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Brevianamide F

Alias: Brevianamide F
Cat No.:V17019 Purity: ≥98%
Brevianamide F (Cyclo(L-Pro-L-Trp)) is a mycotoxin extracted from Colletotrichum gloeosporioides with anti-bacterial effect.
Brevianamide F
Brevianamide F Chemical Structure CAS No.: 38136-70-8
Product category: PI3K
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Brevianamide F (Cyclo(L-Pro-L-Trp)) is a mycotoxin extracted from Colletotrichum gloeosporioides with anti-bacterial effect. Brevianamide F has PI3Kα inhibitory activity with IC50 of 4.8 µM.
Brevianamide F (CAS#: 38136-70-8) is a fungal metabolite belonging to the class of compounds known as diketopiperazines. It is a secondary metabolite produced by various species of Aspergillus and Penicillium. Brevianamide F has been studied for its diverse biological activities, including antimicrobial, antiviral, and cytotoxic properties. Its structure features a unique spiro-oxindole core, which has made it a target for total synthesis and medicinal chemistry studies.
Biological Activity I Assay Protocols (From Reference)
Targets
PI3Kα (IC50 = 4.8 μM)
Brevianamide F's mechanism of action is not fully understood. It has been shown to exhibit antimicrobial activity against various bacterial and fungal strains, as well as antiviral activity against certain viruses. Its cytotoxic effects on cancer cell lines have also been reported, suggesting it may interact with cellular targets involved in cell proliferation and survival.
ln Vitro
Both MSSA and MRSA are moderately active against by brevianamide F[1].
Brevianamide F has demonstrated antimicrobial activity against a range of microorganisms, including Staphylococcus aureus, Escherichia coli, and Candida albicans. It has also shown antiviral activity against herpes simplex virus and influenza virus. In addition, brevianamide F exhibits cytotoxic activity against various cancer cell lines, including HeLa and HL-60 cells.
ln Vivo
In vivo activity data for brevianamide F is limited. As a natural product, its potential therapeutic applications have been explored in preclinical models. Studies have investigated its antimicrobial and anticancer efficacy in animal models. However, more research is needed to fully characterize its in vivo activity and pharmacokinetic properties.
Enzyme Assay
In vitro enzyme assays for brevianamide F are not specific. Its biological activities are typically assessed using cell-based assays for antimicrobial, antiviral, or cytotoxic activity. The compound's mechanism of action may be studied by identifying its molecular targets using techniques such as affinity chromatography or chemical proteomics.
Cell Assay
In vitro cellular assays for brevianamide F involve treating microbial cells or cancer cell lines with the compound and measuring cell viability or growth inhibition. Antimicrobial activity is assessed by measuring the zone of inhibition or the minimum inhibitory concentration (MIC). Cytotoxicity is assessed using metabolic assays such as MTT or by counting viable cells.
Animal Protocol
In vivo animal studies for brevianamide F are limited. Studies may involve administration to animal models of infection or cancer to assess its efficacy. The compound's pharmacokinetic properties and toxicity profile would also be evaluated in these studies.
ADME/Pharmacokinetics
Pharmacokinetic data for brevianamide F is limited. As a natural product, its absorption, distribution, metabolism, and elimination have not been extensively characterized. Further studies are needed to determine its bioavailability and half-life in vivo.
Toxicity/Toxicokinetics
Preclinical toxicity studies of brevianamide F are limited. Its safety profile has not been extensively evaluated. The compound's potential toxicity would need to be assessed in animal models before any clinical development.
References

[1]. Antibacterial Activity of Endophytic Actinomycetes Isolated from the Medicinal Plant Vochysia divergens (Pantanal, Brazil). Front Microbiol. 2017 Sep 6;8:1642.

[2]. Secondary Metabolites and PI3K Inhibitory Activity of Colletotrichum gloeosporioides, a Fungal Endophyte of Uncaria rhynchophylla. Curr Microbiol. 2019 Jul;76(7):904-908.

Additional Infomation
Brevianamide F is a pyrrolopyrazine compound with the structure hexahydropyrrolo[1,2-a]pyrazine-1,4-dione, containing an indole-3-ylmethyl substituent at the 3-position (3S,8aS-diastere, prepared by the cyclocondensation of L-tryptophan and L-proline). It is a metabolite. It belongs to the pyrrolopyrazine class of compounds, specifically the indole class, and is also a dipeptide. Brevianamide F has been reported to be detected in Aspergillus versicolor, Exophiala pisciphila, and other organisms with relevant data.
Brevianamide F is a fungal metabolite belonging to the diketopiperazine class of compounds. It has been studied for its diverse biological activities, including antimicrobial, antiviral, and cytotoxic properties. Its structure features a unique spiro-oxindole core, which has made it a target for total synthesis. Further research is needed to fully characterize its mechanism of action and therapeutic potential.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H17N3O2
Molecular Weight
283.331
Exact Mass
283.132
Elemental Analysis
C, 67.83; H, 6.05; N, 14.83; O, 11.29
CAS #
38136-70-8
Related CAS #
38136-70-8
PubChem CID
181567
Appearance
White to off-white solid powder
Boiling Point
633.2°C
LogP
1.413
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Heavy Atom Count
21
Complexity
453
Defined Atom Stereocenter Count
2
SMILES
O=C1[C@]([H])(C([H])([H])C2=C([H])N([H])C3=C([H])C([H])=C([H])C([H])=C23)N([H])C([C@]2([H])C([H])([H])C([H])([H])C([H])([H])N21)=O
InChi Key
RYFZBPVMVYTEKZ-KBPBESRZSA-N
InChi Code
InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1
Chemical Name
(3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms
Brevianamide F
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: 50~57 mg/mL (176.5~201.2 mM)
Ethanol: ~19 mg/mL (~67.1 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.82 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (8.82 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.82 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.5295 mL 17.6473 mL 35.2945 mL
5 mM 0.7059 mL 3.5295 mL 7.0589 mL
10 mM 0.3529 mL 1.7647 mL 3.5295 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.

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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?
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  • 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:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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