Dinuclear zinc (II) complexes of macrocyclic polyamine ligands containing an imidazolium bridge: Synthesis, characterization, and their interaction with plasmid DNA

International Journal of Molecular Sciences

Volumn 8, Issue 7, 2007, Pages 606-617

  Huang, Jun ^a   Huang, Qing Dong ^a   Zhang, Ji ^a   Zhou, Li Hong ^a   Li, Qiang N ^a   Li, Kun ^a   Jiang, Ning ^b   Lin, Hong Hui ^b   Wu, Jiang ^a   Yu, Xiao Qi ^a,c  

^a Sichuan University   (China)

^b SICHUAN UNIVERSITY   (China)

^c SICHUAN UNIVERSITY   (China)

Author keywords

1, 4, 7, 10 tetraazacyclododecane (cyclen); DNA protection; Imidazolium; Synthesis; Zinc (II) complexes

Indexed keywords

IMIDAZOLE DERIVATIVE; PLASMID DNA; POLYAMINE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; DNA BINDING; EXPERIMENTAL STUDY; FLUORESCENCE; GEL ELECTROPHORESIS; MOLECULAR INTERACTION; SYNTHESIS;

EID: 34547634694     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/i8070606     Document Type: Article

References (32)

1. Dong, S.M.; Fu, P.P.; Shirsat, R.N.; Hwang, H.M.; Leszczynski, J.;Yu, H.T. UVA light-induced DNA cleavage by isomeric methylbenz[a]anthracenes. Chem. Res. Toxicol. 2002, 15, 400-407.
2. Biggins, J.B.; Prudent, J.R.; Marshall, D.J.; Ruppen, M.; Thorson, J.S. A continuous assay for DNA cleavage: the application of "break lights" to enediynes, iron-dependent agents, and nucleases. Proc. Nalt. Acad. Sci. U.S.A. 2000, 97, 13537-13542.
3. Connelly, J.C.; De Leau, E.S.; Leach, D.R.F. DNA cleavage and degradation by the SbcCD protein complex from Escherichia coli. Nucleic. Acids. Res. 1999, 27, 1039-1046.
4. He, X.X.; Wang, K.; Tan, W.; Liu, B.; Lin, X.; He, C.; Li, D.; Huang, S.; Li, J. Bioconjugated nanoparticles for DNA protection from cleavage. J. Am. Chem. Soc. 2003, 125, 7168-7169.
5. Sohail, A.; Hayes, C.S.; Divvela, P.; Setlow, P. Bhagwat, A.S. Protection of DNA by α/β-type small, acid-soluble proteins from bacillus subtilis spores against cytosine deamination. Biochemistry 2002, 41, 11325-11330.
6. Gopal, V.; Prasad, T.K.; Rao N.M.; Takafuji, M.; Rahman, M.M.; Ihara, H. Synthesis and in vitro evaluation of glutamide-containing cationic lipids for gene delivery. Bioconjugate. Chem. 2006, 17, 1530-1536.
7. Su, M.; Cavallo, S.; Stefanini, S.; Chiancone, E.; Chasteen, N.D. The so-called listeria innocua ferritin is a Dps protein. iron incorporation, detoxification, and DNA protection properties. Biochemistry 2005, 44, 5572-5578.
8. Schwaiger, S.; Cervellati, R.; Seger, C.; Ellmerer, E.P.; About, N.; Renimel, I.; Godenir, C.; Andre, P.; Gafner, F.; Stuppner, H. Leontopodic acid - a novel highly substituted glucaric acid derivative from Edelweiss (Leontopodium alpinum Cass.) and its antioxidative and DNA protecting properties. Tetrahedron 2005, 61, 4621-4630.
9. Leone, A.M.; Weatherly, S.C.; Williams, M.E.; Thorp, H.H.; Murray, R.W. An ionic liquid form of DNA: redox-active molten salts of nucleic acids. J. Am. Chem. Soc. 2001, 123, 218-222.
10. Wang, J.H.; Cheng, D.H.; Chen, X.W.; Du, Z.; Fang, Z.L. Direct extraction of double-stranded DNA into ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate and its quantification. Anal. Chem. 2007, 79, 620-625.
11. Ohno, H; Nakamura, N. Ion conductive characteristics of DNA film containing ionic liquids. J. Electrochem. Soc. 2001, 148, E168-170.
12. Nishimura, N; Normura, Y; Nakamura, N; Ohno, H. DNA strands robed with ionic liquid moiety. Biomaterials 2005, 26, 5558-5563.
13. Jacobsen, F.E.; Lewis, J.A.; Cohen, S.M.A new role for old ligands: discerning chelators for zinc metalloproteinases. J. Am. Chem. Soc. 2006, 128, 3156-3157.
14. Lukes, I.; Kotek, J.; Vojtisek, P.; Hermann, P. Complexes of tetraazacycles bearing methylphosphinic/phosphonic acid pendant arms with copper(II), zinc(II) and lanthanides(III). A comparison with their acetic acid analogues. Coord. Chem. Rev. 2001, 216, 287-312.
15. Bencini, A.; Berni, E.; Bianchi, A.; Giorgi, C.; Valtancoli, B.; Chand, D.K.; Schneider, H. Proton and Cu(II) binding to tren-based tris-macrocycles. Affinity towards nucleic acids and nuclease activity. Dalton.Trans. 2003, 5, 793-800.
16. Benniston, A.C.; Gunning, P.; Peacock, R.D. Synthesis and binding properties of hybrid cyclophane-azamacrocyclic receptors. J. Org. Chem. 2005, 70, 115-123.
17. Mancin, F.; Scrimin, P.; Tecilla, P.; Tonellato, U. Artificial metallonucleases. Chem. Commun. 2005, 20, 2540-2548.
18. 2: comparison with other binuclear transition metal complexes. Inorg. Chem. 2002, 41, 913-922.
19. Deck, K.M.; Tseng, T.A.; Burstyn, J.N. Triisopropyltriazacyclononane copper(II): an efficient phosphodiester hydrolysis catalyst and DNA cleavage agent. Inorg. Chem. 2002, 41, 669-677.
20. Ren, R.; Yang, P.; Zheng, W.J.; Hua, Z.C.A simple copper(II)-L-histidine system for efficient hydrolytic cleavage of DNA. Inorg Chem. 2000, 39, 5454-5463.
21. Xiang, Q.X.; Zhang, J.; Liu, P.Y.; Xia, C.Q.; Zhou, Z.Y.; Xie, R.G.; Yu, X.Q. Dinuclear macrocyclic polyamine zinc(II) complexes: Syntheses, characterization and their interaction with plasmid DNA. J. Inorg. Biochem. 2005, 99, 1661-1669.
22. (a). Xia, C.Q.; Jiang, L.; Zhang, J.; Chen, S.Y.; Lin, H.H.; Tan, X.Y.; Yue, Y.; Yu, X.Q. The conjugates of uracil-cyclen Zn(II) complexes: Synthesis, characterization, and their interaction with plasmid DNA. Bioorg. Med. Chem. 2006, 14, 5756-5764;
23. (b). Li, Q.L.; Huang, J.; Wang, Q.; Jiang, N.; Xia, C.Q.; Lin, H.H.; Wu, J.; Yu, X.Q. Monometallic complexes of 1,4,7,10-tetraazacyclododecane containing an imidazolium side: Synthesis, characterization, and their interaction with plasmid DNA. Bioorg. Med. Chem. 2006, 14, 4151-4157;
24. (c). Wang, X.Y.; Zhang, J.; Li, K.; Jiang, N.; Chen, S.Y.; Lin, H.H.; Huang, Y.; Ma, L.J.; Yu, X.Q. Synthesis and DNA cleavage activities of mononuclear macrocyclic polyamine zinc(II), copper(II), cobalt(II) complexes which are linked with uracil. Bioorg. Med. Chem. 2006, 14, 6745-6751;
25. (d). Fang,Y.G.; Zhang, J.; Chen, S.Y.; Jiang, N.; Lin, H.H.; Zhang, Y.; Yu, X.Q. Chiral multinuclear macrocyclic polyamine complexes: Synthesis, characterization and their interaction with plasmid DNA. Bioorg. Med. Chem. 2007, 15, 696-701;
26. (e). Chen, S.Y.; Huang, Y.; Zhang. G.L.; Cheng, H.; Xia, C.Q.; Ma, L.J.; Yu, H.; Yu, X.Q. Synthesis of a cyclen-functionalized α-amino acid and its incorporation into peptide sequence. Synthesis 2005, 6, 888-892.
27. Peng, W.; Liu, P.Y.; Jiang, N.; Lin, H.H.; Zhang, G.L.; Liu, Y.; Yu, X.Q. Dinuclear macrocyclic polyamine zinc(II) complexes linked with flexible spacers: Synthesis, characterization, and DNA cleavage. Bioorg. Chem. 2005, 33, 374-385.
28. Kostiainen, M.A.; Hardy, J.G.; Smith, D.K. High-affinity multivalent DNA binding by using lowmolecular-weight dendrons. Angew. Chem. Int. Ed. 2005, 44, 2556-2559.
29. Wenner, W. Bis(bromomethyl) compounds. J. Org. Chem. 1952, 17, 523-528.
30. Athey P.S.; Kiefer G.E. A new facile synthesis of 1,4,7,10- tetraazacyclododecane: cyclen. J. Org. Chem. 2002, 67, 4081-4085.
31. Brandes, S.; Gros, C.; Denat, F.; Pullumbi, P.; Guilard, R. New facile and convenient synthesis of bispolyazamacrocycles using Boc protection. Determination of geometric parameters of dinuclear copper(II) complexes using ESR spectroscopy and molecular mechanics calculations. Bull. Soc. Chim. Fr. 1996, 133, 65-73.
32. Kimura, E.; Kikuchi, M.; Kitamura, H.; Koike, T. Selective and efficient recognition of thymidylylthymidine (TpT) by bis(ZnII-cyclen) and thymidylylthymidylyl-thymidine (TpTpT) by tris(ZnII-cyclen) at neutral pH in aqueous solution. Chem. Eur. J. 1999, 11, 3113-3123.