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Key Documents

E2028

Sigma-Aldrich

Ethidium bromide monoazide

≥95% (HPLC), solid

Synonym(s):

3-Amino-8-azido-5-ethyl-6-phenylphenanthridinium bromide, Ethidium monoazide bromide

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About This Item

Empirical Formula (Hill Notation):
C21H18BrN5
CAS Number:
Molecular Weight:
420.31
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:

Quality Level

Assay

≥95% (HPLC)

form

solid

color

orange

solubility

DMF: soluble
ethanol: soluble

ε (extinction coefficient)

≥5200 at 459-465 nm

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

−20°C

SMILES string

[Br-].CC[n+]1c(-c2ccccc2)c3cc(ccc3c4ccc(N)cc14)N=[N+]=[N-]

InChI

1S/C21H17N5.BrH/c1-2-26-20-12-15(22)8-10-18(20)17-11-9-16(24-25-23)13-19(17)21(26)14-6-4-3-5-7-14;/h3-13,22H,2H2,1H3;1H

InChI key

GHUXAYLZEGLXDA-UHFFFAOYSA-N

Biochem/physiol Actions

Photoactive stain covalently binds to nucleic acids in solution and in cells with damaged membranes.
Used to footprint drug binding sites on DNA, detect non-viable cells, identify ethidium binding sites on DNA and tRNA, and selectively inactivate gene expression.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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G Loozen et al.
Molecular oral microbiology, 26(4), 253-261 (2011-07-07)
DNA-based methodology for the identification and detection of specific bacteria in dental plaque offers advantages over culturing techniques. One drawback of current molecular techniques like real-time quantitative polymerase chain reaction (RT-QPCR) is that they are not able to distinguish between
G Douglas Inglis et al.
Applied and environmental microbiology, 76(4), 1110-1119 (2009-12-22)
The persistence of naturally occurring campylobacteria in aerobic compost constructed of manure from beef cattle that were administered chlortetracycline and sulfamethazine (AS700) or from cattle not administered antibiotics (control) was examined. Although there were no differences in population sizes of
Takashi Soejima et al.
Analytical biochemistry, 418(1), 37-43 (2011-07-21)
The polymerase chain reaction (PCR) can confirm the presence of bacteria, but it is unable to differentiate between live and dead bacteria. Although ethidium monoazide (EMA)- and propidium monoazide (PMA)-based PCR have been evaluated, a quantity of ≥ 10(3)cells/ml dead
N-T Chen et al.
Journal of applied microbiology, 109(2), 623-634 (2010-02-19)
To optimize ethidium monoazide (EMA) coupled with real-time quantitative PCR (qPCR) and to evaluate its environmental applicability on quantifying viable legionellae in water and biofilm of cooling towers and hot water systems. EMA (0.9-45.5 microg ml(-1)) and propidium monoazide (PMA
K Kim et al.
Water science and technology : a journal of the International Association on Water Pollution Research, 63(3), 502-507 (2011-02-01)
A method was developed for discriminating damaged viruses or naked viral RNA from intact viruses by ethidium monoazide (EMA) treatment before RT-PCR. The applied EMA treatment consisted of three steps: (1) EMA dose, (2) exposure to light, and (3) additional

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