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- W2069384792 endingPage "6966" @default.
- W2069384792 startingPage "6966" @default.
- W2069384792 abstract "Ternary copper(II) complexes [Cu(L-trp)(B)(H2O)](NO3) (1–3) and [Cu(L-phe)(B)(H2O)](NO3) (4–6) of L-tryptophan (L-trp) and L-phenylalanine (L-phe) having phenanthroline bases (B), viz. 1,10-phenanthroline (phen, 1 and 4), dipyrido[3,2-d:2′,3′-f]quinoxaline (dpq, 2 and 5) and dipyrido[3,2-a:2′,3′-c]phenazine (dppz, 3 and 6), were prepared and characterized by physico-chemical techniques. Complexes 3 and 6 were structurally characterized by X-ray crystallography and show the presence of a square pyramidal (4 + 1) CuN3O2 coordination geometry in which the N,O-donor amino acid (L-trp or L-phe) and N,N-donor phenanthroline base bind at the equatorial plane with an aqua ligand coordinated at the elongated axial site. Complex 3 shows significant distortion from the square pyramidal geometry and a strong intramolecular π–π stacking interaction between the pendant indole ring of L-trp and the planar dppz aromatic moiety. All the complexes display good binding propensity to the calf thymus DNA giving an order: 3,6 (dppz) > 2,5 (dpq) > 1,4 (phen). The binding constant (Kb) values are in the range of 2.1 × 104–1.1 × 106 mol−1 with the binding site size (s) values of 0.17–0.63. The phen and dpq complexes are minor groove binders while the dppz analogues bind at the DNA major groove. Theoretical DNA docking studies on 2 and 3 show the close proximity of two photosensitizers, viz. the indole moiety of L-trp and the quinoxaline/phenazine of the dpq/dppz bases, to the complementary DNA strands. Complexes 2 and 3 show oxidative DNA double strand breaks (dsb) of supercoiled (SC) DNA forming a significant quantity of linear DNA along with the nicked circular (NC) form on photoexposure to UV-A light of 365 nm and red light of 647.1 nm (Ar–Kr laser). Complexes 1, 5 and 6 show only single strand breaks (ssb) forming NC DNA. The red light induced DNA cleavage involves metal-assisted photosensitization of L-trp and dpq/dppz base resulting in the formation of a reactive singlet oxygen (1O2) species." @default.
- W2069384792 created "2016-06-24" @default.
- W2069384792 creator A5010638335 @default.
- W2069384792 creator A5021880943 @default.
- W2069384792 creator A5024930481 @default.
- W2069384792 creator A5047863865 @default.
- W2069384792 creator A5082282211 @default.
- W2069384792 date "2008-01-01" @default.
- W2069384792 modified "2023-09-25" @default.
- W2069384792 title "DNA cleavage in red light promoted by copper(ii) complexes of α-amino acids and photoactive phenanthroline bases" @default.
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- W2069384792 doi "https://doi.org/10.1039/b802948b" @default.
- W2069384792 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19050783" @default.
- W2069384792 hasPublicationYear "2008" @default.
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