Stereoselective binding of chiral anti-diabetic drug nateglinide to plasma proteins

Maddi, Srinivas; Scriba, Gerhard K. E.; Yamsani, Madhusudan Rao

doi:10.1515/dmdi.2011.004

Cited by 5 publications

(2 citation statements)

References 12 publications

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“…Most of the drug-protein binding studies used the buffer concentration of 67 mM to mimic the physiological conditions [135,136]. That concentration is also used for immobilization procedures of HSA to a chromatographic support, for packing the CSP into columns as well as for in their storage [78].…”

Section: Zonal Analysismentioning

confidence: 99%

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

et al. 2021

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The interaction between proteins and drugs or other bioactive compounds has been widely explored over the past years. Several methods for analysis of this phenomenon have been developed and improved. Nowadays, increasing attention is paid to innovative methods, such as high performance affinity liquid chromatography (HPALC) and affinity capillary electrophoresis (ACE), taking into account various advantages. Moreover, the development of separation methods for the analysis and resolution of chiral drugs has been an area of ongoing interest in analytical and medicinal chemistry research. In addition to bioaffinity binding studies, both HPALC and ACE al-low one to perform other type of analyses, namely, displacement studies and enantioseparation of racemic or enantiomeric mixtures. Actually, proteins used as chiral selectors in chromatographic and electrophoretic methods have unique enantioselective properties demonstrating suitability for the enantioseparation of a large variety of chiral drugs or other bioactive compounds. This review is mainly focused in chromatographic and electrophoretic methods using human serum albumin (HSA), the most abundant plasma protein, as chiral selector for binding affinity analysis and enantioresolution of drugs. For both analytical purposes, updated examples are presented to highlight recent applications and current trends.

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Section: Zonal Analysismentioning

confidence: 99%

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

et al. 2021

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“…Its mirror image doesn't fit the same receptor, making it ineffective; or if it "fits" another receptor, it can induce a totally different response. between bovine serum albumin and human serum albumin while stereo-selectivity was identical between human serum albumin and human plasma [75]. Based on Easson-Stedman Principle with three-point binding model [76], only one enantiomer binds to enzyme & desired reaction occurs (Figures 20 and 21).…”

Section: Pharmacological Differences Between Two Enantiomers Of a Chimentioning

confidence: 99%

Exploiting the Power of Stereochemistry in Drugs: An Overview of Racemic and Enantiopure Drugs

Sekhon¹

2013

J. Mod. Med. Chem.

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Stereochemistry is one of the essential dimensions in pharmacology as it dictates how enantiomers interact with biological systems. Chirality is very important in drug design. Enantiomers of the same chiral drug can have different pharmacodynamic and/or pharmacokinetic properties. In this context, replacing some existing racemates with single isomers has resulted in improved safety and/or efficacy profile of various racemates. Single enantiomer drug use can potentially lead to simpler and more selective pharmacologic profiles, improved therapeutic indices, simpler pharmacokinetics due to different rates of metabolism of the different enantiomers, decreased drug interactions, and drug companies are increasingly using chiral switching as a marketing strategy. Additionally, due to different pharmacological activity, enantiomers of chiral drugs can differ in toxicity. However, unpredicted toxicity has been reported in some chiral switching cases which has resulted the withdrawal of the enantiomer from the market or a halt in its development. In view of above, before switching to single enantiomer drugs, prescribers should look for evidence from well-conducted clinical trials to prove that the chiral switch is cost-effective and improves the outcomes for patients rather than patents. The U.S. Food and Drug Administration (FDA) have allowed single enantiomers of generic drugs to be patented and marketed under different name. FDA regulations require that all chiral bioactive drug molecules must be isolated and tested for the efficacy and safety, and have to be as pure as possible containing a single pure enantiomer.

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High-Performance affinity chromatographic studies of repaglinide and nateglinide interactions with normal and glyoxal- or methylglyoxal-modified human albumin serum

Ovbude

Tao

Zhao

et al. 2021

Journal of Pharmaceutical and Biomedical Analysis

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Stereoselective binding of chiral anti-diabetic drug nateglinide to plasma proteins

Cited by 5 publications

References 12 publications

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

Exploiting the Power of Stereochemistry in Drugs: An Overview of Racemic and Enantiopure Drugs

High-Performance affinity chromatographic studies of repaglinide and nateglinide interactions with normal and glyoxal- or methylglyoxal-modified human albumin serum

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