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Synthesis and investigation of phthalocyanine-biotin conjugates.

ABSTRACT: An isothiocyanato-functionalized phthalocyanine (Pc) was synthesized in good yield from the corresponding amine-substituted Pc. This Pc reacted with ethanolamine, biotin hydrazine, and biotin diethylamine under mild conditions (room temperature in DMF or DMSO in the presence of TEA) to produce the corresponding thiourea products in 60-75% yields. All Pcs showed intense Q absorptions in DMF around 677 nm, emissions centered at 683 nm, and fluorescence quantum yields in the range 0.18-0.27. The Pcs were phototoxic to human carcinoma HEp2 cells (IC50 ~ 7 at 1.5 J/cm2) and localized in multiple organelles, including the lysosomes, Golgi and ER. One biotin-Pc conjugate was injected via tail vein into nude mice bearing HT-29 tumors and demonstrated selective localization in the tumor tissue.

SUBMITTER: Okoth EA

PROVIDER: S-EPMC7598017 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Synthesis and investigation of phthalocyanine-biotin conjugates.

Okoth Elizabeth A EA Zhou Zehua Z Ongarora Benson B Stutes Alyssa A Mathis J Michael JM Vicente M Graça H MGH

Journal of porphyrins and phthalocyanines 20190101 1n02

An isothiocyanato-functionalized phthalocyanine (Pc) was synthesized in good yield from the corresponding amine-substituted Pc. This Pc reacted with ethanolamine, biotin hydrazine, and biotin diethylamine under mild conditions (room temperature in DMF or DMSO in the presence of TEA) to produce the corresponding thiourea products in 60-75% yields. All Pcs showed intense Q absorptions in DMF around 677 nm, emissions centered at 683 nm, and fluorescence quantum yields in the range 0.18-0.27. The Pc ...[more]

PMID: 33132689

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