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Details

Stereochemistry ACHIRAL
Molecular Formula C34H24N6O14S4.4Na
Molecular Weight 960.805
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of TRYPAN BLUE

SMILES

[Na+].[Na+].[Na+].[Na+].CC1=CC(=CC=C1\N=N\C2=C(C=C3C=C(C=C(N)C3=C2O)S([O-])(=O)=O)S([O-])(=O)=O)C4=CC(C)=C(C=C4)\N=N\C5=C(O)C6=C(N)C=C(C=C6C=C5S([O-])(=O)=O)S([O-])(=O)=O

InChI

InChIKey=GLNADSQYFUSGOU-GPTZEZBUSA-J
InChI=1S/C34H28N6O14S4.4Na/c1-15-7-17(3-5-25(15)37-39-31-27(57(49,50)51)11-19-9-21(55(43,44)45)13-23(35)29(19)33(31)41)18-4-6-26(16(2)8-18)38-40-32-28(58(52,53)54)12-20-10-22(56(46,47)48)14-24(36)30(20)34(32)42;;;;/h3-14,41-42H,35-36H2,1-2H3,(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54);;;;/q;4*+1/p-4/b39-37+,40-38+;;;;

HIDE SMILES / InChI

Molecular Formula C34H24N6O14S4
Molecular Weight 868.846
Charge -4
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 4 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Trypan blue (trade name MembraneBlue, VisionBlue) is a vital stain used to selectively color dead tissues or cells blue. Live cells or tissues with intact cell membranes are not colored. 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 color 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. 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. 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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
MembraneBlue
Diagnostic
VisionBlue
Diagnostic
MembraneBlue

Sourcing

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Before injection of MembraneBlue™ 0.15% perform a ‘fluid-air exchange’, i.e. filling the entire vitreous cavity with air, to prevent aqueous dilution of MembraneBlue™ 0.15%. MembraneBlue™ 0.15% is carefully applied to the retinal membrane using a blunt cannula attached to the MembraneBlue™ 0.15% syringe, without allowing the cannula to contact or damage the retina. Sufficient staining is expected on contact with the membrane. All excess dye should be removed from the vitreous cavity before performing an air-fluid exchange, to prevent unnecessary spreading of the dye. MembraneBlue™ 0.15% can also be injected directly in a BSS filled vitreous cavity (instead of injecting under air). Clinical use demonstrated that, after complete vitreous and posterior hyaloid removal, sufficient staining is achieved after 30 seconds of application under BSS.
Route of Administration: Other
In Vitro Use Guide
Cultured human retinal pigment epithelium cells were exposed for 5 minutes to various concentrations of trypan blue (0.06%, 0.15%, 0.30%), and cell viability was confocally measured.
Substance Class Chemical
Record UNII
I2ZWO3LS3M
Record Status Validated (UNII)
Record Version