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Ternary Copper Complexes for Photocleavage of DNA by Red Light:  Direct Evidence for Sulfur-to-Copper Charge Transfer and d−d Band Involvement

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    Ternary Copper Complexes for Photocleavage of DNA by Red Light:  Direct Evidence for Sulfur-to-Copper Charge Transfer and d−d Band Involvement
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    Contribution from the Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore-560012, India
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    Cite this: J. Am. Chem. Soc. 2003, 125, 40, 12118–12124
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    https://doi.org/10.1021/ja036681q
    Published September 12, 2003
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    A new class of ternary copper(II) complexes of formulation [Cu(Ln)B](ClO4) (1−4), where HLn is a NSO-donor Schiff base (HL1, HL2) and B is a NN-donor heterocyclic base viz. 1,10-phenanthroline (phen) and 2,9-dimethyl-1,10-phenanthroline (dmp), are prepared, structurally characterized, and their DNA binding and photocleavage activities studied in the presence of red light. Ternary complex [Cu(L3)(phen)](ClO4) (5) containing an ONO-donor Schiff base and a binary complex [Cu(L2)2] (6) are also prepared and structurally characterized for mechanistic investigations of the DNA cleavage reactions. While 1−4 have a square pyramidal (4 + 1) CuN3OS coordination geometry with the Schiff base bonded at the equatorial sites, 5 has a square pyramidal (4 + 1) geometry with CuN3O2 coordination with the alcoholic oxygen at the axial site, and 6 has a square planar trans-CuN2O2 geometry. Binding of the complexes 1−4 to calf thymus DNA shows the relative order:  phen ≫ dmp. Mechanistic investigations using distamycin reveal minor groove binding for the complexes. The phen complexes containing the Schiff base with a thiomethyl or thiophenyl moiety show red light induced photocleavage. The dmp complexes are essentially photonuclease inactive. Complexes 5 and 6 are cleavage inactive under similar photolytic conditions. A 10 μM solution of 1 displays a 72% cleavage of SC DNA (0.5 μg) on an exposure of 30 min using a 603 nm Nd:YAG pulsed laser (60 mJ/P) in Tris-HCl buffer (pH 7.2). Significant cleavage of 1 is also observed at 694 nm using a Ruby laser. Complex 1 is cleavage inactive under argon or nitrogen atmosphere. It shows a more enhanced cleavage in pure oxygen than in air. Enhancement of cleavage in D2O and inhibition with sodium azide addition indicate the possibility of the formation of singlet oxygen as a reactive intermediate leading to DNA cleavage. The d−d band excitation with red light shows significant enhancement of cleavage yield. The results indicate that the phen ligand is necessary for DNA binding of the complex. Both the sulfur-to-copper charge transfer band and copper d−d band excitations helped the DNA cleavage. While the absorption of a red photon induces a metal d−d transition, excitation at shorter visible wavelengths leads to the sulfur-to-copper charge transfer band excitation at the initial step of photocleavage. The excitation energy is subsequently transferred to ground state oxygen molecules to produce singlet oxygen that cleaves the DNA.

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    Selected crystallographic data, bond distances and angles for 1, 2, and 4−6 (Tables S1−S3); trigonality parameter values for 1, 2, 4, and 5 (Table S4); chemical nuclease data in the presence of mercaptopropionic acid (Table S5); photonuclease data at 312 nm (Table S6); photonuclease data at 532, 632, and 632.8 nm using a mercury vapor lamp (125 W), halogen lamp (250 W), and CW laser (3 mW), respectively (Table S7); cleavage data in the presence of different inhibiting reagents (Table S8); ORTEP diagrams with 50% probability thermal ellipsoids for the complexes 1, 2, and 4−6 with atom labeling schemes (Figures S1−S5); the DNA binding plots for 1−6 (Figures S6 and S7); gel diagram showing chemical nuclease activity in the presence of mercaptopropionic acid (Figure S8); gel diagram displaying photocleavage data at 312 nm (Figure S9); gel diagram exhibiting photonuclease activity at 532 and 632 nm (Figure S10); gel diagrams showing inhibition reactions (Figure S11); gel diagram showing control experiments using CuCl2·2H2O, bis(phen)copper(II), and Cu(TPP) (Figure S12); full list of bond distances and bond angles, anisotropic thermal parameters, and hydrogen atom coordinates for complexes 1, 2, and 4−6 (CIF). This material is available free of charge via the Internet at http://pubs.acs.org.

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