Abstract
Core–shell architecture of surfactant micelles can act to shield active drug molecules from the adverse environmental conditions and enhance their bioavailability. In the present study the molecular interactions of a fixed dose combination (FDC) containing ofloxacin (OFX) and ornidazole (ORN), with cetyltrimethylammonium bromide (CTAB, a quaternary ammonium surfactant) were investigated under normal physiological pH (pH 7.4 ± 0.1). The impact of the cationic micelle on the spectral and physiochemical properties of the FDC components OFX and ORN was systematically examined by electronic spectroscopy. Micellar liquid chromatography and differential spectral methods were used to optimize analysis of the magnitude of binding constants and related Gibbs energies. The results suggest the potential solubilization of drugs in the external part of the micelles, which may prove to be more helpful for their controlled release. These outcomes have been verified by the binding capacities of drug–CTAB combinational system that may be helpful to customize the uptake of drug molecules in cells.
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Wang, J., Wang, Y., Liang, W.: Delivery of drugs to cell membranes by encapsulation in PEG–PE micelles. J. Control. Release 160, 637–651 (2012)
Chen, Y., Liu, L.: Modern methods for delivery of drugs across the blood–brain barrier. Adv. Drug Deliv. Rev. 64, 640–665 (2012)
Tourné, P.C., Coasneabc, B., Inde, M., Breveta, D., Devoissellea, J.M., Viouxa, A., Viau, L.: Surfactant behavior of ionic liquids involving a drug: from molecular interactions to self-assembly. Langmuir 30, 1229–1238 (2014)
Moghimi, S.M., Hunter, A.C., Murray, J.C., Szewczyk, A.: Cellular distribution of non-ionic micelles. Science 303, 626–627 (2004)
Ménard, N., Tsapis, N., Poirier, C., Arnauld, T., Moine, L., Lefoulon, F., Péan, J.M., Fattal, E.: Drug solubilization and in vitro toxicity evaluation of lipoamino acid surfactants. Int. J. Pharm. 423, 312–320 (2012)
Enache, M., Volanschi, E.: Spectroscopic investigations of the molecular interaction of anticancer drug mitoxantrone with non-ionic surfactant micelles. J. Pharm. Pharmacol. 64, 688–696 (2012)
Tehrani-Baghaa, A.R., Singh, R.G., Holmberg, K.: Solubilization of two organic dyes by cationic ester-containing gemini surfactants. J. Colloid Interface Sci. 376, 112–118 (2012)
Bhattacharjee, J., Verma, G., Aswal, V.K., Patravale, V., Hassan, P.A.: Microstructure, drug binding and cytotoxicity of Pluronic P-123-aerosole OT mixed micelles. RSC Adv. 3, 23080–23089 (2013)
Chakrabarty, A., Das, P., Mallick, A., Chattopadhyay, N.: Effect of surfactant chain length on the binding interaction of a biological photosensitizer with cationic micelles. J. Phys. Chem. B. 112, 3684–3692 (2008)
Banerjee, P., Pramanik, S., Sarkar, A., Bhattacharya, S.C.: Modulated photophysics of 3-pyrazolyl-2-pyrazoline derivative entrapped in micellar assembly. J. Phys. Chem. B 112, 7211–7219 (2008)
Samart, N., Beuning, C.N., Haller, K.J., Rithner, C.D., Crans, D.C.: Interaction of a biguanide compound with membrane model interface systems: probing the properties of antimalaria and antidiabetic compounds. Langmuir 30, 8697–8706 (2014)
Kadam, Y., Yerramilli, U., Bahadur, A.: Solubilization of poorly water-soluble drug carbamezapine in pluronic micelles: effect of molecular characteristics, temperature and added salt on the solubilizing capacity. Colloids Surf. B 72, 141–147 (2014)
Marquezin, C.A., Hirata, I.Y., Juliano, L., Ito, A.S.: Spectroscopic characterization of 2-amino-N-hexadecyl-benzamide (AHBA), a new fluorescence probe for membranes. Biophys. Chem. 124, 125–133 (2006)
Tong, S.W., Xiang, B., Dong, D.W., Qi, X.R.: Enhanced antitumor efficacy and decreased toxicity by self-associated docetaxel in phospholipid-based micelles. Int. J. Pharm. 434, 413–419 (2012)
Badshah, A., Nawaz, S., Nazar, M.F., Shah, S.S., Hasan, A.: Synthesis of novel fluorescent cyclohexenone derivatives and their partitioning study in ionic micellar media. J. Flourescence 20, 1049–1059 (2010)
Nesben, M., Elsayed, G.M., Abdelkawy, M., Elkhateeb, S.Z.: Determination of ofloxacin and dexamethasone in dexaflox eye drops through different ratio spectra manipulating methods. Bull. Fac. Pharm. Cairo Univ. 51, 175–184 (2013)
Vinay, K.B., Ravanasiddappa, H.D., Divya, M.R., Rajendraprasad, N.: Spectrophotometric determination of ofloxacin in pharmaceuticals and human urine. Ecl. Quim. 34, 65–77 (2009)
Feng, Y.L., Dong, C.: Simultaneous determination of trace ofloxacin, ciprofloxacin, and sparfloxacin by micelle TLC-fluorimetry. J. Chromatogr. Sci. 42, 474–477 (2004)
Klosinska, S.E., Grudzien, M., Betlejewska, K.K., Plucinski, F., Biernacka, J., Mazurek, A.P.: Physicochemical properties of lomefloxacin, levofloxacin, and moxifloxacin relevant to the biopharmaceutics classification system. Acta Chim. Slovenica 61, 827–834 (2014)
Okeri, H.A., Arhewoh, I.M.: Analytical profile of the fluoroquinolone antibacterials. I. Ofloxacin. Afr. J. Biotech. 7, 670–680 (2008)
Al Azzam, K.M., Saad, B., Adnan, R., Enein, H.Y.A.: Enantioselective analysis of ofloxacin and ornidazole in pharmaceutical formulations by capillary electrophoresis using single chiral selector and computational calculation of their inclusion complexes. Anal. Chim. Acta 674, 249–255 (2010)
Singh, P., Mittal, R., Sharma, G.C., Singh, S., Singh, A.: Ornidazole: comprehensive profile. Profiles Drug Subst. Excip. Relat. Methodol. 30, 123–184 (2003)
Rizk, M., Toubar, S.S., Alamin, M.M., Azab, M.M.M.: Micellar high performance liquid chromatographic determination of itraconazole in bulk, pharmaceutical dosage forms and human plasma. Eur. J. Chem. 5, 11–17 (2014)
Garcia, A.C.M.C., Torres, L.J.R., Baeza, B.J.J.: Modelling of retention behaviour of solutes in micellar liquid chromatography. J. Chromatogr. A 780, 129–148 (1997)
Ruiz, M.J., Carda, S.B., Torres, L.J.R., Garcia, A.C.M.C.: Retention mechanisms in micellar liquid chromatography. J. Chromatogr. A 1216, 1798–1814 (2009)
El-Shaheny, R.N., El-Maghrabey, M.H., Belal, F.F.: Micellar liquid chromatography from green analysis perspective. Open Chem. 13, 877–892 (2015)
CIR publication, final report on the safety assessment of cetrimonium chloride, cetrimonium bromide, and steartrimonium chloride. Int. J. Toxicol. 16, 195–220 (1997)
Nishiyama, N., Toshima, Y., Ikeda, Y.: Biodegradation of alkyltrimethylammonium salts in activated sludge. Chemosphere 30, 593–603 (1995)
Takenaka, S., Tonoki, T., Taira, K., Murakami, S., Aoki, K.: Adaptation of pseudomonas sp. strain 7-6 to quaternary ammonium compounds and their degradation via dual pathways. Appl. Environ. Microbiol. 73, 1797–1802 (2007)
Gilomen, K., Stauffer, H.P., Meyer, V.R.: Detoxification of acetonitrile–water wastes from liquid chromatography. Chromatographia 41, 488–491 (1995)
Garcia Alvarez-Coque, M.C., Carda, S.B.: Direct injection of physiological fluids in micellar liquid chromatography. J. Chromatogr. B 736, 1–18 (1999)
Khaledi, M.G., Strasters, J.K., Rodgers, A.H., Breyer, E.D.: Simultaneous enhancement of separation selectivity and solvent strength in reversed phase liquid chromatography using micelles in hydro-organic solvents. Anal. Chem. 62, 130–136 (1990)
Cudina, O., Brboric, J., Jankovic, I., Karljikovic, K.: Study of valsartan interaction with micelles as a model system for biomembranes. Colloids Surf. B 65, 80–84 (2008)
Dhandapani, B., Thirumoorthi, N., Rasheed, S.H., Kotaiah, M.R., Anjaneyalu, N.: Method development and validation for the simultaneous estimation of ofloxacin and ornidazole in tablet dosage form by RP-HPLC. Int. J. Pharm. Sci. Res. 1, 78–83 (2010)
Manop, A., Cline, L.L.J.: Model for micellar effects on liquid chromatography capacity factors and for determination of micelle-solute equilibrium constants. Anal. Chem. 56, 1557–1561 (1984)
Tien, T.T.D., Uyen, P.N.D., Huong, T.B., Trang, T.N.: Effect of electrostatic interaction between fluoxetine and lipid membranes on the partitioning of fluoxetine investigated using second derivative spectrophotmetery and FTIR. Chem. Phys. Lipids 207, 10–23 (2017)
Murray, D., Arbuzova, A., Honig, B., Mclaughlint, S.: The role of electrostatic and nonpolar interactions in the association of peripheral proteins with membranes. Curr. Top. Membr. 52, 277–307 (2002)
Pignatello, R., Musumeci, T., Basile, L., Carbone, C., Puglisi, G.: Biomembrane models and drug-biomembrane interaction studies: involvement in drug design and development. J. Pharm. Bioallied Sci. 3, 4–14 (2011)
Carlota, O.R.Y., Adalberto, P.J., Leoberto, C.T.: Micellar solubilization of drugs. J. Pharm. Pharmaceut. Sci. 8, 147–163 (2005)
Sayem, A., Andleeb, Z.N., Kabir, D.: Surface and miceller properties of some amphiphilic drugs in the presence of additives. J. Chem. Eng. Data 52, 1326–1331 (2007)
Nazar, M.F., Shah, S.S., Khosa, M.A.: Interaction of azo dye with cationic surfactant under different pH conditions. J. Surfactants Deterg. 13, 529–537 (2010)
Nazar, M.F., Raheel, M., Shah, S.S., Danish, M., Ashfaq, M., Zafar, M.N.: Thermodynamic characteristics and spectral-luminescent properties of N-m-tolylbenzamide in microhetrogeneous surfactant self assemblies. J. Solution Chem. 43, 632–647 (2014)
Nazar, M.F., Murtaza, S., Ijaz, B., Asfaq, M., Mohsin, M.A.: Photophysical investigations of carmoisine interacting with conventional cationic surfactants under different pH conditions. J. Dispersion Sci. Technol. 36, 18–27 (2015)
Rosen, M.J., Kunjappu, J.T.: Surfactants and Interfacial Phenomena, 4th edn. Willey, Hoboken (2012)
Benesi, H.A., Hildebrand, J.H.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2703–2707 (1949)
Tunc, S., Duman, O., Kancı, B.: Spectrophotometric investigation of the interactions between cationic dye (C.I. Basic Yellow 2) and anionic surfactant (sodium dioctylsulfosuccinate) in the premicellar and micellar region. Dyes Pigm. 94, 233–238 (2012)
Duman, O., Tunc, S., Kancı, B.: Spectrophotometric studies on the interactions of C.I. Basic Red 9 and C.I. Acid Blue 25 with hexadecyltrimethylammonium bromide in cationic surfactant micelles. Fluid Phase Equilib. 301, 56–61 (2011)
Nazar, M.F., Azeem, W., Rana, U.A., Ashfaq, M., Lashin, A., Al-Arifi, N., Rahman, H.M.A., Lazim, A.M., Mehmood, A.: pH-dependent probing of levofloxacin assimilated in surfactant mediated assemblies: insights from photoluminescent and chromatographic measurements. J. Mol. Liq. 220, 26–32 (2016)
Wisplinghoff, H., Schmitt, R., Wohrmann, A., Stefanik, D., Seifert, H.: Resistance to disinfectants in epidemiologically defined clinical isolates of Acinetobacter baumannii. J. Hosp. Infect. 66, 174–181 (2007)
Giraud, I., Rapp, M., Maurizis, J.C., Madelmont, J.C.: Synthesis and in vitro evaluation of quaternary ammonium derivatives of chlorambucil and melphalan, anticancer drugs designed for the chemotherapy of chondrosarcoma. J. Med. Chem. 45, 2116–2119 (2002)
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. 93, 5536–5540 (1989)
Nazar, M.F., Mukhtar, F., Chaudry, S., Ashfaq, M., Mehmood, S., Asif, A., Rana, U.A.: Biophysical probing of antibacterial gemifloxacin assimilated in surfactant mediated molecular assemblies. J. Mol. Liq. 200, 361–368 (2014)
Nazar, M.F., Mukhtar, F., Ashfaq, M., Rahman, H.M.A., Zafar, M.N., Sumrra, S.H.: Physicochemical investigation of antibacterial moxifloxacin interacting with quaternary ammonium disinfectants. Fluid Phase Equilib. 406, 47–54 (2015)
Pedraza, A., Sicilia, M.D., Rubio, S., Pérez-Bendito, D.: Surfactant–dye binding degree method for the determination of amphiphilic drugs. Anal. Chim. Acta 522, 89–97 (2004)
Ulu, S.T.: A new spectrophotometric method for the determination of finasteride in tablets. Spectrochim. Acta, A 67, 778–783 (2007)
Mostafa, S., El-Sadek, M., Alla, E.A.: Spectrophotometric determination of enrofloxacin and pefloxacin through ion-pair complex formation. J. Pharm. Biomed. Anal. 28, 173–180 (2002)
Gomes, A.C.R., Cafer, L.D.F., Mello, P.H., Coutinho-Neto, M.D., Gaubeur, I.: The interaction of an azo compound with a surfactant and ion pair adsorption, to solid phases. J. Colloid Interface Sci. 367, 370–377 (2012)
Rio, J.M.D., Prieto, G., Sarmiento, F., Mosquera, V.: Thermodynamics of micellization of n-octyltrimethylammonium bromide in different media. Langmuir 11, 1511–1514 (1995)
Caetano, W., Tabak, M.: Interaction of chlorpromazine and trifluoperazine with anionic sodium dodecyl sulfate (SDS) micelles: electronic absorption and fluorescence studies. J. Colloid Interface Sci. 225, 69–81 (2000)
Acknowledgements
The authors express their gratitude to the Chemistry Department, Government College University, Lahore, Pakistan for provision of laboratory facilities. The authors also extend their sincere appreciations to the Higher Education Commission of Pakistan for providing financial support through NRPU Project No. 4557.
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Azeem, W., John, P., Nazar, M.F. et al. Fixed-Dose Combination Antibiotics Interacting with a Quaternary Ammonium Disinfectant: Insights from Spectral and Chromatographic Measurements. J Solution Chem 47, 1048–1059 (2018). https://doi.org/10.1007/s10953-018-0773-5
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DOI: https://doi.org/10.1007/s10953-018-0773-5