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 aminederivatized

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 64Cu and its (15[64Cu]) receptor binding affinity to CD44-expressing tumor cells was evaluated.