Citation: LUO Siqi, WANG Meina, ZHAO Weiwei, WANG Yilin. Interactions between Surfactants and Folic Acid and the Effects of Surfactants on the Photodegradation of Folic Acid[J]. Acta Physico-Chimica Sinica, ;2019, 35(7): 766-774. doi: 10.3866/PKU.WHXB201809038 shu

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, yilinwang@iccas.ac.cn
Received Date: 25 September 2018
Revised Date: 1 November 2018
Accepted Date: 5 November 2018
Available Online: 7 July 2018
Fund Project: the National Natural Science Foundation of China 21633002The project was supported by the National Natural Science Foundation of China (21633002)

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.
- Folic acid,
- Surfactant,
- Oligomeric degree,
- Interaction,
- Photo-degradation
1. [1]
  Off, M. K.; Steindal, A. E.; Porojnicu, A. C.; Juzeniene, A.; Vorobey, A.; Johnsson, A.; Moan, J. J. Photochem. Photobiol. B 2005, 80, 47. doi: 10.1016/j.jphotobiol.2005.03.001 doi: 10.1016/j.jphotobiol.2005.03.001
2. [2]
  Juzeniene, A.; Tam, T. T. T.; Iani, V.; Moan, J. T. J. Photochem. Photobiol. B 2013, 126, 11. doi: 10.1016/j.jphotobiol.2013.05.011 doi: 10.1016/j.jphotobiol.2013.05.011
3. [3]
  Hu, J. M.; Qian, Y. F.; Wang, X. F.; Liu, T.; Liu, S. Y. Langmuir 2012, 28, 2073. doi: 10.1021/la203992q doi: 10.1021/la203992q
4. [4]
  Leamon, C. P.; Reddy, J. A. Adv. Drug Deliv. Rev. 2004, 56, 1127. doi: 10.1016/j.addr.2004.01.008 doi: 10.1016/j.addr.2004.01.008
5. [5]
  Li, W. J.; Shi, J.; Zhang, C.; Li, M.; Gan, L.; Xu, H. B.; Yang. X. L. J. Mater. Chem. B 2014, 2, 4901. doi: 10.1039/c4tb00502c doi: 10.1039/c4tb00502c
6. [6]
  Zhu, J.; Liao, L.; Zhu, L. N.; Kong, J. L.; Liu, B. H. Acta Chim. Sinica 2013, 71, 69. doi: 10.6023/A12090680
7. [7]
  Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. doi: 10.1002/anie.199302481 doi: 10.1002/anie.199302481
8. [8]
  Xing, P. Y.; Chu, X. X.; Du, G. Y.; Li, M. Z.; Su, J.; Hao, A. Y.; Hou, Y. H.; Li, S. Y.; Ma, M. F.; Wu, L.; et al. RSC Adv. 2013, 3, 15237. doi: 10.1039/c3ra42129e doi: 10.1039/c3ra42129e
9. [9]
  Xing, P. Y.; Chu, X. X.; Ma, M. F.; Li, S. Y.; Hao, A. Y. Phys. Chem. Chem. Phys. 2014, 16, 8346. doi: 10.1039/c4cp00367e doi: 10.1039/c4cp00367e
10. [10]
  Xing, P. Y.; Chu, X. X.; Ma, M. F.; Li, S. Y.; Zhang, Y. M.; Hao, A. Y. RSC Adv. 2014, 4, 36633. doi: 10.1039/c4ra04585h doi: 10.1039/c4ra04585h
11. [11]
  Akhtar, M. J.; Khan, M. A.; Ahmad, I. J. Pharm. Biomed. Anal. 1999, 19, 269. doi: 10.1016/S0731-7085(98)00038-7 doi: 10.1016/S0731-7085(98)00038-7
12. [12]
  Thomas, A. H.; Suárez, G.; Cabrerizo, F. M.; Martino, R.; Capparelli, A. L. J. Photochem. Photobiol. A: Chem. 2000, 135, 147. doi: 10.1016/S1010-6030(00)00304-X doi: 10.1016/S1010-6030(00)00304-X
13. [13]
  Jamil Akhtar, M.; Ataullah Khan, M.; Ahmad, I. J. Pharm. Biomed. Anal. 1999, 19, 269. doi: 10.1016/S0731-7085(98)00038-7 doi: 10.1016/S0731-7085(98)00038-7
14. [14]
  Vorobey, P.; Steindal, A. E.; Off, M. K.; Vorobey, A.; Moan, J. Photochem. Photobiol. 2006, 82, 817. doi: 10.1562/2005-11-23-RA-739 doi: 10.1562/2005-11-23-RA-739
15. [15]
  Liang, L.; Subirade, M. J. Phys. Chem. B 2010, 114, 6707. doi: 10.1021/jp101096r doi: 10.1021/jp101096r
16. [16]
  Bourassa, P.; Tajmir-Riahi, H. A. J. Phys. Chem. B 2012, 116, 513. doi: 10.1021/jp2083677 doi: 10.1021/jp2083677
17. [17]
  Tavares, G. M.; Croguennec, T.; Le, S.; Lerideau, O.; Hamon, P.; Carvalho, A. F.; Bouhallab, S. Langmuir 2015, 31, 12481. doi: 10.1021/acs.langmuir.5b02299 doi: 10.1021/acs.langmuir.5b02299
18. [18]
  Madziva, H.; Kailasapathy, K.; Phillips, M. J. Microencapsul. 2005, 22, 343. doi: 10.1080/02652040500100931 doi: 10.1080/02652040500100931
19. [19]
  Drummond, C. J.; Fong, C. Curr. Opin. Colloid Interface Sci. 1999, 4, 449. doi: 10.1016/S1359-0294(00)00020-0 doi: 10.1016/S1359-0294(00)00020-0
20. [20]
  Zhang, H. X.; Annunziata, O. Langmuir 2008, 24, 10680. doi: 10.1021/la802080t doi: 10.1021/la802080t
21. [21]
  Bhat, P. A.; Rather, G. M.; Dar, A. A. J. Phys. Chem. B 2009, 113, 997. doi: 10.1021/jp807229c. doi: 10.1021/jp807229c
22. [22]
  Xie, H. J.; Liu, C. C.; Sun, Q.; Gu, Q.; Lei, Q. F.; Fang, W. J. Acta Phys. -Chim. Sin. 2016, 32, 295. doi: 10.3866/PKU.WHXB201609231
23. [23]
  Treger, J. S.; Ma, V. Y.; Gao, Y.; Wang, C. C.; Jeon, S.; Robinson, J. M.; Wang, H. L.; Johal, M. S. Langmuir 2008, 24, 13127. doi: 10.1021/la802080t doi: 10.1021/la802080t
24. [24]
  Carlotti, M. E.; Sapino, S.; Vione, D.; Pelizzetti, E.; Trotta, M. J. Dispersion Sci. Technol. 2004, 25, 193. doi: 10.1081/dis-120030666 doi: 10.1081/dis-120030666
25. [25]
  Leung, M. H. M.; Colangelo, H.; Kee, T. W. Langmuir 2008, 24, 5672. doi: 10.1021/la800780w doi: 10.1021/la800780w
26. [26]
  Wan, Z. Z.; Ke, D.; Hong, J. X.; Wang, X. Y.; Shen, W. G. Colloids Surf., A Physicochem. Eng. Aspects 2012, 414, 267. doi: 10.1016/j.colsurfa.2012.08.046 doi: 10.1016/j.colsurfa.2012.08.046
27. [27]
  Wang, M. N.; Wu, C. X.; Tang, Y. Q.; Fan, Y. X.; Han, Y. C.; Wang, Y. L. Soft Matter 2014, 10, 3432. doi: 10.1039/c4sm00086b doi: 10.1039/c4sm00086b
28. [28]
  Shikata, T.; Hirata, H.; Kotaka, T. Langmuir 1989, 5, 398. doi: 10.1021/la00086a020 doi: 10.1021/la00086a020
29. [29]
  Hassan, P.; Yakhmi, J. Langmuir 2007, 23, 10044. doi: 10.1021/la701542k doi: 10.1021/la701542k
30. [30]
  Wattebled, L.; Laschewsky. Langmuir 2000, 16, 7187. doi: 10.1021/la000517o doi: 10.1021/la000517o
31. [31]
  Yu, D.F.; Huang, X.; Deng, M.L.; Wang, Y. L. J. Phys. Chem. B 2010, 114, 14955. doi: 10.1021/jp106031d doi: 10.1021/jp106031d
32. [32]
  Jiang, L. X.; Huang, J. B.; Bahramian, A.; Li, P. X.; Thomas, R. K.; Penfold, J. Langmuir 2012, 28, 327. doi: 10.1021/la2040938 doi: 10.1021/la2040938
33. [33]
  Wang, R. J.; Tian, M. Z.; Wang, Y. L. Soft Matter 2014, 10, 1705. doi: 10.1039/c3sm52819g doi: 10.1039/c3sm52819g
34. [34]
  Wang, M. N.; Fan, Y. X.; Han, Y. C.; Nie, Z. X.; Wang, Y. L. Langmuir 2013, 29, 14839. doi: 10.1021/la403582y doi: 10.1021/la403582y
35. [35]
  Laschewsky, A.; Wattebled, L.; Arotarena, M.; Habib-Jiwan, J.; Rakotoaly, R. H. Langmuir 2005, 21, 7170. doi: 10.1021/la050952o doi: 10.1021/la050952o
36. [36]
  Hou, Y. B.; Han, Y. C.; Deng, M. L.; Wang, Y. L. Langmuir 2008, 26, 28. doi: 10.1021/la903672r doi: 10.1021/la903672r
37. [37]
  In, M.; Bec, V.; Aguerre-Chariol, O.; Zana, R. Langmuir 2000, 16, 141. doi: 10.1021/la990645g doi: 10.1021/la990645g
38. [38]
  Fan, Y. X.; Han, Y. C.; Wang, Y. L. Acta Phys. -Chim. Sin. 2016, 32, 214. doi: 10.3866/PKU.WHXB201511022
39. [39]
  Zana, R.; Levy, H.; Papoutsi, D.; Beinert, G. Langmuir 1995, 11, 3694. doi: 10.1021/la00010a018 doi: 10.1021/la00010a018
40. [40]
  Lou, P. X.; Wang, Y. J.; Bai, G. Y.; Fan, C. Y.; Wang, Y. L. Acta Phys. -Chim. Sin. 2013, 29, 1401. doi: 10.3866/PKU.WHXB201304282
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