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2-Amino-3-carboxy-1,4-naphthoquinone

CAS# 173043-38-4

2-Amino-3-carboxy-1,4-naphthoquinone

2D Structure

Catalog No. BCN8571----Order now to get a substantial discount!

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Quality Control of 2-Amino-3-carboxy-1,4-naphthoquinone

3D structure

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2-Amino-3-carboxy-1,4-naphthoquinone

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Chemical Properties of 2-Amino-3-carboxy-1,4-naphthoquinone

Cas No. 173043-38-4 SDF Download SDF
PubChem ID 9859229 Appearance Powder
Formula C11H7NO4 M.Wt 217.18
Type of Compound Quinones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-amino-1,4-dioxonaphthalene-2-carboxylic acid
SMILES C1=CC=C2C(=C1)C(=O)C(=C(C2=O)N)C(=O)O
Standard InChIKey GXDIXDKPIUJGOV-UHFFFAOYSA-N
Standard InChI InChI=1S/C11H7NO4/c12-8-7(11(15)16)9(13)5-3-1-2-4-6(5)10(8)14/h1-4H,12H2,(H,15,16)
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 2-Amino-3-carboxy-1,4-naphthoquinone

The herbs of Rubia yunnanensis Diels

Biological Activity of 2-Amino-3-carboxy-1,4-naphthoquinone

Description2-Amino-3-carboxy-1,4-naphthoquinone is a novel growth stimulator for bifidobacteria, it affects the end-product profile of bifidobacteria through the mediated oxidation of NAD(P)H.
TargetsNADPH-oxidase
In vitro

Role of 2-amino-3-carboxy-1,4-naphthoquinone, a strong growth stimulator for bifidobacteria, as an electron transfer mediator for NAD(P)(+) regeneration in Bifidobacterium longum.[Pubmed: 10434042]

Biochim Biophys Acta. 1999 Aug 5;1428(2-3):241-50.

2-Amino-3-carboxy-1,4-naphthoquinone (ACNQ) is a novel growth stimulator for bifidobacteria. The role of ACNQ as a mediator of the electron transfer from NAD(P)H to dioxygen (O(2)) and hydrogen peroxide (H(2)O(2)), proposed in our previous paper, was examined using the cell-free extract and whole cells of Bifidobacterium longum.
METHODS AND RESULTS:
Continuous monitoring of ACNQ, O(2) and H(2)O(2) by several amperometric techniques has revealed that ACNQ works as a good electron acceptor of NAD(P)H diaphorase and that the reduced form of ACNQ is easily autoxidized and also acts as a better electron donor of NAD(P)H peroxidase than NAD(P)H. The generation of H(2)O(2) by B. longum under aerobic conditions is effectively suppressed in the presence of ACNQ. These ACNQ-mediated reactions would play roles as NAD(P)(+)-regeneration processes. The accumulation of ACNQ in the cytosol has been also suggested. These characteristics of ACNQ seem to be responsible for the growth stimulation of bifidobacteria.
CONCLUSIONS:
Vitamin K(3), which has an extremely low growth-stimulating activity and was used as a reference compound, exhibits much lower activity as an electron transfer mediator. The difference in the activity is discussed in terms of the redox potential and partition property of the quinones.

Protocol of 2-Amino-3-carboxy-1,4-naphthoquinone

Cell Research

2-Amino-3-carboxy-1,4-naphthoquinone affects the end-product profile of bifidobacteria through the mediated oxidation of NAD(P)H.[Pubmed: 12073135 ]

Appl Microbiol Biotechnol. 2002 Jun;59(1):72-8.

Glucose metabolism of bifidobacteria in the presence of 2-Amino-3-carboxy-1,4-naphthoquinone (ACNQ), a specific growth stimulator for bifidobacteria, and ferricyanide (Fe(CN)(6)(3-)) as an extracellular electron acceptor was examined using resting cells of Bifidobacterium longum and Bifidobacterium breve.
METHODS AND RESULTS:
NAD(P)H in the cells is oxidized by ACNQ with the aid of diaphorase activity, and reduced ACNQ donates the electron to Fe(CN)(6)(3-). Exogenous oxidation of NADH by the ACNQ/Fe(CN)(6)(3-) system suppresses the endogenous lactate dehydrogenase reaction competitively, which results in the remarkable generation of pyruvate and a decrease in lactate production. In addition, a decrease in acetate generation is also observed in the presence of ACNQ and Fe(CN)(6)(3-). This phenomenon could not be explained in terms of the fructose-6-phosphate phosphoketolase pathway, but suggests rather that glucose is partially metabolized via the hexose monophosphate pathway. This was verified by NADP(+)-induced reduction of Fe(CN)(6)(3-) in cell-free extracts in the presence of ACNQ. Effects of the ACNQ/Fe(CN)(6)(3-) system on anaerobically harvested cells were also examined.
CONCLUSIONS:
Stoichiometric analysis of the metabolites from the pyruvate-formate lyase pathway suggests that exogenous oxidation of NADH is an efficient method to produce ATP in this pathway.

2-Amino-3-carboxy-1,4-naphthoquinone Dilution Calculator

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Preparing Stock Solutions of 2-Amino-3-carboxy-1,4-naphthoquinone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.6045 mL 23.0224 mL 46.0448 mL 92.0895 mL 115.1119 mL
5 mM 0.9209 mL 4.6045 mL 9.209 mL 18.4179 mL 23.0224 mL
10 mM 0.4604 mL 2.3022 mL 4.6045 mL 9.209 mL 11.5112 mL
50 mM 0.0921 mL 0.4604 mL 0.9209 mL 1.8418 mL 2.3022 mL
100 mM 0.046 mL 0.2302 mL 0.4604 mL 0.9209 mL 1.1511 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 2-Amino-3-carboxy-1,4-naphthoquinone

2-Amino-3-carboxy-1,4-naphthoquinone affects the end-product profile of bifidobacteria through the mediated oxidation of NAD(P)H.[Pubmed:12073135]

Appl Microbiol Biotechnol. 2002 Jun;59(1):72-8.

Glucose metabolism of bifidobacteria in the presence of 2-Amino-3-carboxy-1,4-naphthoquinone (ACNQ), a specific growth stimulator for bifidobacteria, and ferricyanide (Fe(CN)(6)(3-)) as an extracellular electron acceptor was examined using resting cells of Bifidobacterium longum and Bifidobacterium breve. NAD(P)H in the cells is oxidized by ACNQ with the aid of diaphorase activity, and reduced ACNQ donates the electron to Fe(CN)(6)(3-). Exogenous oxidation of NADH by the ACNQ/Fe(CN)(6)(3-) system suppresses the endogenous lactate dehydrogenase reaction competitively, which results in the remarkable generation of pyruvate and a decrease in lactate production. In addition, a decrease in acetate generation is also observed in the presence of ACNQ and Fe(CN)(6)(3-). This phenomenon could not be explained in terms of the fructose-6-phosphate phosphoketolase pathway, but suggests rather that glucose is partially metabolized via the hexose monophosphate pathway. This was verified by NADP(+)-induced reduction of Fe(CN)(6)(3-) in cell-free extracts in the presence of ACNQ. Effects of the ACNQ/Fe(CN)(6)(3-) system on anaerobically harvested cells were also examined. Stoichiometric analysis of the metabolites from the pyruvate-formate lyase pathway suggests that exogenous oxidation of NADH is an efficient method to produce ATP in this pathway.

Role of 2-amino-3-carboxy-1,4-naphthoquinone, a strong growth stimulator for bifidobacteria, as an electron transfer mediator for NAD(P)(+) regeneration in Bifidobacterium longum.[Pubmed:10434042]

Biochim Biophys Acta. 1999 Aug 5;1428(2-3):241-50.

2-Amino-3-carboxy-1,4-naphthoquinone (ACNQ) is a novel growth stimulator for bifidobacteria. The role of ACNQ as a mediator of the electron transfer from NAD(P)H to dioxygen (O(2)) and hydrogen peroxide (H(2)O(2)), proposed in our previous paper, was examined using the cell-free extract and whole cells of Bifidobacterium longum. Continuous monitoring of ACNQ, O(2) and H(2)O(2) by several amperometric techniques has revealed that ACNQ works as a good electron acceptor of NAD(P)H diaphorase and that the reduced form of ACNQ is easily autoxidized and also acts as a better electron donor of NAD(P)H peroxidase than NAD(P)H. The generation of H(2)O(2) by B. longum under aerobic conditions is effectively suppressed in the presence of ACNQ. These ACNQ-mediated reactions would play roles as NAD(P)(+)-regeneration processes. The accumulation of ACNQ in the cytosol has been also suggested. These characteristics of ACNQ seem to be responsible for the growth stimulation of bifidobacteria. Vitamin K(3), which has an extremely low growth-stimulating activity and was used as a reference compound, exhibits much lower activity as an electron transfer mediator. The difference in the activity is discussed in terms of the redox potential and partition property of the quinones.

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