IJOC  Vol.1 No.4 , December 2011
Electrochemical Characterization, Detoxification and Anticancer activity of Didodecyldimethylammonium Bromide
Abstract: Quaternaryammonium compounds (QACs) are cationic surfactants with broad range applications. They enter into aquatic environment through the discharge of sewage effluents and adversely affect the ecosystem due to toxicity. Modern electrochemical methods have been used for characterization and detoxification of an extensively used QAC, didodecyldimethylammonium bromide (DDAB) in a wide pH range. The diffusion coefficient of DAAB was determined by Randles-Sevcik equation. In acidic conditions the electrochemical reduction of DAAB occurred by two electrons and two protons process. However, in neutral medium the overall reduction of DAAB followed electronation-protonation mechanism involving 3e– and 3H+. Although DDAB is toxic yet it is bestowed with cancer preventing ability. Hence, for getting insights into the under-standing of DAAB anticancer effect, its DNA binding parameters has been evaluated.
Cite this paper: nullA. Shah, E. Nosheen, R. Qureshi, M. Yasinzai, S. Lunsford, D. Dionysiou, Z. ur-Rehman, M. Siddiq, A. Badshah and S. Ali, "Electrochemical Characterization, Detoxification and Anticancer activity of Didodecyldimethylammonium Bromide," International Journal of Organic Chemistry, Vol. 1 No. 4, 2011, pp. 183-190. doi: 10.4236/ijoc.2011.14027.

[1]   Y. Kuboyama, K. Suzuki and T. Hara, “Nasal Lesions Induced by Intranasal Administration of Benzalkonium Chloride in Rats,” Journal of Toxicological Sciences, Vol. 22, No. 2, 1997, pp. 153-160. doi:10.2131/jts.22.2_153

[2]   B. Nicola, E. Nicolas, R. Junice and V. Glyn, “Paediatric Toxicology Handbook of Poisoning in Children,” Macmillan Reference Ltd., London, 1997.

[3]   R. Beasley, D. Fishwick, J. F. Miles and L. Hendeles, “Preservatives in Nebulizer Solutions: Risks without Benefit,” Pharmacotherapy, Vol. 18, 1998, pp. 130-139.

[4]   P. S. Boeris, A. S. Liffourrena, M. A. Salvano and G. I. Lucchesi, “Physiological Role of Phosphatidylcholine in the Pseudomonas putida A ATCC 12633 Response to Tetradecyltrimethylammonium Bromide and Aluminium,” Letters in Applied Microbiology, Vol. 49, No. 4, 2009, pp. 491-496. doi:10.1111/j.1472-765X.2009.02699.x

[5]   R. P. Singh, N. Gupta, S. Singh, A. Singh, R. Suman and K. Annie, “Toxicity of Ionic and Non Ionic Surfactants to Six Microbes Found in Agra, India,” Bulletin of Environmental Contamination and Toxicology, Vol. 69, No. 2, 2002, pp. 265-270. doi:10.1007/s00128-002-0056-z

[6]   F. Placucci, A. Benini and A. Tosti, “Occupational Allergic Contact Dermatitis from Disinfectant Wipes Used in Dentistry,” Contact Dermatitis, Vol. 35, No. 5, 1996, p. 306. doi:10.1111/j.1600-0536.1996.tb02397.x

[7]   D. Chataigner, R. Garnier, S. Sans and M. L. Efthymiou, “Intoxication Aigue Accidentelle Par un Désinfectant Hospitalier. 45 cas dont 13 d’évolution Mortelle,” La Presse Médicale, Vol. 20, 1991, pp. 741-743.

[8]   M. Van Berkel and F. A. de Wolff, “Survival after Benzalkonium Chloride Poisoning,” Human Toxicology, Vol. 7, 1988, pp. 191-193. doi:10.1177/096032718800700216

[9]   R. Ren, D. Liu, K. Li, J. Sun and C. Zhang, “Adsorption of Quaternary Ammonium Compounds onto Activated Sludge,” Journal of Water Resource and Protection, Vol. 3, No. 2, 2011, pp. 105-113. doi:10.4236/jwarp.2011.32012

[10]   M. T. Garcia, E. Campos, J. Sanchez-Leal and I. Risoba, “Anaerobic Degradation and Toxicity of Commercial Cationic Surfactants in Anaerobic Screening Tests,” Che- mosphere, Vol. 41, No. 5, 2000, pp. 705-710. doi:10.1016/S0045-6535(99)00455-5

[11]   H. T. Chifotides and K. R. Dunbar, “Interactions of Metal-Metal-Bonded Antitumor Active Complexes with DNA Fragments and DNA,” Accounts of Chemical Research, Vol. 38, No. 2, 2005, pp. 146-156. doi:10.1021/ar0302078

[12]   D. D. Li, J. L. Tian, W. Gu, X. Liu, H. H. Zeng and S. P. Yan, “DNA Binding, Oxidative DNA Cleavage, Cytotoxicity, and Apoptosis-Inducing Activity of Copper(II) Complexes with 1,4-Tpbd(N,N,N’,N’-tetrakis(2-yridylme- thyl)benzene-1,4-diamine) Ligand,” Journal of Inorganic Biochemistry, Vol. 105, No. 6, 2011, pp. 894-901. doi:10.1016/j.jinorgbio.2011.03.012

[13]   M. Egli, L. D. Williams, C. A. Frederick and A. Rich, “DNA-Nogalamycin Interactions,” Biochemistry, Vol. 30, No. 5, 1991, pp. 1364-1372.

[14]   A. Fontana, P. D. Maria, G. Siani and B. H. Robinson, “Kinetics of Breakdown of Vesicles from Didodecyldimethylammonium Bromide Induced by Single Chain Surfactants and by Osmotic Stress in Aqueous Solution,” Colloids and Surfaces B: Biointerfaces, Vol. 32, No. 4, 2003, pp. 365-374. doi:10.1016/j.colsurfb.2003.08.003

[15]   M. Gradzielski, “Recent Developments in the Characterization of Microemulsions,” Current Opinion in Colloid & Interface Science, Vol. 13, No. 4, 2008, pp. 263- 269. doi:10.1016/j.cocis.2007.10.006

[16]   K. Kusumoto and T. Ishikawa, “Didodecyldimethylammonium Bromide (DDAB) Induces Caspase-Mediated Apoptosis in Human Leukemia HL-60 Cells,” Journal of Controlled Release, Vol. 147, No. 2, 2010, pp. 246-252. doi:10.1016/j.jconrel.2010.07.114

[17]   T. Neumann, S. Gajria, N. Bouxsein, L. Jaeger and M. Tirrell, “Structural Responses of DNA-DDAB Films to Varying Hydration and Temperature,” Journal of the American Chemical Society, Vol. 132, No. 20, 2010, pp. 7025-7037. doi:10.1021/ja909514j

[18]   N. Subramanian, S. K. Ghosal, A. Acharya and S. P. Moulik, “Formulation and Physicochemical Characterization of Microemulsion System Using Isopropyl Myristate, Medium-Chain Glyceride, Polysorbate 80 and Water,” Chemical & Pharmaceutical Bulletin, Vol. 53, No. 12, 2005, pp. 1530-1535. doi:10.1248/cpb.53.1530

[19]   A. Shah, A. M. Khan, R. Qureshi, F. L. Ansari, M. F. Nazar and S. S. Shah, “Redox Behavior of Anticancer Chalcone on a Glassy Carbon Electrode and Evaluation of Its Interaction Parameters with DNA,” International Journal of Molecular Sciences, Vol. 9, No. 8, 2008, pp. 1424-1434. doi:10.3390/ijms9081424

[20]   M.-J. Han, Z.-M. Duan, et al., “Molecular Light Switches for Calf Thymus DNA Based on Three Ru(II) Bipyridyl Complexes with Variations of Heteroatoms,” The Journal of Physical Chemistry C, Vol. 111, No. 44, 2007, pp. 16577-16585. doi:10.1021/jp075194k

[21]   D. L. Guo, Y. Xin, P. C. Zeng, L. S. Guo and Q. Y. Ru, “Interaction of Metal Complexes of Bis(salicylidene)- ethylenediamine with DNA,” Analytical Sciences, Vol. 16, No. 12, 2000, pp. 1255-1260. doi:10.2116/analsci.16.1255

[22]   C. M. A. Brett and A. M. O. Brett, “Electrochemistry. Principles, Methods and Applications,” Oxford University Press, Oxford, 1993.

[23]   V. C. Diculescu, T. A. Enache, P. J. Oliveira and A. M. O. Brett, “Electrochemical Oxidation of Berberine and of Its Oxidation Products at a Glassy Carbon Electrode,” Electroanalysis, Vol. 21, No. 9, 2009, pp. 1027-1034. doi:10.1002/elan.200804516

[24]   B. M. Asit and U. N. Balachandran, “Cyclic Voltammetric Technique for the Determination of the Critical Micelle Concentration of Surfactants, Self-Diffusion Coefficient of Micelles, and Partition Coefficient of an Electrochemical Probe,” Journal of Physical Chemistry, Vol. 95, No. 22, 1991, pp. 9008-9013. doi:10.1021/j100175a106

[25]   A. Shah, V. C. Diculescu, R. Qureshi and A. M. O. Brett, “Electrochemical Behavior of Dimethyl-2-oxoglutarate on Glassy Carbon Electrode,” Bioelectrochemistry, Vol. 77, No. 2, 2010, pp. 145-150. doi:10.1016/j.bioelechem.2009.07.012

[26]   N. Nishiyama, Y. Toshima and Y. Ikeda, “Biodegradation of Alkyltrimethylammonium Salts in Activated Sludge,” Chemosphere, Vol. 30, 2009, pp. 593-603. doi:10.1016/0045-6535(94)00406-K

[27]   D. Y. Guang, “Fate, Behaviour and Effects of Surfactants and Their Degradation Products in the Environment,” Environmental International, Vol. 32, No. 3, 2006, pp. 417-431. doi:10.1016/j.envint.2005.07.004

[28]   Q. Feng, N. Q. Li and Y. Y. Jiang, “Electrochemical Studies of Porphyrin Interacting with DNA and Determination of DNA,” Analytica Chimica Acta, Vol. 344, No. 1-2, 1997, pp. 97-104. doi:10.1016/S0003-2670(97)00008-1

[29]   M. B. Gholivand, S. Kashanian, H. Peyman and H. Roshanfekr, “DNA-Binding Study of Anthraquinone Derivatives Using Chemometrics Methods,” European Journal of Medicinal Chemistry, Vol. 46, No. 7, 2011, pp. 2630-2638. doi:10.1016/j.ejmech.2011.03.034

[30]   M. Aslanoglu and N. Oge, “Voltammetric, UV Absorption and Viscometric Studies of the Interaction of Norepinephrine with DNA,” Turkish Journal of Chemistry, Vol. 29, 2005, pp. 477-485.

[31]   D. F. Evans and H. Wennerstrom, “The Colloidal Domain: Where Physics, Chemistry, Biology, and Technology Meet,” VCH Publishers Inc., New York, 1994.

[32]   R. Atkin, V. S. J. Craig, E. J. Wanless and S. Biggs, “Mechanism of Cationic Surfactant Adsorption at the Solid-Aqueous Interface,” Advances in Colloid and Interface Science, Vol. 103, No. 3, 2003, pp. 219-304. doi:10.1016/S0001-8686(03)00002-2

[33]   F. Antonella, D. M. Paolo, S. Gabriella and H. R. Brian, “Kinetics of Breakdown of Vesicles from Didodecylammonium Bromide Induced by Single Chain Surfactants and by Osmotic Stress in Aqueous Solution,” Colloids and Surfaces B: Biointerfaces, Vol. 32, No. 4, 2003, pp. 365-374. doi:10.1016/j.colsurfb.2003.08.003