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

Hemanjali Mude; Pranay Amruth Maroju; Aniket Balapure; Ramakrishnan Ganesan; Jayati Ray Dutta

doi:10.1016/j.foodchem.2021.131830

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

Food Chem. 2022 Apr 16:374:131830. doi: 10.1016/j.foodchem.2021.131830. Epub 2021 Dec 9.

Authors

Hemanjali Mude¹, Pranay Amruth Maroju¹, Aniket Balapure², Ramakrishnan Ganesan³, Jayati Ray Dutta⁴

Affiliations

¹ Department of Biological Sciences, Birla Institute of Technology and Science (BITS), Pilani, Hyderabad Campus, Jawahar Nagar, Kapra Mandal, Medchal District, Hyderabad, Telangana 500078, India.
² Department of Chemistry, Birla Institute of Technology and Science (BITS), Pilani, Hyderabad Campus, Jawahar Nagar, Kapra Mandal, Medchal District, Hyderabad, Telangana 500078, India.
³ Department of Chemistry, Birla Institute of Technology and Science (BITS), Pilani, Hyderabad Campus, Jawahar Nagar, Kapra Mandal, Medchal District, Hyderabad, Telangana 500078, India. Electronic address: ram.ganesan@hyderabad.bits-pilani.ac.in.
⁴ 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: jayati@hyderabad.bits-pilani.ac.in.

PMID: 34906806
DOI: 10.1016/j.foodchem.2021.131830

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, ¹H NMR, ¹³C NMR, 2D ¹H-¹H 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.

Keywords: Anticancer; Antimicrobial; Antioxidant; Dopamine; Polyphenol; Water-soluble caffeic acid complex.

MeSH terms

Antioxidants* / analysis
Caffeic Acids
Dopamine*
Solubility
Spectroscopy, Fourier Transform Infrared
Water

Substances

Antioxidants
Caffeic Acids
Water
caffeic acid
Dopamine