Phenosafranine
(Synonyms: 奎诺二甲基酯) 目录号 : GC65334Phenosafranine 是一种吩嗪染料。Phenosafranine 对三链 RNA 比对双链 RNA 具有更高的结合亲和力,通过嵌入与两种 RNA 结合。Phenosafranine 可用于植物细胞染色,测定血红蛋白、多巴胺、血清素等。
Cas No.:81-93-6
Sample solution is provided at 25 µL, 10mM.
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Phenosafranine is a phenazine dye. Phenosafranine has high binding affinity to triplex RNA compared to the parent duplex form, binds through intercalation to both forms of RNA. Phenosafranine can be used for staining plant cells, determination of hemoglobin, dopamine, serotonin and so on[1][2][3].
[1]. Widholm JM. The use of fluorescein diacetate and phenosafranine for determining viability of cultured plant cells. Stain Technol. 1972 Jul;47(4):189-94.
[2]. Liu, W., et al. Characterization of Phenosafranine-Hemoglobin Interactions in Aqueous Solution. J Solution Chem 40, 231-246 (2011).
[3]. Pradhan AB, et al. An overview on the interaction of phenazinium dye phenosafranine to RNA triple and double helices. Int J Biol Macromol. 2016 May;86:345-51.
Cas No. | 81-93-6 | SDF | Download SDF |
别名 | 奎诺二甲基酯 | ||
分子式 | C18H15ClN4 | 分子量 | 322.79 |
溶解度 | DMSO : 125 mg/mL (387.25 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 3.098 mL | 15.4899 mL | 30.9799 mL |
5 mM | 0.6196 mL | 3.098 mL | 6.196 mL |
10 mM | 0.3098 mL | 1.549 mL | 3.098 mL |
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Interaction of Phenosafranine with nucleic acids and model polyphosphates. I. Self-aggregation and complex formation with inorganic polyphosphates
Biophys Chem 1978 Mar;8(1):17-25.PMID:647100doi
Aggregation of Phenosafranine in concentrated aqueous solutions and interaction with polyphosphates was studied by absorption and fluorescence spectroscopy. At concentrations greater than 10(-3)M Phenosafranine forms dimers (Kd = 3.8 x 10(2) 1.mole-1), which are characterized by a hypsochromic shift of the visible and near ultraviolet absorption maxima accompanied by a hypochromic effect. No fluorescence could be detected from Phenosafranine dimers. Analogues spectra changes were observed when a polyphosphate was titrated with Phenosafranine, which indicated that with increasing saturation of the polyphosphate binding sites Phenosafranine gradually became bound in the aggregated form. Full saturation of the polyphosphate binding sites with Phenosafranine was reached only when an excess of free dye was present. The cooperative binding of Phenosafranine to a polyphosphate could be evaluated by means of a theory proposed by Schwarz et al. At the zero ionic strength and at 25 degrees C the binding was characterized by cooperative binding constant K = 6.2 x 10(5) 1.mole-1, number of binding sites per monomeric phosphate residue g = 0.4, and cooperativity parameter q-30. Spectroscopic properties of Phenosafranine in the aggregated and polyphosphate-bound states were compared with those of ethidium bromide.
A docking model of human ribonucleotide reductase with flavin and Phenosafranine
Bioinformation 2009 Sep 30;4(3):123-6.PMID:20198185DOI:10.6026/97320630004123.
Ribonucleotide Reductase (RNR) is an enzyme responsible for the reduction of ribonucleotides to their corresponding Deoxyribonucleotides (DNA), which is a building block for DNA replication and repair mechanisms. The key role of RNR in DNA synthesis and control in cell growth has made this an important target for anticancer therapy. Increased RNR activity has been associated with malignant transformation and tumor cell growth. In recent years, several RNR inhibitors, including Triapine, Gemcitabine and GTI-2040, have entered the clinical trials. Our current work focuses on an attempted to dock this inhibitors Flavin and Phenosafranine to curtail the action of human RNR2. The docked inhibitor Flavin and Phenosafranine binds at the active site with THR176, which are essential for free radical formation. The inhibitor must be a radical scavenger to destroy the tyrosyl radical or iron metal scavenger. The iron or radical site of R2 protein can react with one-electron reductants, whereby the tyrosyl radical is converted to a normal tyrosine residue. However, compounds such as Flavin and Phenosafranine were used in most of the cases to reduce the radical activity. The docking study was performed for the crystal structure of human RNR with the radical scavengers Flavin and Phenosafranine to inhibit the human RNR2. This helps to understand the functional aspects and also aids in the development of novel inhibitors for the human RNR2.
Triplet state quenching of Phenosafranine dye by indolic compounds studied by transient absorption spectroscopy
Photochem Photobiol Sci 2015 Feb;14(2):407-13.PMID:25428794DOI:10.1039/c4pp00365a.
The interaction of the triplet state of the synthetic dye Phenosafranine (3,7-diamino-5-phenylphenazinium chloride) with indolic compounds of biological relevance was investigated in water by means of laser flash photolysis. The rate constants for the triplet quenching were determined. The quenching process may be explained by an electron transfer from the indole to the dye in its triplet state. The rate constants present a typical dependence of an electron transfer process with the one-electron oxidation potential of the indole. Indole-3-acetic acid and its homologous indole propionic and indole butyric acids are the most effective quenchers with rate constants reaching the diffusion limit. Rate constants for indole itself, tryptophan and indole-3 carboxylic acid are one order of magnitude lower. The electron transfer nature of the quenching reaction is further confirmed by the detection of the semi-reduced form of the dye by its transient absorption. The absorption coefficients of the transient species were estimated, and the quantum yield of the charge separation process was determined. The efficiency of formation of radical species is between 60 and 90% of the triplets intercepted.
Phenazinium dyes safranine O and Phenosafranine induce self-structure in single stranded polyadenylic acid: structural and thermodynamic studies
J Photochem Photobiol B 2014 Mar 5;132:17-26.PMID:24565690DOI:10.1016/j.jphotobiol.2014.01.014.
The interaction of phenazinium dyes, safranine O and Phenosafranine with single stranded polyadenylic acid was studied using spectroscopic viscometric and calorimetric techniques. Both dyes bind to polyadenylic acid strongly with association constant of the order of 10(5)M(-1). Safranine O showed higher affinity over Phenosafranine. The binding induced conformational changes in polyadenylic acid, but the extent of change was much higher with safranine O. The bound safranine O molecules acquired strong induced circular dichroism spectra compared to the weak induced circular dichroism of Phenosafranine. Fluorescence polarization, iodide quenching, viscosity results and energy transfer from bases to bound dyes suggested intercalation of the dye molecules to polyadenylic acid structure. The binding was entropy driven in both the cases. Circular dichroism and optical melting studies revealed cooperative melting profiles for dye-polyadenylic acid complexes that provided evidence for the formation of self-structured polyadenylic acid on dye binding. This structural reorganization was further confirmed by differential scanning calorimetry results.
Interaction of Phenosafranine with nucleic acids and model polyphosphates. I. Self-aggregation and complex formation with inorganic polyphosphates
Biophys Chem 1978 Mar;8(1):17-25.PMID:16996450doi
Aggregation or Phenosafranine in concentrated aqueous solutions and its interaction with polyphosphates was Studied by absorption and fluorescence spectroscopy. At concentrations > 10(-3) M Phenosafranine forms dimers (Kd = 3.8 x 10(2) l.mole(-1)), which are characterized by a hypsochromic shift of the visible and near ultraviolet absorption maxima accompanied by a hypochromic effect. No fluorescence could be detected from Phenosafranine dimers. Analogous spectral changes were observed when a polyphosphate was titrated with phenusafranine, which indicated that with increasing saturation of the polyphosphate binding sites Phenosafranine gradually became bound in the aggregated form. Full saturation of the polyphosphate binding sites with Phenosafranine was reached only when an excess of free dye was present. The cooperative binding of Phenosafranine to a polyphosphate could be evaluated by means of a theory proposed by Schwarz et al. At the zero ionic strength and at 25 degrees C the binding was characterized by cooperative binding constant K = 6.2 x 10(5) l.mole(-1), number of binding sites per monomeric phosphate residue g = 0.4, and cooperativity parameter q reverse similar 30. Spectroscopic properties of Phenosafranine in the aggregated and poly phosphate-bound stotes were compared with those of ethidium bromide.