Large-Scale Synthesis of Thio-glucose-Conjugated Chlorin e6 for Photodynamic Therapy

Abstract

Chlorin e6 is a heterocycle exhibiting spectral absorption in the 600-700 nm wavelength range used for photodynamic therapy (PDT). Herein, a sugar-conjugated chlorin e6 derivative was synthesized on a large scale. An alkyl spacer was fabricated by controlling the alkoxylation conditions between the thio-sugar and chlorin e6 and thio-glucose-conjugated chlorin e6 was successfully synthesized.Heterocycles such as porphyrins and chlorins show great potential to be developed as new drugs.Therefore, it is important to develop new synthesis methods and pathways for drugs to fight novel

Vascular‐targeted photodynamic therapy with glucose‐conjugated chlorin e6 for dogs with spontaneously occurring tumours

“…Methyl (7S,8S)−18‐ethyl‐5‐(2‐methoxy‐2‐oxoethyl)−7‐(3‐methoxy‐3‐oxopropyl)−2,8,12,17‐tetramethyl‐13‐(1‐(3‐(((2S,3R,4S,5S,6R)−3,4,5‐trihydroxy‐6‐(hydroxymethyl) tetrahydro‐2H‐pyran‐2‐yl)thio)propoxy) ethyl)−7H,8H‐porphyrin‐3‐carboxylate (G‐Ce6, MW: 893.06) was synthesised as previously described (Nomoto et al., 2021). For intravenous administration in dogs, G‐Ce6 was dissolved in 2.5% Kolliphor (Sigma‐Aldrich, St. Louis, MO, USA) and 97.5% saline.…”

“…Methyl 893.06) was synthesised as previously described (Nomoto et al, 2021). For intravenous administration in dogs, G-Ce6 was dissolved in 2.5% Kolliphor (Sigma-Aldrich, St. Louis, MO, USA) and 97.5% saline.…”

“…Recently, we developed a new photosensitiser, glucose‐conjugated chlorin e6 (G‐Ce6) (Kataoka et al., 2021; Nomoto et al., 2021; Osaki et al., 2019). It is relatively water‐soluble and rapidly excreted from the body.…”