N-(3-Aminoalkyl)proline derivatives with potent antigycation activity

Chilukuri Harsha; Kolekar Yogesh M.; Bhosle Govind S.; Godbole Rashmi K.; Kazi Rubina S.; Kulkarni Mahesh J.; Fernandes Moneesha

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N-(3-Aminoalkyl)proline derivatives with potent antigycation activity

机译：N-（3-氨基烷基）脯氨酸衍生物，具有有效的抗钙化活性

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The importance of amino acids in the therapy of conditions such as renal failure, neurological disorders and congenital defects has been documented. Some amino acids such as lysine and glycine have also been reported to have antiglycating activity. Herein we report the synthesis of a new series of N-(3-aminoalkyl)proline derivatives which are non-natural in nature. The compounds were unambiguously characterized by NMR, mass and IR spectroscopy. Their in vitro antiglycation activity was studied by circular dichroism and fluorescence spectrometry. The mechanism of action was also studied and found to take place by inhibition of Amadori product formation. The inhibition of AGE formation was further confirmed by western blot and LC-MS/MS analyses and the IC50 values of the potent compounds were determined. Compounds containing hydroxyl substituents at C4 were found to have superior antiglycation properties than those containing azide substituents at the same position. The compounds were additionally found to possess good anti-oxidant properties, which could lead to further reduction in AGE formation. Moreover, the title compounds were found to have low cytotoxicity in mammalian cells, another important attribute. Thus, the title compounds represent a novel promising class of antiglycating agents.

机译：记录了氨基酸在诸如肾衰竭，神经障碍和先天性缺陷等条件治疗中的重要性。还据报道，一些氨基酸如赖氨酸和甘氨酸具有抗衰老活性。在此，我们报告了一种新的N-（3-氨基烷基）脯氨酸衍生物的合成，其是非自然的。通过NMR，质量和IR光谱，化合物明确地表征。通过圆形二色性和荧光光谱法研究了它们的体外抗饱和活性。还研究了作用机制，发现通过抑制Amadori产物形成来进行。通过蛋白质印迹和LC-MS / MS分析进一步证实了年龄形成的抑制，并且测定了效溶化合物的IC 50值。发现含有C4的羟基取代基的化合物具有优于含有相同位置的叠氮化物取代基的化合物。另外发现该化合物具有良好的抗氧化剂性能，这可能导致年龄形成进一步降低。此外，发现标题化合物在哺乳动物细胞中具有低细胞毒性，另一个重要属性。因此，标题化合物代表了一种新颖的抗衰老剂类别。

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来源
《RSC Advances》 |2015年第94期|共9页
作者
Chilukuri Harsha; Kolekar Yogesh M.; Bhosle Govind S.; Godbole Rashmi K.; Kazi Rubina S.; Kulkarni Mahesh J.; Fernandes Moneesha;
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CSIR Natl Chem Lab Prote Facil Div Biochem Sci Pune 411008 Maharashtra India;

CSIR Natl Chem Lab Prote Facil Div Biochem Sci Pune 411008 Maharashtra India;

CSIR Natl Chem Lab Organ Chem Div Pune 411008 Maharashtra India;

CSIR Natl Chem Lab Prote Facil Div Biochem Sci Pune 411008 Maharashtra India;

CSIR Natl Chem Lab Prote Facil Div Biochem Sci Pune 411008 Maharashtra India;

CSIR Natl Chem Lab Prote Facil Div Biochem Sci Pune 411008 Maharashtra India;

CSIR Natl Chem Lab Organ Chem Div Pune 411008 Maharashtra India;

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正文语种 eng
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N-(3-Aminoalkyl)proline derivatives with potent antigycation activity

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