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21955

5(6)-Carboxytetramethylrhodamine N-succinimidyl ester

Name: 5(6)-Carboxytetramethylrhodamine <I>N</I>-succinimidyl ester
Brand: SIGMA

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

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₂₅N₃O₇

CAS Number:

150408-83-6

Molecular Weight:

527.52

UNSPSC Code:

12352116

NACRES:

NA.32

PubChem Substance ID:

57647956

MDL number:

MFCD00077324

Beilstein/REAXYS Number:

8739319

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Properties

product line

BioReagent

Quality Level

100

assay

≥70% (coupling to amines)

form

powder

solubility

DMF: soluble, acetonitrile: soluble, methanol: soluble

fluorescence

λ_ex 543 nm; λ_em 576 nm in methanol, λ_ex 554 nm; λ_em 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

Description

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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E. Koller

Appl. Fluoresc. Technol., 3, 20-20 (1991)

Enhancing solid phase synthesis by a noncovalent protection strategy-efficient coupling of rhodamine to resin-bound peptide nucleic acids.

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

Conjugation to the cell-penetrating peptide TAT potentiates the photodynamic effect of carboxytetramethylrhodamine.

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

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Global Trade Item Number

SKU	GTIN
21955-25MG	04061838776020