Shift of acid-base equilibrium of curcumin in its complexes with gemini surfactant hexamethylene-1,6-bis-(dodecyldimethyl ammonium bromide)

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 443, Issue , 2014, Pages 481-487

  Ke, Dan ^a   Wu, Yue ^a   Wang, Xiaoyong ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Absorption; Acid base equilibrium; Curcumin; Fluorescence; Gemini surfactant

Indexed keywords

ABSORPTION; BIOCHEMISTRY; CYCLOHEXANE; FLUORESCENCE;

ABSORPTION AND FLUORESCENCE SPECTRA; ACID-BASE EQUILIBRIA; CURCUMIN; FLUORESCENCE SPECTRA; GEMINI SURFACTANT; PHARMACOLOGICAL ACTIVITY; SURFACTANT CONCENTRATIONS; SURFACTANT MICELLES;

SURFACE ACTIVE AGENTS;

ANION; CATION; CURCUMIN; HEXAMETHYLENE 1,6 BIS(DODECYLDIMETHYL AMMONIUM BROMIDE); MONOMER; SODIUM CHLORIDE; SURFACTANT; UNCLASSIFIED DRUG;

ABSORPTION; ACID BASE BALANCE; ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; CONCENTRATION RESPONSE; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; MICELLE; PRIORITY JOURNAL; STATIC ELECTRICITY; STEADY STATE;

EID: 84891122053     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2013.12.012     Document Type: Article

References (40)

1. Sharma O.P. Antioxidant activity of curcumin and related compounds. Biochem. Pharmacol. 1976, 25:1811-1812.
2. Chan M.M., Huang H.I., Fenton M.R., Fong D. In vivo inhibition of nitric oxide synthase gene expression by curcumin, a cancer preventive natural product with anti-inflammatory properties. Biochem. Pharmacol. 1998, 55:1955-1962.
3. Khar A., Ali A.M., Pardhasaradhi B.V., Begum Z., Anjum R. Antitumor activity of curcumin is mediated through the induction of apoptosis in AK-5 tumor cells. FEBS Lett. 1999, 445:165-168.
4. Aggarwal B.B., Kumar A., Bharti A.C. Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res. 2003, 23:363-398.
5. Zsila F., Bikádi Z., Simonyi M. Unique, pH-dependent biphasic band shape of the visible circular dichroism of curcumin-serum albumin complex. Biochem. Biophys. Res. Commun. 2003, 301:776-782.
6. Zsila F., Bikádi Z., Simonyi M. Circular dichroism spectroscopic studies reveal pH dependent binding of curcumin in the minor groove of natural and synthetic nucleic acids. Org. Biomol. Chem. 2004, 2:2902-2910.
7. Ruby A.J., Kuttan G., Babu K.D., Rajasekharan K.N., Kuttan R. Anti-tumour and antioxidant activity of natural curcuminoids. Cancer Lett. 1995, 94:79-83.
8. Anand P., Kunnumakkara A.B., Newman R.A., Aggarwal B.B. Bioavailability of curcumin: problems and promises. Mol. Pharm. 2007, 4:807-818.
9. Tønnesen H.H., Karlsen J. Studies on curcumin and curcuminoids. VI. Kinetics of curcumin degradation in aqueous solution. Z. Lebensm. Unters. Forsch. 1985, 180:402-404.
10. Wang Y.J., Pan M.H., Cheng A.L., Lin L.I., Ho Y.S., Hsieh C.Y., Lin J.K. Stability of curcumin in buffer solutions and characterization of its degradation products. J. Pharm. Biomed. Anal. 1997, 15:1867-1876.
11. Tønnesen H.H. Studies of curcumin and curcuminoids, XXVIII. Solubility, chemical and photochemical stability of curcumin in surfactant solutions. Pharmazie 2002, 57:820-824.
12. Leung M.H.M., Colangelo H., Kee T.W. Encapsulation of curcumin in cationic micelles suppresses alkaline hydrolysis. Langmuir 2008, 24:5672-5675.
13. Wang Z., Leung M.H.M., Kee T.W., English D.S. The role of charge in the surfactant-assisted stabilization of the natural product curcumin. Langmuir 2010, 26:5520-5526.
14. Ke D., Wang X., Yang Q., Niu Y., Chai S., Chen Z., An X., Shen W. Spectrometric study on the interaction of dodecyltrimethylammonium bromide with curcumin. Langmuir 2011, 27:14112-14117.
15. Zana R. Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: a review. Adv. Colloid Interface Sci. 2002, 97:205-253.
16. Han Y., Wang Y. Aggregation behavior of gemini surfactants and their interaction with macromolecules in aqueous solution. Phys. Chem. Chem. Phys. 2011, 13:1939-1956.
17. Wan Z., Ke D., Hong J., Ran Q., Wang X., Chen Z., An X., Shen W. Comparative study on the interactions of cationic gemini and single-chain surfactant micelles with curcumin. Colloids Surf. A 2012, 414:267-273.
18. Ke D., Yang Q., Yang M., Wu Y., Li J., Zhou H., Wang X. Effect of the spacer length on the electrostatic interactions of cationic gemini surfactant micelles with trianionic curcumin. Colloids Surf. A 2013, 436:80-86.
19. Tønnesen H.H., Karlsen J. Studies on curcumin and curcuminoids. V. Alka-line degradation of curcumin. Z. Lebensm. Unters. Forsch. 1985, 180:132-134.
20. Adhikary R., Carlson P.J., Kee T.W., Petrich J.W. Excited-state intramolecular hydrogen atom transfer of curcumin in surfactant micelles. J. Phys. Chem. B 2010, 114:2997-3004.
21. Bernabé-Pineda M., Ramírez-Silva M.T., Romero-Romo M., González-Vergara E., Rojas-Hernández A. Determination of acidity constants of curcumin in aqueous solution and apparent rate constant of its decomposition. Spectrochim. Acta A 2004, 60:1091-1097.
22. Menger F.M., Littau C.A. Gemini surfactants: a new class of self-assembling molecules. J. Am. Chem. Soc. 1993, 115:10083-10090.
23. Alami E., Beinert G., Marie P., Zana R. Alkanediyl-α,ω-bis(dimethylalkylammonium bromide) surfactants. 3. Behavior at the air-water interface. Langmuir 1993, 9:1465-1467.
24. Wang X., Wang J., Wang Y., Ye J., Yan H., Thomas R.K. Micellization of a series of dissymmetric gemini surfactants in aqueous solution. J. Phys. Chem. B 2003, 107:11428-11432.
25. Wang X., Li Y., Wang J., Wang Y., Ye J., Yan H., Zhang J., Thomas R.K. Interactions of cationic gemini surfactants with hydrophobically modified poly(acrylamides) studied by fluorescence and microcalorimetry. J. Phys. Chem. B 2005, 109:12850-12855.
26. Shinitzky M., Barenholz Y. Fluidity parameters of lipid regions determined by fluorescence polarization. Biochim. Biophys. Acta 1978, 515:367-394.
27. Zsila F., Bikádi Z., Simonyi M. Molecular basis of the cotton effects induced by the binding of curcumin to human serum albumin. Tetrahedron: Asymmetry 2003, 14:2433-2444.
28. Wang F., Yang J., Wu X., Wang F., Ding H. Investigation of the interaction between curcumin and nucleic acids in the presence of CTAB. Spectrochim. Acta A 2007, 67:385-390.
29. Began G., Sudharshan E., Sankar K.U., Rao A.G.A. Interaction of curcumin with phosphatidylcholine: a spectrofluorometric study. J. Agric. Food Chem. 1999, 47:4992-4997.
30. Bernabé-Pineda M., Ramírez-Silva M.T., Romero-Romo M., González-Vergara E., Rojas-Hernández A. Spectrophotometric and electrochemical determination of the formation constants of the complexes curcumin-Fe(III)-water and curcumin-Fe(II)-water. Spectrochim. Acta A 2004, 60:1105-1113.
31. Addicoat M.A., Metha G.F., Kee T.W. Density functional theory investigation of Cu(I)- and Cu(II)-curcumin complexes. J. Comput. Chem. 2011, 32:429-438.
32. Bong P.-H. Spectral and photophysical behaviors of curcumin and curcuminoids. Bull. Korean Chem. Soc. 2000, 21:81-86.
33. Kapoor S., Priyadarsini K.I. Protection of radiation-induced protein damage by curcumin. Biophys. Chem. 2001, 92:119-126.
34. Lawrence M., Marzzacco C.J., Morton C., Schwab C., Halpern A.M. Excited-state deprotonation of 2-naphthol by anions. J. Phys. Chem. 1991, 95:10294-10299.
35. Kunwar A., Barik A., Pandey R., Priyadarsini K.I. Transport of liposo-mal and albumin loaded curcumin to living cells: an absorption and fluorescence spectroscopic study. Biochim. Biophys. Acta 2006, 1760:1513-1520.
36. Iwunze M.O. Binding and distribution characteristics of curcumin solubilized in CTAB. J. Mol. Liq. 2004, 111:161-165.
37. a calculations for carboxylic acids using complete basis set and Gaussian-n models combined with CPCM continuum solvation methods. J. Am. Chem. Soc. 2001, 123:7314-7319.
38. Zana R., In M., Lévy H. Alkanediyl-α,ω-bis(dimethylalkylammonium bromide). 7. Fluorescence probing studies of micelle micropolarity and microviscosity. Langmuir 1997, 13:5552-5557.
39. Böhmer M.R., Koopal L.K., Lyklema J. Micellization of ionic surfactants. Calculations based on a self-consistent field lattice model. J. Phys. Chem. 1991, 95:9569-9578.
40. Quina F.H., Nassar P.M., Bonilha J.B.S., Bales B.L. Growth of sodium dodecyl sulfate micelles with detergent concentration. J. Phys. Chem. 1995, 99:17028-17031.