Selective synthesis and photophysical properties of tailor-made chlorins for photodynamic therapy

Montforts, Franz‐Peter; Gerlach, Benjamin; Haake, Gerold; Hoeper, F.; Kusch, Dirk; Meier, Axel; Scheurich, Gerhard; Brauer, H.‐D.; Schiwon, K.; Schermann, G.

doi:10.1117/12.199155

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“…A few years ago, Bonnett and co-workers showed that, compared to β-hydroxyoctaethylchlorin, the related glycosylated analogue was more effective as a photosensitizing agent in vitro as well as in vivo. Montforts et al further explored this approach by attaching hydrophilic carbohydrate structural units to certain chlorins. Such conjugation increased the water solubility of the parent chlorins by introducing an estradiol with a diethyl spacer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of β-Galactose-Conjugated Chlorins Derived by Enyne Metathesis as Galectin-Specific Photosensitizers for Photodynamic Therapy

et al. 2001

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A first report on the synthesis and biological evaluation of the beta-galactose-conjugated purpurinimides (a class of chlorins containing a six-membered fused imide ring system) as Gal-1 (galectin-1) recognized photosensitizers, prepared from purpurin-N-propargylimide via enyne metathesis, is discussed. On the basis of examination of the available crystal structure of the galectin-1 N-acetyllactose amine complex, it was considered that the chlorin-based photosensitizers could be introduced into a carbohydrate skeleton to expand the repertoire of the galectin-1-specific ligands. Preliminary molecular modeling analysis utilizing the modeled photosensitizers and the available crystal structures of galectin-carbohydrate complexes indicated that addition of the photosensitizer to the carbohydrate moiety at an appropriate position does not interfere with the galectin-carbohydrate recognition. Under similar drug and light doses, compared to the free purpurinimide analogue, the purpurinimides conjugated either with galactose or with lactose (Gal(beta1-4)-Glc) produced a considerable increase in photosensitizing efficacy in vitro. This indicates the possibility for development of a new class of specific photosensitizers for photodynamic therapy (PDT) based on recognition of a cellular receptor.

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Section: Introductionmentioning

confidence: 99%