.2004.02.006 1:CAS:528:DC%2BD2cXivVKrsb4%3D (Pubitemid 38452435)
47. Q. Zhu Y.-X. Lian S. Thyagarajan S.E. Rokita K.D. Karlin N.V. Blough 2008 Hydrogen peroxide and dioxygen activation by dinuclear copper complexes in aqueous solution: hydroxyl radical production initiated by internal electron transfer J. Am. Chem. Soc. 130 6304 6305 10.1021/ja800080z 10.1021/ja800080z 1:CAS:528:DC%2BD1cXkvF2mtbo%3D (Pubitemid 351706074)
48. L.M. Pope K.A. Reich D.R. Graham D.S. Sigman 1982 Products of DNA cleavage by the 1,10-phenanthroline-copper complex. Inhibitors of Escherichia coli DNA polymerase I J. Biol. Chem. 257 12121 12128 1:CAS:528: DyaL38XlvFGju7w%3D
49. N.J. Blackburn F.C. Rhames M. Ralle S. Jaron 2000 Major changes in copper coordination accompany reduction of peptidylglycine monooxygenase: implications for electron transfer and the catalytic mechanism J. Biol. Inorg. Chem. 5 341 353 10.1007/PL00010663 10.1007/PL00010663 1:CAS:528:DC%2BD3cXkvFCksbo%3D
50. Q. Zhu Y. Lian S. Thyagarajan S.E. Rokita K.D. Karlin N.V. Blough 2008 Hydrogen peroxide and dioxygen activation by dinuclear copper complexes in aqueous solution: hydroxyl radical production initiated by internal electron transfer J. Am. Chem. Soc. 130 6304 6305 10.1021/ja800080z 10.1021/ja800080z 1:CAS:528:DC%2BD1cXkvF2mtbo%3D (Pubitemid 351706074)