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Details

Stereochemistry ACHIRAL
Molecular Formula C21H11NO5S
Molecular Weight 389.381
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FLUORESCEIN 5-ISOTHIOCYANATE

SMILES

OC1=CC2=C(C=C1)C3(OC(=O)C4=C3C=CC(=C4)N=C=S)C5=C(O2)C=C(O)C=C5

InChI

InChIKey=MHMNJMPURVTYEJ-UHFFFAOYSA-N
InChI=1S/C21H11NO5S/c23-12-2-5-16-18(8-12)26-19-9-13(24)3-6-17(19)21(16)15-4-1-11(22-10-28)7-14(15)20(25)27-21/h1-9,23-24H

HIDE SMILES / InChI

Molecular Formula C21H11NO5S
Molecular Weight 389.381
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Fluorescein isothiocyanate (FITC) is widely used to attach a fluorescent label to proteins via the amine group. The isothiocyanate group reacts with amino terminal and primary amines in proteins. It has been used for the labeling of proteins including antibodies and lectins. Isomer I (Fluorescein 5-isothiocyanate) has the thiocyanate group on the 4 carbon of the benzene ring, whereas isomer II (Fluorescein 6-isothiocyanate) has the thiocyanate on the 5 carbon. The two isomers are indistinguishable spectrally, either by wavelength or intensity. Isomer I is more easily isolated in pure form, so is less expensive. This may explain why isomer I is more commonly used for labeling. For many purposes, however, the mixed isomers of FITC will be perfectly suitable. Some FITC conjugates are being investigated for diagnostic purposes. Folate-fluorescein isothiocyanate, or folate-FITC, also identified as EC-17, targets folate receptors over expressed in certain cancers and could help in better identifying the margins of the cancer thereby achieving negative margins.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Conjugation of FITC (Fluorescein 5-isothiocyanate) to IgG. A standard solution of 1 mg FITC per ml 0.15 M Na2HPO4 X 2H20 solution (pH 9.0) is made for immediate use. About 10 ml of the FITC solution per gram protein is added to the IgG solution while stirring at room temperature. The pH is adjusted to 9.5 by addition of 0 1 M Na3PO4 X 1OH20 while stirring. The reaction is continued for 60 minutes at room temperature, while pH is maintained at 9.5. The conjugate is put on a 'Sephadex G 25 coarse' column, equilibrated and eluted with PBS, and the free dye is removed.
Substance Class Chemical
Record UNII
I223NX31W9
Record Status Validated (UNII)
Record Version