Petrobactin
Petrobactin is a bis-catechol α-hydroxy acid siderophore, Fe (III) chelator, and oxidative stress protector. Petrobactin is produced by marine bacteria and Bacillus anthracis Sterne strain under iron-starvation conditions. Petrobactin promotes the biodegradation of petroleum hydrocarbons by microorganisms, as well as the proliferation, virulence exertion, vegetative growth, sporulation efficiency, and spore binding of Bacillus anthracis; it also mediates community iron acquisition in the global ocean. Petrobactin can be used in anthrax-related research.
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- No. CAS: 545434-89-7
- Fòrmula: C34H50N6O11
- Peso molecular:718.79
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Almacenamiento:Pure form -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Actividad biológica
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Chemical Information
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Solvente y solubilidad
- Pureza y Documentación
- Referencias
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Help & FAQs
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Actividad biológica
Descripciòn
IC50 & Target
[2]|
Microbial Metabolite |
In Vitro
Petrobactin (25 μM; 12 h) restores efficient 12-h sporulation of Bacillus anthracis Sterne asb mutant strain in ModG medium to wild-type levels (≥107 CFU/mL spores), while the asb mutant shows delayed but full sporulation by 36 h without supplementation[3].
Petrobactin (25 μM; 24 h) restores 24-h growth and spore counts of Bacillus anthracis Sterne asb mutant strain in bovine blood to wild-type levels (≈108 CFU/mL total, ≈107 CFU/mL spores), though it only partially improves 72-h sporulation percentage[3].
Petrobactin (25 μM; 8 h) restores oxidative stress survival of 8-h-grown Bacillus anthracis Sterne asb mutant strain in ModG medium to wild-type levels (≈45-50% survival following 10 mM H2O2 exposure)[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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No. CAS 545434-89-7
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Appearance Liquid (Density: 1.322±0.06 g/cm3)
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Peso molecular 718.79
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Fòrmula C34H50N6O11
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Color Colorless to light yellow
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SMILES
O=C(C(CC(NCCCCNCCCNC(C1=CC=C(C(O)=C1)O)=O)=O)(CC(NCCCCNCCCNC(C2=CC=C(C(O)=C2)O)=O)=O)O)O
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Structure Classification
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Initial Source
Marinobacter hydrocarbonoclasticus
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Pure form -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvente y solubilidad
In Vitro:
DMSO : 100 mg/mL (139.12 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (3.48 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (3.48 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Pureza y Documentación
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Ficha de datos (274 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Barbeau K, et al. Petrobactin, a photoreactive siderophore produced by the oil-degrading marine bacterium Marinobacter hydrocarbonoclasticus. Journal of the American Chemical Society. 2002 Jan 23;124(3):378-9. [Content Brief]
[2]. Koppisch AT, et al. Petrobactin is the primary siderophore synthesized by Bacillus anthracis str. Sterne under conditions of iron starvation. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine. 2005 Dec;18(6):577-85. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 1.3912 mL | 6.9561 mL | 13.9123 mL | 34.7807 mL |
| 5 mM | 0.2782 mL | 1.3912 mL | 2.7825 mL | 6.9561 mL | |
| 10 mM | 0.1391 mL | 0.6956 mL | 1.3912 mL | 3.4781 mL | |
| 15 mM | 0.0927 mL | 0.4637 mL | 0.9275 mL | 2.3187 mL | |
| 20 mM | 0.0696 mL | 0.3478 mL | 0.6956 mL | 1.7390 mL | |
| 25 mM | 0.0556 mL | 0.2782 mL | 0.5565 mL | 1.3912 mL | |
| 30 mM | 0.0464 mL | 0.2319 mL | 0.4637 mL | 1.1594 mL | |
| 40 mM | 0.0348 mL | 0.1739 mL | 0.3478 mL | 0.8695 mL | |
| 50 mM | 0.0278 mL | 0.1391 mL | 0.2782 mL | 0.6956 mL | |
| 60 mM | 0.0232 mL | 0.1159 mL | 0.2319 mL | 0.5797 mL | |
| 80 mM | 0.0174 mL | 0.0870 mL | 0.1739 mL | 0.4348 mL | |
| 100 mM | 0.0139 mL | 0.0696 mL | 0.1391 mL | 0.3478 mL |
Petrobactin Related Classifications
HY-N18050 Related Classifications
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Keywords
- Petrobactin
- 545434-89-7
- Endogenous Metabolite
- Bacterial
- Biochemical Assay Reagents
- Fe(III)
- oxidative stress
- anthrax
- iron starvation
- sporulation
- Bacillus anthracis str. Sterne
- Marinobacter hydrocarbonoclasticus SP.17
- Alteromonas macleodii ATCC 27126
- petroleum hydrocarbon biodegradation
- siderophore
- Inhibitor
- inhibitor
- inhibit