An Alkyne‐Appended, Click‐Ready PtII Complex with an Unusual Arrangement in the Solid State1. Issue 3 (27th November 2014)

• Record Type: Journal Article
• Authors: White, Jonathan D.; Guzman, Lindsay E.; Zakharov, Lev N.; Haley, Michael M.; DeRose, Victoria J.
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 3(2015)
• Page Start: 1032
• Page End: 1035
• Publication Date: 2014-11-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201409853
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>To better understand the range of cellular interactions of Pt^II‐based chemotherapeutics, robust and efficient methods to track and analyze Pt targets are needed. A powerful approach is to functionalize Pt^II compounds with alkyne or azide moieties for post‐treatment conjugation through the azide–alkyne cycloaddition (click) reaction. Herein, we report an alkyne‐appended <italic>cis</italic>‐diamine Pt^II compound, <italic>cis</italic>‐[Pt(2‐(5‐hexynyl)amido‐1, 3‐propanediamine)Cl₂] (<bold>1</bold>), the X‐ray crystal structure of which exhibits a combination of unusual radially distributed CH/π(CC) interactions, PtPt bonding, and NH:O/NH:Cl hydrogen bonds. In solution, <bold>1</bold> exhibits no Ptalkyne interactions and binds readily to DNA. Subsequent click reactivity with nonfluorescent dansyl azide results in a 70‐fold fluorescence increase. This result demonstrates the potential for this new class of alkyne‐modified Pt compound for the comprehensive detection and isolation of Pt‐bound biomolecules.</p> </abstract>