339
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Designing of new cationic surfactant based micellar systems as drug carriers: an investigation into the drug cell membrane interactions

, , , , , & show all
Pages 958-968 | Received 21 Apr 2018, Accepted 10 Jun 2018, Published online: 08 Oct 2018

References

  • Lin, J. ; Zhang, S. ; Chen, T. ; Lin, S. ; Jin, H . Micelle Formation and Drug Release Behavior of Polypeptide Graft Copolymer and Its Mixture with Polypeptide Block Copolymer. Int. J. Pharm. 2007, 336 , 49–57. DOI: 10.1016/j.ijpharm.2006.11.026
  • Torchilin, V. P . Structure and Design of Polymeric Surfactant-Based Drug Delivery Systems. J. Controlled Release 2001, 73 , 137–172. DOI: 10.1016/S0168-3659(01)00299-1
  • Abildskov, J. ; O’Connell, J. P . Molecular Thermodynamic Modeling and Design of Microencapsulation Systems for Drug Delivery. J. Chem. Eng. Data 2011, 56 , 1229–1237. DOI: 10.1021/je1011218
  • Noori, S. ; Naqvi, A. Z. ; Ansari, W. H . Experimental and Theoretical Approach to Cationic Drug-Anionic Gemini Surfactant Systems in Aqueous Medium. Colloids Surf. B 2014, 115 , 71–78. DOI: 10.1016/j.colsurfb.2013.11.023
  • Li, X. ; Xie, Y. ; Chen, Z. ; Zou, G . The Interaction of 2-Hydroquinone-5, 10, 15, 20-Tetra (p-Hydroxyphenyl) Porphyrin with Surfactants: Solubilization and J-Aggregates. Spectrochim. Acta Part A 2005, 61 , 2468–2473. DOI: 10.1016/j.saa.2004.09.011
  • Khan, A. B. ; Naqvi, A. Z . Mixed Micellization of Antidepressant Drug Amitriptyline Hydrochloride with Cationic Surfactants. Colloids Surf. B 2010, 80 , 206–212. DOI: 10.1016/j.colsurfb.2010.06.007
  • Al-Ahmadi, M. D. ; Naqvi, A. Z. ; Akram, M . Conductometric Study of Antidepressant Drug–Cationic Surfactant Mixed Micelles in Aqueous Solution. Colloids Surf. B 2008, 64 , 65–69. DOI: 10.1016/j.colsurfb.2008.01.005
  • Bhat, P. A. ; Dar, A. A. ; Rather, G. M . Solubilization Capabilities of Some Cationic, Anionic, and Nonionic Surfactants toward the Poorly Water-Soluble Antibiotic Drug Erythromycin. J. Chem. Eng. Data 2008, 53 , 1271–1277. DOI: 10.1021/je700659g
  • Desai, K. G. H. ; Kulkarni, A. R. ; Aminabhavi, T. M . Solubility of Rofecoxib in the Presence of Methanol, Ethanol, and Sodium Lauryl Sulfate at (298.15, 303.15, and 308.15) K. J. Chem. Eng. Data 2003, 48 , 942–945. DOI: 10.1021/je020213z
  • Sharma, R. ; Mahajan, R. K . An Investigation of Binding Ability of Ionic Surfactants with Trifluoperazine Dihydrochloride: Insights from Surface Tension, Electronic Absorption and Fluorescence Measurements. RSC Adv. 2012, 2 , 9571–9583. DOI: 10.1039/C2RA21020G
  • Maswal, M. ; Chat, O. A. ; Jabeen, S. ; Ashraf, U. ; Masrat, R. ; Shah, R. A. ; Dar, A. A . Solubilization and Co-Solubilization of Carbamazepine and Nifedipine in Mixed Micellar Systems: Insights from Surface Tension, Electronic Absorption, Fluorescence and HPLC Measurements. RSC Adv. 2015, 5 , 7697–7712. DOI: 10.1039/C4RA09870F
  • Rub, M. A. ; Naqvi, A. Z . Mixed Micelles of Amphiphilic Drug Promethazine Hydrochloride and Surfactants (Conventional and Gemini) at 293.15 K to 308.15 K: Composition, Interaction and Stability of the Aggregates. J. Colloid Interface Sci. 2011, 354 , 700–708. DOI: 10.1016/j.jcis.2010.11.005
  • Rub, M. A. ; Naqvi, A. Z . Micellization of Mixtures of Amphiphilic Drugs and Cationic Surfactants: A Detailed Study. Colloids Surf. B 2012, 92 , 16–24. DOI: 10.1016/j.colsurfb.2011.11.002
  • Quagliotto, P. ; Barbero, N. ; Barolo, C. ; Artuso, E. ; Compari, C. ; Fisicaro, E. ; Viscardi, G . Synthesis and Properties of Cationic Surfactants with Tuned Hydrophylicity. J. Colloid Interface Sci. 2009, 340 , 269–275. DOI: 10.1016/j.jcis.2009.09.009
  • Viscardi, G. ; Quagliotto, P. ; Barolo, C. ; Savarino, P. ; Barni, E. ; Fisicaro, E . Synthesis and Surface and Antimicrobial Properties of Novel Cationic Surfactants. J. Org. Chem. 2000, 65 , 8197–8203. DOI: 10.1021/jo0006425
  • Bijma, K. ; Engberts, J. B . Effect of Counterions on Properties of Micelles Formed by Alkylpyridinium Surfactants. 1. Conductometry and 1H-NMR Chemical Shifts. Langmuir 1997, 13 , 4843–4849. DOI: 10.1021/la970171q
  • Benito, I. ; Garcia, M. ; Monge, C. ; Saz, J. ; Marina, M . Spectrophotometric and Conductimetric Determination of the Critical Micellar Concentration of Sodium Dodecyl Sulfate and Cetyltrimethylammonium Bromide Micellar Systems Modified by Alcohols and Salts. Colloids Surf. A 1997, 125 , 221–224. DOI: 10.1016/S0927-7757(97)00014-9
  • Khan, A. M. ; Shah, S. S . A UV-Visible Study of Partitioning of Pyrene in an Anionic Surfactant Sodium Dodecyl Sulfate. J. Dispers. Sci. Technol. 2008, 29 , 1401–1407. DOI: 10.1080/01932690802313246
  • Gul, F. ; Khan, A. M. ; Shah, S. S. ; Nazar, M. F . Spectroscopic Study of Alizarin Red s Binding with Cetyltrimethylammonium Bromide at Low Concentrations. Color. Technol. 2010, 126 , 109–113. DOI: 10.1111/j.1478-4408.2010.00236.x
  • Akbaş, H. ; Taner, T . Spectroscopic Studies of Interactions between CI Reactive Orange 16 with Alkyltrimethylammonium Bromide Surfactants. Spectrochim. Acta Part A 2009, 73 , 150–153. DOI: 10.1016/j.saa.2009.02.018
  • Zaghbani, N. ; Dhahbi, M. ; Hafiane, A . Spectral Study of Eriochrome Blue Black R in Different Cationic Surfactant Solutions. Spectrochim. Acta Part A 2011, 79 , 1528–1531. DOI: 10.1016/j.saa.2011.05.011
  • Ali, A. ; Afzal, S. ; Ashraf, M. ; Amin, S. ; Javeed, A. ; Usman, M . Pharmacokinetic Study of Ketoprofen in Healthy Sheep under Local Conditions of Pakistan. J. Anim. Plant Sci. 2012, 22 , 588–592. DOI: 10.1016/j.saa.2011.05.011
  • Zaidan, M. ; Noor Rain, A. ; Badrul, A. ; Adlin, A. ; Norazah, A. ; Zakiah, I . In Vitro Screening of Five Local Medicinal Plants for Antibacterial Activity Using Disc Diffusion Method. Trop. Biomed. 2005, 22 , 165–170.
  • Sirajuddin, M. ; Ali, S. ; McKee, V. ; Sohail, M. ; Pasha, H . Potentially Bioactive Organotin (IV) Compounds: Synthesis, Characterization, in Vitro Bioactivities and Interaction with SS-DNA. Eur. J. Med. Chem. 2014, 84 , 343–363. DOI: 10.1016/j.ejmech.2014.07.028
  • Rabbani, M. G. ; Islam, M. R. ; Ahmad, M. ; Hossion, A. M. L . Synthesis of Some NH-Derivatives of Ciprofloxacin as Antibacterial and Antifungal Agents. Bangladesh J. Pharmacol. 2011, 6 , 8–13. DOI: 10.3329/bjp.v6i1.7720
  • Cook, D . Vibrational Spectra of Pyridinium Salts. Can. J. Chem. 1961, 39 , 2009–2024. DOI: 10.1139/v61-271
  • Clark, R. J. ; Williams, C. S . The Far-Infrared Spectra of Metal-Halide Complexes of Pyridine and Related Ligands. Inorg. Chem. 1965, 4 , 350–357. DOI: 10.1021/ic50025a020
  • Gill, N. ; Nuttall, R. H. ; Scaife, D. ; Sharp, D. A . The Infra-Red Spectra of Pyridine Complexes and Pyridinium Salts. J. Inorg. Nucl. Chem 1961, 18 , 79–87. DOI: 10.1016/0022-1902(61)80372-2
  • Engin Özdil, S. ; Akbaş, H. ; Boz, M . ; Synthesis and Physicochemical Properties of Double-Chain Cationic Surfactants. J. Chem. Eng. Data 2016, 61 , 142–150. DOI: 10.1021/acs.jced.5b00367
  • Ruiz, C. C . Thermodynamics of Micellization of Tetradecyltrimethylammonium Bromide in Ethylene Glycol–Water Binary Mixtures. Colloid Polym. Sci. 1999, 277 , 701–707. DOI: 10.1007/s003960050443
  • Manabe, M. ; Kawamura, H. ; Yamashita, A. ; Tokunaga, S . Effect of Alkanols on Intermicellar Concentration and on Ionization of Micelles. J. Colloid Interface Sci. 1987, 115 , 147–154. DOI: 10.1016/0021-9797(87)90019-1
  • Mata, J. ; Varade, D. ; Bahadur, P . Aggregation Behavior of Quaternary Salt Based Cationic Surfactants. Thermochim. Acta 2005, 428 , 147–155. DOI: 10.1016/j.tca.2004.11.009
  • Liu, T. Q. ; Guo, R . Influence of Low Cetyltrimethylammonium Bromide Concentration on the Interactions and Properties of Hemoglobin with Acyclovir. Chin. J. Chem. 2006, 24 , 620–626. DOI: 10.1002/cjoc.200690119
  • Zhang, L. ; Dong, Y. ; Zhang, X. ; Guo, X . Micellization of Lactosylammonium Surfactants with Different Counter Ions and Their Interaction with DNA. J. Chem. Eng. Data 2016, 61 , 2969–2978. DOI: 10.1021/acs.jced.5b01057
  • Shah, S. ; Saeed, A. ; Sharif, Q . A Study of Micellization Parameters and Electrostatic Interactions in Micellar Solution of Sodium Dodecyl Sulfate. Colloids Surf. A 1999, 155 , 405–412. DOI: 10.1016/S0927-7757(99)00021-7
  • Shah, F. A. ; Khan, A. M. ; Sabir, S. ; Ali, S . CTAB–Tributylstannic [3-(3′, 4′-Dichlorophenylamido) Propanoate] Interaction: A Tool for Predicting Organotin (IV) Complex–Cell Membrane Interaction Parameters. Colloid Polym. Sci. 2016, 294 , 87–94. DOI: 10.1007/s00396-015-3738-x
  • Klevens, H . Structure and Aggregation in Dilate Solution of Surface Active Agents. J. Am. Oil Chem. Soc. 1953, 30 , 74–80. DOI: 10.1007/BF02635002
  • Farías, T. ; De Menorval, L.-C. ; Zajac, J. ; Rivera, A . Solubilization of Drugs by Cationic Surfactants Micelles: Conductivity and 1 H NMR Experiments. Colloids Surf. A 2009, 345 , 51–57. DOI: 10.1016/j.colsurfa.2009.04.022
  • Schreier, S. ; Malheiros, S. V. ; de Paula, E . Surface Active Drugs: self-Association and Interaction with Membranes and Surfactants. Physicochemical and Biological Aspects. Biochim. Biophys. Acta 2000, 1508 , 210–234. DOI: 10.1016/S0304-4157(00)00012-5
  • Gantiva, M. ; Yurquina, A. ; Martínez, F . Solution Thermodynamics of Ketoprofen in Ethanol + Water Cosolvent Mixtures. J. Chem. Eng. Data 2010, 55 , 113–118. DOI: 10.1021/je9002866
  • Kantor, T. G . Ketoprofen: A Review of Its Pharmacologic and Clinical Properties. Pharmacotherapy 1986, 6 , 93–102. DOI: 10.1002/j.1875-9114.1986.tb03459.x
  • Mazières, B. ; Rouanet, S. ; Guillon, Y. ; Scarsi, C. ; Reiner, V . Topical Ketoprofen Patch in the Treatment of Tendinitis: A Randomized, Double Blind, Placebo Controlled Study. J. Rheumatol. 2005, 32 , 1563–1570.
  • Sekiya, I. ; Morito, T. ; Hara, K. ; Yamazaki, J. ; Ju, Y.-J. ; Yagishita, K. ; Mochizuki, T. ; Tsuji, K. ; Muneta, T . Ketoprofen Absorption by Muscle and Tendon after Topical or Oral Administration in Patients Undergoing Anterior Cruciate Ligament Reconstruction. AAPS PharmSciTech 2010, 11 , 154–158. DOI: 10.1208/s12249-009-9367-2
  • Altman, R. ; Bosch, B. ; Brune, K. ; Patrignani, P. ; Young, C . Advances in NSAID Development: evolution of Diclofenac Products Using Pharmaceutical Technology. Drugs 2015, 75 , 859–877. DOI: 10.1007/s40265-015-0392-z
  • Zafar, F. ; Shah, A. ; Khan, A. M. ; Rana, U. A. ; Siddiq, Z. A. M. ; Ali, S . A Spectroscopic and Electrochemical Investigation of Interactions of Anticancer Uracil Derivatives with Cationic and Anionic Surfactants. J. Chem. Soc. Pak. 2015, 37 , 290–299.
  • Kawamura, H. ; Manabe, M. ; Miyamoto, Y. ; Fujita, Y. ; Tokunaga, S . Partition Coefficients of Homologous. Omega.-Phenylalkanols between Water and Sodium Dodecyl Sulfate Micelles. J. Phys. Chem. 1989, 93 , 5536–5540. DOI: 10.1021/j100351a042
  • Hosseinzadeh, R. ; Maleki, R. ; Matin, A. A. ; Nikkhahi, Y . Spectrophotometric Study of Anionic Azo-Dye Light Yellow (X6G) Interaction with Surfactants and Its Micellar Solubilization in Cationic Surfactant Micelles. Spectrochim. Acta Part A 2008, 69 , 1183–1187. DOI: 10.1016/j.saa.2007.06.022
  • Abdel-Fattah, L. ; Abdel-Aziz, L. ; Gaied, M . Enhanced Spectrophotometric Determination of Losartan Potassium Based on Its Physicochemical Interaction with Cationic Surfactant. Spectrochim. Acta Part A 2015, 136 , 178–184. DOI: 10.1016/j.saa.2014.09.007
  • Naseem, B. ; Sabri, A. ; Hasan, A. ; Shah, S. S . Interaction of Flavonoids within Organized Molecular Assemblies of Anionic Surfactant. Colloids Surf. B 2004, 35 , 7–13. DOI: 10.1016/j.colsurfb.2004.01.012
  • Awan, M. A. ; Shah, S . Hydrophobic Interaction of Amphiphilic Hemicyanine Dyes with Cationic and Anionic Surfactant Micelles. Colloids Surf. A 1997, 122 , 97–101. DOI: 10.1016/S0927-7757(96)03825-3

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.