title: Solid-Supported Porphyrins Useful for the Synthesis of Conjugates with Oligomeric Biomolecules.
abstract: meso-Tris(pyridin-4-yl)(4-carboxyphenyl)porphyrin and 2-(1-hexyloxyethyl)-2-devinyl pyropheophorbide-a (Photochlor, HPPH) were amide-coupled to 1R,2S,3R,4R-2,3-dihydroxy-4-(hydromethyl)-1-aminocyclopentane and immobilized via an ester linkage to long chain alkyl amine-derivatized controlled pore glass (LCAA-CPG). The applicability of these supports (5 and 6) for the synthesis of porphyrin conjugates with oligomeric biomolecules was demonstrated using an automated phosphoramidite coupling chemistry. Cleavage from the support with concentrated ammonia gave the products, viz., porphyrin conjugates of oligonucleotides (7-9) and dendritic glycoclusters (10-13) and a cyclooctyne derivative (14) in 23-58% yield. In addition, the synthesized cyclooctyne derivative of meso-tris(pyridin-4-yl)(4-carboxyphenyl)porphyrin (14) was conjugated with an azidopropyl-modified hyaluronic acid (19). The hyaluronic acid-porphyrin conjugate (15) was radiolabeled with (64)Cu and its (15[(64)Cu]) receptor binding affinity to CD44-expressing tumor cells was evaluated.
authors.affiliation: Department of Chemistry, University of Turku , FI-20014 Turku, Finland.
authors.forename: Satish
authors.initials: S
authors.lastname: Jadhav
authors.affiliation: Turku PET Centre, Åbo Akademi University , FI-20520 Turku, Finland.
authors.forename: Cheng-Bin
authors.initials: CB
authors.lastname: Yim
authors.affiliation: Turku PET Centre, Åbo Akademi University , FI-20520 Turku, Finland.
authors.forename: Johan
authors.initials: J
authors.lastname: Rajander
authors.affiliation: Turku PET Centre, University of Turku , FI-20520 Turku, Finland.|Medicity Research Laboratory, University of Turku , FI-20520 Turku, Finland.
authors.forename: Tove J
authors.initials: TJ
authors.lastname: Grönroos
authors.affiliation: Department of Chemistry, University of Turku , FI-20014 Turku, Finland.|Turku PET Centre, University of Turku , FI-20520 Turku, Finland.
authors.forename: Olof
authors.initials: O
authors.lastname: Solin
authors.affiliation: Department of Chemistry, University of Turku , FI-20014 Turku, Finland.
authors.forename: Pasi
authors.initials: P
authors.lastname: Virta
mesh_terms: D001704:Biopolymers / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry*
chemical_list: D001704:Biopolymers; D011166:Porphyrins