Peer Reviewed

1

Document Type

Article

Publication Date

21-2-2018

Keywords

Platinum, Near IR, Azadipyrromethene, Strain-promoted azide alkyne cycloaddition, Cytotoxicity, Imaging.

Funder/Sponsor

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.

Comments

The original article is available at www.sciencedirect.com

Abstract

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.

Disciplines

Chemistry | Medicinal-Pharmaceutical Chemistry | Medicine and Health Sciences

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

PubMed ID

29482160

DOI Link

10.1016/j.jinorgbio.2018.02.010

Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 4.0 License.

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