An amine-reactive fluorescent probe
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5-Carboxytetramethylrhodamine succinimidyl ester

Item No. 28509

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-[2-carboxy-4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]phenyl]-3,6-bis(dimethylamino)-xanthylium, inner salt
CAS Number
150810-68-7
Synonyms
  • 5-TAMRA-SE
Molecular Formula
C29H25N3O7
Formula Weight
527.5
Purity
≥90%
Emission
580 nm
Excitation
540-560 nm
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 1.4 mg/mlEthanol: 0.2 mg/mlPBS (pH 7.2): 0.25 mg/ml
λmax
357, 545 nm
SMILES
[O-]C(C(C=C(C(ON1C(CCC1=O)=O)=O)C=C2)=C2C3=C4C=CC(N(C)C)=CC4=[O+]C5=C3C=CC(N(C)C)=C5)=O
InChi Code
InChI=1S/C29H25N3O7/c1-30(2)17-6-9-20-23(14-17)38-24-15-18(31(3)4)7-10-21(24)27(20)19-8-5-16(13-22(19)28(35)36)29(37)39-32-25(33)11-12-26(32)34/h5-10,13-15H,11-12H2,1-4H3
InChi Key
VWFRSNKRTNUMET-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $41

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    5 mg

    $128

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    10 mg

    $235

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    25 mg

    $487

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    Product Description

    5-Carboxytetramethylrhodamine succinimidyl ester (5-TAMRA-SE) is an amine-reactive fluorescent probe.1 It has been used in double site-directed peptide modification to label proteinase substrates for use in FRET assays. It quenches lucifer yellow CH (Item No. 25573) 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 (Item No. 14417), nucleotide diphosphate uridine-5’-diphosphate (UDP; Item No. 18137), and the progesterone receptor antagonist RU486 (mifepristone; Item No. 10006317).2,3,4 5-TAMRA-SE displays excitation maxima ranging from 540 to 560 nm and an emission maximum of 580 nm.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Geoghegan, K.F., Emery, M.J., Martin, W.H., et al. 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. Bioconjug. Chem. 4(6), 537-544 (1993).

    2. Shapiro, A.B., Comita-Prevoir, J., and Sylvester, M. 5-Carboxytetramethylrhodamine-ampicillin fluorescence anisotropy-based assay of Escherichia coli penicillin-binding protein 2 transpeptidase inhibition. ACS Infect. Dis. 5(6), 863-872 (2019).

    3. Qi, J., Oppenheimer, M., and Sobrado, P. Fluorescence polarization binding assay for Aspergillus fumigatus virulence factor UDP-galactopyranose mutase. Enzyme Res. 513905 (2011).

    4. Weinstain, R., Kanter, J., Friedman, B., et al. Fluorescent ligand for human progesterone receptor imaging in live cells. Bioconjug. Chem. 24(5), 766-771 (2013).