Phenoxazine
(Synonyms: 吩噁嗪) 目录号 : GC47948
A heterocyclic building block
Cas No.:135-67-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Phenoxazine is a heterocyclic building block.1 It has been used in the synthesis of phenoxazine derivatives that have anticancer and antimicrobial activities in vitro.2,3 Phenoxazine has also been used in the synthesis of phenoxazine derivatives used as chromogenic substrates.4
1.Shruti, Dwivedi, J., Kishore, D., et al.Recent advancement in the synthesis of phenoxazine derivatives and their analoguesSynthetic Commun.48(12)1377-1402(2018) 2.Shimizu, S., Suzuki, M., Tomoda, A., et al.Phenoxazine compounds produced by the reactions with bovine hemoglobin show antimicrobial activity against non-tuberculosis mycobacteriaTohoku J. Exp. Med.203(1)47-52(2004) 3.Che, X.-F., Zheng, C.-L., Akiyama, S.-I., et al.2-Aminophenoxazine-3-one and 2-amino-4,4α-dihydro-4α,7-dimethyl-3H-phenoxazine-3-one cause cellular apoptosis by reducing higher intracellular pH in cancer cellsProc. Jpn. Acad. Ser. B Phys. Biol. Sci.87(4)199-213(2011) 4.Jana, N.C., Patra, M., BrandÃo, P., et al.Synthesis, structure and diverse coordination chemistry of cobalt(III) complexes derived from a Schiff base ligand and their biomimetic catalytic oxidation of o-aminophenolsPolyhedron16423-34(2019)
| Cas No. | 135-67-1 | SDF | |
| 别名 | 吩噁嗪 | ||
| Canonical SMILES | C12=CC=CC=C1NC3=C(C=CC=C3)O2 | ||
| 分子式 | C12H9NO | 分子量 | 183.2 |
| 溶解度 | DMF: 15mg/mL,DMSO: 10mg/mL,Ethanol: 20mg/mL,Ethanol:PBS (pH 7.2) (1:4): 0.2mg/mL | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.4585 mL | 27.2926 mL | 54.5852 mL |
| 5 mM | 1.0917 mL | 5.4585 mL | 10.917 mL |
| 10 mM | 0.5459 mL | 2.7293 mL | 5.4585 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Medicinal and Biological Significance of Phenoxazine Derivatives
Mini Rev Med Chem 2021;21(12):1541-1555.PMID:33319658DOI:10.2174/1389557520666201214102151.
Since 1887, Phenoxazine derivatives have attracted the attention of chemists due to their versatile utility, industrially and pharmacologically. Literature is found abundant with various pharmacological activities of Phenoxazine derivatives like antitumor, anticancer, antifungal, antibacterial, anti-inflammatory, anti-diabetic, anti-viral, anti-malarial, anti-depressant, analgesic and many other drug resistance reversal activities. This review covers a detailed overview of the pharmacological application of Phenoxazine nucleus, its chemistry and reactivity, and also illustrating the incorporation of different groups at different positions enhancing its biological application, besides some synthetic procedures.
Anticancer activity of G4-targeting Phenoxazine derivatives in vitro
Biochimie 2022 Oct;201:43-54.PMID:35817132DOI:10.1016/j.biochi.2022.07.001.
G4-stabilizing ligands are now being considered as anticancer, antiviral and antibacterial agents. Phenoxazine is a promising scaffold for the development of G4 ligands. Here, we profiled two known phenoxazine-based nucleoside analogs and five new nucleoside and non-nucleoside derivatives against G4 targets from telomere repeats and the KIT promoter region. Leading new derivatives exhibited remarkably high G4-stabilizing effects (comparable or superior to the effects of the commonly used selective G4 ligands PDS and NMM) and selectivity toward G4s over duplex (superior to BRACO-19). All phenoxazine-based ligands inhibited cellular metabolic activity. The Phenoxazine derivatives were particularly toxic for lung adenocarcinoma cells A549' and human liver cancer cells HepG2 (CC50 of the nucleoside analogues in the nanomolar range), but also affected breast cancer cells MCF7, as well as immortalized fibroblasts VA13 and embryonic kidney cells HEK293t (CC50 in the micromolar range). Importantly, the CC50 values varied mostly in accordance with G4-binding affinities and G4-stabilizing effects, and the Phenoxazine derivatives localized in the cell nuclei, which corroborates G4-mediated mechanisms of action.
Phenoxazine-based scaffold for designing G4-interacting agents
Org Biomol Chem 2020 Aug 12;18(31):6147-6154.PMID:32719836DOI:10.1039/d0ob00983k.
G-quadruplexes (G4) represent one class of non-canonical secondary nucleic acid structures that are currently regarded as promising and attractive targets for anti-cancer, anti-viral and antibacterial therapy. Herein, we probe a new i-clamp-inspired Phenoxazine scaffold for designing G4-stabilizing ligands. The length of the protonated aminoalkyl tethers ('arms') of the phenoxazine-based ligand was optimized in silico. Two double-armed ligands differing in the relative orientation of their arms and one single-armed ligand were synthesized. The two-armed ligands significantly enhanced the thermal stability of the G-quadruplex structures (increasing the melting temperature by up to 20 °C) and displayed G4 selectivity over duplex DNA. The ligands look promising for biological studies and the Phenoxazine scaffold could be a starting point for designing new G4-interacting compounds.
Synthetic, biological and optoelectronic properties of Phenoxazine and its derivatives: a state of the art review
Mol Divers 2023 Feb 9;1-43.PMID:36757655DOI:10.1007/s11030-023-10619-5.
Phenoxazines have sparked a lot of interest owing to their numerous applications in material science, organic light-emitting diodes, photoredox catalyst, dye-sensitized solar cells and chemotherapy. Among other things, they have antioxidant, antidiabetic, antimalarial, anti-alzheimer, antiviral, anti-inflammatory and antibiotic properties. Actinomycin D, which contains a Phenoxazine moiety, functions both as an antibiotic and anticancer agent. Several research groups have worked on various structural modifications over the years in order to develop new phenoxazines with improved properties. Both phenothiazines and phenoxazines have gained prominence in medicine as pharmacological lead structures from their traditional uses as dyes and pigments. Organoelectronics and material sciences have recently found these compounds and their derivatives to be quite useful. Due to this, organic synthesis has been used in an unprecedented amount of exploratory alteration of the parent structures in an effort to create novel derivatives with enhanced biological and material capabilities. As a result, it is critical to conduct more frequent reviews of the work done in this area. Various stages of the synthetic transformation of Phenoxazine scaffolds have been depicted in this article. This article aims to provide a state of the art review for the better understanding of the Phenoxazine derivatives highlighting the progress and prospects of the same in medicinal and material applications.
Oligonucleotides Containing Phenoxazine Artificial Nucleobases: Triplex-Forming Abilities and Fluorescence Properties
Chembiochem 2020 Mar 16;21(6):860-864.PMID:31568630DOI:10.1002/cbic.201900536.
1,3-Diaza-2-oxophenoxazine ("Phenoxazine"), a tricyclic cytosine analogue, can strongly bind to guanine moieties and improve π-π stacking effects with adjacent bases in a duplex. Phenoxazine has been widely used for improving duplex-forming abilities. In this study, we have investigated whether Phenoxazine and its analogue, 1,3,9-triaza-2-oxophenoxazine (9-TAP), could improve triplex-forming abilities. A triplex-forming oligonucleotide (TFO) incorporating a Phenoxazine component was found to show considerably decreased binding affinity with homopurine/homopyrimidine double-stranded DNA, so the Phenoxazine system was considered not to function as either a protonated cytosine or thymine analogue. Alternatively, a 9-TAP-containing artificial nucleobase developed by us earlier as a new Phenoxazine analogue functioned as a thymine analogue with respect to AT base pairs in a parallel triplex DNA motif. The fluorescence of the 9-TAP moiety was maintained even in triplex (9-TAP:AT) formation, so 9-TAP might be useful as an imaging tool for various oligonucleotide nanotechnologies requiring triplex formation.