Synthesis of L-selenocystin, N,N'-diacetyl-L-selenocystin and their investigation as antioxidants and glutathione peroxidase mimics
- Авторлар: 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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Мекемелер:
- Penza State University
- “Parapharm” LLC
- Шығарылым: Том 28, № 12 (2025)
- Беттер: 46-57
- Бөлім: Pharmaceutical chemistry
- URL: https://medbiosci.ru/1560-9596/article/view/362635
- DOI: https://doi.org/10.29296/25877313-2025-12-06
- ID: 362635
Дәйексөз келтіру
Ашық рұқсат
Рұқсат берілді
Тек жазылушылар үшін
Аннотация
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.
Авторлар туралы
P. Poluboyarinov
Penza State University
Хат алмасуға жауапты Автор.
Email: poluboyarinovpavel@yandex.ru
ORCID iD: 0000-0001-9870-0272
SPIN-код: 1855-6069
Ph.D. (Agric.), Associate Professor, Department of General and Clinical Pharmacology
Ресей, 40 Krasnaya St., Penza, 440026I. Moiseeva
Penza State University
Email: moiseeva_pharm@mail.ru
ORCID iD: 0000-0003-1168-2871
SPIN-код: 9607-0306
Dr.Sc. (Med.), Professor, Department of General and Clinical Pharmacology
Ресей, 40 Krasnaya St., Penza, 440026A. Mitishev
Penza State University
Email: smitishev@mail.ru
ORCID iD: 0000-0002-3327-9744
SPIN-код: 2831-1792
Senior Lecturer, Department of General and Clinical Pharmacology
Ресей, 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
Ресей, 40 Krasnaya St., Penza, 440026D. Elistratov
“Parapharm” LLC
Email: info@parafarm.ru
ORCID iD: 0000-0001-7809-480X
SPIN-код: 2376-9670
General Director
Ресей, 116-a Kalinina St., Penza, 440033A. Kuznetsova
Penza State University
Email: kuznetanna1@hotmail.com
ORCID iD: 0000-0001-5180-6790
SPIN-код: 4714-6602
Ph.D. (Chem.), Associate Professor, Department of General and Clinical Pharmacology
Ресей, 40 Krasnaya St., Penza, 440026Әдебиет тізімі
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