Abstract
The synthesis and pharmacological activities of anthraquinone-ibuprofen prodrugs for finding new antiinflammatory drugs specifically targeting osseous tissues were studied. Two hydrolytically activated anti-inflammatory prodrugs containing anthraquinone moiety and ibuprofen moiety were designed and synthesized. Rhein was chosen as bone-targeting agent and potentially active drug, which was linked chemically with ibuprofen through glycol ester as bone-targeting anti-inflammatory prodrugs. The chemical structures of the new compounds were confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. The studies of bioactivities demonstrated that both prodrugs showed significant binding capability to hydroxyapatite (HAP), the major component of bone, and were hydrolytically activated under physiological conditions in vitro and better anti-inflammatory activity in vivo.
Keywords: Bone-targeting, prodrug, hydrolysis, hydroxyapatite, bone affinity, anti-inflammatory
Medicinal Chemistry
Title: Synthesis of Anthraquinone-Ibuprofen Prodrugs with Hydroxyapatite Affinity and Anti-Inflammatory Activity Characteristics
Volume: 5 Issue: 6
Author(s): Yanbing Duan, Jia Yu, Shi Liu and Min Ji
Affiliation:
Keywords: Bone-targeting, prodrug, hydrolysis, hydroxyapatite, bone affinity, anti-inflammatory
Abstract: The synthesis and pharmacological activities of anthraquinone-ibuprofen prodrugs for finding new antiinflammatory drugs specifically targeting osseous tissues were studied. Two hydrolytically activated anti-inflammatory prodrugs containing anthraquinone moiety and ibuprofen moiety were designed and synthesized. Rhein was chosen as bone-targeting agent and potentially active drug, which was linked chemically with ibuprofen through glycol ester as bone-targeting anti-inflammatory prodrugs. The chemical structures of the new compounds were confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. The studies of bioactivities demonstrated that both prodrugs showed significant binding capability to hydroxyapatite (HAP), the major component of bone, and were hydrolytically activated under physiological conditions in vitro and better anti-inflammatory activity in vivo.
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Cite this article as:
Duan Yanbing, Yu Jia, Liu Shi and Ji Min, Synthesis of Anthraquinone-Ibuprofen Prodrugs with Hydroxyapatite Affinity and Anti-Inflammatory Activity Characteristics, Medicinal Chemistry 2009; 5 (6) . https://dx.doi.org/10.2174/157340609790170498
DOI https://dx.doi.org/10.2174/157340609790170498 |
Print ISSN 1573-4064 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6638 |
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