RESORUFIN ETHYL ETHER Chemical Properties

Melting point:

223-225 °C (lit.)

Boiling point:

389.3±42.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMF: soluble

form 

Brown solid.

pka

1.43±0.20(Predicted)

color 

Dark Orange to Red

BRN 

225973

Safety Information

WGK Germany 

3

F 

8-10

MSDS

• Language:English Provider:SigmaAldrich

RESORUFIN ETHYL ETHER Usage And Synthesis

Chemical Properties

Red Solid

Uses

A fluorimetric substrate for cytochrome P450 IAI. Inhibits vasorelaxant responses to acetylcholine

Uses

Dealkylase substrate for the microfluorimetric analysis of microsomal cytochrome P-450.

Uses

Resorufin ethyl ether is suitable for the study of dealkylating activity of cytochrome P450 isozymes 1A1 and 1A2, where arylalkyl and alkyl isothiocyanates, and their glutathione, cysteine, and A′-acetylcysteine conjugates are used as inhibitors. It is suitable to study the ethoxyresorufin-O-deethylase (EROD) activity of cytochrome P450 activity (CYP1A1).

Definition

ChEBI: 7-ethoxyresorufin is a phenoxazine.

General Description

Resorufin ethers are used as markers or substrates for different cytochrome P (CYP) isoforms. Resorufin ethyl ether is the preferred resorufin ether to be metabolized by microsomes of 3-methylcholanthrene treated animals.

Biological Activity

cytochrome p450, family 1, subfamily a, polypeptide 1 is a protein that is encoded by human cyp1a1 gene. the protein is a member of the cytochrome p450 superfamily of enzymes. cyp1a1 is involved in phase i xenobiotic and drug metabolism. cyp1a1 is inhibited by fluoroquinolones and macrolides and induced by aromatic hydrocarbons. 7-ethoxyresorufin is a specific subtrate of cyp1a.

in vitro

7-ethoxyresorufin (2-10 microm), a substrate for cytochrome p450, which binds to the heme moiety of the enzyme, reduced responses to acetylcholine concentration-dependently but not the other agonists indicating an effect on nitric oxide synthesis although neither affected the conversion of l-arginine to l-citrulline [1].

in vivo

activities of cyp1a (7-ethoxyresorufin) in the liver was determined for comparative purposes. in mice, lps depressed cyp2a5 at low doses but not at doses that increased pro-inflammatory cytokines and no serum levels, and depressed cyp1a activity. blockade of proinflammatory cytokines extended down-regulation of cyp2a5 while not affecting lps-induced depression of cyp1a [2].

storage

Store at -20°C

References

[1] oyekan ao, mcgiff jc, rosencrantz-weiss p, quilley j. relaxant responses of rabbit aorta: influence of cytochrome p450 inhibitors. j pharmacol exp ther. 1994 jan;268(1):262-9.
[2] de-oliveira ac, poça ks, totino pr, paumgartten fj. modulation of cytochrome p450 2a5 activity by lipopolysaccharide: low-dose effects and non-monotonic dose-response relationship. plos one. 2015 jan 30;10(1):e0117842.
[3] pelkonen o, pasanen m, kuha h, gachalyi b, kairaluoma m, sotaniemi ea, park ss, friedman fk, gelboin hv. the effect of cigarette smoking on 7-ethoxyresorufin o-deethylase and other monooxygenase activities in human liver: analyses with monoclonal antibodies. br j clin pharmacol. 1986 aug;22(2):125-34.

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