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The effect of UV irradiation on air/water interfacial activity of Tween 20–coumarin conjugates

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Abstract

In order to obtain photo-sensitive surfactants, coumarin derivatives were covalently attached, through either ester bond or ether bond, to hydroxyl groups located at the ends of PEO segments of Tween 20. The molar ratios of Tween 20 to coumarin residues in both Tween 20–coumarin conjugate having ester bond (TCES) and ether bond (TCET) were about 1:1 despite the excess coumarin in the reaction mixture. The photo-dimerization degree was in the order of TCET > TCES > a free coumarin derivative. And the air/water interfacial activity was in the order of TCET > Tween 20 > TCES. The interfacial activities of TCES and TCET increased with the UV irradiation time. This is possibly because the coumarin residues of TCES and TCET are photo-dimerized to produce Gemini surfactant-like dimeric surfactants. The photo-induced change in the interfacial activity of TCES was slightly greater than that of TCET, probably due to the difference in the length, the polarity, and the flexibility of the linker between two monomeric conjugates of Gemini-like dimeric surfactants.

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References

  1. Kerwin BA (2008) Polysorbates 20 and 80 used in the formulation of protein biotherapeutics: structure and degradation pathways. J Pharm Sci 97:2924–2935

    Article  CAS  Google Scholar 

  2. Jiao J (2008) Polyoxyethylated nonionic surfactants and their applications in topical ocular drug delivery. Adv Drug Deliv Rev 60:1663–1673

    Article  CAS  Google Scholar 

  3. Frison-Norrie S, Sporns PJ (2001) Investigating the molecular heterogeneity of polysorbate emulsifiers by MALDI-TOF MS. Agri Food Chem 49:3335–3340

    Article  CAS  Google Scholar 

  4. Nair LM, Stephens NV, Vincent S, Raghavan N, Sand PJ (2003) Determination of polysorbate 80 in parenteral formulations by high-performance liquid chromatography and evaporative light scattering detection. J Chromatogr A 1012:81–86

    Article  CAS  Google Scholar 

  5. Mal NK, Fujiwara M, Tanaka Y, Taguchi T, Matsukata M (2003) Photo-switched storage and release of guest molecules in the pore void of coumarin-modified MCM-41. J Chem Mater 15:3385–3394

    Article  CAS  Google Scholar 

  6. Seo HJ, Kim J-C (2012) Light-sensitive liposomes containing coumarin–proteinoid conjugate. J Nanosci Nanotechnol 12:4044–4050

    Article  CAS  Google Scholar 

  7. Jiang J, Qi B, Lepage M, Zhao Y (2007) Polymer micelles stabilization-on-demand through reversible photocrosslinking. Macromolecules 40:790–792

    Article  CAS  Google Scholar 

  8. He J, Zhao Y (2011) Light-responsive polymer micelles nano- and microgels based on the reversible photodimerization of coumarin. Dyes Pigment 89:278–283

    Article  CAS  Google Scholar 

  9. He J, Tong X, Zhao Y (2009) Photoresponsive nanogels based on photocontrollable cross-links. Macromolecules 42:4845–4852

    Article  CAS  Google Scholar 

  10. Nagata M, Yamamoto Y (2008) Photoreversible poly (ethylene glycol)s with pendent coumarin group and their hydrogels. React Funct Polym 68:915–921

    Article  CAS  Google Scholar 

  11. Trenor SR, Long TE, Love BJ (2004) Photoreversible chain extension of poly(ethylene glycol). Macromol Chem Phys 205:715–723

    Article  CAS  Google Scholar 

  12. Harris JM, Struck EC, Case MG, Paley MS, Yalpani M, Van Alstine JM, Brooks DE (1984) Synthesis and characterization of poly (ethylene glycol) derivatives. J Polym Sci Pol Chem 22:341–352

    Article  CAS  Google Scholar 

  13. Tocco G, Carbonaro CM, Meli G, Podda G (2009) Evaluation of photoluminescence properties of some poly(ethylene glycol)-supported coumarin derivatives. Molecules 14:1044–1055

    Article  CAS  Google Scholar 

  14. Jin Q, Liu G, Ji J (2010) Preparation of reversibly photo-cross-linked nanogels from pH-responsive block copolymers and use as nanoreactors for the synthesis of gold nanoparticles. Eur Polym J 46:2120–2128

    Article  CAS  Google Scholar 

  15. Chen Y, Geh J-L (1996) Copolymers derived from 7-acryloyloxy-4-methylcoumarin and acrylates: 1. Copolymerizability and photocrosslinking behaviours. Polymer 20:4481–4486

    Article  Google Scholar 

  16. Nino MRR, Patino JMR (1998) Surface tension of bovine serum albumin and Tween 20 at the air–aqueous interface. J Am Oil Chem Soc 75:1241–1248

    Article  CAS  Google Scholar 

  17. Weiss J, Coupland JN, McClements DJ (1996) Solubilization of hydrocarbon emulsion droplets suspended in nonionic surfactant micelle solutions. J Phys Chem 100:1066–1071

    Article  CAS  Google Scholar 

  18. El-Sadek BM (2011) Synthesis of selected Gemini surfactant: surface, biological activity and corrosion efficiency against hydrochloric acid medium. Chem Sin 2(3):125–137

    CAS  Google Scholar 

  19. Shirai A, Maeda T, Nagamune H, Matsuki H, Kaneshina S, Kourai H (2005) Biological and physicochemical properties of Gemini quaternary ammonium compounds in which the positions of a cross-linking sulfur in the spacer differ. Eur J Med Chem 40:113–123

    Article  CAS  Google Scholar 

  20. Kirby AJ, Camilleri P, Engberts JBFN, Feiters MC, Nolte RJM, Soderman O, Bergsma M, Bell PC, Fielden ML, Garcia Rodriguez CL, Guedat P, Kremer A, McGregor C, Perrin C, Ronsin G, Van Eijk MCP (2003) Gemini surfactants: new synthetic vectors for gene transfection. Angew Chem 42:1448–1457

    Article  CAS  Google Scholar 

  21. Lunkenheimer K, Wantke K-D (1981) Determination of the surface tension of surfactant solutions applying the method of Lecomte du Noiiy (ring tensiometer). Colloid Polym Sci 259:354–366

    Article  CAS  Google Scholar 

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Acknowledgments

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2011-0026059).

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Authors and Affiliations

  1. College of Biomedical Science and Institute of Bioscience and Biotechnology, Kangwon National University, 192-1, Hyoja 2 dong, Chuncheon-si, Kangwon-do, 200-701, Korea

    Hee Jin Seo, Jing Dai & Jin-Chul Kim

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  1. Hee Jin Seo
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  2. Jing Dai
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  3. Jin-Chul Kim
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Correspondence to Jin-Chul Kim.

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Hee Jin Seo and Jing Dai contributed equally to this work.

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Seo, H.J., Dai, J. & Kim, JC. The effect of UV irradiation on air/water interfacial activity of Tween 20–coumarin conjugates. Colloid Polym Sci 291, 2311–2318 (2013). https://doi.org/10.1007/s00396-013-2966-1

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  • DOI: https://doi.org/10.1007/s00396-013-2966-1

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