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Sigma-Aldrich

5(6)-Carboxytetramethylrhodamine N-succinimidyl ester

BioReagent, suitable for fluorescence, ≥70% (coupling to amines)

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Empirical Formula (Hill Notation):
C29H25N3O7
CAS Number:
150408-83-6
Molecular Weight:
527.52
Beilstein:
8739319
MDL number:
MFCD00077324
UNSPSC Code:
12352116
PubChem Substance ID:
57647956
NACRES:
NA.32

product line

BioReagent

Quality Level

100

Assay

≥70% (coupling to amines)

form

powder

solubility

DMF: soluble
acetonitrile: soluble
methanol: soluble

fluorescence

λex 543 nm; λem 576 nm in methanol
λex 554 nm; λem 584 nm in 0.1 M phosphate pH 8.0

suitability

suitable for fluorescence

storage temp.

−20°C

SMILES string

CN(C)c1ccc2c(Oc3cc(ccc3C24OC(=O)c5cc(ccc45)C(=O)ON6C(=O)CCC6=O)N(C)C)c1

InChI

1S/C29H25N3O7/c1-30(2)17-6-9-21-23(14-17)37-24-15-18(31(3)4)7-10-22(24)29(21)20-8-5-16(13-19(20)28(36)38-29)27(35)39-32-25(33)11-12-26(32)34/h5-10,13-15H,11-12H2,1-4H3

InChI key

CXYYHBMOVJJZTD-UHFFFAOYSA-N

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Application

5(6)-Carboxytetramethylrhodamine N-succinimidyl ester (TMR-SE) is used as an amine coupling reagent to form 5(6)-carboxytetramethylrhodamine (TMR) derivatized compounds such as proteins and drugs.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Rhodamine derived label for amine modification and protein conjugation

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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E. Koller
Appl. Fluoresc. Technol., 3, 20-20 (1991)
L D Mayfield et al.
Bioorganic & medicinal chemistry letters, 9(10), 1419-1422 (1999-06-09)
Resins for solid-phase synthesis can affect coupling efficiencies by interacting with reactants. We have observed that polyethylene glycol-polystyrene (PEG-PS) solid support absorbs added activated fluorophores, preventing efficient labeling of peptide nucleic acids (PNAs). We now report that addition of an
Divyamani Srinivasan et al.
PloS one, 6(3), e17732-e17732 (2011-03-23)
Cell-penetrating peptides (CPPs) can transport macromolecular cargos into live cells. However, the cellular delivery efficiency of these reagents is often suboptimal because CPP-cargo conjugates typically remain trapped inside endosomes. Interestingly, irradiation of fluorescently labeled CPPs with light increases the release
P Kask et al.
Biophysical journal, 78(4), 1703-1713 (2000-03-29)
A method of sample analysis is presented which is based on fitting a joint distribution of photon count numbers. In experiments, fluorescence from a microscopic volume containing a fluctuating number of molecules is monitored by two detectors, using a confocal
Yoshiaki Yano et al.
Biochemistry, 41(9), 3073-3080 (2002-02-28)
Investigation of interactions between hydrophobic model peptides and lipid bilayers is perhaps the only way to elucidate the principles of the folding and stability of membrane proteins (White, S. H., and Wimley, W. C. (1998) Biochim. Biophys. Acta 1367, 339-352).
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