Synthesis and photophysics of an octathioglycosylated zinc(II) phthalocyanine

Abstract

A water soluble zinc(II) phthalocyanine symmetrically appended with eight thioglucose units was synthesized from commercially available hexadecafluorophthalocyaninatozinc(II) by controlled nucleophilic substitution of the peripheral fluoro groups. The photophysical properties and cancer cell uptake studies of this nonhydrolyzable thioglycosylated phthalocyanine are reported. The new compound has amphiphilic character, is chemically stable, and can potentially be used as a photosensitizer in photodynamic therapy.

Photophysical properties and photochemistry of a sulfanyl porphyrazine bearing isophthaloxybutyl substituents

“…The low values of fluorescence quantum yields might be explained by the presence of eight sulfur atoms in 4, responsible for heavy-atom deactivation of the excited states. Notably, the relatively low fluorescence quantum yields were also found for zinc(II) phthalocyanine functionalized by eight thioglucose units [31]. Similarly, the influence of sulfur present in the phthalocyanine ring has been observed for octaglucosylated zinc(II) phthalocyanines, containing oxygen or sulfur bridges.…”

“…Similarly, in methanol bi-exponential decay with t F1 (S1 / S0) ¼ 38.5 ps (40%) and t F2 (S1 / S0) ¼ 116.8 ps (60%) was noted. Literature data indicates for some phthalocyanines and porphyrazines mono-exponential decay of the S 1 state on the ns time scale [31,32]. However, bi-exponential fluorescence decay was also noted for porphyrazines with peripheral 2,5-dimethylpyrrol-1-yl and dimethylamino groups dissolved in DMSO.…”

Synthesis of Glycoconjugated Phthalonitriles for New Phthalocyanine-Based Photosensitizers

“…Analytical data were in accordance with the literature. [41] 6-O-(4-Bromobutyl)-1,2:3,4-di-O-isopropylidene-α-Dgalactopyranose (16) Pursuant to general procedure GP1, 2.80 g (10.76 mmol) of saccharide 2, 336 mg (13.99 mmol) sodium hydride, and 6.40 mL (54.00 mmol) 1,4-dibromobutane (13) in 60 mL of dry DMF and chromatographic purification on silica gel using a mixture of toluene/acetone (30:1) gave compound 16 as a colorless oil (3.34 g, 55%). Analytical data were in accordance with the literature.…”

“…[8][9][10][11][12][13] The combination of the hydrophobic macrocycles with hydrophilic carbohydrate moieties has attracted a great deal of attention, mainly due to the fact that several carbohydrates have a specific recognition for cancer cells. [14][15][16] In addition, these carbohydrate residues enhance the solvation properties of the photosensitizer to ensure more effective photocytotoxic activity. [17][18][19][20][21][22][23][24][25][26][27][28] In previous studies we have synthesized and fully characterized a series of peripheral glycosylated and glycoconjugated zinc (II) phthalocyanines bearing galactose, glucose, mannose, maltose, or cellobiose residues at the macrocyclic skeleton.…”

Synthesis and cell phototoxicity of a triply bridged fused diporphyrin appended with six thioglucose units

“…700–1100 nm) especially for deep cancers, 5–7 so bio-targeted dye systems with longer wavelength absorptions are needed for next-generation imaging and PDT agents. 8,9 …”