Synthesis and investigation of phthalocyanine-biotin conjugates

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

Research output: Contribution to journalArticleResearchpeer-review

2 Citations (Scopus)

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
StatePublished - 1 Jan 2019

Fingerprint

Biotin
hydrazine
Tumors
Bearings (structural)
Thiourea
Ethanolamine
Quantum yield
Dimethyl Sulfoxide
Amines
Fluorescence
Tissue
phthalocyanine
Temperature

Keywords

  • PDT
  • biotin
  • isothiocyanate
  • photosensitizer
  • phthalocyanine

Cite this

Okoth, Elizabeth A. ; Zhou, Zehua ; Ongarora, Benson ; Stutes, Alyssa ; Mathis, James Michael ; Vicente, M. Graça H. / Synthesis and investigation of phthalocyanine-biotin conjugates. In: Journal of Porphyrins and Phthalocyanines. 2019 ; Vol. 23, No. 1-2. pp. 125-135.
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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 {\^a} 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.",
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Synthesis and investigation of phthalocyanine-biotin conjugates. / Okoth, Elizabeth A.; Zhou, Zehua; Ongarora, Benson; Stutes, Alyssa; Mathis, James Michael; Vicente, M. Graça H.

In: Journal of Porphyrins and Phthalocyanines, Vol. 23, No. 1-2, 01.01.2019, p. 125-135.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Synthesis and investigation of phthalocyanine-biotin conjugates

AU - Okoth, Elizabeth A.

AU - Zhou, Zehua

AU - Ongarora, Benson

AU - Stutes, Alyssa

AU - Mathis, James Michael

AU - Vicente, M. Graça H.

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AB - 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.

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