Synthesis of inositol 2-phosphate-quercetin conjugates

The antiproliferative flavonoid, quercetin, is limited in its pharmacological utility by its low water solubility. In this paper, we describe the synthesis of two quercetin analogues prepared by linking the hydroxyl group at the 3- or 5-position of the flavonoid to the 1-hydroxyl group of myo-inosit...

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Bibliographic Details
Published in:Carbohydrate research 1996-10, Vol.292 (1), p.83-90
Main Authors: Calias, P, Galanopoulos, T, Maxwell, M, Khayat, A, Graves, D, Antoniades, H N, d'Alarcao, M
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Cell Division - drug effects
Cell Survival - drug effects
Humans
Inositol Phosphates - chemical synthesis
Inositol Phosphates - chemistry
Inositol Phosphates - pharmacology
Magnetic Resonance Spectroscopy
Molecular Structure
Quercetin - analogs & derivatives
Quercetin - chemical synthesis
Quercetin - chemistry
Quercetin - pharmacology
Solubility
Succinates - chemistry
Tumor Cells, Cultured
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Summary:The antiproliferative flavonoid, quercetin, is limited in its pharmacological utility by its low water solubility. In this paper, we describe the synthesis of two quercetin analogues prepared by linking the hydroxyl group at the 3- or 5-position of the flavonoid to the 1-hydroxyl group of myo-inositol-2-phosphate via a succinate diester linkage. The resulting conjugates were found to have dramatically enhanced water solubility relative to quercetin; the 5-linked quercetin analogue 2 had a water solubility of > 300 mg/mL at 20 degrees C. Comparison of the in vitro cytotoxicity and antiproliferative activity of conjugate 2 with those of quercetin toward cultured human colon adenocarcinoma (SW480) and human glioblastoma (U87MG) cells indicated that this modification of quercetin does not significantly diminish its activity in these assays.
ISSN:0008-6215
DOI:10.1016/0008-6215(96)00179-6