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Interaction of Cationic CTAB Surfactant with Curcumin, an Anticarcinogenic Drug: Spectroscopic Investigation

  • Rakesh Sharma and Dipti Jani
Published/Copyright: September 9, 2013
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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 50 Issue 4

Abstract

Curcumin, the most active polyphenolic constituent of turmeric cucuminoids obtained from rhizome Curcuma longa, holds a high place in ayurvedic medicine but its role in conventional disease management is also established. Unfortunately, the compound has poor aqueous solubility, which results in poor bioavailability following high doses by oral administration. In order to enhance its effectiveness and improve bioavailability, surfactant assemblies as the colloidal drug carriers with desired properties have been largely utilized. The interaction of curcumin with cetyltrimethylammonium bromide (CTAB) surfactant has been investigated by absorption spectroscopy as a function of surfactant concentration in pre-micellar and micellar range at acidic pH of 6.4. The pre-micellar and micellar region of pure CTAB surfactant at acidic pH of 6.4 is examined through tensiometry and conductometry techniques. Spectral data shows that in presence of curcumin at lower CCTAB, the change in absorbance and peak form initially was assigned to attraction of positive head group of CTAB towards the β-diketone group of drug. In micellar region including CMC, the type of interaction corresponds to the attachment of C16 chains of CTAB to nonpolar aryl groups of drug and simultaneously displacement of polar head group from β-diketone group of the drug. Finally at post micellar CCTAB, the encapsulation of the curcumin into micelles, predominantly in intact monomeric form is observed with the sharp peak at λmax = 423 nm.

Kurzfassung

Curcumin, die aktivste polyphenolische Verbindung unter den Gelbwurzel Cucminoiden, wird aus dem Wurzelstock Curcuma longa erhalten und hat in der ayurvedischen Medizin einen hohen Stellenwert; ist aber auch in der konventionellen Krankenbehandlung etabliert. Leider ist die Verbindung schlecht wasserlöslich, was zu einer schlechten Bioverfügbarkeit und daher zu hoher Dosierung bei der oralen Verabreichung führt. Zur Erhöhung seiner Wirksamkeit und zur Verbesserung der Bioverfügbarkeit wurden Tensidaggregate als kolloidale Wirkstoffträger mit gewünschten Eigenschaften umfangreich eingesetzt. Die Wechselwirkung von Curcumin mit Cetyltrimethylammoniumbromid (CTAB) wurde abhängig von der Tensidkonzentration im vormizellaren und mizellaren Bereich bei pH 6,4 mit der Absorptionsspektroskopie untersucht. Der vormizellare und mizellare Bereich des reinen CTAB wurde bei pH 6,4 tensiometrisch und konduktometrisch untersucht. Die spektralen Daten zeigen, dass bei Anwesenheit von Curcumin bei niedrigen CTAB-Konzentrationen die Veränderung von Extinktion und ursprünglicher Peakform von der Anziehung der positiven CTAB-Kopfgruppe zur β-Diketongruppe des Wirkstoffs bestimmt wurde. Im mizellaren Bereich einschließlich der CMC, entspricht der Wechselswirkungstyp der Anlagerung der C16-Ketten des CTAB an die unpolaren Arylgruppen des Wirkstoffs bei gleichzeitiger Entfernung der polaren Kopfgruppen von den β-Diketongruppen des Wirkstoffs. Letzlich wird in der post-mizellaren Region des CTAB aufgrund des scharfen Peaks bei λmax = 423 nm beobachtet, dass Curcumin überwiegend in der intakten monomeren Form in die Mizellen eingeschlossen ist.

Key words: Curcumin; CTAB surfactant; CMC; drug-surfactant interaction; UV-Visible spectroscopy
Stichwörter: Curcumin; CTAB; CMC; Wirkstoff-Tensid-Wechselwirkung; UV-Vis-Spektroskopie
1 Dr. Rakesh K. Sharma, Assistant Professor, Applied Chemistry Department, Faculty of Technology & Engineering, The Maharaja Sayajirao University of Baroda, Post Box no. 51, Kala Bhavan, Vadodara-390001 (Gujarat) India, Tel.: (O)+912652434188 (M)+919228499273, Fax: 02652423898, E-Mail:

Dr. Rakesh K. Sharma, M.Sc., M. Phil., Ph.D., is the Assistant Professor in the Applied Chemistry Department, Faculty of Technology & Engineering, The M. S. University of Baroda, Vadodara, Gujarat, India. His research interests are in aggregation and phase behavior of surfactants and EO-PO based block copolymers and its application in drug delivery and detergency. He has published more than ten research papers in reputed international journals.

Dipti Jani, M.Sc., is a project student in the Applied Chemistry Department, Faculty of Technology & Engineering, The M. S. University of Baroda, Vadodara, Gujarat, India. She is working in the area of applications of surfactants in pharmaceutical sciences.

References

1. Aggarwal, B. B., Sundaram, C., Malani, N. and Ichikawa, H.: Curcumin: The Indian Solid Gold, Adv. Exp. Med. Biol.595 (2007) 1–75.Search in Google Scholar

2. Tang, C. H., Lee, C. Y. and Huang, M. T.: Phenolic Compounds in Food and Their Effects on Health I., Washington DC, ACS Symposium Series 506, American Chemical Society (1992).Search in Google Scholar

3. Kita, T., Imai, S., Sawada, H., Kumagai, H. and Seto, H.: Biosci. Biotechnol. Biochem.72 (2008) 1789–1798.10.1271/bbb.80075Search in Google Scholar PubMed

4. Anand, P., Sundaram, C., Jhurani, S., Kunnumakkara, A. B. and Aggarwal, B. B.: Curcumin and Cancer: An “old-age” disease with an “age-old” solution, Cancer Lett.267 (2008) 133–164.Search in Google Scholar

5. Teiten, M. H., Eifes, S., Dicato, M. and Diederich, M.: Curcumin-The Paradigm of a Multi-Target Natural Compound with Applications in Cancer Prevention and Treatment, Toxins2 (2010) 128–162.Search in Google Scholar

6. Hatcher, H., Planalp, R., Cho, J., Torti, F. M. and Torti, S. V.: Cell. Mol. Life Sci.65 (2008) 1631–1652.10.1007/s00018-008-7452-4Search in Google Scholar PubMed PubMed Central

7. Sharma, R. A., Gescher, A. J. and Steward, W. P.: Eur. J. Cancer41 (2005) 1955–1968.10.1016/j.ejca.2005.05.009Search in Google Scholar PubMed

8. Nardo, L., Andreini, A., Masson, M., Haukvik, T. and Tønnesen, H. H.: J. Fluoresc.21 (2011) 627–635.10.1007/s10895-010-0750-xSearch in Google Scholar PubMed PubMed Central

9. Nardo, L., Andreini, A. and Tønnesen, H. H.: In Hydrogen Bonding and Transfer in the Excited State; New York, John Wiley & Sons (2010) pp. 353–375.Search in Google Scholar

10. Patra, D. and Barakat, C.: Spectrochim. ActaA79 (2011) 1034–1041.10.1016/j.saa.2011.04.016Search in Google Scholar PubMed

11. Bong, P. H.: Bull. Korean Chem. Soc.1 (2000) 81–86.Search in Google Scholar

12. Chignell, C. F., Bilski, P., Reszka, K. J., Motten, A. G., Sik, R. H. and Dahl, T. A.: Photochem. Photobiol.59 (1994) 295–302.10.1111/j.1751-1097.1994.tb05037.xSearch in Google Scholar PubMed

13. Wang, Y. J., Pan, M. H., Cheng, A. L., Lin, L. I., Ho, Y. S., Hsich, C. Y. and Lin, J. K.: J. Pharm. Biomed. Anal.15 (1997) 1867.Search in Google Scholar

14. Rangel-Yagui, C., Pessoa, Jr.A. and Tavares, L. C.: J. Pharm. Pharmaceut. Sci.8 (2005) 147–163.Search in Google Scholar

15. Leung, M. H. M., Colangelo, H. and Kee, T. W.: Langmuir24 (2008) 5672–5675.10.1021/la800780wSearch in Google Scholar PubMed

16. Dan, K., Wang, X, Yang, Q., Niu, Y., Chai, S., Chen, Z., An, X. and Shen, W.: Langmuir27 (2011) 14112–14117.10.1021/la104445hSearch in Google Scholar PubMed

17. Iwunze, M. O.: J. Mol. Liquids111 (2004) 161–165.10.1016/j.molliq.2003.12.013Search in Google Scholar

18. Jain, D. V. S. and Singh, S.: Indian J. Chem.10 (1972) 629.Search in Google Scholar

19. Lah, J., Pohar, C. and Vesnaver, G.: J. Phys. Chem.B104 (2000) 2522.Search in Google Scholar

20. Tedeschi, A. M., Franco, L., Ruzzi, M., Paduano, L., Corvajaand, C. and D’Errico, G.: Phys. Chem. Chem. Phys.5 (2003) 4204–4209.10.1039/b305324pSearch in Google Scholar

21. Xiaoli, T., Zhang, L., Zhao, S., Jiayong, Y. and Jingyi, A.: J. of Surfactant Detergents7 (2004) 2.Search in Google Scholar

22. Tonnesen, H. H.: Pharmazie 57(12) (2002) 820-824.Search in Google Scholar

23. Zsila, F., Bikadi, Z. and Simonyi, M.: Tetrahedron Asymmetry14 (2003) 2433–2444.10.1016/S0957-4166(03)00486-5Search in Google Scholar

24. Wang, Z. F., Leung, M. H. M., Kee, T. W. and English, D. S.: Langmuir26 (2010) 5520–5526.10.1021/la903772eSearch in Google Scholar PubMed

Received: 2013-2-24
Revised: 2013-3-28
Published Online: 2013-09-09
Published in Print: 2013-07-15

© 2013, Carl Hanser Publisher, Munich

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  16. Interaction of Cationic CTAB Surfactant with Curcumin, an Anticarcinogenic Drug: Spectroscopic Investigation
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https://doi.org/10.3139/113.110261
Keywords for this article
Curcumin; CTAB surfactant; CMC; drug-surfactant interaction; UV-Visible spectroscopy

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Application
  6. Surface and Interfacial Performance of Unsaturated Octadecyl Carboxybetaine
  7. Synthesis of Thermoresponsive SiO2 Composite Modified by Nonionic Organosilicone Surfactant
  8. Combination of Best Promoter and Micellar Catalyst for Chromic Acid Oxidation of D-Mannitol to Mannose in Aqueous Media
  9. Antimicrobial Efficacy of Hygiene Rinsers under Consumer-Related Conditions
  10. Environmental Chemistry
  11. How Effective are Alternative Ways of Laundry Washing?
  12. Novel Surfactants
  13. Foaming Behavior of Dialdehyde Starch Schiff-base Derivatives
  14. Novel Diphenyl Methane Based Quaternary Ammonium Surfactants: Synthesis, Surface Properties and Antimicrobial Activity
  15. Physical Chemistry
  16. Interaction of Cationic CTAB Surfactant with Curcumin, an Anticarcinogenic Drug: Spectroscopic Investigation
  17. Parametric Optimization and Thermo-dynamic Studies on the Influence of Electrolytes on Sodium Salicylate in Aqueous Solution
  18. Effect of Cationic Surfactant on the Oxidation of Galactose by N-Bromophthalimide in the Presence of Acidic Medium: A Kinetic and Mechanistic Study
  19. News
  20. Retirement of Professor Ulrich Buller
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