Derivation of Oridonin with Bioreduction‐Responsive Disulfide Bond |
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| Authors: | Ming Du Qisang Guo Hua Feng Guolin Lu Xiaoyu Huang |
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| Institution: | 1. Obstetrics & Gynecology Hospital, Shanghai Medical College of Fudan University, Shanghai 200011, China;2. Laboratory of Synthetic and Self‐Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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| Abstract: | A novel oridonin derivative substituted with 3‐((2,3‐dihydroxypropyl)dithio)‐propionyl group at 14‐O position was synthesized through a two‐step procedure: Esterification of oridonin with 3‐(2‐pyridyldithio)propanoic acid and the subsequent thiol‐disul?de exchange reaction with 3‐mercapto‐1,2‐propanediol. The bioreduction‐responsive disulfide bond in the compound leads to high leaving ability of the 14‐O acyl moiety when treated with glutathione as monitored by reverse phase high‐performance liquid chromatography. |
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| Keywords: | oridonin disulfide esterification 3‐mercapto‐1 2‐propanediol glutathione |
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