Aggregation and Solubilization Properties of System Based on Glycine-Calix[4]resorcinol and Sodium Dodecyl Sulfate in Aqueous Medium

Alina M. Bekmukhametova,^a Ruslan R. Kashapov,^a,b@ Maria N. Saifutdinova,^a Elena L. Gavrilova,^a Vakhid A. Mamedov,^a,b Nataliya A. Zhukova,^a,b Lucia Ya. Zakharova,^a,b and Oleg G. Sinyashin^a,b

^aKazan National Research Technological University, 420015 Kazan, Russian Federation

^bA.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, Russian Federation

^@Corresponding author E-mail: kashapov@iopc.ru

DOI: 10.6060/mhc170517k

Macroheterocycles2017 10(2) 164-168

A complex of physicochemical methods showed that the water-insoluble glycine-based сalix[4]resorcinol is solubilized by sodium dodecyl sulfate (SDS) micelles, thus not affecting the character of surfactant aggregation. pH-dependent solubilization of hydrophobic drug 2,2’-bibenzimidazole (BBI) in SDS micellar solutions in the presence of this macrocycle was shown. At acidic conditions the presence of solubilized сalix[4]resorcinol in SDS micelles leads to a decrease in the joint solubilization of BBI in aqueous micellar solutions. In this case, the protonation of the nitrogen atom at the upper rim of calixarene favors its solubilization in the SDS micelles due to electrostatic interaction. This leaves little “room” in the hydrophobic part of the micelles to solubilize the drug. In the alkaline medium, the upper rim of calixarene is recharged to negative values due to the dissociation of hydroxyl and carboxyl groups. The electrostatic repulsion between SDS and calixarene molecules frees the hydrophobic part of the surfactant micelles from the macrocycle, which increases the solubilization capacity with respect to BBI. This result is of importance from the viewpoint of the delivery of lipophilic drugs.

References:

Click here to expand or collapse this section

1. Holmberg K., Jönsson B., Kronberg B., Lindman B. Surfactants and Polymers in Aqueous Solutions. Chichester: John Wiley & Sons, 2007. 528 p.

2. Steed J.W., Atwood J.L. Encyclopedia of Supramolecular Chemistry. New York: Marcel Dekker, 2004. 1649 p.

3. Nanoreactor Engineering for Life Sciences and Medicine (Ostafin A., Landfester K., Eds.) Boston-London: Artech House, 2009. 283 p.

4. Gaynanova G.A., Vagapova G.I., Valeeva F.G., Vasilieva E.A., Galkina I.V., Zakharova L.Ya., Sinyashin O.G. Colloids Surf., A 2016, 489, 95–102.
https://doi.org/10.1016/j.colsurfa.2015.10.032

5. Gabdrakhmanov D.R., Samarkina D.A., Valeeva F.G., Sayfina L.F., Semenov V.E., Reznik V.S., Zakharova L.Ya., Konovalov A.I. Russ. Chem. Bull. 2015, 3, 573–578.
https://doi.org/10.1007/s11172-015-0902-x

6. Gabdrakhmanov D.R., Valeeva F.G., Semenov V.E., Samarkina D.A., Mikhailov A.S., Reznik V.S., Zakharova L.Ya. Macroheterocycles 2016, 9, 29–33.
https://doi.org/10.6060/mhc151194g

7. Han Y., Wang Y. Phys. Chem. Chem. Phys. 2011, 13, 1939–1956.
https://doi.org/10.1039/c0cp01196g

8. Kashapov R.R., Pashirova T.N., Kharlamov S.V., Ziganshina A.Yu., Zhiltsova E.P., Lukashenko S.S., Zakharova L.Ya., Latypov S.K., Konovalov A.I. Phys. Chem. Chem. Phys. 2011, 13, 15891–15898.
https://doi.org/10.1039/c1cp20906j

9. Kharlamov S.V., Kashapov R.R., Pashirova T.N., Zhiltsova E.P., Ziganshina A.Yu., Zakharova L.Ya., Latypov Sh.K., Konovalov A.I. J. Phys. Chem. C 2013, 117, 20280–20288.
https://doi.org/10.1021/jp406643g

10. Basilio N., Garcia-Rio L., Martin-Pastor M. Langmuir 2012, 28, 2404–2414.
https://doi.org/10.1021/la204004h

11. Kashapov R.R., Rassadkina R.I., Ziganshina A.Yu., Mukhitova R.K., Mamedov V.A., Zhukova N.A., Kadirov M.K., Nizameev I.R., Zakharova L.Y., Sinyashin O.G. RSC Adv. 2016, 6, 38548–38552.
https://doi.org/10.1039/C6RA03838G

12. Gaynanova G.A., Bekmukhametova A.M., Kashapov R.R., Ziganshina A.Y., Zakharova L.Y. Chem. Phys. Lett. 2016, 652, 190–194.
https://doi.org/10.1016/j.cplett.2016.04.021

13. Kashapov R.R., Zakharova L.Ya., Saifutdinova M.N., Kochergin Y.S., Gavrilova E.L., Sinyashin O.G. J. Mol. Liq. 2015, 208, 58–62.
https://doi.org/10.1016/j.molliq.2015.04.025

14. Kashapov R.R., Zakharova L.Ya., Saifutdinova M.N., Gavrilova E.L., Sinyashin O.G. Tetrahedron Lett. 2015, 56, 2508–2511.
https://doi.org/10.1016/j.tetlet.2015.03.113

15. Casnati A., Sansone F., Ungaro R. Acc. Chem. Res. 2003, 36, 246–254.
https://doi.org/10.1021/ar0200798

16. Khairutdinov B., Ermakova E., Sitnitsky A., Stoikov I., Zuev Y. J. Mol. Struct. 2014, 1074, 126–133.
https://doi.org/10.1016/j.molstruc.2014.05.073

17. Khanpour M., Taghvaei-Ganjali S., Zadmard R. Orient. J. Chem. 2017, 33, 274–281.
https://doi.org/10.13005/ojc/330132

18. Mamedov V.A., Beschastnova T.N., Zhukova N.A., Kadyrova S.F., Gubaidullin A.T., Sinyashin O.G. RF patent 2413722, 2011.

19. Mamedov V.A. RSC Adv. 2016, 6, 42132–42172.
https://doi.org/10.1039/C6RA03907C

20. Rahman A., Brown C.W. J. Appl. Polym. Sci. 1983, 28, 1331–1334.
https://doi.org/10.1002/app.1983.070280407

Attachment	Size
mhc170517k.pdf	1.89 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Aggregation and Solubilization Properties of System Based on Glycine-Calix[4]resorcinol and Sodium Dodecyl Sulfate in Aqueous Medium

References: