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Solid‐phase Synthesis of Folate–Chlorin Conjugates for Selective Photodynamic Therapy and the Effect of Linker Variation
Author(s) -
Lee SeonMin,
Ahn YoungDeok,
Mun Hyoyoung,
Goh Byoungsook,
Kim TaeYoung,
Seo Jiwon,
Kim MinGon
Publication year - 2016
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11028
Subject(s) - photodynamic therapy , peptoid , linker , photosensitizer , chemistry , chlorin , polyethylene glycol , peptide , conjugate , combinatorial chemistry , folic acid , peg ratio , conjugated system , in vitro , biophysics , photochemistry , biochemistry , organic chemistry , polymer , medicine , mathematical analysis , mathematics , finance , computer science , economics , operating system , biology
Here, we evaluated the effect of linkers conjugating a chlorin‐based photosensitizer, 2‐[1‐hexyloxyethyl]‐2‐devinyl pyropheophorbide‐a ( HPPH ), and folic acid to target cancer cells. Folate– HPPH conjugates with peptide, polyethylene glycol ( PEG ), peptoid, or 7‐aminoheptanoic acid ( AHA ) linkers were synthesized on a solid‐phase and evaluated for photodynamic therapy ( PDT ) efficacy. Compared to free HPPH , the folate‐linker‐ HPPHs were effectively internalized into tumor cells and exhibited superior PDT effect upon irradiation. Tumor‐targeting PDT efficacy was influenced by linker variation, with in vitro photocytotoxicities of peptide > PEG > AHA > peptoid, paralleling water solubility of the linkers. Thus, linker choice significantly affects targeted PDT efficacy providing useful information for linker design.