Abstract
A homologous series of cationic surfactants with a pyrrolidinium head group containing a hydroxyethyl moiety was studied for the solubilization of nonsteroidal anti-inflammatory drugs, indomethacin and meloxicam, and the antioxidant quercetin. For indomethacin, the solubilization capacity linearly increases with increasing number of carbon atoms in the alkyl chain. In the case of quercetin and meloxicam, the solubilization capacity passes through a maximum for the hexadecyl derivative. The possibility of solubilization by premicellar surfactant aggregates was shown for indomethacin and meloxicam.
Similar content being viewed by others
References
D. A. Samarkina, D. R. Gabdrakhmanov, V. E. Semenov, F. G. Valeeva, A. E. Nikolaev, L. F. Saifina, L. Ya. Zakharova, Russ. J. Gen. Chem., 2017, 87, 1977; DOI: https://doi.org/10.1134/s1070363217090134.
D. A. Kuznetsova, D. R. Gabdrakhmanov, S. S. Lukashenko, A. D. Voloshina, A. S. Sapunova, R. R. Kashapov, L. Ya. Zakharova, Chem. Phys. Lipids, 2019, 223, 104791; DOI: https://doi.org/10.1016/j.chemphyslip.2019.104791.
X. Liu, N. L. Abbott, J. Phys. Chem. B, 2010, 114, 15554; DOI: https://doi.org/10.1021/jp107936b.
F. E. Heakal, A. E. Elkholy, J. Mol. Liq., 2017, 230, 395; DOI: https://doi.org/10.1016/j.molliq.2017.01.047.
R. V. Pavlov, G. A. Gaynanova, D. A. Kuznetsova, L. A. Vasileva, I. V. Zueva, A. S. Sapunova, D. N. Buzyurova, V. M. Babaev, A. D. Voloshina, S. S. Lukashenko, I. Kh. Rizvanov, K. A. Petrov, L. Ya. Zakharova, O. G. Sinyashin, Int. J. Pharm., 2020, 587, 119640; DOI: https://doi.org/10.1016/j.ijpharm.2020.119640.
S. Younis, M. Usman, A. U. Haq, N. Akram, M. Saeed, S. Raza, M. Siddiq, F. Bukhtawar, Chem. Phys. Lett., 2020, 738, 136890; DOI: https://doi.org/10.1016/j.cplett.2019.136890.
D. R. Gabdrakhmanov, D. A. Samarkina, E. S. Krylova, I. V. Kapitanov, Y. Karpichev, S. K. Latypov, V. E. Semenov, I. R. Nizameev, M. K. Kadirov, L. Ya. Zakharova, J. Surfactants Deterg., 2019, 22, 865; DOI: https://doi.org/10.1002/jsde.12257.
M. Jabbari, A. Jabbari, Colloids Surf., A, Physicochem. Eng. Asp., 2016, 489, 392; DOI: https://doi.org/10.1016/j.colsurfa.2015.11.022.
M. O. Jibrin, Q. Liu, J. B. Jones, S. Zhang, Plant Pathol., 2020, 1; DOI: https://doi.org/10.1111/ppa.13318.
A. A Revina, K. F. Chernyshova, N. Y. Tabachkova, Y. N. Parkhomenko, Russ. Chem. Bull., 2019, 68, 1164; DOI: https://doi.org/10.1007/s11172-019-2534-z.
X. Gao, B. R. Jasti, M. Huang, X. Wang, R. Mahalingam, X. LiInt, J. Pharm., 2020, 588, 119789; DOI: https://doi.org/10.1016/j.ijpharm.2020.119789.
M. Jabbari, F. Teymoori, J. Mol. Liq., 2018, 262, 1; DOI: https://doi.org/10.1016/j.molliq.2018.04.054.
Z. Vinarov, V. Katev, D. Radeva, S. Tcholakova, N. D. Denkov, Drug Dev. Ind. Pharm., 2018, 44, 677; DOI: https://doi.org/10.1080/03639045.2017.1408642.
H. D. Williams, N. L. Trevaskis, S. A. Charman, R. M. Shanker, W. N. Charman, C. W. Pouton, C. J. H. Porter, Pharmacol. Rev., 2013, 65, 315; DOI: https://doi.org/10.1124/pr.112.005660.
A. Saraf, S. Sharma, S. Sachar, J. Mol. Liq., 2020, 319, 114060; DOI: https://doi.org/10.1016/j.molliq.2020.114060.
M. Dasgupta, E. Judy, N. Kishore, Colloid. Surface B., 2020, 187, 110730; DOI: https://doi.org/10.1016/j.colsurfb.2019.110730.
C. K. Kim, S. J. Lim, Arch. Pharm. Res., 2002, 25, 229; DOI: https://doi.org/10.1007/BF02976620.
P. A. Bhat, G. M. Rather, A. A. Dar, J. Phys. Chem. B., 2009, 113, 997; DOI: https://doi.org/10.1021/jp807229c.
V. P. Torchilin, J. Control. Release, 2001, 73, 137; DOI: https://doi.org/10.1016/S0168-3659(01)00299-1.
O. Sunnapu, P. Ravipati, P. Srinath, S. Kalita, P. P. Bhat, S. R. Harshitha, K. Sekar, P. K. Vemula, M. Mahato, Bull. Mater. Sci., 2020, 43, 172; DOI: https://doi.org/10.1007/s12034-020-02089-4.
M. Shakeel, K. Mehmood, M. Siddiq, Proc. Natl. Acad. Sci. India, Sect. A: Phys. Sci., 2020, 90, 389; DOI: https://doi.org/10.1007/s40010-018-0587-2.
M. Spaglova, M. Cuchorova, V. Simunkova, D. Matusova, M. Cierna, L. Starychova, K. Bauerova, Drug. Dev. Ind. Pharm., 2020, 46, 1468; DOI: https://doi.org/10.1080/03639045.2020.1802483.
J. Swarbrick, J. Pharm. Sci., 1965, 54, 1229; DOI: https://doi.org/10.1002/jps.2600540902.
L. Pathania, S. Chauhan, J. Mol. Liq., 2020, 299, 112210; DOI: https://doi.org/10.1016/j.molliq.2019.
M. F. Nazar, F. Mukhtar, S. Chaudry, M. Ashfaq, S. Mehmood, A. Asif, U. A. Rana, J. Mol. Liq., 2014, 200, 361; DOI: https://doi.org/10.1016/j.molliq.2014.11.007.
B. Ahmad, S. Parveen, R. H. Khan, Biomacromolecules, 2006, 7, 1350; DOI: https://doi.org/10.1021/bm050996b.
B. C. Stephenson, C. O. Rangel-Yagui, A. Pessoa, L. C. Tavares, K. Beers, D. Blankschtein, Langmuir, 2006, 22, 1514; DOI: https://doi.org/10.1021/la052530k.
P. A. Bhat, A. A. Dar, G. M. Rather, J. Chem. Eng. Data, 2008, 53, 1271; DOI: https://doi.org/10.1021/je700659g.
A. Rehman, M. Usman, T. H. Bokhari, H. M. A. U. Rahman, A. Mansha, M. Siddiq, A. Rasheedd, M. U. Nisa, Colloids Surf. A Physicochem. Eng. Asp., 2020, 586, 124241; DOI: https://doi.org/10.1016/j.colsurfa.2019.124241.
R. A. Kushnazarova, A. B. Mirgorodskaya, S. S. Lukashenko, A. D. Voloshina, A. S. Sapunova, I. R. Nizameev, M. K. Kadirov, L. Ya. Zakharova, J. Mol. Liq., 2020, 318, 113894; DOI: https://doi.org/10.1016/j.molliq.2020.113894.
Z. Vinarov, P. Dobreva, S. Tcholakova, J. Drug. Deliv. Sci. Technol., 2018, 43, 44; DOI: https://doi.org/10.1016/j.jddst.2017.09.014.
T. N. Pashirova, E. A. Burilova, S. S. Lukashenko, N. K. Gaysin, O. I. Gnezdilov, A. S. Sapunova, A. R. Fernandes, A. D. Voloshina, E. B. Souto, E. P. Zhiltsova, L. Ya. Zakharova, J. Mol. Liq., 2019, 296, 112062; DOI: https://doi.org/10.1016/j.molliq.2019.112062.
D. A. Kuznetsova, D. R. Gabdrakhmanov, L. R. Ahtamyanova, S. S. Lukashenko, A. M. Kusova, Y. F. Zuev, A. D. Voloshina, A. S. Sapunova, N. V. Kulik, D. M. Kuznetsov, I. R. Nizameev, M. K. Kadirov, L. Ya. Zakharova, J. Mol. Liq., 2020, 298, 111961; DOI: https://doi.org/10.1016/j.molliq.2019.111961.
E. A. Vasilieva, S. S. Lukashenko, A. D. Voloshina, A. S. Strobykina, L. A. Vasileva, L. Y. Zakharova, Russ. Chem. Bull., 2018, 67, 1280; DOI: https://doi.org/10.1007/s11172-018-2213-5.
B. Vyas, S. Pillai, A. Bahadur, P. Bahadur, Polymers, 2018, 10, 76; DOI: https://doi.org/10.3390/polym10010076.
E. A. Vasilieva, S. S. Lukashenko, L. A. Vasileva, R. V. Pavlov, G. A. Gaynanova, L. Y. Zakharova, Russ. Chem. Bull., 2019, 68, 341; DOI: https://doi.org/10.1007/s11172-019-2390-x.
H. Pool, S. Mendoza, H. Xiao, D. J. McClements, Food Funct., 2013, 4, 162; DOI: https://doi.org/10.1039/c2fo30042g.
I. Casero, D. Sicilia, S. Rubio, D. Pérez-Bendito, Talanta, 1997, 45, 167; DOI: https://doi.org/10.1016/S0039-9140(97)00117-3.
P. Bilski, R. N. Holt, C. F. Chignell, J. Photochem. Photobiol. A. Chem., 1997, 110, 67; DOI: https://doi.org/10.1016/S1010-6030(97)00166-4.
R. Hadgiivanova, H. Diamant, J. Chem. Phys., 2009, 130, 114901; DOI: https://doi.org/10.1063/1.3088828.
W. Zhao, K. Song, Y. Chen, H. Wang, Z. Liu, Q. Shi, J. Huang, Y. Wang, Langmuir, 2017, 33, 12719; DOI: https://doi.org/10.1021/acs.langmuir.7b03137.
P. Sieger, Y. Cui, S. Scheuerer, Eur. J. Pharm. Sci., 2017, 105, 82; DOI: https://doi.org/10.1016/j.ejps.2017.04.016.
I. Ullah, M. K. Baloch, G. F. Durrani, J. Solution Chem., 2011, 40, 1341; DOI: https://doi.org/10.1007/s10953-011-9709-z.
A. B. Mirgorodskaya, R. A. Kushnazarova, S. S. Lukashenko, L. Ya. Zakharova, J. Mol. Liq., 2019, 292, 111407; DOI: https://doi.org/10.1016/j.molliq.2019.111407.
A. B. Mirgorodskaya, R. A. Kushnazarova, S. S. Lukashenko, L. Ya. Zakharova, Russ. Chem. Bull., 2019, 68, 328; DOI: https://doi.org/10.1007/s11172-019-2388-4.
I. G. Zenkevich, A. Yu. Eshchenko, S. V. Makarova, A. G. Vitenberg, Yu. G. Dobryakov, V. A. Utsal, Molecules, 2007, 12, 654; DOI: https://doi.org/10.3390/12030654.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1341-1348, July, 2021.
To the 75th anniversary of the A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences.
Based on the materials of the 2nd Scientific Conference “Dynamic Processes in the Chemistry of Organoelement Compounds” (November 11–13, 2020, Kazan, Russia).
This study was financially supported by the Russian Foundation for Basic Research and the Cabinet of Ministers of the Republic of Tatarstan (Project No. 18-43-160015).
This paper does not contain descriptions of studies on animals or humans.
The authors declare no competing interests.
Rights and permissions
About this article
Cite this article
Vasileva, L.A., Kuznetsova, D.A., Valeeva, F.G. et al. Micellar nanocontainers based on cationic surfactants with a pyrrolidinium head group for increasing drug bioavailability. Russ Chem Bull 70, 1341–1348 (2021). https://doi.org/10.1007/s11172-021-3221-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-021-3221-4