Glycoconjugated hypocrellin: synthesis of [(beta-D-glucosyl)ethylthiyl]hypocrellins and photosensitized generation of singlet oxygen.
In order to improve the water solubility and specific affinity for malignant tumors of hypocrellin, glycoconjugated hypocrellins have been synthesized using an improved Königs-Knörr reaction from mercaptoethanol substituted hypocrellin B and 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide precursors. Deprotection of glucose moieties allows the production of derivatives which had improved solubility in neutral aqueous solution and covered a range of amphiphilic character. The structures of these new protected and unprotected compounds were characterized by UV-Vis, IR, 1H-NMR and MS data. The present strategy should prove applicable to the synthesis of other glycoconjugated perylenequinone compounds. In addition, the quantum yield of singlet oxygen generation photosensitized by these glycoconjugated hypocrellins has been determined.
He
Y Y
YY
Institute of Photographic Chemistry, Academia Sinica, Beijing, PR China.
An
J Y
JY
Jiang
L J
LJ
D006001:Glycoconjugates / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D019800:Phenol; D010777:Photochemistry; D011809:Quinones / Q000737:chemistry / Q000378:metabolism*; D026082:Singlet Oxygen; D013057:Spectrum Analysis
D006001:Glycoconjugates; D011809:Quinones; D026082:Singlet Oxygen; D019800:Phenol; D010569:Perylene; D010100:Oxygen; C048388:hypocrellin A