7-Ethoxyresorufin is a fluorimetric substrate and suicide inhibitor of CYP (cytochrome P450). Also shown to inhibit several reductase enzymes, specifically CYPOR (NADPH-P450 reductase). The binding to CYP (cytochrome P450) is thought to inhibit the vasorelaxant response to acetylcholine. 7-Ethoxyresorufin has also demonstrated inhibition of NO synthesis by uncoupling neuronal NOS1 (nitric oxide synthase); it is a noncompetitive inhibitor of neuronal NOS1 with respect to L-arginine with a Ki value of 0.76 +/- 0.06 μM. 7-Ethoxyresorufin is a substate of CYP1A1. 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.
Fluorogenic microsomal dealkylase and CYP450 substrate. Produces the red fluorescent dye resorufin (Ex/Em 571/585 nm). Suitable for\xa0differentiating CYP isoenzymes, 1A1 and 1A2. Substrate for microsomal\xa0cytochrome P450\xa0enzyme systems from microbes
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
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Note
Refer to SDS for further information Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
This compound belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring.
External Descriptors
phenoxazine
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Soluble in DMSO (5 mg/mL), ethanol (5 mg/mL), chloroform, dichloromethane, DMF (5 mg/mL), alcohols, and methanol. Insoluble in water.
Molecular Weight
241.240 g/mol
XLogP3
1.800
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Exact Mass
241.074 Da
Monoisotopic Mass
241.074 Da
Topological Polar Surface Area
47.900 Ų
Heavy Atom Count
18
Formal Charge
0
Complexity
450.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
References
1.Wei Liu, Mi Zhang, Yan Xiao, Zhaoyang Ye, Yan Zhou, Meidong Lang, Wen-Song Tan. (2020) Fabrication and in vitro evaluation of a packed-bed bioreactor based on galactosylated poly(ethylene terephthalate) microfibrous scaffolds. BIOCHEMICAL ENGINEERING JOURNAL, [PMID:][10.1016/j.bej.2020.107565]
2.Tongtong Shen, Yufan Miao, Chenchen Ding, Wentao Fan, Shuhui Liu, Yanan Lv, Xiaona Gao, Marthe De Boevre, Liping Yan, Sheila Okoth, Sarah De Saeger, Suquan Song. (2019) Activation of the p38/MAPK pathway regulates autophagy in response to the CYPOR-dependent oxidative stress induced by zearalenone in porcine intestinal epithelial cells. FOOD AND CHEMICAL TOXICOLOGY, [PMID:31173817][10.1016/j.fct.2019.05.035]
3.Yingchang Song, Jiayu Zeng, Jianglan Long, Aiting Wang, Kuan Chen, Jia'an Qin, Dan Yan. (2024) Rapid multichannel fluorescent probe assay for CYP450 inhibition screening and drug interaction monitoring. MICROCHEMICAL JOURNAL, [PMID:][10.1016/j.microc.2024.110185]
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L1811136