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93862

Sigma-Aldrich

Nitrotetrazolium Blue chloride

90.0-110.0% (calc. on dry substance, T)

Synonym(s):

2,2′-bis(4-Nitrophenyl)-5,5′-diphenyl-3,3′-(3,3′-dimethoxy-4,4′-diphenylene)ditetrazolium chloride, 3,3′-(3,3′-Dimethoxy-4,4′-biphenylene)bis[2-(4-nitrophenyl)-5-phenyl-2H-tetrazolium chloride], p-Nitro-Blue tetrazolium chloride, p-Nitrotetrazolium blue, NBT, Nitro BT

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About This Item

Linear Formula:
C40H30N10O6 · 2Cl
CAS Number:
298-83-9
Molecular Weight:
817.64
Beilstein/REAXYS Number:
4115923
MDL number:
MFCD00012159
UNSPSC Code:
12352200
PubChem Substance ID:
329770281
NACRES:
NA.54

Quality Level

100

assay

90.0-110.0% (calc. on dry substance, T)

form

powder

impurities

≤10% solvent content
≤10% water

λ

in methanol

UV absorption

λ: 252-262 nm Amax

storage temp.

2-8°C

SMILES string

[Cl-].[Cl-].COc1cc(ccc1-[n+]2nc(nn2-c3ccc(cc3)[N+]([O-])=O)-c4ccccc4)-c5ccc(c(OC)c5)-[n+]6nc(nn6-c7ccc(cc7)[N+]([O-])=O)-c8ccccc8

InChI

1S/C40H30N10O6.2ClH/c1-55-37-25-29(13-23-35(37)47-43-39(27-9-5-3-6-10-27)41-45(47)31-15-19-33(20-16-31)49(51)52)30-14-24-36(38(26-30)56-2)48-44-40(28-11-7-4-8-12-28)42-46(48)32-17-21-34(22-18-32)50(53)54;;/h3-26H,1-2H3;2*1H/q+2;;/p-2

InChI key

FSVCQIDHPKZJSO-UHFFFAOYSA-L

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Biochem/physiol Actions

Nitrotetrazolium blue chloride (NBT) is used in staining, visualizing and evaluating the damage in brain sections or heart tissues. The principle of the technique is that the redox enzymes like nicotinamide adenine dinucleotide NAD(H) and cofactors present in the cell convert colorless tetrazolium salt to blue formazan. The dead cells remain unstained. It is used in the dual-staining along with methyl green for the hyperspectral microscopic imaging analysis of colon tissues for the diagnosis of colon diseases. NBT is also used for diagnosing microbial infections and phagocytic defects. In conventional chromogenic methods, NBT/ 5-bromo-4-chloro-3-indolyl phosphate (BCIP) is used as a substrate for alkaline phosphatase enzyme reaction, in which NBT is reduced to insoluble purple diformazan.

Analysis Note

solubility:
250 mg in 5 mL methanol: yellow to very dark yellow and light brown-yellow to very dark brown-yellow

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Methyl green and nitrotetrazolium blue chloride co-expression in colon tissue: A hyperspectral microscopic imaging analysis.
Li Q, et al.
Optics & Laser technology, 64, 337-342 (2014)
Technique for the performance of the nitro-blue tetrazolium (NBT) test.
Freeman R and King B
Journal of Clinical Pathology, 25(10), 912-912 (1972)
Fluorescent in situ hybridization employing the conventional NBT/BCIP chromogenic stain.
Trinh L A, et al.
Biotechniques, 42(6), 756-759 (2007)
Irina S Balan et al.
Brain research, 1316, 112-119 (2009-12-29)
A histo-enzymatic technique for visualizing and quantifying endogenous NAD(H) in brain tissue was developed, based on coupled enzymatic cycling reactions that reduce nitrotetrazolium blue chloride to produce formazan. Conditions were used where the endogenous level of nicotinamide adenine dinucleotides (NAD(H))

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