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Photoactive platinum(iv) complex conjugated to a cancer-cell-targeting cyclic peptide

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Shi, Huayun, Wang, Qian, Venkatesh, Venkatesh, Feng, Guokai, Young, Lawrence S., Romero-Canelón, Isolda, Zeng, Musheng and Sadler, P. J. (2019) Photoactive platinum(iv) complex conjugated to a cancer-cell-targeting cyclic peptide. Dalton Transactions . doi:10.1039/c9dt00909d (In Press)

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Official URL: http://dx.doi.org/10.1039/c9dt00909d

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Abstract

A conjugate of cancer-cell targeting cyclic disulphide non a-peptide c(CRWYDENAC) consisting of nine L-amino acids with the photoactive succinate platinum(IV)complex trans, trans-[Pt(N3)2(py)2(OH)(succinate)] (Pt-cP) has been synthesised and characterised. The conjugate was stable in dark, but released succinate–peptide and Pt(II) species upon irradiation with visible light, and formed photoproducts with guanine. Conjugate Pt-cP exhibited higher photocytotoxicity than parent complextrans, trans, trans-[Pt(N3)2(OH)2(py)2] (FM-190) towards cancer cells, including ovarian A2780, lung A549 and prostate PC3 human cancer cells upon irradiation with blue light (465 nm, 17.28 J cm−2) with IC50values of 2.8–22.4μM and the highest potency for A549 cells. Even though the dark cellular accumulation of Pt-cP in A2780 cells was lower than that of parent FM-190, Pt from Pt-cP accumulated in cancer cells upon irradiation to a level >3× higher than that fromFM-190. In addition, the cellular accumulation of Pt from Pt-cPwas enhanced ca. 47× after irradiation.

Item Type: Journal Article
Subjects: R Medicine > RM Therapeutics. Pharmacology
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Prodrugs, Cyclic peptides
Journal or Publication Title: Dalton Transactions
Publisher: Royal Society of Chemistry
ISSN: 1477-9226
Official Date: 31 May 2019
Dates:
DateEvent
31 May 2019Available
26 April 2019Accepted
Date of first compliant deposit: 3 June 2019
DOI: 10.1039/c9dt00909d
Status: Peer Reviewed
Publication Status: In Press
Access rights to Published version: Open Access
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
EP/G006792[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
EP/F034210/1[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
247450 European Research Councilhttp://viaf.org/viaf/130022607
UNSPECIFIEDUniversity of Warwickhttp://dx.doi.org/10.13039/501100000741
E131109[RS] Royal Societyhttp://dx.doi.org/10.13039/501100000288
AL170006\1Isaac Newton Trusthttp://dx.doi.org/10.13039/501100004815

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