Synthesis of L-selenocystin, N,N'-diacetyl-L-selenocystin and their investigation as antioxidants and glutathione peroxidase mimics
- 作者: Poluboyarinov P.A.1, Moiseeva I.Y.1, Mitishev A.V.1, Pogodina V.S.1, Elistratov D.G.2, Kuznetsova A.V.1
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隶属关系:
- Penza State University
- “Parapharm” LLC
- 期: 卷 28, 编号 12 (2025)
- 页面: 46-57
- 栏目: Pharmaceutical chemistry
- URL: https://bakhtiniada.ru/1560-9596/article/view/362635
- DOI: https://doi.org/10.29296/25877313-2025-12-06
- ID: 362635
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详细
Introduction. Cysteine and its derivatives have unique biological functions; acetylcysteine and carbocysteine are registered and marketed drugs. Selenium cysteine derivatives have to be a great challenge due to their vital role in natural redox catalysis and their use in dietary supplements. The adequate space for chemical modification creates a complex interests to manipulate their properties for pharmacological and nutritional purposes.
The aim of this study was to synthesize and investigate the antioxidant and glutathione peroxidase mimic properties of L-selenocystine and N,N'-diacetyl-L-selenocystine.
Material and Methods. Chemical synthesis of selenocystine from serine, acetylation of the amino group of selenocystine, to get acetylselenocystine. Coulometric assays of the antioxidant capacity and activity of cysteine and its derivatives. The reduction reactions of the diselenide with mercaptoethanol and N-acetylcysteine were studied spectrophotometrically. The glutathione peroxidase mimic properties of L-selenocysteine were modeled by bromine oxidation and sodium borohydride reduction.
Results. Sulfur-containing antioxidants have higher antioxidant capacity than selenium-containing. The antioxidant capacity in acidic solutions decreases in the following order: Cystine > L-selenocystine > N-acetylcysteine > N,N'-diacetyl-L-selenocystine > Methionine. An experimental coulometric conditions were developed for antioxidant activity assays. The antioxidant activity of N-acetylcysteine was higher than that of N,N'-diacetyl-L-selenocystine. Diselenide exhibits the glutathione peroxidase mimic properties: 1) accelerates the thiol oxidation and 2) is capable for reversible oxidation. In the red-ox model of selenocystine bromine oxidation and sodium borohydride reduction the 93% of substance were regenerated.
Conclusions. Diselenide bond of selenocysteine can be used as a chromophore for the spectrophotometric assays. N-acetylcysteine is weaker reductant for the diselenide bond than mercaptoethanol.
作者简介
P. Poluboyarinov
Penza State University
编辑信件的主要联系方式.
Email: poluboyarinovpavel@yandex.ru
ORCID iD: 0000-0001-9870-0272
SPIN 代码: 1855-6069
Ph.D. (Agric.), Associate Professor, Department of General and Clinical Pharmacology
俄罗斯联邦, 40 Krasnaya St., Penza, 440026I. Moiseeva
Penza State University
Email: moiseeva_pharm@mail.ru
ORCID iD: 0000-0003-1168-2871
SPIN 代码: 9607-0306
Dr.Sc. (Med.), Professor, Department of General and Clinical Pharmacology
俄罗斯联邦, 40 Krasnaya St., Penza, 440026A. Mitishev
Penza State University
Email: smitishev@mail.ru
ORCID iD: 0000-0002-3327-9744
SPIN 代码: 2831-1792
Senior Lecturer, Department of General and Clinical Pharmacology
俄罗斯联邦, 40 Krasnaya St., Penza, 440026V. Pogodina
Penza State University
Email: lerapogodina75@gmail.com
ORCID iD: 0009-0002-2504-3130
Student, Department of General and Clinical Pharmacology
俄罗斯联邦, 40 Krasnaya St., Penza, 440026D. Elistratov
“Parapharm” LLC
Email: info@parafarm.ru
ORCID iD: 0000-0001-7809-480X
SPIN 代码: 2376-9670
General Director
俄罗斯联邦, 116-a Kalinina St., Penza, 440033A. Kuznetsova
Penza State University
Email: kuznetanna1@hotmail.com
ORCID iD: 0000-0001-5180-6790
SPIN 代码: 4714-6602
Ph.D. (Chem.), Associate Professor, Department of General and Clinical Pharmacology
俄罗斯联邦, 40 Krasnaya St., Penza, 440026参考
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