Theoretical Calculation and Experimental Verification Demonstrated the Impossibility of Finding Haptens Identifying Triphenylmethane Dyes and Their Leuco Metabolites Simultaneously

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2018 Mar 16

PMID 29543738

Authors

De-Xin Kong

Fang Lv

Ben Hu

Li-Min Cao

Affiliations

Soon will be listed here.

Abstract

Detection of triphenylmethane dyes (TDs), especially the widely used malachite green (MG) and crystal violet (CV), plays an important role in safety control of aquatic products. There are two chromatic forms of TDs: oxidized or reduced. Usually, only one form can be detected by reported ELISA antibodies. In this article, molecular shape superimposing and quantum mechanics calculation were employed to elucidate the differences between MG, CV, and their reduced chromatic forms (leucomalachite green, LMG and leucocrystal violet, LCV). A potential hapten was rationally designed and synthesized. Polyclonal antibodies were raised through immunizing New Zealand white rabbits and BALB/C mice. We tested the cross-reactivity ratios between the hapten and TDs. The cross-reactivity ratios were correlated with the difference in surface electrostatic potential. The determination coefficients (²) of the correlations are 0.901 and 0.813 for the rabbit and mouse antibody, respectively. According to this linear model, the significant difference in the atomic charge seemed to make it impossible to find a hapten that can produce antibodies with good cross-reactivities with both reduced and oxidized TDs.

References

Bergwerff A, Scherpenisse P . Determination of residues of malachite green in aquatic animals. J Chromatogr B Analyt Technol Biomed Life Sci. 2003; 788(2):351-9. DOI: 10.1016/s1570-0232(03)00042-4. View

Cao L, Kong D, Sui J, Jiang T, Li Z, Ma L . Broad-specific antibodies for a generic immunoassay of quinolone: development of a molecular model for selection of haptens based on molecular field-overlapping. Anal Chem. 2009; 81(9):3246-51. DOI: 10.1021/ac802403a. View

Irwin J, Shoichet B . ZINC--a free database of commercially available compounds for virtual screening. J Chem Inf Model. 2005; 45(1):177-82. PMC: 1360656. DOI: 10.1021/ci049714+. View

Galve R, Camps F, Sanchez-Baeza F, Marco M . Development of an immunochemical technique for the analysis of trichlorophenols using theoretical models. Anal Chem. 2000; 72(10):2237-46. DOI: 10.1021/ac991336y. View

Oplatowska M, Connolly L, Stevenson P, Stead S, Elliott C . Development and validation of a fast monoclonal based disequilibrium enzyme-linked immunosorbent assay for the detection of triphenylmethane dyes and their metabolites in fish. Anal Chim Acta. 2011; 698(1-2):51-60. DOI: 10.1016/j.aca.2011.04.047. View

Singh G, Koerner T, Gelinas J, Abbott M, Brady B, Huet A . Design and characterization of a direct ELISA for the detection and quantification of leucomalachite green. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2011; 28(6):731-9. PMC: 3118533. DOI: 10.1080/19440049.2011.567360. View

Broughton H . Molecular modeling. Curr Opin Chem Biol. 1998; 1(3):392-8. DOI: 10.1016/s1367-5931(97)80079-8. View

Spreter Von Kreudenstein T, Lario P, Dixit S . Protein engineering and the use of molecular modeling and simulation: the case of heterodimeric Fc engineering. Methods. 2013; 65(1):77-94. DOI: 10.1016/j.ymeth.2013.10.016. View

Shen Y, Deng X, Xu Z, Wang Y, Lei H, Wang H . Simultaneous determination of malachite green, brilliant green and crystal violet in grass carp tissues by a broad-specificity indirect competitive enzyme-linked immunosorbent assay. Anal Chim Acta. 2011; 707(1-2):148-54. DOI: 10.1016/j.aca.2011.09.006. View

10.

Albrecht M, Muller M, Mergel O, Rissanen K, Valkonen A . CH-directed anion-pi interactions in the crystals of pentafluorobenzyl-substituted ammonium and pyridinium salts. Chemistry. 2010; 16(17):5062-9. DOI: 10.1002/chem.200903016. View

11.

Nichkova M, Galve R, Marco M . Biological monitoring of 2,4,5-trichlorophenol (I): preparation of antibodies and development of an immunoassay using theoretical models. Chem Res Toxicol. 2002; 15(11):1360-70. DOI: 10.1021/tx025555h. View

12.

Mu H, Lei H, Wang B, Xu Z, Zhang C, Ling L . Molecular modeling application on hapten epitope prediction: an enantioselective immunoassay for ofloxacin optical isomers. J Agric Food Chem. 2014; 62(31):7804-12. DOI: 10.1021/jf404449n. View

13.

Yang M, Fang J, Kuo T, Wang D, Huang Y, Liu L . Production of antibodies for selective detection of malachite green and the related triphenylmethane dyes in fish and fishpond water. J Agric Food Chem. 2007; 55(22):8851-6. DOI: 10.1021/jf071195y. View

14.

Valle L, Diaz C, Zanocco A, Richtera P . Determination of the sum of malachite green and leucomalachite green in salmon muscle by liquid chromatography-atmospheric pressure chemical ionisation-mass spectrometry. J Chromatogr A. 2005; 1067(1-2):101-5. DOI: 10.1016/j.chroma.2004.10.049. View

15.

Dowling G, Mulder P, Duffy C, Regan L, Smyth M . Confirmatory analysis of malachite green, leucomalachite green, crystal violet and leucocrystal violet in salmon by liquid chromatography-tandem mass spectrometry. Anal Chim Acta. 2007; 586(1-2):411-9. DOI: 10.1016/j.aca.2006.08.045. View

16.

Snider B, Gu Y . Total synthesis of (-)- and (+)-dysibetaine. Org Lett. 2001; 3(11):1761-3. DOI: 10.1021/ol015954o. View

17.

Arroyo D, Ortiz M, Sarabia L, Palacios F . Determination and identification, according to European Union Decision 2002/657/EC, of malachite green and its metabolite in fish by liquid chromatography-tandem mass spectrometry using an optimized extraction procedure and three-way calibration. J Chromatogr A. 2009; 1216(29):5472-82. DOI: 10.1016/j.chroma.2009.05.076. View

18.

Hurtaud-Pessel D, Couedor P, Verdon E, Dowell D . Determination of residues of three triphenylmethane dyes and their metabolites (malachite green, leuco malachite green, crystal violet, leuco crystal violet, and brilliant green) in aquaculture products by LC/MS/MS: first action 2012.25. J AOAC Int. 2013; 96(5):1152-7. DOI: 10.5740/jaoacint.13-142. View

19.

Liu Y, Jin M, Gui W, Cheng J, Guo Y, Zhu G . Hapten design and indirect competitive immunoassay for parathion determination: correlation with molecular modeling and principal component analysis. Anal Chim Acta. 2007; 591(2):173-82. DOI: 10.1016/j.aca.2007.03.071. View