6-CARBOXYTETRAMETHYLRHODAMINE N-HYDROXYSUCCINIMIDE ESTER Chemical Properties

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

DMF: soluble

form 

A solid

color 

Pale purple to purple

Appearance

Dark red amorphous solid

InChIKey

VWFRSNKRTNUMET-UHFFFAOYSA-N

SMILES

C(C1C=C(C(=O)ON2C(CCC2=O)=O)C=CC=1C1=C2C=CC(N(C)C)=CC2=[O+]C2C=C(N(C)C)C=CC1=2)(=O)[O-]

Safety Information

WGK Germany 

3

HS Code 

32049010

6-CARBOXYTETRAMETHYLRHODAMINE N-HYDROXYSUCCINIMIDE ESTER Usage And Synthesis

Description

5-Carboxytetramethylrhodamine succinimidyl ester (5-TAMRA-SE) is an amine-reactive fluorescent probe. It has been used in double site-directed peptide modification to label proteinase substrates for use in FRET assays. It quenches lucifer yellow CH fluorescence by greater than 90% in uncleaved proteinase substrates, which allows for the detection of enzyme-cleaved substrates by an increase in fluorescence intensity. It has also been used in the synthesis of fluorescent derivatives of a variety of compounds, including the antibiotic ampicillin , nucleotide diphosphate uridine-5’-diphosphate (UDP; ), and the progesterone receptor antagonist RU486 (mifepristone; ). 5-TAMRA-SE displays excitation maxima ranging from 540 to 560 nm and an emission maximum of 580 nm.

Uses

Amine-reactive form of 5-carboxytetramethylrhodamine single isomer.

Uses

Amine-Reactive Fluorescent Probe for labeling of DNA and RNA

storage

Store at -20°C

References

[1] KIERAN F. GEOGHEGAN. Site-directed double fluorescent tagging of human renin and collagenase (MMP-1) substrate peptides using the periodate oxidation of N-terminal serine. An apparently general strategy for provision of energy-transfer substrates for proteases[J]. Bioconjugate Chemistry Bioconjugate, 1993, 4 6: 537-544. DOI: 10.1021/bc00024a017
[2] ADAM B. SHAPIRO*  Mark S  Janelle Comita Prevoir. 5-Carboxytetramethylrhodamine-Ampicillin Fluorescence Anisotropy-Based Assay of Escherichia coli Penicillin-Binding Protein 2 Transpeptidase Inhibition[J]. ACS Infectious Diseases, 2019, 5 6: 863-872. DOI: 10.1021/acsinfecdis.8b00351
[3] JUN QI  Pablo S  Michelle Oppenheimer. Fluorescence Polarization Binding Assay for Aspergillus fumigatus Virulence Factor UDP-Galactopyranose Mutase.[J]. Enzyme Research, 2011, 2011: 513905. DOI: 10.4061/2011/513905
[4] ROY WEINSTAIN. Fluorescent Ligand for Human Progesterone Receptor Imaging in Live Cells[J]. Bioconjugate Chemistry Bioconjugate, 2013, 24 5: 766-771. DOI: 10.1021/bc3006418

Abs/Em Maxima

553/575 nm

Excitation / Emission Maximum

546 nm/580 nm

Extinction Coefficient

92,000

Microscopy Laser Line

532 nm or 555 nm

Flow Cytometry Laser Line

532 nm or 555 nm

Spectrally Similar Dyes

Alexa Fluor® 555, CF® 555, DyLight® 549

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