Water-Soluble Quaternized Serotonin Substituted Zinc-Phthalocyanine for Photodynamic Therapy Applications

Ebru Yabaş; Fuat Erden

doi:10.17776/csj.1191282

EN

Water-Soluble Quaternized Serotonin Substituted Zinc-Phthalocyanine for Photodynamic Therapy Applications

Abstract

Poor water solubility is the main drawback of phthalocyanine (Pc)-based second generation photosensitizing agents in photodynamic therapy (PDT). To resolve this, we proposed preparation of quaternized serotonin substituted zinc phthalocyanine (q-Ser-ZnPc) since the positive charge on quaternary amines could improve water-solubility and might limit self-interactions of hydrophobic aromatic surface of Pc in aqueous solutions. Briefly, serotonin substituted phthalonitrile was prepared by reaction of 4-nitrophthalonitrile with 5-hydroxytryptamine (Serotonin). Serotonin substituted zinc(II) phthalocyanine (Ser-ZnPc) was prepared by cyclotetramerization of serotonin substituted phthalonitrile. Then, q-Ser-ZnPc was prepared by the quaternization reaction of Ser-ZnPc. The synthesized compounds were characterized by 1H-NMR, UV-Vis, FT-IR, fluorescence, and elemental analysis. Importantly, unlike ZnPc, which is among most widely used second generation photosensitizing agents, we report that q-Ser-ZnPc is actually water-soluble. Besides, q-Ser-ZnPc also absorbs light in the wavelengths corresponding to the therapeutic window. What’s more, q-Ser-ZnPc exhibits a higher fluorescence quantum yield than that of ZnPc. Thus, the material might be useful particularly for image-guided PDT applications.

Keywords

References

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Details

Primary Language

English

Subjects

-

Journal Section

Research Article

Authors

Ebru Yabaş
0000-0001-7163-3057
Türkiye

Fuat Erden ^*
0000-0002-8261-4844
Türkiye

Publication Date

March 26, 2023

Submission Date

October 18, 2022

Acceptance Date

March 9, 2023

Published in Issue

Year 2023 Volume: 44 Number: 1

DOI

https://doi.org/10.17776/csj.1191282

IZ

https://izlik.org/JA57GL45KF

Cite

RIS / Bibtex

APA

Yabaş, E., & Erden, F. (2023). Water-Soluble Quaternized Serotonin Substituted Zinc-Phthalocyanine for Photodynamic Therapy Applications. Cumhuriyet Science Journal, 44(1), 99-105. https://doi.org/10.17776/csj.1191282