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Phenazine-1-carboxylic acid

Cat No.:V53261 Purity: ≥98%
Phenazine-1-carboxylic acid has strong antifungal activity against plant pathogenic fungi.
Phenazine-1-carboxylic acid
Phenazine-1-carboxylic acid Chemical Structure CAS No.: 2538-68-3
Product category: Fungal
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
1g
Other Sizes
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Product Description
Phenazine-1-carboxylic acid has strong antifungal activity against plant pathogenic fungi.
Phenazine-1-carboxylic acid is a naturally occurring antifungal agent and a secondary metabolite produced by bacteria such as Pseudomonas spp. and Streptomycetes. It exhibits strong antifungal activity against phytopathogenic fungi, inhibiting fungal growth by approximately 90-100%. Additionally, it demonstrates anticancer activity by inducing apoptosis in cancer cells through the regulation of reactive oxygen species (ROS) generation. The compound also shows antibacterial, bacterial metabolic, and immunomodulatory activities. It upregulates IL-8 and ICAM-1 expression while inhibiting RANTES and MCP-1 release, holding significant research value in anti-infection, anticancer, and immune response modulation.
Biological Activity I Assay Protocols (From Reference)
Targets
Phenazine-1-carboxylic acid primarily targets microbial cells, specifically fungal and bacterial pathogens. Its primary mechanism of action involves the regulation of ROS generation, leading to oxidative stress and apoptosis in cancer cells. The compound also modulates immune responses by affecting cytokine and chemokine expression. Its antifungal activity is directed against a broad spectrum of phytopathogenic fungi.
ln Vitro
Phenazine-1-carboxylic acid demonstrates potent in vitro antifungal activity against all tested phytopathogenic fungi, with inhibition rates of about 90-100%. It exhibits anticancer activity by inducing apoptosis in cancer cells through ROS generation. The compound shows antibacterial activity and modulates immune responses by upregulating IL-8 and ICAM-1 while inhibiting RANTES and MCP-1 release. Its broad-spectrum antimicrobial and anticancer activities make it a valuable tool for research.
ln Vivo
In vivo activity of phenazine-1-carboxylic acid has been demonstrated in a zebrafish model, where it showed antagonistic activity against Vibrio anguillarum. Its strong antifungal activity against plant pathogenic fungi suggests potential for agricultural applications in controlling grapevine trunk diseases and other phytopathogenic infections. The compound's anticancer and immunomodulatory activities warrant further in vivo investigation in mammalian models.
Enzyme Assay
In vitro enzyme/receptor binding assays for phenazine-1-carboxylic acid are not extensively documented, as the compound's primary mechanism involves ROS generation rather than specific enzyme inhibition. However, its ability to modulate cytokine expression can be assessed using ELISA or multiplex assays in cell culture supernatants. Antifungal activity is evaluated using standard agar diffusion or broth microdilution methods against phytopathogenic fungi.
Cell Assay
In vitro cellular assays for phenazine-1-carboxylic acid involve treating cancer cell lines with varying concentrations of the compound and measuring cell viability using MTT or other assays. Apoptosis is evaluated by Annexin V staining, caspase activity assays, or ROS detection using fluorescent probes. Immunomodulatory effects are assessed by measuring cytokine and chemokine levels in treated immune cells or epithelial cells using ELISA.
Animal Protocol
In vivo animal experiments for phenazine-1-carboxylic acid have been conducted in a zebrafish model to evaluate its antagonistic activity against Vibrio anguillarum. For agricultural applications, the compound can be tested in plant models infected with phytopathogenic fungi to evaluate disease control efficacy. Further studies in mammalian models of cancer and infection are needed to fully characterize its therapeutic potential.
ADME/Pharmacokinetics
Pharmacokinetic data for phenazine-1-carboxylic acid are limited. The compound has a molecular weight of 224.22 and a molecular formula of C13H8N2O2. It is soluble in DMSO and should be stored under recommended conditions. Its absorption, distribution, metabolism, and excretion properties have not been fully characterized. Further pharmacokinetic studies are needed to determine its bioavailability and tissue distribution for potential therapeutic applications.
Toxicity/Toxicokinetics
Toxicological data for phenazine-1-carboxylic acid are limited. As a naturally occurring compound with antimicrobial and anticancer activities, it is generally considered to have moderate toxicity, but comprehensive toxicological studies have not been reported. The compound is intended for research use only and is not for human therapeutic application. Standard laboratory safety precautions should be followed when handling this compound.
References

[1]. Phenazine-1-Carboxylic Acid (PCA), Produced for the First Time as an Antifungal Metabolite by Truncatella angustata, a Causal Agent of Grapevine Trunk Diseases (GTDs) in Iran. J Agric Food Chem. 2021 Oct 20;69(41):12143-12147.

Additional Infomation
Phenazine-1-carboxylic acid is an aromatic carboxylic acid derived from phenazine by replacing the carboxyl group at the C-1 position. It possesses antibacterial, bacterial metabolic, and antifungal activities. It belongs to the phenazine class of compounds and is a monocarboxylic and aromatic carboxylic acid. It is the conjugate acid of phenazine-1-carboxylate. Phenazine-1-carboxylic acid has been reported to be detected in Pseudomonas fluorescens, Streptomyces diastaticus, and other organisms with relevant data.
Phenazine-1-carboxylic acid (CAS#: 2538-68-3) has the molecular formula C13H8N2O2 and a molecular weight of 224.22. It is a naturally occurring antifungal agent produced by Pseudomonas spp. and Streptomycetes. The compound exhibits strong antifungal, antibacterial, anticancer, and immunomodulatory activities. It is used in research on anti-infection, anticancer, and immune response modulation. The compound is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C13H8N2O2
Molecular Weight
224.21
Exact Mass
224.058
CAS #
2538-68-3
Related CAS #
1144-02-1 (hydrochloride salt)
PubChem CID
95069
Appearance
Light yellow to green yellow solid powder
Density
1.4±0.1 g/cm3
Boiling Point
494.6±10.0 °C at 760 mmHg
Melting Point
241-241ºC
Flash Point
252.9±19.0 °C
Vapour Pressure
0.0±1.3 mmHg at 25°C
Index of Refraction
1.769
LogP
1.75
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
17
Complexity
308
Defined Atom Stereocenter Count
0
InChi Key
JGCSKOVQDXEQHI-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H8N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7H,(H,16,17)
Chemical Name
phenazine-1-carboxylic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : 5 mg/mL (22.30 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.4601 mL 22.3005 mL 44.6010 mL
5 mM 0.8920 mL 4.4601 mL 8.9202 mL
10 mM 0.4460 mL 2.2301 mL 4.4601 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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