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Development of a novel carboplatin like cytoplasmic trackable near infrared fluorophore conjugate via strain-promoted azide alkyne cycloaddition.

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posted on 23.11.2019 by Eolann Kitteringham, Dan Wu, Shane Cheung, Brendan Twamley, Donal F. O'Shea, Darren M. Griffith

The successful design and pre-clicked synthesis of a non-toxic and cytosol trackable carboplatin-like near infrared fluorophore conjugate via strain-promoted azide alkyne cycloaddition (SPAAC) is reported. Reaction of cis-[Pt(2-azidopropane-1,3-diamine)(cbdca)] (cbdca = cyclobutane-1,1-dicarboxylato) and a bicyclo[6.1.0]non-4-yne near-infrared (NIR) azadipyrromethene fluorophore gave the corresponding clicked Pt-Fluorophore conjugate. The X-ray crystal structure of cis-[Pt(2-azidopropane-1,3-diamine)(cbdca)] was determined featuring the azide on the bidentate 1,3-diaminopropane ligand. The Pt-fluorophore conjugate is the first example of a Pt conjugate clicked via strain-promoted azide alkyne cycloaddition (SPAAC) where the reactive azide handle is on the amine carrier ligand. The in vitro cytotoxicity and widefield fluorescence imaging of the Pt-Fluorophore conjugate in A2780P and A2780cisR cells are described.

Funding

EK sincerely thanks the Royal College of Surgeons in Ireland for financial support through the RCSI Apjohn Scholarship and DOS gratefully acknowledges Science Foundation Ireland grant number 11/PI/1071(T) for financial support.

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The original article is available at www.sciencedirect.com

Published Citation

Kitteringham E, Wu D, Cheung S, Twamley B, O'Shea DF, Griffith DM. Development of a novel carboplatin like cytoplasmic trackable near infrared fluorophore conjugate via strain-promoted azide alkyne cycloaddition. Journal of Inorganic Biochemistry. 2018;182:150-15

Publication Date

21/02/2018

Publisher

Elsevier

PubMed ID

29482160

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