4.7 Article

Phthalocyanine-Peptide Conjugates via Palladium-Catalyzed Cross-Coupling Reactions

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 6, Pages 1887-1890

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo102083g

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Funding

  1. Centre de recherche clinique Etienne-Le Bel of the Centre Hospitalier Universitaire de Sherbrooke
  2. Naturel Sciences and Engineering Research council of Canada (NSERC)
  3. Jeanne and J.-Louis Levesque Chair in Radiobiology

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Phthalocyanines (Pc) were conjugated with peptide moieties to improve their target selectivity for potential use as fluorescence and/or positron emission tomography (PET) probes in medical imaging. Three synthetic methods based on palladium-catalyzed cross-coupling reactions (Sonogashira, Buchwald-Hartwig, and Suzuki-Miyaura) were investigated. Using these methods, a series of peptides monofunctionalized with Pc at the N/C-terminal position or on a phenylalanine side chain was obtained in good yields and characterized.

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