263893
Phenoxazine
≥99%, purified by sublimation
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About This Item
Empirical Formula (Hill Notation):
C12H9NO
CAS Number:
Molecular Weight:
183.21
EC Number:
205-210-8
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
143234
MDL number:
InChI key
TZMSYXZUNZXBOL-UHFFFAOYSA-N
InChI
1S/C12H9NO/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H
SMILES string
N1c2ccccc2Oc3ccccc13
assay
≥99%
purified by
sublimation
mp
156-159 °C (lit.)
solubility
benzene: freely soluble(lit.), chloroform: freely soluble(lit.), diethyl ether: freely soluble(lit.), ethanol: freely soluble(lit.), petroleum ether: very slightly soluble(lit.)
General description
Phenoxazine dyes, including several Nile blue analogs, are known to localize selectively in animal tumors.
Application
Phenoxazine is a tricyclic 2′deoxycytidine analog that has been used to improve stacking interactions between heterocycles of oligonucleotide/RNA hybrids and to enhance cellular uptake.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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W M Flanagan et al.
Nature biotechnology, 17(1), 48-52 (1999-01-27)
One of the major barriers to the development of antisense therapeutics has been their poor bioavailability. Numerous oligonucleotide modifications have been synthesized and evaluated for enhanced cellular permeation with limited success. Phenoxazine, a tricyclic 2' deoxycytidine analog, was designed to
C W Lin et al.
Cancer research, 51(4), 1109-1116 (1991-02-15)
The overall goal of our research is to develop effective new photosensitizers for tumor-selective photodynamic therapy. Phenoxazine dyes, including several Nile blue analogues, are known to localize selectively in animal tumors. Structural modifications yielded several series of analogues with substantially
Karina Mondragón-Vásquez et al.
Chemical communications (Cambridge, England), (44)(44), 6726-6728 (2009-11-04)
N(6)-(N'-Arylcarbamoyl)-2'-deoxyadenosine-H-phosphonates displayed molecular recognition towards cationic phenothiazinium and phenoxazinium dyes in aqueous solutions; studies have shown that binding is driven mainly by aromatic interactions and that size and shape-complementarity of the aromatic rings in host and guest provides selectivity.
Michael J Rose et al.
Inorganic chemistry, 48(14), 6904-6917 (2009-06-02)
Three ruthenium nitrosyl-dye conjugates, namely, [((OMe)(2)bQb)Ru(NO)(Resf)] (RuNO-Resf), [((OMe)(2)bQb)Ru(NO)(Thnl)] (RuNO-Thnl), and [((OMe)(2)bQb)Ru(NO)(Seln)] (RuNO-Seln) have been synthesized using the tetradentate N4 dicarboxamido ligand H(2)(OMe)(2)bQb. Each nitrosyl of this series is conjugated to a phenoxazine-type heterotricyclic chromophore which has been systematically varied in
Guo-Xiang Li et al.
Journal of biochemical and molecular toxicology, 23(4), 280-286 (2009-08-26)
Phenothiazine (PtzNH) and phenoxazine (PozNH) can protect human erythrocytes against hemolysis induced by 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH), a peroxyl radical supplier. However, an antioxidant may be a pro-oxidant to accelerate the oxidation in the presence of radicals. The aim of this
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