Assessing Photosensitizer Targeting Using Meso-Tetra(Carboxyphenyl) Porphyrin

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,...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2018-04, Vol.23 (4), p.892
Main Authors: Chitgupi, Upendra, Lovell, Jonathan F, Rajendiran, Venugopal
Format: Article
Language:English
Subjects:
Amines
Amino acids
Cancer
Carboxylic acids
Cell Line
Cellulose
Cholic acid
Functional groups
Humans
Hydrophobic and Hydrophilic Interactions
Hydrophobicity
Incubation
Irradiation
Large Neutral Amino Acid-Transporter 1 - metabolism
Ligands
Lysine
Molecular chains
Molecular Structure
mTCPP
PDT
Photodynamic therapy
photosensitizer
Photosensitizing Agents - chemical synthesis
Photosensitizing Agents - chemistry
Photosensitizing Agents - pharmacology
Pollutants
porphyrin
Porphyrins - chemical synthesis
Porphyrins - chemistry
Porphyrins - pharmacology
Radiation
Surfactants
Tumors
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules23040892