Literature DB >> 31902097

A new derivative of acetylsalicylic acid and carnosine: synthesis, physical and chemical properties, biological activity.

Olga I Kulikova1, Sergey L Stvolinsky2, Vasily A Migulin3, Ludmila A Andreeva4, Igor Yu Nagaev4, Olga M Lopacheva2, Ksenia N Kulichenkova2, Alexander V Lopachev2, Irina E Trubitsina5, Tatiana N Fedorova2.   

Abstract

PURPOSE: The aim of this study was to create and assess biological activity of a new compound based on carnosine and acetylsalicylic acid (ASA) that will comprise antioxidant effect with antiplatelet activity, while simultaneously preventing side effects on the gastrointestinal tract.
METHODS: Salicyl-carnosine (SC) was synthesized by condensation of ASA and carnosine. Antioxidant activity was determined by spectrophotometric and chemiluminescence methods. Antiplatelet activity was carried out by the light transmission-aggregometry method using the inductor ADP. Chronic gastric ulcer in rats was modeled using glacial acetic acid.
RESULTS: Using SOD-like activity, iron-induced chemiluminescence, BaSO4-activated respiratory burst, and evaluation of red blood cell structure stabilization during oxidative damage induced by sodium hypochlorite, it was shown that SC possesses antioxidant activity analogous, or better, than that of carnosine. Antiplatelet activity of SC was evaluated in the blood of healthy individuals, and was also shown to be comparable to, or exceeding that of ASA. Also SC demonstrates high resistance to hydrolysis by tissue and serum carnosinases. Most importantly, it was shown that SC has protected the gastric mucosa against the formation of stomach ulcerative lesions and promoted their epithelization, therefore overcoming the undesirable inherent side effects of ASA.
CONCLUSIONS: SC preserves pharmacologically significant properties of ASA and carnosine while retaining an anti-ulcer activity and resistance to the carnosinase hydrolysis at the same time. These properties are particularly promising for the potential development of new anti-inflammatory and antithrombotic drugs. Graphical abstract .

Entities:  

Keywords:  Acetylsalicylic acid; Antioxidant; Antiplatelet action; Carnosine; Gastrointestinal ulcer; Salicylic acid

Year:  2020        PMID: 31902097      PMCID: PMC7214588          DOI: 10.1007/s40199-019-00323-x

Source DB:  PubMed          Journal:  Daru        ISSN: 1560-8115            Impact factor:   3.117


  40 in total

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Review 4.  Salicylic acid derivatives: synthesis, features and usage as therapeutic tools.

Authors:  Deniz Ekinci; Murat Sentürk; Ömer İrfan Küfrevioğlu
Journal:  Expert Opin Ther Pat       Date:  2011-12       Impact factor: 6.674

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Authors:  A Corina Vlot; D'Maris Amick Dempsey; Daniel F Klessig
Journal:  Annu Rev Phytopathol       Date:  2009       Impact factor: 13.078

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Journal:  Xenobiotica       Date:  1988-04       Impact factor: 1.908

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8.  Biological activity of novel synthetic derivatives of carnosine.

Authors:  S L Stvolinsky; E R Bulygina; T N Fedorova; K Meguro; T Sato; O V Tyulina; H Abe; A A Boldyrev
Journal:  Cell Mol Neurobiol       Date:  2009-10-02       Impact factor: 5.046

9.  [Lipoilcarnosine: synthesis, study of physico-chemical and antioxidant properties, biological activity].

Authors:  S L Stvolinsky; N A Antonova; O I Kulikova; A V Lopachev; D A Abaimov; I Al-Baidani; O M Lopacheva; T N Fedorova; A P Kaplun; G M Sorokoumova
Journal:  Biomed Khim       Date:  2018-06

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Authors:  Vincent Dj-P Dubois; Andrew Bastawrous
Journal:  Cochrane Database Syst Rev       Date:  2017-02-28
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Authors:  Shu Fu; Jiamei Chen; Chen Zhang; Jinfeng Shi; Xin Nie; Yichen Hu; Chaomei Fu; Xiaofang Li; Jinming Zhang
Journal:  Front Pharmacol       Date:  2021-12-15       Impact factor: 5.810

4.  Pharmacological evaluation of newly synthesized organotin IV complex for antiulcer potential.

Authors:  Syed Azmatullah; Arif-Ullah Khan; Neelam Gul Qazi; Humaira Nadeem; Nadeem Irshad
Journal:  BMC Pharmacol Toxicol       Date:  2022-07-29       Impact factor: 2.605

  4 in total

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