Lipoilcarnosine: synthesis, study of physico-chemical and antioxidant properties, biological activity

Stvolinsky S.L.1 , Antonova N.A.2, Kulikova O.I.3, Lopachev A.V.1, Abaimov D.A.1, Al-Baidani I.2, Lopacheva O.M.4, Fedorova T.N.1, Kaplun A.P.2, Sorokoumova G.M.2

1. Research Center of Neurology, Moscow, Russia
2. Moscow Technological University, Moscow, Russia
3. Research Center of Neurology, Moscow, Russia; Peoples' Friendship University of Russia, Moscow, Russia
4. Research Center of Neurology, Moscow, Russia; Lomonosov Moscow State University, International Biotechnological Center, Moscow, Russia
Section: Experimental Study
DOI: 10.18097/PBMC20186403268      PubMed Id: 29964264
Year: 2018  Volume: 64  Issue: 3  Pages: 268-275
Synthesis of lipoilcarnosine (LipC) – a conjugated molecule based on two natural antioxidants, carnosine and a-lipoic acid, is described. Its physico-chemical, antioxidant properties and biological activity are characterized. According to reversed-phase HPLC with a UV detector, purity of the final product was 89.3%. The individuality of the obtained sodium salt of LipC was confirmed by tandem HPLC-mass spectrometry. High resistance of LipC to hydrolysis with serum carnosinase was demonstrated. The antioxidant activity of LipC measured by reaction with the formation of thiobarbituric acid reacting substances and kinetic parameters of iron-induced chemiluminescence was higher than that of carnosine and lipoic acid. LipC did not affect viability of SH-SY5Y human neuroblastoma culture cells, differentiated towards the dopaminergic type, at concentrations not exceeding 5 mM. At the concentration range of 0.1-0.25 mM LipC protected neuronal cells against 1-methyl-4-phenylpyridinium (MPP + )-induced toxicity.
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Keywords: carnosine, a-lipoic acid, lipoilcarnosine, antioxidant, carnosinase, parkinsonism

Stvolinsky, S. L., Antonova, N. A., Kulikova, O. I., Lopachev, A. V., Abaimov, D. A., Al-Baidani, I., Lopacheva, O. M., Fedorova, T. N., Kaplun, A. P., Sorokoumova, G. M. (2018). Lipoilcarnosine: synthesis, study of physico-chemical and antioxidant properties, biological activity. Biomeditsinskaya Khimiya, 64(3), 268-275.
This paper is also available as the English translation: 10.1134/S199075081804008X
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