Synthesis and investigation of phthalocyanine-biotin conjugates

Elizabeth A. Okoth, Zehua Zhou, Benson Ongarora, Alyssa Stutes, J. Michael Mathis, M. Graça H. Vicente

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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 â 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.

Original languageEnglish
Pages (from-to)125-135
Number of pages11
JournalJournal of Porphyrins and Phthalocyanines
Volume23
Issue number1-2
DOIs
Publication statusPublished - 1 Jan 2019

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Keywords

  • PDT
  • biotin
  • isothiocyanate
  • photosensitizer
  • phthalocyanine

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