Stable and potent analogues derived from the modification of the dicarbonyl moiety of curcumin

Chakraborti S.; Dhar G.; Dwivedi V.; Das A.; Poddar A.; Chakraborti G.; Basu G.; Chakrabarti P.; Surolia A.; Bhattacharyya B.

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Stable and potent analogues derived from the modification of the dicarbonyl moiety of curcumin

机译：姜黄素二羰基部分修饰得到的稳定有效的类似物

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Curcumin has shown promising therapeutic utilities for many diseases, including cancer; however, its clinical application is severely limited because of its poor stability under physiological conditions. Here we find that curcumin also loses its activity instantaneously in a reducing environment. Curcumin can exist in solution as a tautomeric mixture of keto and enol forms, and the enol form was found to be responsible for the rapid degradation of the compound. To increase the stability of curcumin, several analogues were synthesized in which the diketone moiety of curcumin was replaced by isoxazole (compound 2) and pyrazole (compound 3) groups. Isoxazole and pyrazole curcumins were found to be extremely stable at physiological pH, in addition to reducing atmosphere, and they can kill cancer cells under serum-depleted condition. Using molecular modeling, we found that both compounds 2 and 3 could dock to the same site of tubulin as the parent molecule, curcumin. Interestingly, compounds 2 and 3 also show better free radical scavenging activity than curcumin. Altogether, these results strongly suggest that compounds 2 and 3 could be good replacements for curcumin in future drug development.

机译：姜黄素已显示出对包括癌症在内的许多疾病的治疗作用。然而，由于其在生理条件下的稳定性差，其临床应用受到严重限制。在这里，我们发现姜黄素在还原性环境中也会瞬间失去活性。姜黄素可以酮和烯醇形式的互变异构混合物形式存在于溶液中，并且发现烯醇形式是该化合物迅速降解的原因。为了提高姜黄素的稳定性，合成了几种类似物，其中姜黄素的二酮部分被异恶唑（化合物2）和吡唑（化合物3）取代。发现异恶唑和吡唑姜黄素除了具有还原性的气氛外，在生理pH下也非常稳定，并且它们可以在血清缺乏的情况下杀死癌细胞。使用分子建模，我们发现化合物2和3都可以与母体分子姜黄素对接在微管蛋白的同一部位。有趣的是，化合物2和3还显示出比姜黄素更好的清除自由基的活性。总之，这些结果强烈表明化合物2和3可能是姜黄素在未来药物开发中的良好替代品。

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《Biochemistry》 |2013年第42期|共12页
作者
Chakraborti S.; Dhar G.; Dwivedi V.; Das A.; Poddar A.; Chakraborti G.; Basu G.; Chakrabarti P.; Surolia A.; Bhattacharyya B.;
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正文语种 eng
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Stable; potent; dicarbonyl moiety; curcumin;

机译：稳定;有效;二羰基部分;姜黄素;

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1. Stable and potent analogues derived from the modification of the dicarbonyl moiety of curcumin [J] . Chakraborti S., Dhar G., Dwivedi V., Biochemistry . 2013,第42期

机译：姜黄素二羰基部分修饰得到的稳定有效的类似物
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6. 14-Dideoxy-14-imino-d-arabinitol(DAB) Analogues Possessing a Hydrazide Imide Moiety as Potent andSelective α-Mannosidase Inhibitors [O] . MarianneB. Haarr, Óscar Lopéz, Ljupcho Pejov, 2020

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7. 17(R),18(S)-Epoxyeicosatetraenoic Acid, a Potent Eicosapentaenoic Acid (EPA) Derived Regulator of Cardiomyocyte Contraction: Structure–Activity Relationships and Stable Analogues [O] . John R. Falck, Gerd Wallukat, Narender Puli, 2011

机译：17（r），18（S）-exyeicosate4甲酸，有效的eicosapentaeno酸（EPA）衍生的心肌细胞收缩调节剂：结构 - 活性关系和稳定的类似物
8. Photochemistry and Electronic Structure of Bis(dicarbonyl(pi5-Cyclopentadienyl)Ruthenium) and Its Iron Analogue. [R] . Abrahamson, H. B., Palazzotto, M. C., Reichel, C. L., 1979

机译：双（二羰基（pi5-环戊二烯基）钌）及其铁类似物的光化学和电子结构。

Stable and potent analogues derived from the modification of the dicarbonyl moiety of curcumin

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