Synthesis and investigation of phthalocyanine-biotin conjugates

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

doi:10.1142/S1088424619500056

Synthesis and investigation of phthalocyanine-biotin conjugates

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

Research output: Chapter in Book/Report/Conference proceeding › Chapter › peer-review

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 HE_p2 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.

Original language	English
Title of host publication	Porphyrin Science By Women (In 3 Volumes)
Publisher	World Scientific Publishing Co.
Pages	238-248
Number of pages	11
ISBN (Electronic)	9789811223556
DOIs	https://doi.org/10.1142/S1088424619500056
State	Published - 1 Jan 2020

Keywords

Biotin
Isothiocyanate
PDT
Photosensitizer
Phthalocyanine

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10.1142/S1088424619500056

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title = "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.",

keywords = "Biotin, Isothiocyanate, PDT, Photosensitizer, Phthalocyanine",

author = "Okoth, {Elizabeth A.} and Zehua Zhou and Benson Ongarora and Alyssa Stutes and Mathis, {J. Michael} and Vicente, {M. Gra{\c c}a H.}",

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doi = "10.1142/S1088424619500056",

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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, J. Michael

AU - Vicente, M. Graça H.

PY - 2020/1/1

Y1 - 2020/1/1

N2 - 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.

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 ~ 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.

KW - Biotin

KW - Isothiocyanate

KW - PDT

KW - Photosensitizer

KW - Phthalocyanine

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DO - 10.1142/S1088424619500056

M3 - Chapter

AN - SCOPUS:85109739330

SP - 238

EP - 248

BT - Porphyrin Science By Women (In 3 Volumes)

PB - World Scientific Publishing Co.

ER -

Synthesis and investigation of phthalocyanine-biotin conjugates

Abstract

Keywords

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