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263893

Sigma-Aldrich

Phenoxazine

≥99%, purified by sublimation

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About This Item

Empirical Formula (Hill Notation):
C12H9NO
CAS Number:
135-67-1
Molecular Weight:
183.21
Beilstein:
143234
EC Number:
205-210-8
MDL number:
MFCD00005014
UNSPSC Code:
12352100
PubChem Substance ID:
24855892

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.)

SMILES string

N1c2ccccc2Oc3ccccc13

InChI

1S/C12H9NO/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H

InChI key

TZMSYXZUNZXBOL-UHFFFAOYSA-N

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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 Code

13 - Non 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Kyoko Hayashi et al.
Journal of pharmacological sciences, 114(1), 85-91 (2010-08-26)
We examined the in vivo antiviral activities of 2-amino-4,4α-dihydro-4α-7-dimethyl-3H-phenoxazine-3-one (Phx-1), 3-amino-1,4α-dihydro-4α-8-dimethyl-2H-phenoxazine-2-one (Phx-2), and 2-aminophenoxazine-3-one (Phx-3) against herpes viruses. The virus yield three days after administration, changes in the 6-degree's lesion scores, and the morbidity were assessed after herpes simplex virus
Steve H Thorne et al.
Molecular cancer therapeutics, 8(2), 333-341 (2009-02-05)
We report the discovery of a new prodrug, 6-chloro-9-nitro-5-oxo-5H-benzo(a)phenoxazine (CNOB). This prodrug is efficiently activated by ChrR6, the highly active prodrug activating bacterial enzyme we have previously developed. The CNOB/ChrR6 therapy was effective in killing several cancer cell lines in
Martin Link et al.
Bioorganic & medicinal chemistry letters, 21(18), 5538-5542 (2011-08-02)
Novel amino-reactive phenoxazines were obtained by reasonably simple synthetic protocols and characterized in terms of their use as fluorescent labels for amines, amino acids and proteins in general. Purple labels (alternatives to Texas Red) and blue labels (alternatives to Cy-1)
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