Issue 24, 2019

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


A conjugate of cancer-cell targeting cyclic disulphide nona-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 complex trans,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 IC50 values of 2.8–22.4 μM 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 from FM-190. In addition, the cellular accumulation of Pt from Pt-cP was enhanced ca. 47× after irradiation.

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

Supplementary files

Article information

Article type
28 Feb 2019
26 Apr 2019
First published
31 May 2019
This article is Open Access
Creative Commons BY license

Dalton Trans., 2019,48, 8560-8564

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

H. Shi, Q. Wang, V. Venkatesh, G. Feng, L. S. Young, I. Romero-Canelón, M. Zeng and P. J. Sadler, Dalton Trans., 2019, 48, 8560 DOI: 10.1039/C9DT00909D

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