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Strategies for conjugating iridium(III) anticancer complexes to targeting peptides via copper-free click chemistry

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Zhang, Wen-Ying, Banerjee, Samya, Imberti, Cinzia, Clarkson, Guy J., Wang, Qian, Zhong, Qian, Young, Lawrence S., Romero-Canelón, Isolda, Zeng, Musheng, Habtemariam, Abraha and Sadler, Peter J. (2020) Strategies for conjugating iridium(III) anticancer complexes to targeting peptides via copper-free click chemistry. Inorganica Chimica Acta, 503 . 119396. doi:10.1016/j.ica.2019.119396 ISSN 0020-1693.

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Official URL: http://dx.doi.org/10.1016/j.ica.2019.119396

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Abstract

We report the synthesis and characterisation of novel pentamethylcyclopentadienyl (Cp*) iridium(III) complexes [(Cp*)Ir(4-methyl-4'-carboxy-2,2'-bipyridine)Cl]PF6 (Ir-I), the product from amide coupling of Ir-I to dibenzocyclooctyne-amine (Ir-II), and its conjugate with the cyclic nona-peptide c(CRWYDENAC) (Ir-CP). The familiar three-legged ‘piano-stool’ configuration for complex Ir-I was confirmed by its single crystal X-ray structure. Significantly, copper-free click strategy has been developed for site-specific conjugation of the parent complex Ir-I to the tumour targeting nona-cyclic peptide. The approach consisted of two steps: (i) the carboxylic acid group of the bipyridine ligand in complex Ir-I was first attached to a amine functionalized dibenzocyclooctyne group via amide formation to generate complex Ir-II; and (ii) the alkyne bond of dibenzocyclooctyne in complex Ir-II underwent a subsequent strain-promoted copper-free cycloaddition with the azide group of the modified peptide. Interestingly, while complex Ir-I was inactive towards A2780 human ovarian cancer cells, complex Ir-II exhibited moderate cytotoxic activity. Targeted complexes such as Ir-CP offer scope for enhanced activity and selectivity of this class of anticancer complexes.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
R Medicine > RC Internal medicine
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH): Organoindium compounds, Antineoplastic agents, Azides, Ring formation (Chemistry), Cyclic peptides
Journal or Publication Title: Inorganica Chimica Acta
Publisher: Elsevier BV
ISSN: 0020-1693
Official Date: 1 April 2020
Dates:
DateEvent
1 April 2020Published
23 December 2019Available
20 December 2019Accepted
Volume: 503
Article Number: 119396
DOI: 10.1016/j.ica.2019.119396
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access (Creative Commons)
Date of first compliant deposit: 10 January 2020
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
EP/P030572/1 [EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
Chancellor’s International PhD ScholarshipUniversity of Warwickhttp://dx.doi.org/10.13039/501100000741
NF151429Royal Societyhttp://dx.doi.org/10.13039/501100000288
IE131109Royal Societyhttp://dx.doi.org/10.13039/501100000288
[209173/Z/17/Z]Wellcome Trusthttp://dx.doi.org/10.13039/100010269

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