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Applicant:
Central University of Tamil Nadu 
Author:
Upendra Chitgupi, Jonathan F. Lovell, and Venugopal Rajendiran 
Corresponding Authors:
Jonathan F. Lovell and Venugopal Rajendiran 
DOI #:
10.3390/molecules23040892 
Title:
Assessing Photosensitizer Targeting Using Meso-Tetra(Carboxyphenyl) Porphyrin 
Journal:
Molecules 
Year:
2018 
Volume:
23 
Page:
892 
Keywords:
porphyrin; photosensitizer; mTCPP; photodynamic therapy; PDT 
Abstract:
Mesotetra(4-carboxyphenyl)porphyrin (mTCPP) is a commercially available small molecule fluorophore and photosensitizer with four free carboxylic acid groups. mTCPP can readily be conjugated with amines for facile attachment of functional groups. In this work, we synthesized and assessed tetravalent, lysine-conjugated mTCPP, for its potential applications in targeted imaging and photodynamic therapy. Fmoc-protected D-lysine or L-lysine was conjugated to mTCPP via amide coupling with the epsilon amine group of lysine, followed by Fmoc deprotection. The resulting compounds did not dissolve well in aqueous solvent, but could be solubilized with the assistance of surfactants, including cholic acid. The L-amino acid transporter (LAT1) can uptake diverse neutral L-amino acids. In vitro studies with U87 cells revealed a non-specific uptake of the hydrophobic Fmoc-protected lysine-conjugated mTCPP precursors, but not D- or L-lysine mTCPP. Likewise, only the Fmoc-protected compounds induced substantial phototoxicty in cells following incubation and irradiation with blue light. These experimental results do not provide evidence to suggest that lysine-mTCPP is able to specifically target cancer cells. However, they do highlight mTCPP as a convenient and accessible framework for assessing molecular targeting of photosensitizers. 
Entered by:
Rajendiran Venugopal on 2020-08-29 
 
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