Resorufin ethyl ether

Name: Resorufin ethyl ether
Brand: SIGMA

suitable for fluorescence, ≥95% (UV)

Sinónimos:

7-Ethoxy-3H-phenoxazin-3-one, Ethoxyresorufin, O⁷-Ethylresorufin

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Fórmula empírica (notación de Hill):

C₁₄H₁₁NO₃

Número CAS:

5725-91-7

Peso molecular:

241.24

UNSPSC Code:

12161501

NACRES:

NA.32

PubChem Substance ID:

329757074

MDL number:

MFCD00037661

Beilstein/REAXYS Number:

225973

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InChI

1S/C23H14F5NO4.C14H11NO3/c24-17-18(25)20(27)22(21(28)19(17)26)33-16(30)9-29-23(31)32-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15;1-2-17-10-4-6-12-14(8-10)18-13-7-9(16)3-5-11(13)15-12/h1-8,15H,9-10H2,(H,29,31);3-8H,2H2,1H3

SMILES string

CCOc1ccc2N=C3C=CC(=O)C=C3Oc2c1.Fc4c(F)c(F)c(OC(=O)CNC(=O)OCC5c6ccccc6-c7ccccc57)c(F)c4F

InChI key

ZOSYTBPPLWBBKM-UHFFFAOYSA-N

assay

≥95% (UV)

form

solid

mp

223-225 °C (lit.)

solubility

DMF: soluble, DMSO: soluble, alcohols: soluble

fluorescence

λ_ex 464 nm; λ_em 540 nm in methanol(lit.), λ_ex 571 nm; λ_em 585 nm in dealkylase(lit.)

suitability

suitable for fluorescence

storage temp.

2-8°C

Quality Level

100

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Este artículo	E3763	M1544	B1532
Sigma-Aldrich 46121 Resorufin ethyl ether	Sigma-Aldrich E3763 Resorufin ethyl ether	Sigma-Aldrich M1544 Resorufin methyl ether	Sigma-Aldrich B1532 Resorufin benzyl ether
assay ≥95% (UV)	assay ≥98% (TLC)	assay ≥98.0% (HPLC)	assay ≥98% (TLC)
solubility DMF: soluble, alcohols: soluble, DMSO: soluble	solubility chloroform: 9.80-10.20 mg/mL, clear, orange	solubility dichloromethane: 0.95-1.05 mg/mL, clear, orange to very deep orange	solubility chloroform: 9.80-10.20 mg/mL, clear, orange
suitability suitable for fluorescence	suitability suitable for fluorescence	suitability -	suitability -
Quality Level 100	Quality Level 200	Quality Level 200	Quality Level 200
form solid	form powder	form powder	form powder
storage temp. 2-8°C	storage temp. −20°C	storage temp. 2-8°C	storage temp. 2-8°C

Application

7-Ethoxyresorufin (7-ER) is a substrate used in environmental toxicology studies to monitor ethoxyresorufin-O-deethylase catalytic activity in the EROD assay. The EROD assay monitors the induction of the xenobiotic-metabolizing enzyme cytochrome P-450 (CYP) 1A1 and is a widely used biomarker for exposure of wildlife to substances that bind the aryl hydrocarbon (Ah) receptor. It provides evidence of receptor-mediated induction of cytochrome P450-dependant monooxygenases (the CYP1A subfamily specifically) by xenobiotic chemicals.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Dealkylase substrate for the microfluorimetric analysis of microsomal cytochrome P-450[1][2]

Clase de almacenamiento

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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Cytochrome P4501A induction in avian hepatocyte cultures exposed to polychlorinated biphenyls: comparisons with AHR1-mediated reporter gene activity and in ovo toxicity.

Gillian E Manning et al.

Toxicology and applied pharmacology, 266(1), 38-47 (2012-11-13)

Avian-specific toxic equivalency factors (TEFs) were developed by the World Health Organization to simplify environmental risk assessments of dioxin-like compounds (DLCs), but TEFs do not account for differences in the toxic and biochemical potencies of DLCs among species of birds.

Fluorescence-microscopic measurement of intracellular cytochrome P-450 enzyme activity (ethoxyresorufin O-de-ethylation) in unfixed liver section.

M D Burke et al.

The Biochemical journal, 212(1), 15-24 (1983-04-15)

A fluorescence-microscopic method has been developed for measurement of the intracellular kinetics of the cytochrome P-450 reaction, ethoxyresorufin O-de-ethylation, in individual hepatocytes in unfixed non-frozen liver sections obtained from control or 3-methylcholanthrene-pretreated mice. De-ethylation was enhanced in the presence of

Ethoxyresorufin-O-deethylase (EROD) activity in fish as a biomarker of chemical exposure.

J J Whyte et al.

Critical reviews in toxicology, 30(4), 347-570 (2000-08-24)

This review compiles and evaluates existing scientific information on the use, limitations, and procedural considerations for EROD activity (a catalytic measurement of cytochrome P4501A induction) as a biomarker in fish. A multitude of chemicals induce EROD activity in a variety

How flood events affect rainbow trout: evidence of a biomarker cascade in rainbow trout after exposure to PAH contaminated sediment suspensions.

Markus Brinkmann et al.

Aquatic toxicology (Amsterdam, Netherlands), 128-129, 13-24 (2012-12-25)

Increasing frequency and intensity of flood events are major concerns in the context of climate change. In addition to the direct hydrological implications of such events, potential ecotoxicological impacts are of increasing interest. It is vital to understand mechanisms of

Fluorescence assay for per-cell estimation of cytochrome P-450-dependent monooxygenase activities in keratinocyte suspensions and cultures.

J J Reiners et al.

Analytical biochemistry, 188(2), 317-324 (1990-08-01)

An assay was characterized that facilitated per-cell estimation of cytochrome P-450-dependent monooxygenase activities in whole-cell suspensions and cultures of murine epidermal keratinocytes (MEKs). 7-Ethoxycoumarin O-deethylase (7-ECD), 7-ethoxyresorufin O-deethylase (7-ERD), and 7-pentoxyresorufin O-deethylase (7-PRD) activities were monitored by fluorescent detection of

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