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Molecules 2018, 23(4), 892; https://doi.org/10.3390/molecules23040892

Assessing Photosensitizer Targeting Using Meso-Tetra(Carboxyphenyl) Porphyrin

1
Department of Biomedical Engineering, University at Buffalo, State University of New York, Buffalo, New York, NY 14260, USA
2
Department of Chemistry, School of Basic and Applied Sciences, Central University of Tamil Nadu, Thiruvarur 610005, India
*
Authors to whom correspondence should be addressed.
Academic Editor: Michael R. Hamblin
Received: 6 March 2018 / Revised: 28 March 2018 / Accepted: 10 April 2018 / Published: 12 April 2018
(This article belongs to the Special Issue Advances in Photodynamic Therapy 2018)
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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. View Full-Text
Keywords: porphyrin; photosensitizer; mTCPP; photodynamic therapy; PDT porphyrin; photosensitizer; mTCPP; photodynamic therapy; PDT
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Chitgupi, U.; Lovell, J.F.; Rajendiran, V. Assessing Photosensitizer Targeting Using Meso-Tetra(Carboxyphenyl) Porphyrin. Molecules 2018, 23, 892.

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