69-48-7

Usage

Uses

Used in Biological Staining Applications:
1,6-Phenazinediol is used as a biological stain for visualizing cytoplasmic granules and nuclei in cell culture. Its staining properties allow researchers to examine cellular structures and monitor cell health in laboratory settings.
Used in Anticancer Applications:
1,6-Phenazinediol is used as a potential anti-cancer agent, as it has been found to inhibit the growth of certain cancer cell lines. Its ability to target cancer cells makes it a candidate for further research and development in oncology.
Used in Antimicrobial Applications:
1,6-Phenazinediol is used for its antimicrobial properties, exhibiting antibacterial and antifungal activity. This makes it a potential candidate for use in the development of new antimicrobial agents to combat drug-resistant infections.
Used in Research and Development:
1,6-Phenazinediol is used in research and development for exploring its potential applications in medicine and biology. Its unique properties and effects on cellular structures make it a valuable tool for scientific investigations.
Note: Due to its known toxicity and mutagenicity, caution should be exercised when handling and using 1,6-phenazinediol, and appropriate safety measures should be implemented.

InChI:InChI=1/C12H8N2O2/c15-9-5-1-3-7-11(9)14-8-4-2-6-10(16)12(8)13-7/h1-6,13,16H

Upstream product

• 16582-03-9 1,6-diaminophenazine 
• 13398-79-3 1,6-dimethoxyphenazine 
• 7294-03-3 1,6-diethoxy-phenazine 
• 68-81-5 iodinin 
• 92-82-0 Phenazin 
• 91-23-6 2-Nitroanisole 
• 934-00-9 3-methocycatechol 
• 610-67-3 1-ethoxy-2-nitrobenzene 
• 500298-30-6 2-bromo-6-methoxynitrobenzene 
• 16554-45-3 2-methoxy-6-nitroaniline 
• 36848-41-6 1,6-dinitrophenazine 
• 408509-15-9 (2-methoxy-6-nitro-phenyl)-(3-methoxy-2-nitro-phenyl)-amine 
• 90-04-0 2-methoxy-phenylamine 
• 94-70-2 ortho-phenitidine 

Downstream Products

• 68-81-5 iodinin 
• 1478263-83-0 (E)-6-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-1-hydroxyphenazine 
• 13925-12-7 1-hydroxy-6-methoxy-phenazine-N₅,N₁₀-dioxide 
• 13129-58-3 1-hydroxy-6-methoxyphenazine 
• 69-86-3 1,6-dihydroxyphenazine N₅-monooxide 
• 13925-10-5 1,6-dimethoxy-phenazinol-5-oxide 

Relevant academic research and scientific papers

Baraphenazines A-G, Divergent Fused Phenazine-Based Metabolites from a Himalayan Streptomyces

The structures and bioactivities of three unprecedented fused 5-hydroxyquinoxaline/alpha-keto acid amino acid metabolites (baraphenazines A-C, 1-3), two unique diastaphenazine-type metabolites (baraphenazines D and E, 4 and 5) and two new phenazinolin-type (baraphenazines F and G, 6 and 7) metabolites from the Himalayan isolate Streptomyces sp. PU-10A are reported. This study highlights the first reported bacterial strain capable of producing diastaphenazine-type, phenazinolin-type, and izumiphenazine A-type metabolites and presents a unique opportunity for the future biosynthetic interrogation of late-stage phenazine-based metabolite maturation.

Generation of strong, homochiral bases by electrochemical reduction of phenazine derivatives

Electrochemical reduction of enantiomerically pure amino- and alkoxy-phenazine derivatives forms strongly basic radical anions which give asymmetric induction in the conversion of 3,4-epoxytetrahydrothiophene-1,1- dioxide 7 into the allylic ester 9 with f

Dual phenazine gene clusters enable diversification during biosynthesis

Biosynthetic gene clusters (BGCs) bridging genotype and phenotype continuously evolve through gene mutations and recombinations to generate chemical diversity. Phenazine BGCs are widespread in bacteria, and the biosynthetic mechanisms of the formation of the phenazine structural core have been illuminated in the last decade. However, little is known about the complex phenazine core-modification machinery. Here, we report the diversity-oriented modifications of the phenazine core through two distinct BGCs in the entomopathogenic bacterium Xenorhabdus szentirmaii, which lives in symbiosis with nematodes. A previously unidentified aldehyde intermediate, which can be modified by multiple enzymatic and non-enzymatic reactions, is a common intermediate bridging the pathways encoded by these BGCs. Evaluation of the antibiotic activity of the resulting phenazine derivatives suggests a highly effective strategy to convert Gram-positive specific phenazines into broad-spectrum antibiotics, which might help the bacteria–nematode complex to maintain its special environmental niche.

Functional and Structural Analysis of Phenazine O -Methyltransferase LaPhzM from Lysobacter antibioticus OH13 and One-Pot Enzymatic Synthesis of the Antibiotic Myxin

Myxin is a well-known antibiotic that had been used for decades. It belongs to the phenazine natural products that exhibit various biological activities, which are often dictated by the decorating groups on the heteroaromatic three-ring system. The three rings of myxin carry a number of decorations, including an unusual aromatic N5,N10-dioxide. We previously showed that phenazine 1,6-dicarboxylic acid (PDC) is the direct precursor of myxin, and two redox enzymes (LaPhzS and LaPhzNO1) catalyze the decarboxylative hydroxylation and aromatic N-oxidations of PDC to produce iodinin (1.6-dihydroxy-N5,N10-dioxide phenazine). In this work, we identified the LaPhzM gene from Lysobacter antibioticus OH13 and demonstrated that LaPhzM encodes a SAM-dependent O-methyltransferase converting iodinin to myxin. The results further showed that LaPhzM is responsible for both monomethoxy and dimethoxy formation in all phenazine compounds isolated from strain OH13. LaPhzM exhibits relaxed substrate selectivity, catalyzing O-methylation of phenazines with non-, mono-, or di-N-oxide. In addition, we demonstrated a one-pot biosynthesis of myxin by in vitro reconstitution of the three phenazine-ring decorating enzymes. Finally, we determined the X-ray crystal structure of LaPhzM with a bound cofactor at 1.4 ? resolution. The structure provided molecular insights into the activity and selectivity of the first characterized phenazine O-methyltransferase. These results will facilitate future exploitation of the thousands of phenazines as new antibiotics through metabolic engineering and chemoenzymatic syntheses.

Total synthesis and antileukemic evaluations of the phenazine 5,10-dioxide natural products iodinin, myxin and their derivatives

A new efficient total synthesis of the phenazine 5,10-dioxide natural products iodinin and myxin and new compounds derived from them was achieved in few steps, a key-step being 1,6-dihydroxyphenazine di-N-oxidation. Analogues prepared from iodinin, including myxin and 2-ethoxy-2-oxoethoxy derivatives, had fully retained cytotoxic effect against human cancer cells (MOLM-13 leukemia) at atmospheric and low oxygen level. Moreover, iodinin was for the first time shown to be hypoxia selective. The structure-activity relationship for leukemia cell death induction revealed that the level of N-oxide functionality was essential for cytotoxicity. It also revealed that only one of the two phenolic functions is required for activity, allowing the other one to be modified without loss of potency.

Heterocyclic Aromatic N-Oxidation in the Biosynthesis of Phenazine Antibiotics from Lysobacter antibioticus

Heterocyclic aromatic N-oxides often have potent biological activities, but the mechanism for aromatic N-oxidation is unclear. Six phenazine antibiotics were isolated from Lysobacter antibioticus OH13. A 10 gene cluster was identified for phenazine biosynthesis. Mutation of LaPhzNO1 abolished all N-oxides, while non-oxides markedly increased. LaPhzNO1 is homologous to Baeyer-Villiger flavoproteins but was shown to catazlye phenazine N-oxidation. LaPhzNO1 and LaPhzS together converted phenazine 1,6-dicarboxylic acid to 1,6-dihydroxyphenazine N5,N10-dioxide. LaPhzNO1 also catalyzed N-oxidation of 8-hydroxyquinoline.

Synthesis of phenazine derivatives for use as precursors to electrochemically generated bases

1,6-Disubstituted phenazine derivatives for use as precursors to electrochemically generated bases have been synthesized from readily available starting materials. Reaction of 1,6-dihydroxyphenazine with 1,10-diododecane, 1,1 1-diiodo-3,6,9-trioxaundecane

NEUROLOGICALLY-ACTIVE COMPOUNDS

The present invention relates to neurologically-active compounds, being heterocyclic compounds having two fused 6-membered rings with a nitrogen atom at position 1 and a hydroxy or mercapto group at position 8 with at least one ring being aromatic. Also disclosed are processes for the preparation of these compounds and their use as pharmaceutical or veterinary agents, in particular for the treatment of neurological conditions, more specifically neurodegenerative conditions such as Alzheimer's disease.

Studies on the Coordination Polymer of Niobium(V) with 1,6-Dihydroxyphenazine

Complexation reaction between niobium(V) and 1,6-dihydroxyphenazine has been investigated with a view to isolate the brown complex and to study its stoichiometry on the basis of elemental analysis, ir spectra, magnetic studies and thermogravimetric analysis.Infrared spectra show 1,6-dihydroxyphenazine acting as a tetradentate ligand coordinating through oxygen and nitrogen since two oxine functions are present in the structure of the ligand.A possible polymeric structure of the complex involving ligand and anion bridge has been suggested.