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Article: Double-strand DNA cleavage by copper complexes of 2,2′-dipyridyl with guanidinium/ammonium pendants

TitleDouble-strand DNA cleavage by copper complexes of 2,2′-dipyridyl with guanidinium/ammonium pendants
Authors
Issue Date2008
PublisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/dalton
Citation
Dalton Transactions, 2008 n. 24, p. 3207-3214 How to Cite?
AbstractTwo ligands with guanidinium/ammonium groups were synthesized and their copper complexes, [Cu(L 1)Cl 2](ClO 4) 2•H 2O (1) and [Cu(L 2)Cl 2](ClO 4) 2 (2) (L 1 = 5,5′-di[1-(guanidyl)methyl]-2,2′-bipyridyl cation and L 2 = 5,5′-di[1-(amino)methyl]-2,2′-bipyridyl cation), were prepared to serve as nuclease mimics. X-Ray analysis revealed that Cu(ii) ion in 1 has a planar square CuN 2Cl 2-configuration. The shortest distance between the nitrogen of guanidinium and copper atoms is 6.5408(5) Å, which is coincident with that of adjacent phosphodiesters in DNA (ca. 6 Å). In the absence of reducing agent, supercoiled plasmid DNA cleavage by the complexes were performed and their hydrolytic mechanisms were demonstrated with radical scavengers and T4 ligase. The pseudo-Michaelis-Menten kinetic parameters (k cat, K M) were calculated to be 4.42 h -1, 7.46 × 10 -5 M for 1, and 4.21 h -1, 1.07 × 10 -4 M for 2, respectively. The result shows that their cleavage efficiency is about 10-fold higher than the simple analogue [Cu(bipy)Cl 2] (3) (0.50 h -1, 3.5 × 10 -4 M). The pH dependence of DNA cleavage by 1 and its hydroxide species in solution indicates that mononuclear [Cu(L 1)(OH)(H 2O)] 3+ ion is the active species. Highly effective DNA cleavage ability of 1 is attributed to the effective cooperation of the metal moiety and two guanidinium pendants with the phosphodiester backbone of nucleic acid. © The Royal Society of Chemistry 2008.
Persistent Identifierhttp://hdl.handle.net/10722/168307
ISSN
2015 Impact Factor: 4.177
2015 SCImago Journal Rankings: 1.404
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorHe, Jen_US
dc.contributor.authorHu, Pen_US
dc.contributor.authorWang, YJen_US
dc.contributor.authorTong, MLen_US
dc.contributor.authorSun, Hen_US
dc.contributor.authorMao, ZWen_US
dc.contributor.authorJi, LNen_US
dc.date.accessioned2012-10-08T03:17:19Z-
dc.date.available2012-10-08T03:17:19Z-
dc.date.issued2008en_US
dc.identifier.citationDalton Transactions, 2008 n. 24, p. 3207-3214en_US
dc.identifier.issn1477-9226en_US
dc.identifier.urihttp://hdl.handle.net/10722/168307-
dc.description.abstractTwo ligands with guanidinium/ammonium groups were synthesized and their copper complexes, [Cu(L 1)Cl 2](ClO 4) 2•H 2O (1) and [Cu(L 2)Cl 2](ClO 4) 2 (2) (L 1 = 5,5′-di[1-(guanidyl)methyl]-2,2′-bipyridyl cation and L 2 = 5,5′-di[1-(amino)methyl]-2,2′-bipyridyl cation), were prepared to serve as nuclease mimics. X-Ray analysis revealed that Cu(ii) ion in 1 has a planar square CuN 2Cl 2-configuration. The shortest distance between the nitrogen of guanidinium and copper atoms is 6.5408(5) Å, which is coincident with that of adjacent phosphodiesters in DNA (ca. 6 Å). In the absence of reducing agent, supercoiled plasmid DNA cleavage by the complexes were performed and their hydrolytic mechanisms were demonstrated with radical scavengers and T4 ligase. The pseudo-Michaelis-Menten kinetic parameters (k cat, K M) were calculated to be 4.42 h -1, 7.46 × 10 -5 M for 1, and 4.21 h -1, 1.07 × 10 -4 M for 2, respectively. The result shows that their cleavage efficiency is about 10-fold higher than the simple analogue [Cu(bipy)Cl 2] (3) (0.50 h -1, 3.5 × 10 -4 M). The pH dependence of DNA cleavage by 1 and its hydroxide species in solution indicates that mononuclear [Cu(L 1)(OH)(H 2O)] 3+ ion is the active species. Highly effective DNA cleavage ability of 1 is attributed to the effective cooperation of the metal moiety and two guanidinium pendants with the phosphodiester backbone of nucleic acid. © The Royal Society of Chemistry 2008.en_US
dc.languageengen_US
dc.publisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/daltonen_US
dc.relation.ispartofDalton Transactionsen_US
dc.subject.mesh2,2'-Dipyridyl - Chemistry - Metabolismen_US
dc.subject.meshCopper - Chemistry - Metabolismen_US
dc.subject.meshCrystallography, X-Rayen_US
dc.subject.meshDna - Chemistry - Metabolismen_US
dc.subject.meshDna Cleavageen_US
dc.subject.meshGuanidine - Chemistry - Metabolismen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshPotentiometryen_US
dc.subject.meshQuaternary Ammonium Compounds - Chemistry - Metabolismen_US
dc.titleDouble-strand DNA cleavage by copper complexes of 2,2′-dipyridyl with guanidinium/ammonium pendantsen_US
dc.typeArticleen_US
dc.identifier.emailSun, H:hsun@hkucc.hku.hken_US
dc.identifier.authoritySun, H=rp00777en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1039/b801549jen_US
dc.identifier.pmid18688419-
dc.identifier.scopuseid_2-s2.0-44949241350en_US
dc.identifier.hkuros146179-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-44949241350&selection=ref&src=s&origin=recordpageen_US
dc.identifier.issue24en_US
dc.identifier.spage3207en_US
dc.identifier.epage3214en_US
dc.identifier.isiWOS:000256597100011-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridHe, J=35310626100en_US
dc.identifier.scopusauthoridHu, P=34872289200en_US
dc.identifier.scopusauthoridWang, YJ=7601499567en_US
dc.identifier.scopusauthoridTong, ML=7202033871en_US
dc.identifier.scopusauthoridSun, H=7404827446en_US
dc.identifier.scopusauthoridMao, ZW=23989068600en_US
dc.identifier.scopusauthoridJi, LN=20734334600en_US

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