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Sudan II

(Synonyms: Sudan Red II, Solvent Orange 7, Color Index No:12140, C.I. 12140) 目录号 : GC25971

Sudan II (Sudan Red II, Solvent Orange 7, Color Index No: 12140, C.I. 12140) is a lysochrome (fat-soluble dye) azo dye used for staining of triglycerides in frozen sections, and some protein bound lipids and lipoproteins on paraffin sections.

Sudan II Chemical Structure

Cas No.:3118-97-6

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100mg
¥556.00
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产品描述

Sudan II (Sudan Red II, Solvent Orange 7, Color Index No: 12140, C.I. 12140) is a lysochrome (fat-soluble dye) azo dye used for staining of triglycerides in frozen sections, and some protein bound lipids and lipoproteins on paraffin sections.

[1] Carolina V Di Anibal, et al. Talanta. 2009 Aug 15;79(3):887-92.

Chemical Properties

Cas No. 3118-97-6 SDF Download SDF
别名 Sudan Red II, Solvent Orange 7, Color Index No:12140, C.I. 12140
分子式 C18H16N2O 分子量 276.33
溶解度 DMSO: 30 mg/mL (108.57 mM);Water: Insoluble;Ethanol: 1 mg/mL (3.62 mM) 储存条件 Store at -20°C
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1 mM 3.6189 mL 18.0943 mL 36.1886 mL
5 mM 0.7238 mL 3.6189 mL 7.2377 mL
10 mM 0.3619 mL 1.8094 mL 3.6189 mL
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Research Update

Molecular Modeling Study of the Genotoxicity of the Sudan I and Sudan II Azo Dyes and Their Metabolites

Front Chem 2022 Jun 23;10:880782.PMID:35815205DOI:10.3389/fchem.2022.880782.

Azo dyes are defined by the presence of a characteristic N=N group. Sudan I and Sudan II are synthetic azo dyes that have been used as coloring agents. Although animal toxicity studies suggest that Sudan dyes are mutagenic, their molecular mechanism of action is unknown, thus making it challenging to establish thresholds for tolerable daily intake or to understand how these molecules could be modified to ameliorate toxicity. In addition, dye metabolites, such as azobiphenyl and 4-aminobiphenyl, have been correlated with epigenetic alterations. We shed some light on the mechanisms of Sudan dye genotoxicity through a molecular modeling study of Sudan I and Sudan II dyes and two common metabolites interacting with DNA as adducts. The results suggest that all four adducts cause significant perturbations to the DNA helical conformation and structure; thus, it can be inferred that DNA repair and replication processes would be significantly impacted.

Binding of Sudan II and IV to lecithin liposomes and E. coli membranes: insights into the toxicity of hydrophobic azo dyes

BMC Struct Biol 2007 Mar 27;7:16.PMID:17389047DOI:10.1186/1472-6807-7-16.

Background: Sudan red compounds are hydrophobic azo dyes, still used as food additives in some countries. However, they have been shown to be unsafe, causing tumors in the liver and urinary bladder in rats. They have been classified as category 3 human carcinogens by the International Agency for Research on Cancer. A number of hypotheses that could explain the mechanism of carcinogenesis have been proposed for dyes similar to the Sudan red compounds. Traditionally, investigations of the membrane toxicity of organic substances have focused on hydrocarbons, e.g. polycyclic aromatic hydrocarbons (PAHs), and DDT. In contrast to hydrocarbons, Sudan red compounds contain azo and hydroxy groups, which can form hydrogen bonds with the polar head groups of membrane phospholipids. Thus, entry may be impeded. They could have different toxicities from other lipophilic hydrocarbons. The available data show that because these compounds are lipophilic, interactions with hydrophobic parts of the cell are important for their toxicity. Lipophilic compounds accumulate in the membrane, causing expansion of the membrane surface area, inhibition of primary ion pumps and increased proton permeability. Results: This work investigated the interactions of the amphiphilic compounds Sudan II and IV with lecithin liposomes and live Escherichia coli (E. coli). Sudan II and IV binding to lecithin liposomes and live E. coli corresponds to the Langmuir adsorption isotherm. In the Sudan red compounds--lecithin liposome solutions, the binding ratio of Sudan II to lecithin is 1/31 and that of Sudan IV to 1/314. The binding constant of the Sudan II-lecithin complex is 1.75 x 104 and that of the Sudan IV-lecithin complex 2.92 x 105. Besides, the influences of pH, electrolyte and temperature were investigated and analyzed quantitatively. In the Sudan red compounds--E.coli mixture, the binding ratios of Sudan II and Sudan IV to E.coli membrane phospholipid are 1/29 and 1/114. The binding constants of the Sudan II--and Sudan IV- E.coli membrane phospholipid complexes are 1.86 x 104 and 6.02 x 104. Over 60% of Sudan II and 75% of Sudan IV penetrated into E.coli, in which 90% of them remained in the E.coli membrane. Conclusion: Experiments of Sudan II and IV binding to lecithin liposomes and live E. coli indicates that amphiphilic compounds may be sequestered in the lecithin liposomes and membrane phospholipid bilayer according to the Langmuir adsorption law. Penetration into the cytosol was impeded and inhibited for Sudan red compounds. It is possible for such compounds themselves (excluding their metabolites and by-products)not result directly in terminal toxicity. Therefore, membrane toxicity could be manifested as membrane blocking and membrane expansion. The method established here may be useful for evaluating the interaction of toxins with membranes.

Determination of Sudan I and II in Food by High-Performance Liquid Chromatography after Simultaneous Adsorption on Nanosilica

J Anal Methods Chem 2021 Feb 15;2021:6664463.PMID:33628578DOI:10.1155/2021/6664463.

Analytical techniques for analyte quantification are often complex, time-consuming, and costly. Further, samples must be carefully prepared to make them suitable for each analytical technique, thus increasing complexity and cost and often requiring toxic solvents. In this paper, we propose a simple and quick method for the pre-concentration of analytes using a nonporous adsorbent: nanosilica, which is prepared from rice husks, an ecofriendly waste material. Subsequently, analysis using high-performance liquid chromatography with a photodiode array detector was used for accurate analyte quantification. To test our method, Sudan I and II dyes were selected because these are potential carcinogens that are often used to adulterate foods because of their bright colors. Although nanosilica has been used as an adsorbent before, the adsorption of hydrophobic organic dyes has not been investigated to date. Thus, the optimal conditions for dye adsorption on nanosilica were systematically studied and found to be 1 mM KCl, pH 3.0, and an adsorption time of 120 min, and the maximum adsorption capacities of the nanosilica for Sudan I and II were 0.619 and 0.699 mg·g-1, respectively. The adsorption of the dyes on the nanosilica is discussed in detail with respect to the surface area, functional groups, zeta potential, and adsorption isotherms. Under optimal conditions, the extraction efficiencies of Sudan I and Sudan II reached 98.3% and 92.8%, respectively, and the proposed method was applied for the analysis of several foods and achieved high recoveries (80-100%).

Binding of Sudan II and Sudan IV to bovine serum albumin: comparison studies

Food Chem Toxicol 2011 Dec;49(12):3158-64.PMID:21951948DOI:10.1016/j.fct.2011.09.011.

In this paper, we report the interaction of Sudan II and Sudan IV to bovine serum albumin (BSA). Structural analysis showed that both Sudan II and Sudan IV interact mainly with BSA at the hydrophobic pocket and via Van der Waals forces. The number of bound Sudan molecule for each protein molecule was approximately 1. The overall binding constants at 293 K (20°C) estimated for Sudan II and Sudan IV were 1.22 × 10(4)M(-1) and 1.48 × 10(4)M(-1), respectively. BSA backbone structure was damaged by the dyes with more severe phenomenon observed for Sudan IV. For two Sudan dyes with the same concentration, Sudan IV could cause more alterations on CD spectra of BSA with slight decrease of α-helical content and increase of β-sheet content, suggesting a partial protein unfolding.

Comparison of the toxicity of the dyes Sudan II and Sudan IV to catalase

J Biochem Mol Toxicol 2017 Oct;31(10).PMID:28613393DOI:10.1002/jbt.21943.

The mechanisms of the toxicity of Sudan dyes to the key antioxidant enzyme catalase (CAT) were investigated by spectroscopic methods, calorimetry techniques, enzyme activity assay, and molecular docking. Results showed that Sudan dyes bound to CAT through hydrophobic force, which changed the microenvironment of tryptophan and tyrosine residues, leading to a conformational alteration and shrinkage of the protein. Enzyme activity assay and molecular docking revealed that the activity of CAT was slightly inhibited in the presence of Sudan dyes. In comparison, the binding of Sudan II with CAT was slightly stronger than Sudan IV. Also, Sudan II and Sudan IV showed a different impact on the microenvironment of aromatic amino acid residues. But the dyes had very similar effects on conformation and activity of the protein. This work provides an essential reference for the evaluation of Sudan dyes' effects on body's antioxidant defense system and safe use of Sudan dyes.