Trypan blue

Trypan Blue
Names
IUPAC name
(3Z,3'Z)-3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)di(1Z)hydrazin-2-yl-1-ylidene]bis(5-amino-4-oxo-3,4-dihydronaphthalene-2,7-disulfonic acid)
Identifiers
72-57-1 (tetrasodium salt) YesY
ChEBI CHEBI:78897 N
ChEMBL ChEMBL1640 YesY
ChemSpider 10482308 YesY
Jmol 3D image Interactive graph
KEGG C19307 N
PubChem 5904246
UNII I2ZWO3LS3M YesY
Properties
C34H28N6O14S4
Molar mass 872.88
Appearance deep blue in aqueous solution[1]
Melting point > 300 °C (572 °F; 573 K)
<0.1 mg/mL in water [2]
Solubility 20 mg/mL in methyl Cellosolve, and 0.6 mg/mL in ethanol
Hazards
Lethal dose or concentration (LD, LC):
6200 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Trypan blue is a vital stain used to selectively colour dead tissues or cells blue. It is a diazo dye.

Live cells or tissues with intact cell membranes are not coloured. Since cells are very selective in the compounds that pass through the membrane, in a viable cell trypan blue is not absorbed; however, it traverses the membrane in a dead cell. Hence, dead cells are shown as a distinctive blue colour under a microscope. Since live cells are excluded from staining, this staining method is also described as a dye exclusion method. This dye may be a cause of certain birth defects such as encephalocele.

Background & chemistry

Trypan blue is derived from toluidine, that is, any of several isomeric bases, C14H16N2, derived from toluene. Trypan blue is so-called because it can kill trypanosomes, the parasites that cause sleeping sickness. An analog of trypan blue, suramin is used pharmacologically against trypanosomiasis. Trypan blue is also known as diamine blue and Niagara blue.

The extinction coefficient for trypan blue is 6 x 104 M−1 cm−1 at 607nm in methanol.[3]

Trypan red and Trypan blue were first synthesized by the German scientist Paul Ehrlich in 1904.

Uses of trypan blue

Observation with an optical microscope of Hyaloperonospora parasitica within a leaf of Arabidopsis thaliana by using the trypan blue staining.

Trypan blue is commonly used in microscopy (for cell counting) and in laboratory mice for assessment of tissue viability. The method cannot distinguish between necrotic and apoptotic cells.

It may be used to observe fungal hyphae[4] and stramenopiles.

Trypan blue is also used in ophthalmic cataract surgery to stain the anterior capsule in the presence of a mature cataract, to aid in visualization, before creating the continuous curvilinear capsulorhexis.

Synonyms

Further reading

References

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