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Gallocyanine

(Synonyms: 花菁) 目录号 : GC43725

A Dkk1 inhibitor

Gallocyanine Chemical Structure

Cas No.:1562-85-2

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10mg
¥385.00
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25mg
¥770.00
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50mg
¥1,232.00
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100mg
¥1,925.00
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产品描述

Gallocyanine is a small molecule blue dye used to stain nuclei. It is known to inhibit Dickkopf-1 (Dkk1), an antagonist of the Wnt pathway. Gallocyanine can disrupt the interaction of Dkk1 with its receptor LRP5/6 (IC50 = 3 µM), thereby activating Wnt/β-catenin signaling. Modulation of the Dkk1-LRP5/6 interaction via gallocyanine has been shown to inhibit prostaglandin J2-induced tau phosphorylation at serine396 in primary cortical neurons in vitro.

Chemical Properties

Cas No. 1562-85-2 SDF
别名 花菁
Canonical SMILES OC(C1=CC(O)=C(O)C2=[O+]C3=CC(N(C)C)=CC=C3N=C21)=O.[Cl-]
分子式 C15H13N2O5•Cl 分子量 336.7
溶解度 DMSO 74 mg/mL (219.76 mM) 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 2.97 mL 14.85 mL 29.7 mL
5 mM 0.594 mL 2.97 mL 5.94 mL
10 mM 0.297 mL 1.485 mL 2.97 mL
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Research Update

Design and synthesis of Gallocyanine inhibitors of DKK1/LRP6 interactions for treatment of Alzheimer's disease

Bioorg Chem 2018 Oct;80:230-244.PMID:29966869DOI:10.1016/j.bioorg.2018.06.018.

Based on NCI8642, a series of Gallocyanine derivatives was synthesized with modifications of the substituent groups in position 1, 2 and 4 of the phenoxazinone scaffold. The effectiveness of gallocyanines to inhibit DKK1/LRP6 interactions and Tau phosphorylation induced by prostaglandin J2 and DKK1 was elucidated by both experimental data and molecular docking simulations. Bis-alkylated with flexible alkyl ester groups on C1 and bis-benzyl gallocyanines provided the most active inhibitors, while amino derivatives on C2 of NCI8642 that have alkoxy or benzyloxy substituents on C4, were less active. Furthermore, it is shown that treating of SHSY5Y cells with NCI8642 derivatives activates Wnt signaling and increases the levels of pGSK3β kinase and β-catenin.

Synthesis and evaluation of Gallocyanine dyes as potential agents for the treatment of Alzheimer's disease and related neurodegenerative tauopathies

Eur J Med Chem 2016 Jan 27;108:28-38.PMID:26629858DOI:10.1016/j.ejmech.2015.11.024.

In search of safe and effective anti-Alzheimer disease agents a series of Gallocyanine dyes have been synthesized and evaluated for their ability to inhibit LRPs/DKK1 interactions. Modulation of the interactions between LRPS and DKK1, regulate Wnt signaling pathway and affect Tau phosphorylation. The current efforts resulted in the identification of potent DKK1 inhibitors which are able to inhibit prostaglandin J2-induced tau phosphorylation at serine 396.

Spectrophotometric reaction rate method for the determination of osmium by its catalytic effect on the oxidation of Gallocyanine by bromate

Talanta 1994 Oct;41(10):1651-5.PMID:18966116DOI:10.1016/0039-9140(94)e0095-9.

A simple kinetic spectrophotometric method was developed for the determination of osmium. The method is based on the catalytic effect of osmium as osmium tetroxide on the oxidation of Gallocyanine by bromate at pH 7. The reaction is monitored spectrophotometrically by measuring the decreasing absorbance of Gallocyanine at 620 nm by the fixed-time method. A detection limit of 0.01 ng/ml and linear calibration curve from 0.1 to 100 and from 100 to 1200 ng/ml Os(VIII) is reported. The relative standard deviation for 0.0100 microg/ml Os(VIII) is 0.8% (N = 10). The method is free from most interferences. Osmium in synthetic samples is determined by this method, with satisfactory results.

Removal of uranyl ions in aquatic mediums by using a new material: Gallocyanine grafted hydrogel

J Hazard Mater 2013 Jun 15;254-255:397-405.PMID:23669652DOI:10.1016/j.jhazmat.2013.04.004.

A new material containing Gallocyanine (GC) grafted polyacyril amide (PAA) was synthesized and its adsorption ability was examined for the removal of uranyl ions from aqueous media. The new developed adsorbent was characterized by FTIR, SEM, and PZC analysis. Adsorption of UO₂(2+) ions from aqueous solution as a function of ion concentration, pH, ionic strength, temperature, and reusability of adsorbent was investigated in detail. The adsorption data were analyzed by using the Langmuir, Freundlich and Dubinin-Radushkevich (DR) models. The adsorption of UO₂(2+) increased with pH and reached a plateau value in the pH range 5-6. The adsorption of UO₂(2+) ions were not affected by increasing ionic strength. The adsorption mechanism followed an endothermic and spontaneous process with increased disorderliness at adsorbate/adsorbent interface. The adsorption process followed a pseudo-second-order kinetics. The new developed material is a potential adsorbent for effective removal of uranyl ions from aquatic solutions.

Specific staining of nuclei with aqueous solutions of celestin blue B and Gallocyanine

Microsc Acta 1982 Sep;86(3):201-5.PMID:6183561doi

This paper presents methods for specific staining of nuclei with aqueous solutions of celestin blue B and Gallocyanine in tissue sections from which RNA has been extracted selectively with concentrated phosphoric acid at 5 degrees C for 20 min or by hydrolysis in 6 N HCl at 28 degrees C for 15 min. It has been found that pH of the freshly prepared celestin blue B dye solution is 3.0 and that of an aqueous solution of Gallocyanine is 2.8. These pHs can be lowered to 1.5 with concentrated sulphuric or nitric acid and at this pH staining of the nuclei is possible. But with concentrated sulphuric or nitric acid and at this pH staining of the nuclei is possible. But if the pHs are lowered with concentrated hydrochloric or phosphoric acid, effective use of these dyes is not possible. It has been suggested that some dispersion of the two dyes takes place with concentrated sulphuric or nitric acid which are used to lower the pH. Staining of the nuclei is also possible with an aqueous solution of celestin blue B at pH 3.0 but the same is not possible with Gallocyanine at pH 2.8. The absorption spectra of nuclei stained with an aqueous solution of celestin blue B at pH 1.5 and 3.0 are fairly identical, the peak of maximum absorption being at 620 nm. Those of nuclei stained with an aqueous solution of Gallocyanine reveal irregular peaks. Possible implications of these findings have been discussed.