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• W2000188786 abstract "It is generally accepted that, within the cell, DNA is the primary target of the active aquated forms of the antitumor cis-[Pt(NH3)2Cl2] drug (cis-DDP) [1, 2]. The fact that only the cis isomer of the complex exhibits antineoplastic activity, suggests that the cytotoxic lesion could result from a particular bifunctional coordination of the cis-PtII(NH3)2 moiety [1]. Intrastrand cross-linking is one possibility [3] and platinum chelation by two adjacent guanines has received much support from studies with various DNAs [4–8] and oligonucleotide models [9–14]. We report here that the three d(T-G-G-C-C-A), d(A-T-G-G) and d(C-C-A-T-G-G) oligonucleotides give GG-platinum chelates. We have studied the stoichiometric reactions between cis-[Pt(NH3)2(H2O)2](NO3)2 and the deoxyoligonucleotides d(T-G-G-C-C-A), d(A-T-G-G) and d(C-C-A-T-G-G) (1 Pt per oligonucleotide) in the 10−5–10−4M concentration range, in water at 37 °C. In the reaction conditions 1H NMR shows that the self complementary hexanucleotides are essentially in the single strand form. For the three reactions, HPLC and 1H NMR analyses show that the oligonucleotide is completely converted to a single complex. The same complex is obtained from the reaction with cis-DDP. High pressure gel permeation chromatography and atomic absorption spectroscopy coupled with the UV absorption of the complex, show that one platinum atom is bound per oligonucleotide. 1H NMR (400 and 500 MHz) of the two hexanucleotide complexes (1–5 × 10−3M) shows that they are single stranded in conditions where the free self-complementary oligonucleotides adopt a duplex structure [14, 15]. The metal binding sites in the d(T-G-G-C-C-A)[Pt], d(A-T-G-G)[Pt] and d(C-C-A-T-G-G)[Pt] complexes have been determined by the analysis of the pH dependence of the chemical shifts of the non exchangeable base protons. In the three cases, on going from basic to acidic pH, one observes the successive protonations of the thymine N3 (apparent pKaca. 10), of the N1 of the two guanines (app. pKa ≈ 8.3–8.5 instead of ca. 10 for the free oligonucleotides), of the N3 of the two cytosines (app. pKa ≈ 4.1–4.5) and the adenine N1 (app. pKa ≈ 3.4–3.5). These data, together with the two different GH8 downfield shifts already encountered for the d(G-G)[Pt] and d(C-C-G-G)[Pt] chelates [10, 11] show that the cis-PtII(NH3)2 moiety is chelated by the N7 atoms of the adjacent guanines. T1 relaxation times of the base protons, nuclear Overhauser enhancements between the GH8 and deoxy-ribose H2′ and H3′, allowed the assignment of the external and internal guanines and together with two dimensional NMR (J-δ) allowed the identification of the C3′-endo deoxy-ribose that is characteristic of the diguanosine chelates [10, 16]." @default.
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• W2000188786 title "Chelation of the cis-PtII(NH3)2 moiety by the guanines of the oligonucleotides d(T-G-G-C-C-A), d(A-T-G-G) and d(C-C-A-T-G-G)" @default.
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• W2000188786 doi "https://doi.org/10.1016/s0020-1693(00)95291-5" @default.
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