Water-soluble caffeic acid-dopamine acid-base complex exhibits enhanced bactericidal, antioxidant, and anticancer properties.

Food Chem

Department of Biological Sciences, Birla Institute of Technology and Science (BITS), Pilani, Hyderabad Campus, Jawahar Nagar, Kapra Mandal, Medchal District, Hyderabad, Telangana 500078, India. Electronic address:

Published: April 2022

AI Article Synopsis

  • Caffeic acid (CA) has limited applications due to its poor water solubility, but a new method using dopamine hydrochloride (Dopa.HCl) allows for the formation of a water-soluble complex without covalent bonds.
  • The solubility is achieved after using sodium bicarbonate to neutralize the mineral acid in the mixture, resulting in a water-soluble CA-Dopa complex.
  • This complex has been shown to have strong bactericidal, antibiofilm, antioxidant, and anticancer properties in a pH range relevant to physiological conditions (5.5 to 7.5), highlighting its potential for various applications.

Article Abstract

Despite the highly potent biological characteristics, the poor water-solubility of caffeic acid (CA) limits its applications in various domains. Here, we present a facile approach, wherein CA has been treated with dopamine hydrochloride (Dopa.HCl) to obtain a water-soluble acid-base complex, which does not possess any covalent bond between the individual components and thus retains their nativity. Simple mixing of CA and Dopa.HCl did not provide water solubility to CA, but the complex became readily soluble in water when the mineral acid was scavenged using sodium bicarbonate. The obtained CA-Dopa complex had been characterized using FT-IR, H NMR, C NMR, 2D H-H NOESY NMR, XPS, and DSC techniques. The complex was found to exhibit excellent bactericidal, antibiofilm, antioxidant, and anticancer properties in the physiologically relevant pH range of 5.5 to 7.5. The results have revealed the high potential of the simple acid-base complex of CA in diverse domains.

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Source
http://dx.doi.org/10.1016/j.foodchem.2021.131830DOI Listing

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