English

Interactions between Surfactants and Folic Acid and the Effects of Surfactants on the Photodegradation of Folic Acid

• LUO Siqi ^1,2, ,
• WANG Meina ^1, ,
• ZHAO Weiwei ^1, ,
• WANG Yilin ^{1,2, ,}

• 1.

  Key Laboratory of Colloid, Interface and Chemical Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China

• 2.

  University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Corresponding author: WANG Yilin, Email: yilinwang@iccas.ac.cn; Tel.: +86-10-82615802

• Received Date: 25 September 2018
  Accepted Date: 05 November 2018
  Revised Date: 01 November 2018
  Available Online: 15 July 2019
• Fund Project:

  The project was supported by the National Natural Science Foundation of China (21633002)

Abstract: Interactions between surfactants and small organic molecules not only enhance the surface activity of the surfactants and induce aggregate transitions in them, but also improve the solubility and stability of the organic molecules. Understanding the interaction between surfactants and small molecules will help in widening the scope of application of surfactants. Folic acid, a member of the vitamin B family, has a pteridine ring, para-aminobenzoic acid, and glutamic acid, and is crucial for many reactions inside the human body. The unique structure of folic acid also facilitates the preparation of functional materials such as liquid crystals and gels. However, the poor solubility and precipitation of folic acid limit its applications. Therefore, it is essential to improve the solubility and stability of folic acid. Surfactants are efficient in solubilizing and stabilizing small molecules. The interactions of folic acid with four types of surfactants, namely, an anionic surfactant, sodium dodecyl sulfate (SDS); a cationic surfactant, dodecyl trimethylammonium bromide (DTAB); a cationic ammonium gemini surfactant, 12-6-12; and a cationic ammonium trimeric surfactant, 12-3-12-3-12; have been investigated at pH 7.0 by surface tension measurements, ultraviolet-visible (UV) absorption spectroscopy, dynamic light scattering, isothermal titration calorimetry, and nuclear magnetic resonance spectroscopy. At pH 7.0, the carboxylic acid groups of folic acid are deprotonated, so each folic acid molecule carries two negative charges. The addition of a small amount of folic acid sharply reduces the critical micelle concentration (CMC) of cationic surfactants and their surface tension at the CMC. However, the surface activity and aggregation of SDS show only minimal changes with the introduction of folic acid. In addition, the photodegradation of folic acid in the presence of different surfactants is studied by fluorescence and UV absorption spectroscopy. When irradiated with UV light, folic acid undergoes rapid degradation in aqueous solution, in the absence of any surfactants. In contrast, the degradation is greatly suppressed in the presence of surfactants. The extent of suppression by cationic surfactants is more significant than that by the anionic surfactant. The residual folic acid concentration increases from nearly 0 in the absence of any surfactant to 43%, 89%, 96%, and 96% in the presence of SDS, DTAB, 12-6-12, and 12-3-12-3-12, respectively, in the concentration range studied. The amount of surfactant required to prevent the degradation decreases with an increase in the degree of oligomerization of the cationic surfactants. The greater number of binding sites and hydrophobic tails in the gemini and oligomeric surfactants result in much stronger electrostatic and hydrophobic interactions with folic acid. In addition, the close and compact packing in these surfactant molecules prevents folic acid from coming in contact with oxygen, thereby retaining its stability and preserving its properties. This work provides a new methodology for regulating the surface activity of the surfactants and their aggregation in the presence of small functional molecules, which in turn improves the stability of the small molecules that are otherwise unstable.

Key words:
• Folic acid
•  /  Surfactant
•  /  Oligomeric degree
•  /  Interaction
•  /  Photo-degradation

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