Effect of pH and amphiphile concentration on the gel-emulsion of sodium salt of 2-dodecylpyridine-5-boronic acid: Entrapment and release of vitamin B12

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 461, Issue 1, 2014, Pages 76-84

  Maiti, Monali ^a   Roy, Aparna ^a   Roy, Sumita ^a  

^a VIDYASAGAR UNIVERSITY   (India)

Author keywords

Boronic acid based amphiphile; Entrapment; Gel emulsion; Microscopy; Rheology; XRD

Indexed keywords

ELASTICITY; EMULSIFICATION; MICROSCOPIC EXAMINATION; MORPHOLOGY; RHEOLOGY; SALTS; ULTRAVIOLET VISIBLE SPECTROSCOPY; XEROGELS;

ENTRAPMENT; GEL-EMULSION; LOW CONCENTRATIONS; PHARMACEUTICAL INDUSTRY; RHEOLOGICAL MEASUREMENTS; STRUCTURE AND ACTIVITIES; UV-VIS SPECTROSCOPY; XRD; BORONIC ACID; EFFECT OF PH; SODIUM SALT; VITAMIN B-12;

AMPHIPHILES; MICROSCOPIC EXAMINATION;

1,3,5 TRIMETHYLBENZENE; 2 DODECYLPYRIDINE 5 BORONIC ACID; AMPHOPHILE; BENZENE; BORONIC ACID DERIVATIVE; CHLOROFORM; CYANOCOBALAMIN; CYCLOHEXANE; KEROSENE; META XYLENE; ORTHO XYLENE; SODIUM; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; DISPERSION; EMULSION; FIELD EMISSION SCANNING ELECTRON MICROSCOPY; FLOW KINETICS; GELATION; MICROSCOPY; PH; PRIORITY JOURNAL; ROOM TEMPERATURE; SOLUBILIZATION; THERMOSTABILITY; ULTRAVIOLET SPECTROSCOPY; VISCOELASTICITY; X RAY DIFFRACTION; DRUG INDUSTRY; ENCAPSULATION; MORPHOLOGY; SUSTAINED DRUG RELEASE; XEROGEL;

EID: 84905675365     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2014.07.030     Document Type: Article

References (43)

1. Lehn J.M. Supramolecular Chemistry: Concepts and Perspectives 1995, VCH, Weinheim.
2. Hirst A.R., Escuder B., Miravet J.F., Smith D.K. High-tech applications of self-assembling supramolecular nanostructured gel-phase materials: from regenerative medicine to electronic devices. Angew. Chem. Int. Ed. 2008, 47:8002-8018.
3. Jadhav S.R., Kumar P., Kumar V.R., Raghavan S.R., John G. Sugar-derived phase-selective molecular gelators as model solidifiers for oil spills. Angew. Chem. Int. Ed. 2010, 49:7695-7698.
4. Estroff L.A., Hamilton A.D. Water gelation by small organic molecules. Chem. Rev. 2004, 104:1201-1218.
5. de Loos M., Friggeri A., Van Esch J., Kellogg R.M., Feringa B.L. Cyclohexane bis-urea compounds for the gelation of water and aqueous solutions. Org. Biomol. Chem. 2005, 3:1631-1639.
6. Suzuki M., Saito H., Shirai H., Hanabusa K. Supramolecular organogel formation triggered by acid-base interaction in two-component system consisting of l-lysine derivative and aliphatic acids. New J. Chem. 2007, 31:1654-1660.
7. Tiller J.C. Increasing the local concentration of drugs by hydrogel formation. Angew. Chem. Int. Ed. 2003, 42:3072-3075.
8. Yu C.W., Chow K.H., Ho P.L., Fu D., Xu B. Hydrophobic interaction and hydrogen bonding cooperatively confer a vancomycin hydrogel: a potential candidate for biomaterials. J. Am. Chem. Soc. 2002, 124:14846-14847.
9. Kobayashi S., Hamasaki N., Suzuki M., Kimura M., Shirai H., Hanabusa K. Preparation of helical transition-metal oxide tubes using organogelators as structure-directing agents. J. Am. Chem. Soc. 2002, 124:6550-6551.
10. Shumburo A., Biewer M.C. Stabilization of an organic photochromic material by incorporation in an organogel. Chem. Mater. 2002, 14:3745-3750.
11. Huang Y., Lin Y., Zeng G., Liang Z., Liu X., Hong X., Zhang G., Tsang S.C. Thermoreversible organogels formed in a polyol system for the preparation of Sn nanoparticlesencapsulated in carbon. J. Mater. Chem. 2008, 18:5445-5447.
12. Ajayaghosh A., Praveen V.K., Vijayakumar C. Organogels as scaffolds for excitation energy transfer and light harvesting. Chem. Soc. Rev. 2008, 37:109-122.
13. Wilder E.A., Wilson K.S., Quinn J.B., Skrtic D., Antonucci J.M. Effect of an organogelator on the properties of dental composites. Chem. Mater. 2005, 17:2946-2952.
14. Kubo W., Kitamura T., Hanabusa K., Wada Y., Yanagida S. Quasi-solid-state dye-sensitized solar cells using room temperature molten salts and a low molecular weight gelator. Chem. Commun. 2002, 374-375.
15. Love C.S., Chechik V., Smith D.K., Wilson K., Ashworth I., Brennan C. Synthesis of gold nanoparticles within a supramolecular gel-phase network. Chem. Commun. 2005, 1971-1973.
16. Adhikari B., Nanda J., Banerjee A. Pyrene-containing peptide-based fluorescent organogels: inclusion of graphene into the organogel. Chem. Eur. J. 2011, 17:11488-11496.
17. Giansante C., Raffy G., Schafer C., Rahma H., Kao M.T., Olive A.G.L., Guerzo A.D. White-light-emitting self-assembled nanofibers and their evidence by microspectroscopy of individual objects. J. Am. Chem. Soc. 2011, 133:316-325.
18. Reynolds P.A., Gilbert E.P., Henderson M.J., White J.W. Structure of high internal phase aqueous-in-oil emulsions and related inverse micelle solutions. 3. Variation of surfactant. J. Phys. Chem. B 2009, 113:12231-12242.
19. Sun G., Li Z., Ngai T. Inversion of particle-stabilized emulsions to form high-internal-phase emulsions. Angew. Chem. Int. Ed. 2010, 49:2163-2166.
20. Yaron P.N., Reynolds P.A., McGillivray D.J., Mata J.P., White J.W. Nano-microstructure of high-internal phase emulsions under shear. J. Phys. Chem. B 2010, 114:3500-3509.
21. Gokmen M.T., Camp W.V., Colver P.J., Bon S.A.F., Du Prez F.E. Fabrication of porous "clickable" polymer beads and rods through generation of high internal phase emulsion (HIPE) droplets in a simple microfluidic device. Macromolecules 2009, 42:9289-9294.
22. Ikem V.O., Menner A., Horozov T.S., Bismarck A. Highly permeable macroporous polymers synthesized from pickering medium and high internal phase emulsion templates. Adv. Mater. 2010, 22:3588-3592.
23. Ikem V.O., Menner A., Bismarck A. Tailoring the mechanical performance of highly permeable macroporous polymers synthesized via Pickering emulsion templating. Soft Matter 2011, 7:6571-6577.
24. Lim H.N., Kassim A., Huang N.M., Khiewc P.S., Chiu W.S. Three-dimensional flower-like brushite crystals prepared from high internal phase emulsion for drug delivery application. Colloids Surf., A 2009, 345:211-218.
25. Dunstan T.S., Fletcher P.D.I. Compartmentalization and separation of aqueous reagents in the water droplets of water-in-oil high internal phase emulsions. Langmuir 2011, 27:3409-3415.
26. Caldero G., Llina's M., Garci'a-Celma M.J., Solans C. Studies on controlled release of hydrophilic drugs from W/O high internal phase ratio emulsions. J. Pharm. Sci. 2010, 99:701-711.
27. Pinazo A., Infante M.R., Izquierdo P., Solans C. Synthesis of arginine-based surfactants in highly concentrated water-in-oil emulsions. J. Chem. Soc. Perkin Trans. 2000, 2:1535-1539.
28. Pons R., Carrera I., Erra P., Kunieda H., Solans C. Novel preparation methods for highly concentrated water-in-oil emulsions. Colloids Surf., A 1994, 91:259-266.
29. Li J., Zhang J., Zhao Y., Han B., Yang G. High-internal-ionic liquid-phase emulsions. Chem. Commun. 2012, 48:994-996.
30. Chen X., Liu K., He P., Zhang H., Fang Y. Preparation of novel W/O gel-emulsions and their application in the preparation of low-density materials. Langmuir 2012, 28:9275-9281.
31. 12. J. Mater. Chem. B 2013, 1:5588-5601.
32. Kobayashi H., Amaike M., Jung J.H., Friggeri A., Shinkai S., Reinhoudt D.N. Organogel or polymer gel; facilitated gelation of a sugar-based organic gel by the addition of a boronic acid-appended polymer. Chem. Commun. 2001, 1038-1039.
33. Moy C.L., Kaliappan R., McNeil A.J. Aryl trihydroxyborate salts: thermally unstable species with unusual gelation abilities. J. Org. Chem. 2011, 76:8501-8507.
34. Grigoriou S., Johnson E.K., Chen L., Adams D.J., James T.D., Cameron P.J. Dipeptide hydrogel formation triggered by boronic acid-sugar recognition. Soft Matter 2012, 8:6788-6791.
35. Zhou C., Gao W., Yang K., Xu L., Ding J., Chen J., Liu M., Huang X., Wang S., Wu H. A novel glucose/pH responsive low-molecular-weight organogel of easy recycling. Langmuir 2013, 29:13568-13575.
36. Guan Y., Zhang Y. Boronic acid-containing hydrogels: synthesis and their applications. Chem. Soc. Rev. 2013, 42:8106-8121.
37. Maiti M., Roy A., Roy S. Effect of pH and oxygen atom of the hydrophobic chain on the self-assembly property and morphology of the pyridyl boronic acid based amphiphiles. Langmuir 2013, 29:13329-13338.
38. α-(4-n-Alkyloxybenzoyl)-l-histidine exhibiting pH-modulated properties. Langmuir 2010, 26:7761-7767.
39. Zweep N., Hopkinson A., Meetsma A., Browne W.R., Feringa B.L., Esch J.H.V. Balancing hydrogen bonding and van der Waals interactions in cyclohexane-based bisamide and bisurea organogelators. Langmuir 2009, 25:8802-8809.
40. Banerjee S., Vidya V.M., Savyasachi A.J., Maitra U. Perfluoroalkyl bile esters: a new class of efficient gelators of organic and aqueous-organic media. J. Mater. Chem. 2011, 21:14693-14705.
41. Ku C.Y., Nostro P.L., Chen S.H. Structural study of the gel phase of a semifluorinated alkane in a mixed solvent. J. Phys. Chem. B 1997, 101:908-914.
42. Bhattacharya S., Acharya S.N.G. Pronounced hydrogel formation by the self-assembled aggregates of N-alkyl disaccharide amphiphiles. Chem. Mater. 1999, 11:3504-3511.
43. Nanda J., Biswas A., Banerjee A. Single amino acid based thixotropic hydrogel formation and pH-dependent morphological change of gel nanofibers. Soft Matter 2013, 9:4198-4208.