CHEBI:50010 - 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid

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ChEBI Name 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid ChEBI ID CHEBI:50010 Definition An organosulfonic acid comprising stilbene having 4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino groups at the 4 and 4'-positions and sulfo groups at the 2- and 2'-positions. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information ChemicalBook:CB6918820, ZINC000001554588 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C40H44N12O10S2 Net Charge 0 Average Mass 916.98424 Monoisotopic Mass 916.27448 InChI InChI=1S/C40H44N12O10S2/c53-21-17-51(18-22-54)39-47-35(41-29-7-3-1-4-8-29)45-37(49-39)43-31-15-13-27(33(25-31)63(57,58)59)11-12-28-14-16-32(26-34(28)64(60,61)62)44-38-46-36(42-30-9-5-2-6-10-30)48-40(50-38)52(19-23-55)20-24-56/h1-16,25-26,53-56H,17-24H2,(H,57,58,59)(H,60,61,62)(H2,41,43,45,47,49)(H2,42,44,46,48,50) InChIKey CNGYZEMWVAWWOB-UHFFFAOYSA-N SMILES [H]C(=C([H])c1ccc(Nc2nc(Nc3ccccc3)nc(n2)N(CCO)CCO)cc1S(O)(=O)=O)c1ccc(Nc2nc(Nc3ccccc3)nc(n2)N(CCO)CCO)cc1S(O)(=O)=O Roles Classification Application(s): fluorochrome A fluorescent dye used to stain biological specimens. (via 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid ) View more via ChEBI Ontology ChEBI Ontology Outgoing 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid (CHEBI:50010) has parent hydride stilbene (CHEBI:26775) 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid (CHEBI:50010) has role fluorochrome (CHEBI:51217) 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid (CHEBI:50010) is a 1,3,5-triazines (CHEBI:26588) 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid (CHEBI:50010) is a organosulfonic acid (CHEBI:33551) 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid (CHEBI:50010) is conjugate acid of 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonate (CHEBI:50012) Incoming 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonate (CHEBI:50012) is conjugate base of 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid (CHEBI:50010) IUPAC Name 2,2'-ethene-1,2-diylbis[5-({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)benzenesulfonic acid] Synonyms Sources 4,4'-bis((4-(bis(2-hydroxyethyl)amino)-6-anilino-1,3,5-triazin-2-yl)amino)stilbene-2,2'-disulphonic acid ChemIDplus 4,4'-bis((4-anilino-6-(bis(2-hydroxyethyl)amino)-1,3,5-triazin-2-yl)amino)stilbene-2,2'-disulfonic acid ChemIDplus 4,4'-bis((4-anilino-6-(bis(2-hydroxyethyl)amino)-s-triazin-2-yl)amino)-2,2'-stilbenedisulfonic acid ChemIDplus C.I. Fluorescent brightening agent 28 ChemIDplus Calcofluor M2R ChemIDplus Calcofluor White M2R ChemIDplus Registry Numbers Types Sources 4404-43-7 CAS Registry Number ChemIDplus 604239 Beilstein Registry Number Beilstein 8385272 Reaxys Registry Number Reaxys Citations Zhu R, Liu K, Peng J, Yang H, Hong H (2007) Optical brightener M2R destroys the peritrophic membrane of Spodoptera exigua (Lepidoptera: Noctuidae) larvae. Pest management science 63, 296-300 [PubMed:17252623] [show Abstract] Observations under an environmental scanning electron microscope showed that the peritrophic membrane (PM) of Spodoptera exigua (Hübner) was smooth without pores, but there were many pores and slits in the PM of larvae fed with 10 g L(-1) optical brightener Calcofluor white M2R. After incubation of S. exigua PM in vitro with 10 g L(-1) M2R, a significant amount of proteins was released from the PM structure. M2R disrupted the structure of larval PM, resulting in greatly increased permeability and increased larval susceptibility to Syngrapha falcifera multiple nucleopolyhedrovirus infection. Continuous feeding of larvae on a diet treated with a 10 g L(-1) M2R solution significantly retarded larval development and resulted in high mortality. The destructive effect of M2R on PM was transient and reversible, depending on the presence of M2R within the midgut. Stagoj MN, Komel R, Comino A (2004) Microtiter plate assay of yeast cell number using the fluorescent dye calcofluor white M2R. BioTechniques 36, 380-382 [PubMed:15038150] Green LC, LeBlanc PJ, Didier ES (2000) Discrimination between viable and dead Encephalitozoon cuniculi (Microsporidian) spores by dual staining with sytox green and calcofluor white M2R. Journal of clinical microbiology 38, 3811-3814 [PubMed:11015407] [show Abstract] Microsporidia are obligate intracellular parasites, recognized as causing chronic diarrhea and systemic disease in AIDS patients, organ transplant recipients, travelers, and malnourished children. Species of microsporidia that infect humans have been detected in drinking-water sources, and methods are needed to ascertain if these microsporidia are viable and capable of causing infections. In this study, Calcofluor White M2R and Sytox Green stains were used in combination to differentiate between live (freshly harvested) and dead (boiled) Encephalitozoon cuniculi spores. Calcofluor White M2R binds to chitin in the microsporidian spore wall. Dual-stained live spores appeared as turquoise-blue ovals, while dead spores appeared as white-yellow ovals at an excitation wavelength of 395 to 415 nm used for viewing the Calcofluor stain. Sytox Green, a nuclear stain, is excluded by live spores but penetrates compromised spore membranes. Dual-stained dead spores fluoresced bright yellow-green when viewed at an excitation wavelength of 470 to 490 nm, whereas live spores failed to stain with Sytox Green. After live and dead spores were mixed at various ratios, the number of viably stained spores detected in the dual-staining procedure correlated (P = 0.0025) with the expected numbers of viable spores. Spore mixtures were also assayed for infectivity in a focus-forming assay, and a correlation (P = 0.0002) was measured between the percentage of focus-forming microsporidia and the percentage of expected infectious spores in each mixture. By analysis of variance, no statistically significant differences were measured between the percentage of viably stained microsporidia and the percentage of infectious microsporidia (P = 0.964) in each mixture. These results suggest that Calcofluor White M2R and Sytox Green stains, when used together, may facilitate studies to identify viable microsporidia. Wachsmuth ED (1988) A comparison of the highly selective fluorescence staining of fungi in tissue sections with Uvitex 2B and Calcofluor White M2R. The Histochemical journal 20, 215-221 [PubMed:3061981] [show Abstract] The selective fluorescence staining of two fungi, Candida albicans and Blastomyces dermatitides, with Uvitex 2B and Calcofluor White M2R was studied in deparaffinized and frozen sections of mouse kidney and lung. Both fluorochromes emitted maximally at about 430 nm, independent of the mounting media (Kaiser's gelatin or Entellan). In addition to fungi, both fluorochromes also stained elastic fibres. The fluorescence intensity remained unchanged after storage of sections for more than 6 months in conventional slide boxes. The two fluorochromes showed the following differences: Calcofluor faded 1.25 times faster than Uvitex when illuminated with ultraviolet light. Calcofluor showed a greater affinity for tissues in general, and red cells and renal tubular casts in particular. Counterstaining of deparaffinized sections with Hemalum and Eosin reduced the fungi fluorescence and suppressed the general background fluorescence. However, it led to an intensification of Eosin staining and the fluorescence of red cells in Calcofluor-stained sections but not in Uvitex-stained ones. Similarly, the background fluorescence in frozen sections was reduced by Evans Blue, although elastic fibres still fluoresced after staining with Calcofluor. The degree of staining selectivity, and thus the contrast produced within a histological specimen, was greater with Uvitex 2B than with Calcofluor White M2R. Fischer JM, Peterson CA, Bols NC (1985) A new fluorescent test for cell vitality using calcofluor white M2R. Stain technology 60, 69-79 [PubMed:2580370] [show Abstract] The fluorescent fabric-brightener dye, Calcofluor white M2R (CFW), can be used to distinguish between living and dead cells from a variety of animal and plant sources. CFW does not stain living mouse fibroblasts or trout red blood cells and stains only the cell walls in living cells from the epidermis of onion bulb scale, staminal hairs of Tradescantia, and longitudinal sections of broad bean stems and roots. Heat-killed plant or animal cells are recognized by their lightly stained cytoplasm and brightly stained nuclei. The optimum staining concentrations were very low (0.01% to 0.03%) and nontoxic. Using onion scale epidermis in which some cells had been killed by heating as a test system, and the plasmolysis-deplasmolysis rection as the ultimate test for cell vitality, results from CFW staining correctly predicted cell vitality for about 98% of the cells tested. This success rate was comparable to those for Evans blue, uranin or neutral red in this test system. Arroyo-Begovich A, Almanza de Celis S (1982) [Changes in the encystment of Entamoeba invadens caused by Calcofluor M2R]. Archivos de investigacion medica 13 Suppl 3, 13-16 [PubMed:7181601] Last Modified 19 July 2011