title: An alkyne-appended, click-ready Pt(II) complex with an unusual arrangement in the solid state.
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)Cl2] (1), 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, 1 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.
authors.affiliation: Department of Chemistry & Biochemistry and Institute of Molecular Biology, University of Oregon, Eugene, OR 97403-1253 (USA).
authors.forename: Jonathan D
authors.initials: JD
authors.lastname: White
authors.forename: Lindsay E
authors.initials: LE
authors.lastname: Guzman
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.forename: Michael M
authors.initials: MM
authors.lastname: Haley
authors.forename: Victoria J
authors.initials: VJ
authors.lastname: DeRose
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D057930:Click Chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D004247:DNA / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D009944:Organoplatinum Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010984:Platinum / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D000480:Alkynes; D001386:Azides; D005456:Fluorescent Dyes; D009944:Organoplatinum Compounds; D010984:Platinum; D004247:DNA
keywords: bioorthogonal chemistry; click chemistry; fluorescent probes; metallodrugs; platinum