Synthesis and characterization of monodeoxynucleotide tethered platinum-(II) and -(IV) complexes †

Ren, Sumei; Cai, Lisheng; Segal, Brent M.

doi:10.1039/a808705i

Cited by 13 publications

(10 citation statements)

References 16 publications

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“…The chloride ligands were then substituted by azido ligands by stirring the complexes with an excess of sodium azide in DMF. The reaction of complexes 1–3 with H 2 O 2 in acetic acid resulted in oxidation 31,32. The main products in all three cases were the monohydroxido, monoacetato species [Pt(L)(N 3 ) 2 (OAc)(OH)] (L = bpy, phen, (py) 2 ), which were then readily converted to the diacetato complexes 4–6 by stirring in acetic anhydride.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterisation and photochemistry of PtIV pyridyl azido acetato complexes

et al. 2009

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Pt II azido complexes [Pt(bpy) (N 3 ) 2 ] (1), [Pt(phen) (N 3 ) 2 ] (2) and trans-[Pt(N 3 ) 2 (py) 2 ] (3) incorporating the bidentate diimine ligands 2,2′-bipyridine (bpy), 1,10-phenanthroline (phen) or the monodentate pyridine (py) respectively, have been synthesised from their chlorido precursors and characterised by x-ray crystallography; complex 3 shows significant deviation from squareplanar geometry (N 3 -Pt-N 3 angle 146.7°) as a result of steric congestion at the Pt centre. The novel Pt IV complexes trans, cis-[Pt(bpy)(OAc) 2 (N 3 ) 2 ] (4), trans, cis-[Pt(phen)(OAc) 2 (N 3 ) 2 ] (5), trans, trans, trans-[Pt(OAc) 2 (N 3 ) 2 (py) 2 ] (6), were obtained from 1-3 via oxidation with H 2 O 2 in acetic acid followed by reaction of the intermediate with acetic anhydride. Complexes 4-6 exhibit interesting structural and photochemical properties that were studied by x-ray, NMR and UV-vis spectroscopy and TDDFT. These Pt IV complexes exhibit greater absorption at longer wavelengths (ε = 9756 M −1 cm −1 at 315 nm for 4; ε = 796 M −1 cm −1 at 352 nm for 5; ε = 16900 M −1 cm −1 at 307 nm for 6, in aqueous solution) than previously reported Pt IV azide complexes, due to the presence of aromatic amines, and 4-6 undergo photoactivation with both UVA (365 nm) and visible green light (514 nm). The UV-vis spectra of complexes 4-6 were calculated using TD-DFT; the nature of the transitions contributing to the UV-vis bands provide insight into the mechanism of production of the observed photoproducts. The UV-vis spectra of 1-3 were also simulated by computational methods and comparison between Pt II and Pt IV electronic and structural properties allowed further elucidation of the photochemistry of 4-6.

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Section: Resultsmentioning

confidence: 99%

Synthesis, characterisation and photochemistry of PtIV pyridyl azido acetato complexes

et al. 2009

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“…When the platinum complex (4) was treated with phosphoramidite coupling agent to synthesize the corresponding phosphoramidite, intramolecular coordination by the phosphite center to the platinum was observed (Scheme 2), a similar observation was made by Ren et al [36]. Thus we decided to synthesize a chelator-containing oligonucleotide, after its complete deprotection the chelator attached ODN can be subjected to platinum complexation in solution phase thus avoiding the possibility of the formation of inactivated species due to ammonia treatment.…”

Section: Resultsmentioning

confidence: 59%

Triplex mediated delivery of a platinum complex to a specific DNA target site

Sharma

McLaughlin

2004

Journal of Inorganic Biochemistry

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“…6) at 70 C for 24e30 h, until complete conversion [19]. The products precipitated in the reaction medium and they were separated by filtration.…”

Section: Synthesis Of Platinum(iv) Complexesmentioning

confidence: 99%

Synthesis, biological evaluation and SAR studies of novel bicyclic antitumor platinum(IV) complexes

Lorenzo

Delgado

Montaña

et al. 2014

European Journal of Medicinal Chemistry

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Synthesis and characterization of monodeoxynucleotide tethered platinum-(II) and -(IV) complexes †

Cited by 13 publications

References 16 publications

Synthesis, characterisation and photochemistry of PtIV pyridyl azido acetato complexes

Synthesis, characterisation and photochemistry of PtIV pyridyl azido acetato complexes

Triplex mediated delivery of a platinum complex to a specific DNA target site

Synthesis, biological evaluation and SAR studies of novel bicyclic antitumor platinum(IV) complexes

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