ArticleChemistry (Weinheim an der Bergstrasse, Germany)2013
Diazido mixed-amine platinum(IV) anticancer complexes activatable by visible-light form novel DNA adducts.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- What is the Reason That the Pharmacological Future of Chemotherapeutics in the Treatment of Lung Cancer Could Be Most Closely Related to Nanostructures? Platinum Drugs in Therapy of Non-Small and Small Cell Lung Cancer and Their Unexpected, Possible Interactions. The Review.International journal of nanomedicine · 2024Review
- Development of Photoremovable Linkers as a Novel Strategy to Improve the Pharmacokinetics of Drug Conjugates and Their Potential Application in Antibody-Drug Conjugates for Cancer Therapy.Pharmaceuticals (Basel, Switzerland) · 2022Review
- Ligand Evolution in the Photoactivatable Platinum(IV) Anticancer Prodrugs.Frontiers in chemistry · 2022Review
- The Role of Triplet States in the Photodissociation of a Platinum Azide Complex by a Density Matrix Renormalization Group Method.The journal of physical chemistry letters · 2021Article
- DFT Study on the Substituent Effect of Anticancer Picoline-Diazido-Pt(IV) Compounds.Frontiers in oncology · 2021Article
- Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.Chemical reviews · 2020Article
- Bis[pyrrolyl Ru(ii)] triads: a new class of photosensitizers for metal-organic photodynamic therapy.Chemical science · 2020Article
- Gd(iii)-Pt(iv) theranostic contrast agents for tandem MR imaging and chemotherapy.Chemical science · 2020Article
- Platinum(iv) dihydroxido diazidoChemical science · 2019Article
- Biological activity of PtScientific reports · 2018Article
- Photoactivatable Cell-Selective Dinuclear trans-Diazidoplatinum(IV) Anticancer Prodrugs.Inorganic chemistry · 2018Article
- Platinum(iv) azido complexes undergo copper-free click reactions with alkynes.Dalton transactions (Cambridge, England : 2003) · 2018Article
- Oncosis-inducing cyclometalated iridium(iii) complexes.Chemical science · 2018Article
- Riboflavin as a bioorthogonal photocatalyst for the activation of a PtChemical science · 2017Article
- Activation of Platinum(IV) Prodrugs By Motexafin Gadolinium as a Redox Mediator.Angewandte Chemie (International ed. in English) · 2016Article
- Green light-induced apoptosis in cancer cells by a tetrapyridyl ruthenium prodrug offering twoChemical science · 2016Article
- Comprehensive Vibrational Spectroscopic Investigation of trans,trans,trans-[Pt(N3)2(OH)2(py)2], a Pt(IV) Diazido Anticancer Prodrug Candidate.Inorganic chemistry · 2016Article
- Characterisation of the DNA sequence specificity, cellular toxicity and cross-linking properties of novel bispyridine-based dinuclear platinum complexes.BMC cancer · 2016Article
- The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs.Chemical reviews · 2016Review
- Novel delivery approaches for cancer therapeutics.Journal of controlled release : official journal of the Controlled Release Society · 2015Review
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14 authors.
Funding
Abstract
Platinum diam(m)ine complexes, such as cisplatin, are successful anticancer drugs, but suffer from problems of resistance and side-effects. Photoactivatable Pt(IV) prodrugs offer the potential of targeted drug release and new mechanisms of action. We report the synthesis, X-ray crystallographic and spectroscopic properties of photoactivatable diazido complexes trans,trans,trans-[Pt(N3)2(OH)2(MA)(Py)] (1; MA=methylamine, Py=pyridine) and trans,trans,trans-[Pt(N3)2(OH)2(MA)(Tz)] (2; Tz=thiazole), and interpret their photophysical properties by TD-DFT modelling. The orientation of the azido groups is highly dependent on H bonding and crystal packing, as shown by polymorphs 1p and 1q. Complexes 1 and 2 are stable in the dark towards hydrolysis and glutathione reduction, but undergo rapid photoreduction with UVA or blue light with minimal amine photodissociation. They are over an order of magnitude more potent towards HaCaT keratinocytes, A2780 ovarian, and OE19 oesophageal carcinoma cells than cisplatin and show particular potency towards cisplatin-resistant human ovarian cancer cells (A2780cis). Analysis of binding to calf-thymus (CT), plasmids, oligonucleotide DNA and individual nucleotides reveals that photoactivated 1 and 2 form both mono- and bifunctional DNA lesions, with preference for G and C, similar to transplatin, but with significantly larger unwinding angles and a higher percentage of interstrand cross-links, with evidence for DNA strand cross-linking further supported by a comet assay. DNA lesions of 1 and 2 on a 50 bp duplex were not recognised by HMGB1 protein, in contrast to cisplatin-type lesions. The photo-induced platination reactions of DNA by 1 and 2 show similarities with the products of the dark reactions of the Pt(II) compounds trans-[PtCl2(MA)(Py)] (5) and trans-[PtCl2(MA)(Tz)] (6). Following photoactivation, complex 2 reacted most rapidly with CT DNA, followed by 1, whereas the dark reactions of 5 and 6 with DNA were comparatively slow. Complexes 1 and 2 can therefore give rapid potent photocytotoxicity and novel DNA lesions in cancer cells, with no activity in the absence of irradiation.
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