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Mixed Micellization and Interfacial Properties of Ionic Liquid-Type Imidazolium Gemini Surfactant with Amphiphilic Drug Amitriptyline Hydrochloride and its Thermodynamics

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Journal of Surfactants and Detergents

Abstract

The thermodynamics of mixed micellization of amitriptyline hydrochloride (AMT) with ionic liquid-type imidazolium gemini surfactant ([C10-4-C10im] Br2), was investigated at different mole fractions and temperatures by surface tension measurements. The deviation of the critical micelle concentration (CMC) from the ideal critical micelle concentration (CMC*), micellar mole fraction (\(X_{1}^{m}\)) from ideal micellar mole fraction (\(X_{1}^{\text{ideal}}\)), the values of interaction parameter (\(\beta\)) and activity coefficients (\(f_{i}\)) (for both mixed micelles and mixed monolayer) explained the non-ideal behavior (i.e., synergistic behavior) of binary mixtures. The excess free energy (∆G ex) for the AMT-[C10-4-C10im] Br2 binary mixtures explained the mixed micelles stability in comparison to micelles of [C10-4-C10im] Br2 and pure AMT. Interfacial parameters, i.e., Gibbs surface excess (\(\varGamma_{\hbox{max} }\)), minimum head group area at air/water interface (\(A_{\hbox{min} }\)), free energy of micellization (\(\Delta G_{m}^{o}\)), and standard Gibbs energy of adsorption (∆G oads ) were also evaluated for the systems. The standard entropy of adsorption (∆S oads ) was found higher than the standard entropy of micellization (∆S o m ) at all mole fractions of AMT (α 1).

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References

  1. Rodriguez A, Junquera E, del Burgo P, Aicart E (2004) Conductometric and spectrofluorimetric characterization of the mixed micelles constituted by dodecyltrimethylammonium bromide and a tricyclic antidepressant drug in aqueous solution. J Colloid Interface Sci 269:476–483

    Article  CAS  Google Scholar 

  2. Mohamed DE, Negm NA, Mishrif MR (2013) Micellization and interfacial interaction behaviors of gemini cationic surfactants-CTAB mixed surfactant systems. J Surfact Deterg 16:723–731

    Article  CAS  Google Scholar 

  3. Fernandez-Leyes MD, Messina PV, Schulz PC (2007) Aqueous sodium dehydrocholate–sodium deoxycholate mixtures at low concentration. J Colloid Interface Sci 314:659–664

    Article  CAS  Google Scholar 

  4. Hu J, Zhou L, Feng J, Liu H, Hu Y (2007) Nonideal mixed micelles of gemini surfactant homologues and their application as templates for mesoporous material MCM-48. J Colloid Interface Sci 315:761–767

    Article  CAS  Google Scholar 

  5. Tikariha D, Kumar B, Ghosh S, Tiwari AK, Saha SK, Barbero N, Quagliotto P, Ghosh KK (2013) Interaction between cationic gemini and monomeric surfactants: micellar and surface properties. J Nanofluids 2:316–324

    Article  CAS  Google Scholar 

  6. Das S, Maiti S, Ghosh S (2014) Synthesis of two biofriendly anionic surfactants (N-n-decanoyl-l-valine and N-n-decanoyl-l-leucine) and their mixed micellization with nonionic surfactant Mega-10 in Tris-buffer medium at pH 9. RSC Adv 4:12275–12286

    Article  CAS  Google Scholar 

  7. Shirzad S, Sadeghi R (2014) Micellization properties and related thermodynamic parameters of aqueous sodium dodecyl sulfate and sodium dodecyl sulfonate solutions in the presence of 1-propanol. Fluid Phase Equilib 377:1–8

    Article  CAS  Google Scholar 

  8. Harutyunyan LR (2014) Effect of amino acids on micellization, surface activity and micellar properties of nonionic surfactant hexadecyl alcohol ethoxylate (25EO) in aqueous solutions. J Surfact Deterg 18:73–81

  9. Sood AK, Singh K, Banipal TS (2011) Micellization behavior of the 14-2-14 gemini surfactant with some conventional surfactants at different temperatures. J Surfact Deterg 14:235–244

    Article  Google Scholar 

  10. Sood AK, Singh K, Kaur J, Banipal TS (2012) Mixed micellization behavior of m-2-m gemini surfactants with some conventional surfactants at different temperatures. J Surfact Deterg 15:327–338

    Article  CAS  Google Scholar 

  11. Matsubara H, Nakano T, Matsuda T, Takiue T, Aratono M (2005) Effects of alkyl chain length on synergetic adsorption and micelle formation in homologous cationic surfactant mixtures. Langmuir 21:8131–8137

    Article  CAS  Google Scholar 

  12. Lipinski CA (2001) Avoiding investment in doomed drugs. Curr Drug Disc 4:17–19

  13. Lipinski CA (2002) Poor aqueous solubility—an industry wide problem in drug discovery. Am Pharm Rev 5:82–85

    Google Scholar 

  14. Barenholz Y (2001) Liposome application: problems and prospects. Curr Opin Colloid Interface Sci 6:66–77

    Article  CAS  Google Scholar 

  15. Akers MM (2002) Excipient–drug interactions in parenteral formulations. J Pharm Sci 91:2283–2300

    Article  CAS  Google Scholar 

  16. Rabinow BE (2004) Nanosuspensions in drug delivery. Nat Rev Drug Discov 3:785–796

    Article  CAS  Google Scholar 

  17. Lawrence MJ, Rees GD (2000) Microemulsion-based media as novel drug delivery systems. Adv Drug Deliv Rev 45:89–121

    Article  CAS  Google Scholar 

  18. Nakano M (2000) Places of emulsions in drug delivery. Adv Drug Deliv Rev 45:1–4

    Article  CAS  Google Scholar 

  19. Torchilin VP (2001) Structure and design of polymeric surfactant-based drug delivery systems. J Control Release 73:137–172

    Article  CAS  Google Scholar 

  20. Menger FM, Keiper JS (2000) Gemini surfactants. Angew Chem Int Ed 39:1906–1920

    Article  Google Scholar 

  21. Bernd T (2005) Polymerisation of styrene in microemulsion with catanionic surfactant mixtures. Colloid Polym Sci 283:421–430

    Article  Google Scholar 

  22. Bell PC, Bergsma M, Dolbnya IP (2003) Transfection mediated by gemini surfactants: engineered escape from the endosomal compartment. J Am Chem Soc 125:1551–1558

    Article  CAS  Google Scholar 

  23. Zana R (2002) Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: a review. Adv Colloid Interface Sci 97:205–253

    Article  CAS  Google Scholar 

  24. Chakraborty T, Ghosh S (2007) Mixed micellization of an anionic gemini surfactant (GA) with conventional polyethoxylated nonionic surfactants in brine solution at pH 5 and 298 K. Colloid Polym Sci 285:1665–1673

    Article  CAS  Google Scholar 

  25. Bhadani A, Singh S (2009) Novel gemini pyridinium surfactants: synthesis and study of their surface activity, DNA binding, and cytotoxicity. Langmuir 25:11703–11712

    Article  CAS  Google Scholar 

  26. Fisicaro E, Compari C, Biemmi M, Duce E, Peroni M, Barbero N, Viscardi G, Quagliotto P (2008) Unusual behavior of the aqueous solutions of gemini bispyridinium surfactants: apparent and partial molar enthalpies of the dimethanesulfonates. J Phys Chem B 112:12312–12317

    Article  CAS  Google Scholar 

  27. Bhadani A, Kataria H, Singh S (2011) Synthesis, characterization and comparative evaluation of phenoxy ring containing long chain gemini imidazolium and pyridinium amphiphiles. J Colloid Interface Sci 361:33–41

    Article  CAS  Google Scholar 

  28. Ding YS, Zha M, Zhang J, Wang SS (2007) Synthesis, characterization and properties of geminal imidazolium ionic liquids. Colloids Surf A 298:201–205

    Article  CAS  Google Scholar 

  29. Baltazar QQ, Chandawalla J, Sawyer K, Anderson JL (2007) Interfacial and micellar properties of imidazolium-based monocationic and dicationic ionic liquids. Colloids Surf A 302:150–156

    Article  CAS  Google Scholar 

  30. Ao M, Huang P, Xu G, Yang X, Wang Y (2009) Aggregation and thermodynamic properties of ionic liquid-type gemini imidazolium surfactants with different spacer length. Colloid Polym Sci 287:395–402

    Article  CAS  Google Scholar 

  31. Menger FM, Keiper JS, Azov V (2000) Gemini surfactants with acetylenic spacers. Langmuir 16:2062–2067

    Article  CAS  Google Scholar 

  32. Akbay C, Hoyos Y, Hooper E, Arslan H, Rizvi SAA (2010) Cationic gemini surfactants as pseudostationary phases in micellar electrokinetic chromatography. Part I: effect of head group. J Chromatogr A 1217:5279–5287

    Article  CAS  Google Scholar 

  33. Perez L, Pinazo A, Rosen MJ, Infante MR (1998) Surface activity properties at equilibrium of novel gemini cationic amphiphilic compounds from arginine, bis(args). Langmuir 14:2307–2315

    Article  CAS  Google Scholar 

  34. Perez L, Torres JL, Manresa A, Solans C, Infante MR (1996) Synthesis, aggregation, and biological properties of a new class of gemini cationic amphiphilic compounds from arginine, bis(args). Langmuir 12:5296–5301

    Article  CAS  Google Scholar 

  35. Schreier S, Malheiros SVP, de Paula E (2000) Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochim Biophys Acta 1508:210–234

    Article  CAS  Google Scholar 

  36. Kabir-ud-Din Khan AB, Naqvi AZ (2010) Mixed micellization of antidepressant drug amitriptyline hydrochloride with cationic surfactants. Colloids Surf B 80:206–212

    Article  CAS  Google Scholar 

  37. Kabir-ud-Din Rub MA, Naqvi AZ (2010) Mixed micelle formation between amphiphilic drug amitriptyline hydrochloride and surfactants (conventional and gemini) at 293.15–308.15 K. J Phys Chem B 114:6354–6364

    Article  CAS  Google Scholar 

  38. Kabir-ud-Din Khan AB, Naqvi AZ (2011) Micellization behavior of an amphiphilic drug promethazine hydrochloride-surfactant system in an aqueous medium. Acta Phys Chim Sin 27:1900–1906

    CAS  Google Scholar 

  39. Kabir-ud-Din Khan AB, Naqvi AZ (2012) Mixed micellization and interfacial properties of nonionic surfactants with the phenothiazine drug promazine hydrochloride at 30 °C. J Solut Chem 41:1587–1599

    Article  CAS  Google Scholar 

  40. Kabir-ud-Din Rub MA, Naqvi AZ (2012) Micellization of mixtures of amphiphilic drugs and cationic surfactants: a detailed study. Colloids Surf B 92:16–24

    Article  CAS  Google Scholar 

  41. Aslam J, Siddiqui US, Ansari W, Kabir-ud-Din (2013) Micellization studies of dicationic gemini surfactants (m-2-m type) in the presence of various counter- and co-ions. J Surfact Deterg 16:693–707

    Article  CAS  Google Scholar 

  42. Kabir-ud-Din Khan AB, Naqvi AZ (2013) A study of the interaction between a phenothiazine drug promazine hydrochloride with cationic surfactants. J Mol Liquid 187:374–380

    Article  CAS  Google Scholar 

  43. Taboada P, Attwood D, Ruso JM, García M, Sarmiento F, Mosquera V (1999) Influence of molecular structure on the ideality of mixing in micelles formed in binary mixtures of surface-active drugs. J Colloid Interface Sci 216:270–275

    Article  CAS  Google Scholar 

  44. Blanco E, Verdes PV, Ruso JM, Prieto G, Sarmiento F (2009) Interactions in binary mixed systems involving betablockers with different lipophilicity as a function of temperature and mixed ratios. Colloids Surf A 334:116–123

    Article  CAS  Google Scholar 

  45. Inoue T, Yamakawa H (2011) Micelle formation of nonionic surfactants in a room temperature ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate: surfactant chain length dependence of the critical micelle concentration. J Colloid Interface Sci 356:798–802

    Article  CAS  Google Scholar 

  46. Bowers J, Butts CP, Martin PJ, Vergara-Gutierrez MC (2004) Aggregation behavior of aqueous solutions of ionic liquids. Langmuir 20:2191–2198

    Article  CAS  Google Scholar 

  47. Galgano PD, El Seoud OA (2011) Surface active ionic liquids: study of the micellar properties of 1-(1-alkyl)-3-methylimidazolium chlorides and comparison with structurally related surfactants. J Colloid Interface Sci 361:186–194

    Article  CAS  Google Scholar 

  48. Mahajan S, Sharma R, Mahajan RK (2012) An investigation of drug binding ability of a surface active ionic liquid: micellization, electrochemical, and spectroscopic studies. Langmuir 28:17238–17246

    Article  CAS  Google Scholar 

  49. Khan AB, Ali M, Malik NA, Ali A, Patel R (2013) Role of 1-methyl-3-octylimidazolium chloride in the micellization behavior of amphiphilic drug amitriptyline hydrochloride. Colloids Surf B 112:460–465

    Article  CAS  Google Scholar 

  50. Kresheck GC, Franks F (1975) Water. Plenum, New York

    Google Scholar 

  51. Menguro K, Takasawa Y, Kawahashi N, Tabata Y, Ueno MJ (1981) Micellar properties of a series of octa(ethylene glycol)-n-alkyl ethers with homogeneous ethylene oxide chain and their temperature dependence. Colloid Interface Sci 83:50–56

    Article  Google Scholar 

  52. Ruiz CC, Diaz-Lopez L, Aguiar J (2007) Self-assembly of tetradecyltrimethylammonium bromide in glycerol aqueous mixtures: a thermodynamic and structural study. J Colloid Interface Sci 305:293–300

    Article  Google Scholar 

  53. Das C, Das B (2009) Thermodynamic and interfacial adsorption studies on the micellar solutions of alkyltrimethylammonium bromides in ethylene glycol (1) + water (2) mixed solvent media. J Chem Eng Data 54:559–565

    Article  CAS  Google Scholar 

  54. Ghosh S, Burman AD, De GC, Das AR (2011) Interfacial and self-aggregation of binary mixtures of anionic and nonionic amphiphiles in aqueous medium. J Phys Chem B 115:11098–11112

    Article  CAS  Google Scholar 

  55. Rosen MJ (2004) Surfactants and interfacial phenomena. Wiley-Interscience, New York

    Book  Google Scholar 

  56. Ghosh S (2001) Surface chemical and micellar properties of binary and ternary surfactant mixtures (cetyl pyridinium chloride, Tween-40, and Brij-56) in an aqueous medium. J Colloid Interface Sci 244:128–138

    Article  CAS  Google Scholar 

  57. Rubingh DN (1979) In: Mittal KL (ed) Solution chemistry of surfactants, vol 1. Plenum, New York, p 337

  58. Hall DG (1991) Electrostatic effects in dilute solutions containing charged colloidal entities. J Chem Soc Faraday Trans 87:3529–3535

    Article  CAS  Google Scholar 

  59. Zhou Q, Rosen MJ (2003) Molecular interactions of surfactants in mixed monolayers at the air/aqueous solution interface and in mixed micelles in aqueous media: the regular solution approach. Langmuir 19:4555–4562

    Article  CAS  Google Scholar 

  60. Motomura K, Ando N, Mtasuki H, Aratono M (1990) Thermodynamic studies on adsorption at interfaces: VII. Adsorption and micelle formation of binary surfactant mixtures. J Colloid Interface Sci 139:188–197

    Article  CAS  Google Scholar 

  61. Iyota H, Todoraki N, Ikeda N, Motomura K, Ohta A, Aratono M (1999) Structure effect on nonideal mixing of alkyl methyl sulfoxide and alkyldimethylphosphine oxide in adsorbed film and micelle. J Colloid Interface Sci 216:41–49

    Article  CAS  Google Scholar 

  62. Aratono M, Villeneuve M, Takiue T, Ikeda N, Iyota H (1998) Thermodynamic consideration of mixtures of surfactants in adsorbed films and micelles. J Colloid Interface Sci 200:161–171

    Article  CAS  Google Scholar 

  63. Rosen MJ, Chosen AW, Dahanayaki M, Hua XY (1982) Relationship of structure to properties in surfactants. 10. Surface and thermodynamic properties of 2 dodecyloxypoly(ethenoxyethanol)s, C12H25(OC2H4)xOH, in aqueous solution. J Phys Chem 86:541–545

    Article  CAS  Google Scholar 

  64. Sansanwal PK (2006) Effect of co-solutes on the physico-chemical properties of surfactant solutions. J Sci Ind Res 65:57–64

    CAS  Google Scholar 

  65. Sugihara G, Miyazono AM, Nagadome S, Oida T, Hayashi Y, Ko JS (2003) Adsorption and micelle formation of mixed surfactant systems in water ii: a combination of cationic gemini-type surfactant with mega-10. J Oleo Sci 52:449–461

    Article  CAS  Google Scholar 

  66. Rosen MJ, Aronson S (1981) Standard free energies of adsorption of surfactants at the aqueous solution/air interface from surface tension data in the vicinity of the critical micelle concentration. Colloids Surf A 3:201–208

    Article  CAS  Google Scholar 

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Acknowledgments

Dr. Rajan Patel thanks the Science and Engineering Research Board (SERB), New Delhi for providing research grant with Sanction Order No. (SR/S1/PC-19/2011). Dr. Abbul Bashar Khan is also thankful to SERB, New Delhi for providing research grant with Sanction Order No. (SB/FT/CS-031/2013).

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Authors and Affiliations

  1. Biophysical Chemistry Laboratory, Centre for Interdisciplinary Research in Basic Sciences, Jamia Millia Islamia (Central University), New Delhi, 110025, India

    Rajan Patel, Abbul Bashar Khan & Neeraj Dohare

  2. Department of Chemistry, Aligarh Muslim University, Aligarh, UP, India

    Mohd. Maroof Ali

  3. Department of Chemistry, Ramjas College, University of Delhi, New Delhi, India

    Hament Kumar Rajor

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  1. Rajan Patel
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Patel, R., Khan, A.B., Dohare, N. et al. Mixed Micellization and Interfacial Properties of Ionic Liquid-Type Imidazolium Gemini Surfactant with Amphiphilic Drug Amitriptyline Hydrochloride and its Thermodynamics. J Surfact Deterg 18, 719–728 (2015). https://doi.org/10.1007/s11743-015-1709-3

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