Detection of <i>Para</i>-Chloroaniline Resulting from the Interaction between Sodium Hypochlorite and Chlorhexidine Analyzed by Mass Spectrometry — Oak Academic Publishing
Research ArticleOpen AccessGoogle Scholar indexed
Detection of <i>Para</i>-Chloroaniline Resulting from the Interaction between Sodium Hypochlorite and Chlorhexidine Analyzed by Mass Spectrometry
Instituto de Estudios Avanzados en Odontología “Yury Kutler”, Mexico City, Mexico
,
Instituto de Estudios Avanzados en Odontología “Yury Kutler”, Mexico City, Mexico
,
Instituto de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico
,
Departamento de Microbiología y Parasitología, Facultad de Medicina, Universidad Nacional Autónoma de México, Mexico City, Mexico
,
Departamento de Bioquímica y Biología Estructural, Instituto de Fisiología Celular, Universidad Nacional Autónoma de México, México City, Mexico
,
Instituto de Estudios Avanzados en Odontología “Yury Kutler”, Mexico City, Mexico
1 Instituto de Estudios Avanzados en Odontología “Yury Kutler”, Mexico City, Mexico
2 Instituto de Estudios Avanzados en Odontología “Yury Kutler”, Mexico City, Mexico
3 Instituto de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico
4 Departamento de Microbiología y Parasitología, Facultad de Medicina, Universidad Nacional Autónoma de México, Mexico City, Mexico
5 Departamento de Bioquímica y Biología Estructural, Instituto de Fisiología Celular, Universidad Nacional Autónoma de México, México City, Mexico
6 Instituto de Estudios Avanzados en Odontología “Yury Kutler”, Mexico City, Mexico
5.1% of sodium hypochlorite (NaOCl) mixed with 2% of chlorhexidine (CHX) forms a brown precipitate that corresponds to para -chloroaniline (PCA), whether PCA is formed after the combination of NaOCl, CHX, and ethylenediaminetetraacetic acid (EDTA) by means of electron impact (high resolution and interlaced scanning) and ionization by fast atom bombardment (FAB), was analyzed. The brown precipitate, showed signals 127 and 153 Da, corresponding to p -chloroaniline and p -chlorophenyl isocyanate, respectively. These results were analyzed and compared with signals from the interlaced scanning program and confirmed with high resolution mass spectrometry analysis and compared with the NIST database. The mass spectra of this precipitated after different days confirmed the evolution of byproducts with the presence of a peak m/z = 127, due to the decrease of the fragment m/z = 153, which disappeared after 180 days. A blue and a white precipitate were observed by the addition of CHX (2%) with or without polyethylene glycol, respectively, EDTA (17%) and NaOCl (5.1%) precipitates contain chlorhexidine ( m/z = 505), but no PCA was detected. We confirmed that PCA is not formed directly as a byproduct of CHX oxidation, but through the formation of the para -chlorophenyl isocyanate intermediate, which degrades slowly to PCA.
Kakehashi, S., Stanley, H.R. and Fitzgerald, R.J. (1965) The Effects of Surgical Exposures of Dental Pulps in Germ-Free and Conventional Laboratory Rats. Oral Surgery, Oral Medicine, Oral Pathology, Oral Radiology, and Endodontology, 20, 340-349. https://doi.org/10.1016/0030-4220(65)90166-0
Moller, A.J., Fabricius, L., Dahlen, G., Ohlman, A.E. and Heyden, G. (1981) Influence on Periapical Tissues of Indigenous Oral Bacteria and Necrotic Pulp Tissue in Monkeys. Scandinavian Journal of Dental Research, 89, 475-484. https://doi.org/10.1111/j.1600-0722.1981.tb01711.x
Baumgartner, J.C. (2004) Microbiological and Molecular Analysis of Endodontic Infections. Endodontic Topics, 7, 35-51. https://doi.org/10.1111/j.1601-1546.2004.00061.x
Byström, A. and Sundqvist, G. (1981) Bacteriologic Evaluation of the Efficacy of Mechanical Root Canal Instrumentation in Endodontic Therapy. Scandinavian Journal of Dental Research, 89, 321-328. https://doi.org/10.1111/j.1600-0722.1981.tb01689.x
Thomas, J.E. and Sem, D.S. (2010) An in Vitro Spectroscopic Analysis to Determine Whether Para-Chloroaniline Is Produced from Mixing Sodium Hypochlorite and Chlorhexidine. Journal of Endodontics, 36, 315-317. https://doi.org/10.1016/j.joen.2009.10.028
Gutmann, J.L. and Lovdahl, P. (2010) Problem Solving in Endodontics. Prevention, Identification and Management. 5th Edition, Mosby, London.
Leonardo, M.R., Tanomaru, F.M., Silva, L.A., et al. (1999) In Vivo Antimicrobial Activity of 2% Chlorhexidine Used as a Root Canal Irrigating Solution. Journal of Endodontics, 25, 167-171. https://doi.org/10.1016/S0099-2399(99)80135-6
Kuruvilla, J.R. and Kamath, M.P. (1998) Antimicrobial Activity of 2.5% Sodium Hypochlorite and 0.2% Chlorhexidine Gluconate Separately and Combined, as Endodontic Irrigants. Journal of Endodontics, 24, 472-476. https://doi.org/10.1016/S0099-2399(98)80049-6
Jeansonne, M.J. and White, R.R. (1994) A Comparison of 2.0% Chlorhexidine Gluconate and 5.25% Sodium Hypochlorite as Antimicrobial Endodontic Irrigants. Journal of Endodontics, 20, 276-278. https://doi.org/10.1016/S0099-2399(06)80815-0
Zehnder, M. (2006) Root Canal Irrigants. Journal of Endodontics, 32, 389-398. https://doi.org/10.1016/j.joen.2005.09.014
Komorowski, R., Grad, H., Wu, X.Y. and Friedman, S. (2000) Antimicrobial Substantivity of Chlorhexidine-Treated Bovine Root Dentin. Journal of Endodontics, 26, 315-317. https://doi.org/10.1097/00004770-200006000-00001
Goldman, M., Goldman, L.B., Cavaleri, R., Bogis, J. and Lin, P.S. (1982) The Efficacy of Several Irrigating Solutions for Endodontics: A Scanning Electron Microscopic Study, Part 2. Journal of Endodontics, 8, 487-492. https://doi.org/10.1016/S0099-2399(82)80073-3
Yamada, R.S., Armas, A., Goldman, M. and Lin, P.S. (1983) A Scanning Electron Microscopic Comparison of a High Volume Final Flush with Several Irrigating Solutions: Part 3. Journal of Endodontics, 9, 137-142. https://doi.org/10.1016/S0099-2399(83)80032-6
Baumgartner, J.C. and Mader, C.L. (1987) A Scanning Electron Microscopic Evaluation of Four Root Canal Irrigation Regimens. Journal of Endodontics, 13, 147-157. https://doi.org/10.1016/S0099-2399(87)80132-2
Rosenthal, S., Spångberg, L. and Safavi, K. (2004) Chlorhexidine Substantivity in Root Canal Dentin. Oral Surgery, Oral Medicine, Oral Pathology, Oral Radiology, and Endodontology, 98, 488-492. https://doi.org/10.1016/j.tripleo.2003.07.005
White, R.R., Hays, G.L. and Janer, L.R. (1997) Residual Antimicrobial Activity after Canal Irrigation with Chlorhexidine. Journal of Endodontics, 23, 229-217. https://doi.org/10.1016/S0099-2399(97)80052-0
Kishen, A., Sum, C.P., Mathew, S. and Lim, C.T. (2008) Influence of Irrigation Regimens on the Adherence of Enterococcus faecalis to Root Canal Dentin. Journal of Endodontics, 34, 850-854. https://doi.org/10.1016/j.joen.2008.04.006
Basrani, B.R., Manek, S., Sodhi, R.N. and Fillery, E. (2007) Interaction between Sodium Hypochlorite and Chlorhexidine Gluconate. Journal of Endodontics, 33, 966-969. https://doi.org/10.1016/j.joen.2007.04.001
Bui, T.B., Baumgartner, J.C. and Mitchell, J.C. (2008) Evaluation of the Interaction between Sodium Hypochlorite and Chlorhexidine Gluconate and Its Effect on Root Dentin. Journal of Endodontics, 34, 181-185. https://doi.org/10.1016/j.joen.2007.11.006
Basrani, B.R., Manek, S. and Mathers, D. (2010) Determination of 4-Chloroaniline and Its Derivatives Formed in the Interaction of Sodium Hypochlorite and Chlorhexidine by Using Gas Chromatography. Journal of Endodontics, 36, 312-314. https://doi.org/10.1016/j.joen.2009.10.031
Kolosowski, K.P., Sodhi, R.N., Kishen, A. and Basrani, B.R. (2014) Qualitative Analysis of Precipitate Formation on the Surface and in the Tubules of Dentin Irrigated with Sodium Hypochlorite and a Final Rinse of Chlorhexidine or QMiX. Journal of Endodontics, 40, 2036-2040. https://doi.org/10.1016/j.joen.2014.08.017
Mortenson, D., Sadilek, M., Flake, N.M., et al. (2012) The Effect of Using an Alternative Irrigant between Sodium Hypochlorite and Chlorhexidine to Prevent the Formation of Para-Chloroaniline within the Root Canal System. International Endodontic Journal, 45, 878-882. https://doi.org/10.1111/j.1365-2591.2012.02048.x
Havlíková, L., Matysová, L., Nováková, L., Hájková, R. and Solich, P. (2007) HPLC Determination of Chlorhexidine Gluconate and p-Chloroaniline in Topical Ointment. Journal of Pharmaceutical and Biomedical Analysis, 43, 1169-1173. https://doi.org/10.1016/j.jpba.2006.09.037
World Health Organization. International Agency for Research on Cancer (IARC) (1993) Occupational Exposures of Hairdressers and Barbers and Personal Use of Hair Colourants; Some Hair Dyes, Cosmetic Colourants, Industrial Dyestuffs and Aromatic Amines. Monography on the Evaluation of Carcinogenic Risks to Human Volume 57, Lyon, 305-321.
Orban, E.O., Irmak, Ô., Yaman, B.C. and Karabucak, B. (2016) Does Para-Chloroaniline Really Form after Mixing Sodium Hypochlorite and Chlorhexidine? Journal of Endodontics, 42, 455-459. https://doi.org/10.1016/j.joen.2015.12.024
Krishnamurthy, S. and Sudhakaran, S. (2010) Evaluation and Prevention of the Precipitate Formed on Interaction between Sodium Hypochlorite and Chlorhexidine. Journal of Endodontics, 36, 1154-1157. https://doi.org/10.1016/j.joen.2010.01.012
Chhabra, R.S., Huff, J.E., Haseman, J.K., et al. (1991) Carcinogenicity of p-Chloroaniline in Rats and Mice. Food and Chemical Toxicology, 29, 119-124. https://doi.org/10.1016/0278-6915(91)90166-5
Valera, M.C., Chung, A., Menezes, M.M., et al. (2010) Scanning Electron Microscope Evaluation of Chlorhexidine Gel and Liquid Associated with Sodium Hypochlorite Cleaning on the Root Canal Walls. Oral Surgery, Oral Medicine, Oral Pathology, 110, e82-e87. https://doi.org/10.1016/j.tripleo.2010.04.051
Vivacqua-Gomes, N., Ferraz, C.C.R., Gomes, B.P.F.A., et al. (2002) Influence of Irrigants on the Coronal Microleakage of Laterally Condensed Gutta-Percha Root Filling. International Endodontic Journal, 35, 791-795. https://doi.org/10.1046/j.1365-2591.2002.00569.x
Giampiero Rossi, F., Dogramaci, E.J., Guastalli, A.R., Steier, L. and de Figueiredo, J.A. (2012) Antagonistic Interactions between Sodium Hypochlorite, Chlorhexidine, EDTA, and Citric Acid. Journal of Endodontics, 38, 426-431. https://doi.org/10.1016/j.joen.2012.01.006
Barbin, L.E., Estrela, C., Costa Guedes, D.F., Emboava Spanó, J.C., Sousa-Neto, M.D. and Djalma Pécora, J. (2013) Detection of Para-Chloroaniline, Reactive Oxygen Species, and 1-Chloro-4-Nitrobenzene in High Concentrations of Chlorhexidine and in a Mixture of Chlorhexidine and Calcium Hydroxide. Journal of Endodontics, 39, 664-668. https://doi.org/10.1016/j.joen.2012.10.018
Nowicki, J. and Sem, D. (2011) An in Vitro Spectroscopic Analysis to Determine the Chemical Composition of the Precipitate Formed by Mixing Sodium Hypochlorite and Chlorhexidine. Journal of Endodontics, 37, 983-988. https://doi.org/10.1016/j.joen.2011.03.033
Aizawa, H. (1982) Metabolic Maps of Pesticides. Academic Press, New York, 128. https://doi.org/10.1016/B978-0-12-046480-7.50007-3
Nimmo, W.B., Willems, A.G.M., Joustra, K.D. and Verloop, A. (1986) The Degradation of Diflubenzuron and Its Chief Metabolites in Soil. Part II: Fate of Chlorophenylurea. Pesticide Science, 17, 403-411. https://doi.org/10.1002/ps.2780170411
Ozgür, I., Ekim, O.O., Kamarun, G. and Batu, C.Y. (2018) Nuclear Magnetic Resonance Spectroscopy and Infrared Spectroscopy Analysis of Precipitate Formed after Mixing Sodium Hypochlorite and QMix 2in1. PLoS ONE, 13, e0202081. https://doi.org/10.1371/journal.pone.0202081
Clarkson, R.M., Podlich, H.M. and Moule, A.J. (2011) Influence of Ethylenediaminetetraacetic Acid on the Active Chlorine Content of Sodium Hypochlorite Solutions When Mixed in Various Proportions. Journal of Endodontics, 37, 538-543. https://doi.org/10.1016/j.joen.2011.01.018
Grande, N.M., Plotino, G., Falanga, A., Pomponi, M. and Somma, F. (2006) Interaction between EDTA and Sodium Hypochlorite: A Nuclear Magnetic Resonance Analysis. Journal of Endodontics, 32, 460-464. https://doi.org/10.1016/j.joen.2005.08.007
Rasimick, B.J., Nekich, M., Hladek, M.M., Musikant, B.L. and Deutsch, A.S. (2008) Interaction between Chlorhexidine Digluconate and EDTA. Journal of Endodontics, 34, 1521-1523. https://doi.org/10.1016/j.joen.2008.08.039