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De novo generation of singlet oxygen and ammine ligands by photoactivation of a platinum anticancer complex.

Zhao Y, Farrer NJ, Li H, Butler JS, McQuitty RJ, Habtemariam A, Wang F, Sadler PJ - Angew. Chem. Int. Ed. Engl. (2013)

Bottom Line: Worth the excitement: Highly reactive oxygen and nitrogen species are generated by photoactivation of the anticancer platinum(IV) complex trans,trans,trans-[Pt(N3 )2 (OH)2 (MA)(Py)] (MA=methylamine, Py=pyridine).Singlet oxygen is formed from the hydroxido ligands and not from dissolved oxygen, and ammine ligands are products from the conversion of azido ligands to nitrenes.Both processes can induce oxidation of guanine.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Warwick, Coventry CV4 7AL (United Kingdom); Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Analytical Chemistry for Living Biosystems, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China).

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Two possible mechanisms for the oxidation of 5′-GMP. Charges are omitted for clarity.
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sch1: Two possible mechanisms for the oxidation of 5′-GMP. Charges are omitted for clarity.

Mentions: Two pathways can be proposed for the oxidation of guanine. The first involves a nitrene intermediate (Scheme 1, Mechanism 1). This can arise from loss of N2 from the {Pt-N3} fragment upon irradiation with UVA.6 Two electrons are transferred from guanine to the nitrene, and the guanine itself is oxidized to give 8-OH-G on addition of H2O. The nitrene is reduced and finally forms the ammine adduct {Pt-NH3}. Another possible oxidant is singlet oxygen. The 1O2 generated by photolysis of 1 can oxidize guanine to 8-OH-G by a direct [4+2] cycloaddition (Scheme 1, Mechanism 2).8a


De novo generation of singlet oxygen and ammine ligands by photoactivation of a platinum anticancer complex.

Zhao Y, Farrer NJ, Li H, Butler JS, McQuitty RJ, Habtemariam A, Wang F, Sadler PJ - Angew. Chem. Int. Ed. Engl. (2013)

Two possible mechanisms for the oxidation of 5′-GMP. Charges are omitted for clarity.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4230391&req=5

sch1: Two possible mechanisms for the oxidation of 5′-GMP. Charges are omitted for clarity.
Mentions: Two pathways can be proposed for the oxidation of guanine. The first involves a nitrene intermediate (Scheme 1, Mechanism 1). This can arise from loss of N2 from the {Pt-N3} fragment upon irradiation with UVA.6 Two electrons are transferred from guanine to the nitrene, and the guanine itself is oxidized to give 8-OH-G on addition of H2O. The nitrene is reduced and finally forms the ammine adduct {Pt-NH3}. Another possible oxidant is singlet oxygen. The 1O2 generated by photolysis of 1 can oxidize guanine to 8-OH-G by a direct [4+2] cycloaddition (Scheme 1, Mechanism 2).8a

Bottom Line: Worth the excitement: Highly reactive oxygen and nitrogen species are generated by photoactivation of the anticancer platinum(IV) complex trans,trans,trans-[Pt(N3 )2 (OH)2 (MA)(Py)] (MA=methylamine, Py=pyridine).Singlet oxygen is formed from the hydroxido ligands and not from dissolved oxygen, and ammine ligands are products from the conversion of azido ligands to nitrenes.Both processes can induce oxidation of guanine.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Warwick, Coventry CV4 7AL (United Kingdom); Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Analytical Chemistry for Living Biosystems, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China).

Show MeSH