Effect of pH on the Binding of Sodium, Lysine, and Arginine Counterions to l-Undecyl Leucinate Micelles

Journal of Surfactants and Detergents

Volumn 19, Issue 6, 2016, Pages 1175-1188

  Lewis, Corbin ^a   Hughes, Burgoyne H ^b   Vasquez, Mariela ^a   Wall, Alyssa M ^b   Northrup, Victoria L ^b   Witzleb, Tyler J ^b   Billiot, Eugene J ^a   Fang, Yayin ^c   Billiot, Fereshteh H ^a   Morris, Kevin F ^b  

^a TEXAS A AND M UNIVERSITY CORPUS CHRISTI   (United States)

^b CARTHAGE COLLEGE   (United States)

^c HOWARD UNIVERSITY COLLEGE OF MEDICINE   (United States)

Author keywords

Amino acid surfactant; Counterion; Micelle; NMR

Indexed keywords

AMIDES; ARGININE; BINS; DYNAMIC LIGHT SCATTERING; FLUORESCENCE SPECTROSCOPY; IONS; LIGHT SCATTERING; MICELLES; MOLECULES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; SURFACE ACTIVE AGENTS;

AMINE FUNCTIONAL GROUPS; AMINO ACID SURFACTANT; AMINO ACID-BASED SURFACTANTS; COUNTERIONS; MICELLE FORMATION; SURFACTANT MOLECULES; SURFACTANT MONOMERS; TWO-DIMENSIONAL NMR;

AMINO ACIDS;

EID: 84988662481     PISSN: 10973958     EISSN: 15589293     Source Type: Journal    
DOI: 10.1007/s11743-016-1875-y     Document Type: Article

References (50)

1. Azarmi R, Ashjaran A (2015) Type and application of some common surfactants. J Chem Pharm Res 7:632–640
2. Tamrakar S, Darwhekar GN, Sharma R, Mantry P, Soudawat R (2014) Self-emulsifying drug delivery systems: a review of the applicability in drug delivery technologies. ARPB 4:785–790
3. Eastoe J, Tabor RF (2014) Surfactants and nanoscience, colloidal foundations of nanoscience. In: Berti D, Palazzo G (eds) Colloidal foundations of nanoscience. Elsevier, Amsterdam
4. Felhofer JL, Chumbimuni-Torres KY, Mora MF, Haby GG, Garcia CD (2013) In: Garcia CD, Chumbimuni-Torres KY, Carrilho E (eds) Capillary electrophoresis and microchip capillary electrophoresis: principles, applications, and limitations. Wiley, Hoboken
5. Negm NA, Tawfik SM (2013) Environmentally friendly surface active agents and their applications. In: Biresaw G, Mittal KL (eds) Surfactants in tribology. CRC, Boca Raton
6. Kumar N, Tyagi R (2014) Applications of dimeric surfactants: a review. J Disper Sci Technol 35:205–214
7. Somasundaran P (2012) Self-assembly and self-organization of surfactants in agriculture. Encyclopedia of surface and colloid science 2. CRC, Boca Raton
8. Moradi M, Yamini Y (2012) Surfactant roles in modern sample preparation techniques: a review. J Sep Sci 35:2319–2340
9. Kamal MS (2016) A review of gemini surfactants: potential application in enhanced oil recovery. J Surfactants Deterg 19:223–236
10. Mwangi PM, Rao DN (2014) An overview of surfactants in enhanced oil recovery. In: Romsted LS (ed) Surfactant science and technology. CRC, Boca Raton
11. Chandra N, Tyagi VK (2013) Synthesis, properties, and applications of amino acids based surfactants: a review. J Disper Sci Technol 34:800
12. Brito RO, Silva S (2011) Enhanced interfacial properties of novel amino acid-derived surfactants: effects of headgroup chemistry and of alkyl chain length and unsaturation. Colloid Surf B 86:65–70
13. Bordes R, Tropsch J, Holmberg K (2010) Role of an amide bond for self-assembly of surfactants. Langmuir 26:3077–3083
14. Pinazo A, Manresa MA, Marques AM, Bustelo M, Espuny MJ, Perez L (2016) Amino acid-based surfactant: new antimicrobial agents. Adv Colloid Interfac 228:17–39
15. Kim SH, Satcher JH, Han TY (2012) Hierarchical ZnO structures templated with amino acid based surfactants. Micropor Mesopor Mat 151:64–69
16. Li Y, Holmberg K, Bordes R (2013) Micellization of true amphoteric surfactants. J Colloid Interfac Sci 411:47–52
17. Fan H, Han F (2008) Active control of surface properties and aggergation behavior in amino acid-based gemini surfactant systems. J Colloid Intefac Sci 321:227–234
18. Bordes R, Holmberg K (2015) Amino acid-based surfactants—do they deserve more attention? Adv Colliod Interfac 222:79–91
19. Infante M, Perez L, Pinazo A, Vinardell MP (2004) Amino acid-based surfactants. Green Chem 7:583–592
20. Lv J, Qiao W (2015) Unusual pH-regulated surface adsorption and aggregation behavior of a series of asymmetric gemini amino-acid surfactants. Soft Matter 13:2577–2585
21. Perrin CL, Chen JH, Ohta BK (1999) Amide proton exchange in micelles. J Am Chem Soc 121:2448–2455
22. Perez L, Pinazo A, Pons R, Infante M (2014) Gemini surfactants from natural amino acids. Adv Colloid Interfac 205:134–155
23. Billiot FH, McCarroll ME, Billiot EJ, Rugutt JK, Morris KF, Warner IM (2002) Comparison of the aggregation behavior of fifteen polymeric and monomeric dipeptide surfactants in aqueous solution. Langmuir 18:2993–2997
24. Stilbs P (1987) Fourier transform pulsed-graident spin-echo studies of molecular diffusion. Prog Nucl Mag Reson Spectrosc 19:1–45
25. Willis SA, Stait-Gardner T, Virk AS, Masuda R, Zubkov M, Zheng G, Price WS (2015) Diffusion: definition, description, and measurement. In: Fisher J (ed) Modern NMR techniques for synthetic chemistry. CRC, Boca Raton
26. Heisel KA, Goto JJ, Krishnan VV (2012) NMR chromatography: molecular diffusion in the presence of pulsed field gradients in analytical chemistry applications. Am J Anal Chem 3:401–409
27. Cohen Y, Avram L, Evan-Salem T, Slovak S, Shemesh N, Frish L (2012) Diffusion NMR in supramolecular chemistry and complex systems. In: Schalley CA (ed) Analytical methods in supramolecular chemistry, 2nd edn. Wiley, Hoboken
28. Käerger J (2008) Diffusion measurements by NMR techniques. Mol Sieves 7:85–133
29. Stilbs P, Lindman B (1981) Determination of organic counterion binding to micelles through Fourier transform NMR self-diffusion measurements. J Phys Chem 85:2587–2589
30. Rashidi-Alavijeh M, Javadian S, Gharibi H, Moradi M, Tehrani-Bagha AR, Shahir AA (2011) Intermolecular interactions between a dye and cationic surfactants: effects of alkyl chain, headgroup, and counterion. Colloid Surf A 380:119–127
31. Zuev YF, Gnezdilov OI, Zueva OS, Us’yarov OG (2011) Effective self-diffusion coefficients of ions in sodium dodecyl sulfate micellar solutions. Colloid J 73:59–64
32. Gnezdilov OI, Zuev YF, Zueva OS, Potarikina KS, Us’yarov OG (2011) Self diffusion of ionic surfactants and counterions in premicellar and micellar solutions of sodium, lithium, and cesium dodecyl sulfates as studied by NMR-diffusometry. Appl Magn Reson 40:91–103
33. Deaton K, Feyen E, Nkulabi H, Morris K (2001) Pulsed-field gradient NMR study of sodium dodecyl sulfate micelle-peptide association. Magn Reson Chem 39:276–282
34. Begotka BA, Hunsader JL, Oparaeche C, Vincent JK, Morris KF (2006) A pulsed field gradient NMR diffusion investigation of encephalin peptide-dodium dodecyl sulfate micelle association. Magn Reson Chem 44:586–593
35. Lipidot Y, Rappoport S, Wolman YJ (1967) Use of esters of N-hydroxysuccinimide in the synthesis of N-acylamino acids. J Lipid Res 8:142–145
36. Kalyanasundaram K, Thomas JK (1977) Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J Am Chem Soc 99:2039–2044
37. Wu D, Chen A, Johnson CS Jr (1995) An improved diffusion ordered spectroscopy experiment incorporating bipolar gradient pulses. J Magn Reson 115:260–264
38. Piotto M, Saudek V, Skienar V (1992) Gradient-tailored excitation for single quantum NMR spectroscopy of aqueous solutions. J Biomol NMR 2:661–665
39. Forsen S, Hoffman RA (1963) Study of moderately rapid chemical exchange reactions by means of nuclear magnetic double resonance. J Chem Phys 39:2892–2901
40. O’Neil JDJ, Sykes BD (1989) NMR studies of the influence of dodecyl sulfate on the amide hydrogen exchange kinetics of a micelle-solubilized hydrophobic tripeptide. Biochemistry 28:699–707
41. Lide DR (ed) (2003) CRC handbook of chemistry and physics, 84th edn. CRC, Boca Raton
42. Wilkins DK, Grimshaw SB, Receveur V, Dobson CM, Jones JA, Smith LJ (1999) Hydrodynamic radii of native and denatured proteins measured by pulse field gradient NMR techniques. Biochemistry 38:16424–16431
43. Berg JM, Tymoczko JL, Gatto GJ Jr, Stryer L (2015) Biochemistry, 8th edn. Freeman, New York
44. Bax A, Davis DG (1985) Practical aspects of two-dimensional transverse noe spectroscopy. J Magn Reson 63:207–213
45. Narutis VP, Kopple KD (1983) Substrate specificities and structure-activity relationships for acylation of antibiotics catalyzed by kanamycin acetyltransferase. Biochemistry 22:6233–6239
46. Lenkinski RE, Stephens RL, Krishna NR (1981) Conformation of angiotensin II: evidence for a specific hydrogen bonded conformation. Biochemistry 20:3122–3126
47. 1H nuclear magnetic resonance transfer of solvent saturation method. Conformations of oxytocin and lysine vasopressin in aqueous solution. Biophys J 26:345–366
48. Jamin Y, Eykyn TR, Poon E, Springer CJ, Robinson SP (2014) Detection of the prodrug-activating enzyme carboxypeptidase G2 activity with chemical exchange saturation transfer magnetic resonance. Mol Imaging Biol 16:152–157
49. Zheng Z, Brockel C, Ganter B, Lipsick J, Sasaki M, Ogata K, Nishimura Y, Jardetzky O (1996) Amide proton exchange rates in c-Myb DNA binding domain. Quart Magn Reson Biol Med 3:33–45
50. Assfalg M, Ragona L, Pagano K, D’Onofrio M, Zanzoni S, Tomaselli S, Molinari H (2016) The study of transient protein-nanoparticle interactions by solution NMR spectroscopy. Biochim Biophys Acta 1864:102–114