Sigma Dyes, Stains, and Natural Pigments
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New Nile Blue Derivatives As NIR Fluorescent Probes and Antifungal Agents †
Proceedings New Nile Blue Derivatives as NIR Fluorescent Probes † and Antifungal Agents Rui P. C. L. Sousa 1,2, João C. C. Ferreira 1,2, Maria João M. F. Sousa 2 and M. Sameiro T. Gonçalves 1,* 1 Centre of Chemistry, University of Minho, Campus of Gualtar, 4710-057 Braga, Portugal 2 Centre of Molecular and Environmental Biology, University of Minho, Campus of Gualtar, 4710-057 Braga, Portugal * Correspondence: [email protected] † Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November– 15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22. Published: 14 November 2018 Abstract: The synthesis of four new Nile Blue derivatives with hydrogen, propyl and/or aminopropyl groups as substituents of the amines of 5- and 9-positions is described. Photophysical properties were evaluated in acidified ethanol and aqueous solution at physiological pH. Antifungal activity is also studied through the obtention of MIC values. Keywords: benzo[a]phenoxazines; Nile Blue derivatives; NIR fluorescent probes; antifungal agents 1. Introduction The development of new near-Infrared (NIR) fluorescent probes is a very important issue due to the wide range of applications [1–4]. These probes are an excellent choice to label biological material since its emission will not interfere with the natural fluorescence of biological compounds. Benzo[a]phenoxazinium salts, with Nile Blue being the best known, display fluorescence at around 600 nm and have been used as covalent and non-covalent fluorescent probes for amino acids, proteins and DNA, among other biological material [5–10]. In addition, applications as sensors or agents for photodynamic therapy (PDT) have been described [11,12]. -
Lysochrome Dyes Sudan Dyes, Oil Red Fat Soluble Dyes Used for Biochemical Staining of Triglycerides, Fatty Acids, and Lipoproteins Product Description
FT-N13862 Lysochrome dyes Sudan dyes, Oil red Fat soluble dyes used for biochemical staining of triglycerides, fatty acids, and lipoproteins Product Description Name : Sudan IV Other names: Sudan R, C.I. Solvent Red 24, C.I. 26105, Lipid Crimson, Oil Red, Oil Red BB, Fat Red B, Oil Red IV, Scarlet Red, Scarlet Red N.F, Scarlet Red Scharlach, Scarlet R Catalog Number : N13862, 100g Structure : CAS: [85-83-6] Molecular Weight : MW: 380.45 λabs = 513-529 nm (red); Sol(EtOH): 0.09%abs =513-529nm(red);Sol(EtOH):0.09% S:22/23/24/25 Name : Sudan III Other names: Rouge Sudan ; rouge Ceresin ; CI 26100; CI Solvent Red 23 Catalog Number : 08002A, 25g Structure : CAS:[85-86-9] Molecular Weight : MW: 352.40 λabs = 513-529 nm (red); Sol(EtOH): 0.09%abs =503-510nm(red);Sol(EtOH):0.15% S:24/25 Name : Sudan Black B Other names: Sudan Black; Fat Black HB; Solvent Black 3; C.I. 26150 Catalog Number : 279042, 50g AR7910, 100tests stain for lipids granules Structure : CAS: [4197-25-5] S:22/23/24/25 Molecular Weight : MW: 456.54 λabs = 513-529 nm (red); Sol(EtOH): 0.09%abs=596-605nm(blue-black) Name : Oil Red O Other names: Solvent Red 27, Sudan Red 5B, C.I. 26125 Catalog Number : N13002, 100g Structure : CAS: [1320-06-5 ] Molecular Weight : MW: 408.51 λabs = 513-529 nm (red); Sol(EtOH): 0.09%abs =518(359)nm(red);Sol(EtOH): moderate; Sol(water): Insoluble S:22/23/24/25 Storage: Room temperature (Z) P.1 FT-N13862 Technical information & Directions for use A lysochrome is a fat soluble dye that have high affinity to fats, therefore are used for biochemical staining of triglycerides, fatty acids, and lipoproteins. -
Study of the Effect of Sudan II and Treatment Water Coupled with Fe2+ in Modulating Hematological and Biochemical Changes in Rabbits’
J Biochem Tech (2019) 10(1): 79-84 ISSN: 0974-2328 Study of the Effect of Sudan II and Treatment water Coupled with Fe2+ in Modulating Hematological and Biochemical Changes in Rabbits’ Elham M. Hussien*, Sawsan M. Abu El Hassan and Ferial M.N. Fudllalah Received: 19 November 2018 / Received in revised form: 02 March 2019, Accepted: 07 March 2019, Published online: 24 March 2019 © Biochemical Technology Society 2014-2019 © Sevas Educational Society 2008 Abstract Throughout the years, azo compounds including Sudan dyes have Finally, the present study proved that Sudan II treated with ferrous been widely used in industry as colorants in food, cosmetics, sulfate can keep hematological parameters, liver and kidney waxes, solvents, textiles, plastics and printing inks. Sudan dyes I, functions near the physiological normal state. II, III, IV, and their degradation products have been regarded to hurt human health. They cause cancer due to their teratogenicity, Keywords: Ferrous sulfate, Sudan dyes, liver and kidney genotoxicity and carcinogenicity effects. In the present work, the functions and rabbits. efficiency of ferrous sulfate with low cost and the first choice in the treatment of printing, dyeing and electroplating wastewater to Introduction reduce the toxicity of Sudan II-induced oxidative damage to hematological parameters, liver and kidney functions in adult Synthetic or natural food additives may be used as flavoring or female and male rabbits was investigated. Animals which received coloring tools (Sayed et al., 2012). Moreover, Amin et al. (2010) Sudan II were treated with ferrous sulfate as the sole source of explained that colorants provide an aesthetic appearance to foods potent liquid for 14 days at the dose of 111mg/kg B.wt before preferred by consumers. -
Student Safety Sheets Dyes, Stains & Indicators
Student safety sheets 70 Dyes, stains & indicators Substance Hazard Comment Solid dyes, stains & indicators including: DANGER: May include one or more of the following Acridine orange, Congo Red (Direct dye 28), Crystal violet statements: fatal/toxic if swallowed/in contact (methyl violet, Gentian Violet, Gram’s stain), Ethidium TOXIC HEALTH with skin/ if inhaled; causes severe skin burns & bromide, Malachite green (solvent green 1), Methyl eye damage/ serious eye damage; may cause orange, Nigrosin, Phenolphthalein, Rosaniline, Safranin allergy or asthma symptoms or breathing CORR. IRRIT. difficulties if inhaled; may cause genetic defects/ cancer/damage fertility or the unborn child; causes damages to organs/through prolonged or ENVIRONMENT repeated exposure. Solid dyes, stains & indicators including Alizarin (1,2- WARNING: May include one or more of the dihydroxyanthraquinone), Alizarin Red S, Aluminon (tri- following statements: harmful if swallowed/in ammonium aurine tricarboxylate), Aniline Blue (cotton / contact with skin/if inhaled; causes skin/serious spirit blue), Brilliant yellow, Cresol Red, DCPIP (2,6-dichl- eye irritation; may cause allergic skin reaction; orophenolindophenol, phenolindo-2,6-dichlorophenol, HEALTH suspected of causing genetic PIDCP), Direct Red 23, Disperse Yellow 7, Dithizone (di- defects/cancer/damaging fertility or the unborn phenylthiocarbazone), Eosin (Eosin Y), Eriochrome Black T child; may cause damage to organs/respiratory (Solochrome black), Fluorescein (& disodium salt), Haem- HARMFUL irritation/drowsiness or dizziness/damage to atoxylin, HHSNNA (Patton & Reeder’s indicator), Indigo, organs through prolonged or repeated exposure. Magenta (basic Fuchsin), May-Grunwald stain, Methyl- ene blue, Methyl green, Orcein, Phenol Red, Procion ENVIRON. dyes, Pyronin, Resazurin, Sudan I/II/IV dyes, Sudan black (Solvent Black 3), Thymol blue, Xylene cyanol FF Solid dyes, stains & indicators including Some dyes may contain hazardous impurities and Acid blue 40, Blue dextran, Bromocresol green, many have not been well researched. -
Solarbio Science & Technology Co., Ltd Tel: 010-56371207 Solarbio Fax: 010-56371281/82
Beijing Solarbio Science & Technology Co., Ltd Tel: 010-56371207 Fax: 010-56371281/82 Solarbio Http://www.solarbio.cn Neutral Red CAS Number: 553-24-2 Storage Temperature: 2-8 °C Product Description : Appearance: Fine dark green-black powder Molecular Formula: C15H17ClN4 Molecular Weight: 288.78 Synonyms: toluylene red, basic red 5 Neutral Red is a weak cationic azine dye that is used extensively as a nuclear stain in a variety of biological stain applications. It is a pH indicator as well, changing color from red to yellow over the pH range 6.8-8.0. It is also incorporated into bacteriological growth media. This product is often used for supravital staining of fresh peripheral blood. It can also be used for staining Nissl granules of neuroglial cells. However, this stain is not as permanent as another dye, Cresyl Violet acetate, for this application. Buffered 0.5% Neutral Red solutions are used as a counterstain for Naphthol AS acetate esterase, peroxidase and iron stains. Solutions can also be used to stain plankton for viability. Using 1 part Neutral Red to 10,000 parts sea water, dead cells were stained red and live cells remained unchanged. In addition, aqueous solutions of Neutral Red (0.1% in saline, pH 6.5) can be used as a fluorescent stain for lipids. Lipids will fluoresce blue-geen or yellow, depending on their composition. It has been used also as a Twort's stain for parasites in combination with Light Green SF, as a general histological stain for embryonic tissue in combination with Janus green,and for demostrating hydrolysis of fats. -
STUDIES of MITOCHONDRIAL STAINING with PINACYANOLE, EMPLOYI}.TG YOSHIDA Ascittss SARCOMA CEI-L
247 STUDIES OF MITOCHONDRIAL STAINING WITH PINACYANOLE, EMPLOYI}.TG YOSHIDA ASCITtsS SARCOMA CEI-L KryosARU TexrrAwA, Kyoreno Aen, Krsuro Kero, Tnnuo Yosnloa AND Kyorcnr MesurANr Department of Internal Meclictne, I(omatsujima RerI Cross Hospital (Chief : Dr. Riyoharu Takikau)a) 7st Departntent of Internal Medicine, Nagoya Uniuersity School of Medicine (Director : Prof . Susumu Hibino) Because of potent activities of respiratory enzymes found in isolated mito- chondria, morphological changes in mitochondria have again attracted attention as indicative of cell's functional potentialities. Mitochondria in the cell can be visualized by employing, 1) Altmann's stain- ing method or Heidenhain's iron hematoxylin stain on fixed preparations, 2) the supravital staining method using Janus green, and recently 3) the supravital observation by means of the phase contrast microscope. Among these, the supravital method with Janus green is widely employed because of its simplicity and high specificity. But this Janus green method is not free from faults : namely difficulty in differentiating the types of cells and quick fading of the stained mitochondria. In 1936 Hetheringtonl) introduced a dyestuff named pinacyanole into the su- pravital staining method of mitochondria, and this method has been investigated by J. L. Schwind,2) showing that nuclei are stained supravitally and the types of cells are easily differentiated, stainability of neutral red vacuoleg is not dis- turbed and the colored mitochondria do not fade away for several hours. This pinacyanole (Consolidated Midland Corporation) and vital neutral red have been obtained lately, and we are discussing the usefulness of the former dyestuff in the study of mitochondria, comparing it with the above-mentioned various mitochondrial methods, and the nature of its staining mechanism. -
The Sensitizing and Indicator Action of Victoria Blue and Janus Green on the Flocculation Reaction for Syphilis
In the case of sulphonamides, cultures resistant to sulphanilamide were resistant or partially resistant to the other members of this group with the exception of marfanil. Resistance once acquired seems to be permanent, and so far we have not been successful in reducing it in vitro. REFERENCES. ALBERT, A., FRANCIS, A. E., GARROD, L. P., AND LINNELL, W. H.-(1938) Brit. J. exp. Path., 19, 41. LANDY, M., LARKUM, N. W., OswALD, E. J., AND STREIGHTOFF, F.-(1943) Science, 97, 265. LEVADITI, C., AND MCINTOSH, J.-(1910) Bull. Soc. Path. exot., 3, 368. MACLEAN, I. H., ROGERS, K. B., AND FLEMING, A.-(1939) Lancet, i, 562. MACLEOD, C. M.-(1940) J. exp. Med., 72, 217. RAMMELKAMP, C. H., AND MAXON, T.-(1942) Proc. Soc. exp. Biol., N.Y., 51, 386. RUBBO, S. D., ALBERT, A., AND MAxWELL, M.-(1942) Brit. J. exp. Path., 23, 69. TILLETT, W. S., CAMBIER, M. J., AND HARRIS, W. H.-(1943) J. clin. Invest., 22, 249. THE SENSITIZING AND INDICATOR ACTION OF VICTORIA BLUE AND JANUS GREEN ON THE FLOCCULATION REACTION FOR SYPHILIS. F. M. BERGER. From the Public Health Laboratory, County Hall, Wakefield. Received for publication November 9, 1943. DEAN (1937) found that isamine blue could act as an indicator of the reaction between an antigen and its homologous antibody. The addition of the dye to a mixture of horse serum and dilute antiserum produced a precipitate which was easily visible because it took up all the dye from the supernatant fluid. Prof. P. L. Suther- land suggested the possibility of using isamine blue as indicator in serological tests for syphilis. -
Nile Blue Is a Basic Dye of the Oxazine Group, Which Has Been Used in Several Microscopic and Histochemical Techniques (4, 6)
ACTA HISTOCHEM. CYTOCHEM. Vol. 16, No. 3, 1983 LETTER TO THE EDITOR NILE BLUE SULFATE STAINING FOR DEMONSTRATION OF LIPIDS IN FLUORESCENCE MICROSCOPY Nile blue is a basic dye of the oxazine group, which has been used in several microscopic and histochemical techniques (4, 6) . A staining method based on application of Nile blue sulfate was introduced early for the cytochemical demon- stration of lipids (3, 8, 9), showing neutral fats and fatty acids in red and blue, respectively. There is evidence (1, 10) that aqueous solutions of Nile blue sulfate contain the blue cation of the dye, a red oxidation product (Nile red), and the orange-red imino base. According to this view, phospholipids and fatty acids stain blue because they react with the Nile blue cation, meanwhile neutral fats appear in red color. Other observations seem to be in disagreement with this staining mecha- nism (5, 6) . A fluorescence reaction in tissues after staining with Nile blue sulfate and brilliant cresyl blue has been found by Bozzo and Campos Vidal (2). During the course of investigations by using oxazine dyes we have observed that Nile blue sulfate produces a strong fluorescence reaction in lipid droplets. The fat body of Drosophila larvae is a continuous tissue mass which has been chosen as test material because of its abundance in lipidic inclusions. Drosophila hydei testes, surrounded by the fat body, were fixed in 5 % formaldehyde for 1-24 hr, washed, and then immersed in 0.1 mg/ml aqueous Nile blue sulfate (Fluka) for 30 min. After staining, the material was briefly washed and mounted with a drop of water. -
Sudan Dyes and Other Illegal Dyes
Sudan dyes and other illegal dyes Analysis in spices and food Sudan dyes, e.g. Sudan I to IV, Sudan In October 2004, the governmental Orange G, Sudan Red B, Sudan Red G, chemical institute “Bergisches Land” in Sudan Red 7B, and Sudan Black B as Wuppertal, Germany, reported the well as other dyes like 4-(Dimethylamino)- identification of two prohibited colours: azobenzene (Butter Yellow) and Para Butter Yellow and Para Red in bell pepper Red are basically synthetically produced powder and curry. azo dyes. Their degradation products are In February 2005, Great Britain experi- considered to be carcinogens and enced an extensive Rapid Alert action teratogens. Due to this fact, the EU does cycle. Due to the widespread use of one not permit the use of these colours as batch of chilli powder contaminated with food additives. However, in some Sudan I, batches of different products like countries, these dyes are still occasionally Worcester sauce, pizzas, pot noodles and used in order to intensify the colour of bell seafood sauces were subjected to com- pepper and chilli powder. plete recalls. Background Another recent concern is the discovery of the natural colour annatto in food and During 2003, the EU-Rapid Alert System spice mixes. Annatto (E 160b) is permit- (RASFF) issued a series of notifications ted by the EU for use in a variety of foods concerning the presence of Sudan dyes and beverages but not in spices and in chilli products and others such as spice mixtures. Its main colouring constit- spices, mixtures of spices, tomato uent is Bixin, with Norbixin being present sauces, pastas and sausages. -
Dna Revealed
Staining DNA on electrophoresis gels dna revealed Ethidium bromide, a potent mutagen Staining DNA on the move Concentrated In research laboratories, ethidium bromide and similar Recently, several commercial products have emerged that DNA Stain Dil e ute wi volum o th an equal f di use stilled water before fluorescent compounds are normally used to visualise DNA enable the DNA to be seen as it moves across the gel. Sto . re eze N at 4 °C. Do not fre AT N IO IO NA AT L C DUC ENTR GY E E FOR BIOTECHNOLO T HE U ING on a gel. Unfortunately, ethidium bromide and its breakdown Suppliers seldom reveal their composition, but several of NIVERSITY OF READ products are potent mutagens and carcinogens and therefore these stains contain Nile blue sulphate (also known as they should not be used in schools. Such dyes are often flat Nile blue A), a dye which had not previously been noted molecules with similar dimensions to DNA base pairs. When for its ability to stain DNA. Adkins and Burmeister (1996) ethidium bromide binds to DNA, it slips between adjacent give useful guidance as to its use as well as hints for identifying base pairs and stretches the double helix. This explains the other dyes which may be useful for visualising DNA. resources Methylene blue dye’s mutagenic effect — the ‘extra bases’ cause errors when the DNA replicates. In addition, short-wavelength UV light All of the dyes used for staining ‘mobile’ DNA are cationic Yung-Sharp, D. and (which itself is harmful) is required for ethidium bromide — that is, they are positively charged in the gel buffer, at Kumar, R. -
||||||||||||III USO0575109A United States Patent (19) 11) Patent Number: 5,175,109 Sakata Et Al
||||||||||||III USO0575109A United States Patent (19) 11) Patent Number: 5,175,109 Sakata et al. (45) Date of Patent: " Dec. 29, 1992 54 REAGENT FOR CLASSIFYING 4,666.82 5/1987 Wiedemann et al. ................. 430/78 LEUKOCYTES BY FLOW CYTOMETRY 4,751,179 6/1988 Ledis et al. ........... ... 424/3 X 4,751,188 6/1988 Valet ............. 436/10 X 4.760.006 7/1988 Pawlowski ............................ 430/78 75) Inventors: Takashi Sakata; Tomoyuki Kuroda, both of Kakogawa, Japan 4.882,284 1 1/1989 Kirchanski et al. .. ... 436/63 73 Assignee: Toa Medical Electronics Co., Ltd., 4,933,293 6/1990 Kuroda et al. ........................ 436/63 Kobe, Japan FOREIGN PATENT DOCUMENTS *) Notice: The portion of the term of this patent O086951 8/1983 European Pat. Off. subsequent to Jun. 12, 2007 has been 1560729 2/1980 France . disclaimed. 55-18860 5/1980 Japan . (21) Appl. No.: 663,090 OTHER PUBLICATIONS Kamentsky, Blood Cells, 6, 121-140 (1980). (22 Filed: Feb. 28, 1991 Shapiro et al., J. Histochem. Cytochem., 24, 396-41 1, Related U.S. Application Data (1976). Shapiro et al., J. Histochem. Cytochem., 25, 976–989 63 Continuation of Ser. No. 91.663, Sep. 1, 1987, aban (1977). doned. Colour Index, vol. 4, published by The Society of Dyers (30) Foreign Application Priority Data and Colourists, pp. 4417-4459 (1971). Sep. 10, 1986 JP Japan ................................ 6-21376 Steinkamp, "Flow Cytometry," Rey. Sci. Instrum... pp. Nov. 27, 1986 JP Japan ................................ 6.-28.2697 1375-1400 (1974). W. Groner & D. Tycko, "Characterizing Blooc Cells 51) Int. Cl. .............................................. C09K11/06 52) U.S. -
STAINING TECHNIQUES Staining Is an Auxiliary Technique Used in Microscopy to Enhance Contrast in the Microscopic Image
STAINING TECHNIQUES Staining is an auxiliary technique used in microscopy to enhance contrast in the microscopic image. Stains or dyes are used in biology and medicine to highlight structures in biological tissues for viewing with microscope. Cell staining is a technique that can be used to better visualize cells and cell components under a microscope. Using different stains, it is possible to stain preferentially certain cell components, such as a nucleus or a cell wall, or the entire cell. Most stains can be used on fixed, or non-living cells, while only some can be used on living cells; some stains can be used on either living or non-living cells. In biochemistry, staining involves adding a class specific (DNA, lipids, proteins or carbohydrates) dye to a substrate to qualify or quantify the presence of a specific compound. Staining and fluorescence tagging can serve similar purposes Purposes of Staining The most basic reason that cells are stained is to enhance visualization of the cell or certain cellular components under a microscope. Cells may also be stained to highlight metabolic processes or to differentiate between live and dead cells in a sample. Cells may also be enumerated by staining cells to determine biomass in an environment of interest. Stains may be used to define and examine bulk tissues (e.g. muscle fibers or connective tissues), cell populations (different blood cells) or organelles within individual cells. Biological staining is also used to mark cells in flow cytometry, flag proteins or nucleic acids on gel electrophoresis Staining is not limited to biological materials, it can also be used to study the morphology (form) of other materials e.g.