Indigo

CAS# 482-89-3

Indigo

Catalog No. BCN1091----Order now to get a substantial discount!

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Quality Control of Indigo

Number of papers citing our products

Chemical structure

Indigo

3D structure

Chemical Properties of Indigo

Cas No. 482-89-3 SDF Download SDF
PubChem ID 5354391 Appearance Purple powder
Formula C16H10N2O2 M.Wt 262.26
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Indigo
Solubility Very slightly soluble in water
Chemical Name (2Z)-2-(3-oxo-1H-indol-2-ylidene)-1H-indol-3-one
SMILES C1=CC=C2C(=C1)C(=O)C(=C3C(=O)C4=CC=CC=C4N3)N2
Standard InChIKey COHYTHOBJLSHDF-YPKPFQOOSA-N
Standard InChI InChI=1S/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17-18H/b14-13-
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Indigo

1 Isatis sp.

Biological Activity of Indigo

DescriptionIndigo and indirubin are potent aryl hydrocarbon receptor ligands present in human urine, the endogenous levels and potencies of indirubin and indigo are such that they activate aryl hydrocarbon receptor (AhR) -mediated signaling mechanisms in vivo . Indigo participates in isolating oxygenase genes, indigo carmine angiography provides visual information on foot perfusion, using indigo dye and synergistic halide additives can inhibit mild steel corrosion in sulphuric acid.
TargetsSrc | Antifection | AhR
In vitro

Isolation of oxygenase genes for indigo-forming activity from an artificially polluted soil metagenome by functional screening using Pseudomonas putida strains as hosts.[Pubmed: 25573469]

Appl Microbiol Biotechnol. 2015 May;99(10):4453-70.

Metagenomes contain the DNA from many microorganisms, both culturable and non-culturable, and are a potential resource of novel genes.
METHODS AND RESULTS:
In this study, a 5.2-Gb metagenomic DNA library was constructed from a soil sample (artificially polluted with four aromatic compounds, i.e., biphenyl, phenanthrene, carbazole, and 3-chlorobenzoate) in Escherichia coli by using a broad-host-range cosmid vector. The resultant library was introduced into naphthalene-degrading Pseudomonas putida-derived strains having deficiencies in their naphthalene dioxygenase components, and Indigo-forming clones on the indole-containing agar plates were screened. Cosmids isolated from 29 positive clones were classified by their various properties (original screening hosts, hosts showing Indigo-forming activity, and digestion patterns with restriction enzymes), and six representative cosmids were chosen. Sequencing and in vitro transposon mutagenesis of the six cosmids resulted in the identification of genes encoding putative class B and D flavoprotein monooxygenases, a multicomponent hydroxylase, and a reductase that were responsible for the Indigo-forming activity in the host cells.
CONCLUSIONS:
Among them, the genes encoding the multicomponent hydroxylase were demonstrated to be involved in phenol degradation. Furthermore, two genes encoding ring-cleavage dioxygenases were also found adjacent to the genes responsible for the Indigo formation, and their functions were experimentally confirmed.

Indirubin and Indigo Are Potent Aryl Hydrocarbon Receptor Ligands Present in Human Urine.[Pubmed: 11425848]

J. Biol. Chem., 2001, 276(34):31475-8.

Aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that regulates genes involved in xenobiotic metabolism, cellular proliferation, and differentiation. Numerous xenobiotic and biological compounds are known to interact with AhR, but it remains an orphan receptor, because its physiological ligand is unknown.
METHODS AND RESULTS:
We identified AhR ligands in human urine using a yeast AhR signaling assay and then characterized their properties. Two ligands, indirubin and Indigo, were both present at average concentrations of approximately 0.2 nm in the urine of normal donors. Indirubin was also detected in fetal bovine serum and contributed half of the total AhR ligand activity. The activities of indirubin and Indigo were comparable with or more potent than that of the archetypal ligand, 2,3,7,8-tetrachlorodibenzo-p-dioxin, in yeast AhR activation assays.
CONCLUSIONS:
We suggest that the endogenous levels and potencies of indirubin and Indigo are such that they activate AhR-mediated signaling mechanisms in vivo.

In vivo

Use of Indigo Carmine Angiography to Qualitatively Assess Adequate Distal Perfusion After Endovascular Revascularization in Critical Limb Ischemia.[Pubmed: 25887729]

J Endovasc Ther. 2015 Apr 17.

To report a novel technique to visualize the efficacy of revascularization in critical limb ischemia patients with ischemic foot ulcers.
METHODS AND RESULTS:
An 80-year-old man was admitted with nonhealing ulcers on his left second toe and lateral border of the foot owing to in-stent restenosis of the left popliteal artery. After dilation of the popliteal in-stent restenosis, below-the-knee angiography revealed that the anterior tibial artery (ATA) was occluded, the posterior tibial artery was hypoplastic, and the peroneal artery was enlarged, with 2 plantar arteries. To evaluate the foot circulation before performing additional procedures, a 4-F multipurpose catheter was advanced into the peroneal artery, and 5 mL of Indigo carmine was injected. Immediately, the patient's second toe and lateral border ulcers were dyed blue. We concluded that sufficient blood flow had been obtained to the ulcerated area by balloon angioplasty alone, so the procedure was terminated. The ulcers completely healed at 1 month.
CONCLUSIONS:
Indigo carmine angiography provides visual information on foot perfusion, yielding new insights into microcirculation and helping to determine the effectiveness of treatment and procedure endpoint.

Protocol of Indigo

Kinase Assay

Inhibition of mild steel corrosion in sulphuric acid using indigo dye and synergistic halide additives[Reference: WebLink]

Mater. Chem. Phys., 2004, 84(2-3): 363-8.

Gravimetric method was used to study the inhibitory properties of Indigo dye during corrosion of mild steel in aerated sulphuric acid solutions at 30-50°C. The effect of addition of halide salts KCl, KBr and KI was also investigated. The corrosion rates in all systems studied increased with rise in temperature. The inhibition efficiency of Indigo dye increased with concentration and synergistically increased on addition of halide salts. Temperature studies revealed increased inhibition efficiency at higher temperatures, which is suggestive of chemisorption mechanism. The inhibitor adsorption characteristics were approximated by Frumkins isotherm and Flory-Huggins isotherm. Activation energy for Fe dissolution in sulphuric acid was observed to reduce from 54.6kJmol-1 in the uninhibited system to 34.9kJmol-1 in the inhibited system.

Indigo Dilution Calculator

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Indigo Molarity Calculator

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Preparing Stock Solutions of Indigo

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.813 mL 19.065 mL 38.1301 mL 76.2602 mL 95.3252 mL
5 mM 0.7626 mL 3.813 mL 7.626 mL 15.252 mL 19.065 mL
10 mM 0.3813 mL 1.9065 mL 3.813 mL 7.626 mL 9.5325 mL
50 mM 0.0763 mL 0.3813 mL 0.7626 mL 1.5252 mL 1.9065 mL
100 mM 0.0381 mL 0.1907 mL 0.3813 mL 0.7626 mL 0.9533 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Indigo

Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine.[Pubmed:11425848]

J Biol Chem. 2001 Aug 24;276(34):31475-8.

Aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that regulates genes involved in xenobiotic metabolism, cellular proliferation, and differentiation. Numerous xenobiotic and biological compounds are known to interact with AhR, but it remains an orphan receptor, because its physiological ligand is unknown. We identified AhR ligands in human urine using a yeast AhR signaling assay and then characterized their properties. Two ligands, indirubin and Indigo, were both present at average concentrations of approximately 0.2 nm in the urine of normal donors. Indirubin was also detected in fetal bovine serum and contributed half of the total AhR ligand activity. The activities of indirubin and Indigo were comparable with or more potent than that of the archetypal ligand, 2,3,7,8-tetrachlorodibenzo-p-dioxin, in yeast AhR activation assays. We suggest that the endogenous levels and potencies of indirubin and Indigo are such that they activate AhR-mediated signaling mechanisms in vivo.

Isolation of oxygenase genes for indigo-forming activity from an artificially polluted soil metagenome by functional screening using Pseudomonas putida strains as hosts.[Pubmed:25573469]

Appl Microbiol Biotechnol. 2015 May;99(10):4453-70.

Metagenomes contain the DNA from many microorganisms, both culturable and non-culturable, and are a potential resource of novel genes. In this study, a 5.2-Gb metagenomic DNA library was constructed from a soil sample (artificially polluted with four aromatic compounds, i.e., biphenyl, phenanthrene, carbazole, and 3-chlorobenzoate) in Escherichia coli by using a broad-host-range cosmid vector. The resultant library was introduced into naphthalene-degrading Pseudomonas putida-derived strains having deficiencies in their naphthalene dioxygenase components, and Indigo-forming clones on the indole-containing agar plates were screened. Cosmids isolated from 29 positive clones were classified by their various properties (original screening hosts, hosts showing Indigo-forming activity, and digestion patterns with restriction enzymes), and six representative cosmids were chosen. Sequencing and in vitro transposon mutagenesis of the six cosmids resulted in the identification of genes encoding putative class B and D flavoprotein monooxygenases, a multicomponent hydroxylase, and a reductase that were responsible for the Indigo-forming activity in the host cells. Among them, the genes encoding the multicomponent hydroxylase were demonstrated to be involved in phenol degradation. Furthermore, two genes encoding ring-cleavage dioxygenases were also found adjacent to the genes responsible for the Indigo formation, and their functions were experimentally confirmed.

Use of indigo carmine angiography to qualitatively assess adequate distal perfusion after endovascular revascularization in critical limb ischemia.[Pubmed:25887729]

J Endovasc Ther. 2015 Jun;22(3):352-5.

PURPOSE: To report a novel technique to visualize the efficacy of revascularization in critical limb ischemia patients with ischemic foot ulcers. TECHNIQUE: An 80-year-old man was admitted with nonhealing ulcers on his left second toe and lateral border of the foot owing to in-stent restenosis of the left popliteal artery. After dilation of the popliteal in-stent restenosis, below-the-knee angiography revealed that the anterior tibial artery (ATA) was occluded, the posterior tibial artery was hypoplastic, and the peroneal artery was enlarged, with 2 plantar arteries. To evaluate the foot circulation before performing additional procedures, a 4-F multipurpose catheter was advanced into the peroneal artery, and 5 mL of Indigo carmine was injected. Immediately, the patient's second toe and lateral border ulcers were dyed blue. We concluded that sufficient blood flow had been obtained to the ulcerated area by balloon angioplasty alone, so the procedure was terminated. The ulcers completely healed at 1 month. CONCLUSION: Indigo carmine angiography provides visual information on foot perfusion, yielding new insights into microcirculation and helping to determine the effectiveness of treatment and procedure endpoint.

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