Preparation, characterization, antioxidant evaluation of new curcumin derivatives and effects of forming HSA-bound nanoparticles on the stability and activity

Tiantian Hao; Kai Wang; Shutong Zhang; Shuyan Yang; Pingxi Wang; Feng Gao; Yufan Zhao; Na Guo; Peng Yu

doi:10.1016/j.ejmech.2020.112798

Preparation, characterization, antioxidant evaluation of new curcumin derivatives and effects of forming HSA-bound nanoparticles on the stability and activity

Eur J Med Chem. 2020 Dec 1:207:112798. doi: 10.1016/j.ejmech.2020.112798. Epub 2020 Sep 5.

Authors

Tiantian Hao¹, Kai Wang¹, Shutong Zhang¹, Shuyan Yang¹, Pingxi Wang¹, Feng Gao¹, Yufan Zhao¹, Na Guo², Peng Yu³

Affiliations

¹ China International Science and Technology Cooperation Base of Food Nutrition/Safety and Medicinal Chemistry, College of Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, China.
² China International Science and Technology Cooperation Base of Food Nutrition/Safety and Medicinal Chemistry, College of Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, China; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, PR China. Electronic address: guona@tust.edu.cn.
³ China International Science and Technology Cooperation Base of Food Nutrition/Safety and Medicinal Chemistry, College of Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, China. Electronic address: yupeng@tust.edu.cn.

PMID: 32920425
DOI: 10.1016/j.ejmech.2020.112798

Abstract

Curcumin (CCM) is a well-known active component, which has been studied extensively in food and medicine field since it showed various activities. However, some serious issues limit its application, for example, the extremely low solubility, stability and bioavailability. In this study, 10 Curcumin derivatives were synthesized and characterized by ¹H NMR, ¹³C NMR and HR-MS, then their antioxidant activity was evaluated. Compound 2 and curcumin were further investigated by preparing HSA-bound nanoparticles (NP-2 and NP-CCM) to surmount the difficulties mentioned above. The nanoparticles obtained were about 110 nm in size measured by Dynamic light scattering (DLS), the stability of compound 2 in NP-2 was significantly increased. Above all, NP-2 showed more efficient antioxidant and antitumor activity, which was probably attributed to the introduced isopentenyl groups in 2, it was supposed that the isopentenyl groups increased the interaction between compound 2 and HSA. Overall, NP-2 has great potential for some food and pharmaceutical applications.

Keywords: Antioxidant activity; Antitumor activity; Curcumin; HSA; Nanoparticles.

MeSH terms

Curcumin / chemical synthesis
Curcumin / chemistry*
Curcumin / pharmacology*
Drug Carriers / chemistry*
Drug Stability
Humans
Nanoparticles / chemistry*
Particle Size
Serum Albumin, Human / chemistry*

Substances

Drug Carriers
Curcumin
Serum Albumin, Human