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An Alkyne‐Appended, Click‐Ready Pt II Complex with an Unusual Arrangement in the Solid State
Author(s) -
White Jonathan D.,
Guzman Lindsay E.,
Zakharov Lev N.,
Haley Michael M.,
DeRose Victoria J.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201409853
Subject(s) - alkyne , click chemistry , chemistry , cycloaddition , azide , reactivity (psychology) , biomolecule , hydrogen bond , combinatorial chemistry , stereochemistry , molecule , catalysis , organic chemistry , medicine , biochemistry , alternative medicine , pathology
Abstract 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 cis ‐diamine Pt II compound, cis ‐[Pt(2‐(5‐hexynyl)amido‐1,3‐propanediamine)Cl 2 ] ( 1 ), the X‐ray crystal structure of which exhibits a combination of unusual radially distributed CH/π(CC) interactions, PtPt bonding, and NH:O/NH:Cl hydrogen bonds. In solution, 1 exhibits no Ptalkyne 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.