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| 1mg |
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| ln Vitro |
Pytoxin, an antifungal chemical, was discovered inside a 24 kb genomic region of Pseudomonas fluorescens Pf-5. It is composed of pyrrole dichloride coupled to a resorcin moiety [1]. MCF-7 is significantly cytotoxically affected by septin (IC50=1.84 μM). Significant selective cytotoxicity was also demonstrated by pyroluteorin against BT474, HCC1954, MAD-MB-468, MDA-MB-231, and MCF-10A cells, with IC50 values of 9.75±0.16, 0.94±0.01, 3.89±0.08, and 0.97±, respectively, 0.01 and 57.01±0.76 μM [2]. For 24 hours, 0.1–10 μM of Helicobacter pylori causes alterations in the expression of proteins linked to apoptosis. The caspase cascade and Bcl-2 family proteins are linked to the septoxin-induced apoptosis in MDA-MB-231 [2]. Human triple-negative breast cancer cells MDA-MB-231 undergo cell cycle arrest and death when exposed to helicobacterin (0.1–10 μM) for a full day [2].
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| Cell Assay |
Cell proliferation assay [2]
Cell Types: human triple-negative breast cancer cells MDA-MB-231 Tested Concentrations: 0, 0.032, 0.16, 0.8, 4, 20, 100 μM Incubation Duration: 24, 48, 72 hrs (hours) Experimental Results: Inhibited cells Proliferated in a dose- and time-dependent manner. Western Blot Analysis[2] Cell Types: MDA-MB-231 Cell Tested Concentrations: 0.1, 0.3, 1, 3, 10 μM Incubation Duration: 24 hrs (hours) Experimental Results: Anti-apoptotic proteins Bcl-2, Bcl-XL and Bcl-2 The levels of PARP were Dramatically diminished, while the pro-apoptotic proteins BAX and caspase 3 were increased in a dose-dependent manner. |
| References |
[1]. B Nowak-Thompson, et al. Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5. J Bacteriol. 1999 Apr;181(7):2166-74.
[2]. Ting Ding, et al. Pyoluteorin induces cell cycle arrest and apoptosis in human triple-negative breast cancer cells MDA-MB-231. J Pharm Pharmacol. 2020 Jul;72(7):969-978. |
| Additional Infomation |
Pyoluteorin is a member of the class of resorcinols that is resorcinol in which the hydrogen at position 2 is replaced by a 4,5-dichloro-1H-pyrrole-2-carbonyl group. It is a natural product found in Pseudomonas fluorescens which exhibits antibacterial properties and is a strong inducer of caspase-3-dependent apoptosis. It has a role as a bacterial metabolite, an apoptosis inducer, an antifungal agent, a marine metabolite and an antibacterial agent. It is a member of resorcinols, a member of pyrroles, an organochlorine compound, a diol, a beta-hydroxy ketone, a polyketide, an aromatic ketone and an organochlorine pesticide.
Pyoluteorin has been reported in Pseudomonas fluorescens with data available. |
| Molecular Formula |
C11H7CL2NO3
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|---|---|
| Molecular Weight |
272.08
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| Exact Mass |
270.98
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| CAS # |
25683-07-2
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| PubChem CID |
33137
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| Appearance |
Off-white to yellow solid powder
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| Density |
1.632g/cm3
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| Boiling Point |
436.9ºC at 760mmHg
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| Flash Point |
218ºC
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| Vapour Pressure |
3.06E-08mmHg at 25°C
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| Index of Refraction |
1.694
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| LogP |
2.963
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
17
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| Complexity |
292
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1=C(Cl)NC(C(C2C(O)=CC=CC=2O)=O)=C1
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| InChi Key |
JPGWTZORMBTNMF-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H7Cl2NO3/c12-5-4-6(14-11(5)13)10(17)9-7(15)2-1-3-8(9)16/h1-4,14-16H
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| Chemical Name |
Ketone, 4,5-dichloropyrrol-2-yl 2,6-dihydroxyphenyl
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| Synonyms |
Pyoluteorin NSC143092 NSC143092NSC 143092
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6754 mL | 18.3769 mL | 36.7539 mL | |
| 5 mM | 0.7351 mL | 3.6754 mL | 7.3508 mL | |
| 10 mM | 0.3675 mL | 1.8377 mL | 3.6754 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.
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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