Abstract
Lipoamide (LM), amide of α-lipoic acid, is a very powerful antioxidant. However, information on its physicochemical properties, in particular on its thermal behavior, is very limited. In the present work, a DSC study of LM showed that heating above the melting point led to formation of a mixture of polymeric and crystalline forms of LM. In order to increase thermal stability of the drug, LM was encapsulated in colloid silica with various surface chemistry. It was found that encapsulation of LM in unmodified and organomodified silica materials slowed down the process of thermal degradation of the drug. The effect of silica matrix modification on the thermal degradation was revealed. It was shown that the interactions in the drug-silica composites play an important role in thermal stabilization of LM. The indicated thermal behavior of LM and α-lipoic acid in free form and in the synthesized composites was compared.
Graphic abstract
Similar content being viewed by others
References
P. Bomzan, N. Roy, A. Sharma, V. Rai, S. Ghosh, A. Kumar, M.N. Roy, Molecular encapsulation study of indole-3-methanol in cyclodextrins: effect on antimicrobial activity and cytotoxicity. J. Mol. Struct. 1225, 129093 (2021)
A. Celebioglu, Z.I. Yildiz, T. Uyar, Thymol/cyclodextrin inclusion complex nanofibrous webs: enhanced water solubility, high thermal stability and antioxidant property of thymol. Food Res. Int. 106, 280 (2018)
C. Cheng, Z. Wu, D.J. McClements, L. Zou, S. Peng, W. Zhou, W. Liu, Improvement on stability, loading capacity and sustained release of rhamnolipids modified curcumin liposomes. Colloid. Surf. B 183, 110460 (2019)
Y.-X. Li, E.Y. Park, S.-T. Lim, Stabilization of alpha-lipoic acid by complex formation with octenylsuccinylated high amylose starch. Food Chem. 242, 389 (2018)
A. Shetta, J. Kegere, W. Mamdouh, Comparative study of encapsulated peppermint and green tea essential oils in chitosan nanoparticles: encapsulation, thermal stability, in vitro release, antioxidant and antibacterial activities. Int. J. Biol. Macromol. 126, 731 (2019)
Z.-L. Lia, S.-F. Penga, X. Chena, Y.-Q. Zhua, L.-Q. Zoua, W. Liua, C.-M. Liu, Pluronics modified liposomes for curcumin encapsulation: sustained release, stability and bioaccessibility. Food Res. Int. 108, 246 (2018)
X. Wang, G. Zhou, H. Zhang, S. Du, Y. Xu, C. Wang, Immobilization and catalytic activity of lipase on mesoporous silica prepared from biocompatible gelatin organic template. J. Non-Cryst. Solid 357, 3027 (2011)
N. Liédana, E. Marín, C. Téllez, J. Coronas, One-step encapsulation of caffeine in SBA-15 type and non-ordered silicas. Chem. Eng. J. 223, 714 (2013)
Y. Zhu, W. Shen, X. Dong, J. Shi, Immobilization of hemoglobin on stable Mesoporous multilamellar silica vesicles and their activity and stability. J. Mater. Res. 20, 2682 (2005)
H.S. Neto, G.L.B. de Araujo, L.L. dos Santos, I.C. Cosentino, F.M. de Souza Carvalho, J. do Rosário Matos, Inclusion of prednicarbate in the SBA-15 silica. J. Therm. Anal. Calorim. 123, 2297 (2016)
Use of lipoamide in preventing and treating insulin resistance. Patent CN101396357B https://patents.google.com/patent/CN101396357B/en
B. Zhou, M. Wen, X. Lin, Y.-H. Chen, Y. Gou, Y. Li, Y. Zhang, H.-W. Li, L. Tang, Alpha lipoamide ameliorates motor deficits and mitochondrial dynamics in the Parkinson’s disease model induced by 6-hydroxydopamine. Neurotox. Res. 33, 759 (2018)
L. Zhao, Z. Liu, H. Jia, Z. Feng, J. Liu, X. Li, Lipoamide acts as an indirect antioxidant by simultaneously stimulating mitochondrial biogenesis and phase II antioxidant enzyme systems in ARPE-19 cells. PLoS ONE 10, e0128502 (2015)
E. Zabados, G.M. Fischer, F. Gallyas Jr., G. Kispal, B. Sumegi, Enhanced ADP-ribosylation and its diminution by lipoamide after ischemia-reperfusion in perfused rat heart. Free Radic Biol. Med. 27, 1103 (1999)
H.L. Persson, A.I. Svensson, U.T. Brunk, α-Lipoic acid and α-lipoamide prevent oxidant-induced lysosomal rupture and apoptosis. Redox Rep. 6, 327 (2001)
R.C. Thomas, L.J. Reed, Disulfide polymers of DL-α-lipoic acid. J. Am. Chem. Soc. 78, 6148 (1956)
G.P. Biewenga, G.R.M.M. Haenen, A. Bast, An overview of lipoate chemistry, in Lipoic Acid in Health and Disease, ed. by J. Fuchs, L. Packer, G. Zimmer (Marcel Dekker Inc., New York, 1977), pp. 1–32
A. Kisanuki, Y. Kimpara, Y. Oikado, N. Kado, M. Matsumoto, K. Endo, Ring-opening polymerization of lipoic acid and characterization of the polymer. J. Polym. Sci. A. 48, 5247 (2010)
C.H. Park, J. Lee, pH-dependent sustained release characteristics of disulfide polymers prepared by simple thermal polymerization. J. Biomater. Sci. Polymer Ed. 24, 1847 (2013)
Y. Nambu, M.H. Acar, T. Suzuki, T. Endo, Thermal and photoinitiated copolymerhation of the cyclic disulfide lipoamide with styrene. Makromol. Chem. 189, 495 (1988)
T. Suzuki, Y. Nambu, T. Endo, Radical copolymerization of lipoamide with vinyl monomers. Macromolecules 23, 1579 (1990)
J. Wang, J. Tang, X. Zhou, Q. Xia, Physicochemical characterization, identification and improved photo-stability of alpha-lipoic acid-loaded nanostructured lipid carrier. Drug Dev. Ind. Pharm. 40, 201 (2014)
H. Takahashi, Y. Bungo, K. Mikuni, The aqueous solubility and thermal stability of α-lipoic acid are enhanced by cyclodextrin. Biosci. Biotechnol. Biochem. 75, 633 (2011)
E.S. Dolinina, EYu. Akimsheva, E.V. Parfenyuk, Development of novel silica-based formulation of α-lipoic acid: evaluation of photo and thermal stability of the encapsulated drug. Pharmaceutics 12, 228 (2020)
R. Al-Oweini, H. El-Rassy, Synthesis and characterization by FTIR spectroscopy of silica aerogels prepared using several Si(OR)4 and R’’ Si(OR’)3 precursors. J. Mol. Struct. 919, 140 (2009)
R.M. Silverstein, G.C. Bassler, T.C. Morrill, Spectrometric Identification of Organic Compounds, 3rd edn. (Willey, New York, 1974)
J. Ashenhurst. The amide functional group: properties, synthesis, nomenclature. https://www.masterorganicchemistry.com/2018/02/28/amides-properties-synthesis-and-nomenclature/. Accessed 18 Sept 2020
R.B. Homer, C.D. Johnson, Acid-base and complexing properties of amides, in Amides, Chpt. 3, ed. by J. Zabicki (Wiley, New York, 1970), pp. 187–243
Lipoamide. https://pubchem.ncbi.nlm.nih.gov/compound/863. Accessed 15 Sept 2020
(±)-α-Lipoamide. https://www.sigmaaldrich.com/catalog/product/sial/62330?lang=en®ion=RU. Accessed 6 Oct 2020
G. Bergson, G. Claeson, L. Schotte, Ultraviolet absorption spectra of saturated disulphides and diselenides. Acta Chem. Scand. 16, 1159 (1962)
Acknowledgments
This work was funded by Russian Science Foundation (Grant No. 19-73-00040).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Dolinina, E.S., Akimsheva, E.Y. & Parfenyuk, E.V. Study of thermal properties of antioxidant lipoamide and its composites with colloid silica. Journal of Materials Research 36, 499–507 (2021). https://doi.org/10.1557/s43578-020-00021-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1557/s43578-020-00021-4