| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| Other Sizes |
|
Purity: ≥98%
Prodigiosin (Prodigiosine) is a naturally occuring and secondary metabolite from Serratia marcescens. It exhibits a wide range of biological activities, including acting as an antimalarial, antifungal, immunosuppressant, and antibiotic agent.
| ln Vitro |
Prodigiosin treatment (25–500 nM; 24 hours) decreased the viability of breast cancer cells, with an IC50 value of 261.2 in MDA-MB-468 cells and 62.52 nM in MDA-MB-231 cells at 48 hours. nM[1]. Prodigiosin treatment (25-500 nM; 24 hours) markedly decreased the levels of total β-catenin, active β-catenin, and phosphorylated LRP6 and DVL2. In HEK293T cells, prodigiosin strongly suppresses GSK3β Ser9 phosphorylation, indicating increased GSK3β activity [1]. Breast cancer cells can undergo apoptosis and be inhibited from proliferating when exposed to prodigiosine [1]. In transfected HEK293T cells, prodigiosin treatment (25–500 nM; 24 hours) dose-dependently inhibits Wnt signaling triggered by Wnt1, Wnt3, Wnt1/LRP6, Wnt3/LRP6, and Disheveled 2 (DVL2). The Wnt3A-CM-induced transcription was dose-dependently suppressed by prodigiosin administration. When Wnt transfection or Wnt3A therapy is applied, the SuperTopFlash reporter gene's transcription is inhibited by prodigiosin [1]. Applying this substance to cultures of Batrachochytrium dendrobatidis and B. Prodigiosin and salamandrivorans both significantly restrict growth, having MIC values of 10 μM and 50 μM, respectively [2].
|
|---|---|
| ln Vivo |
Tumor growth was markedly reduced by prodigiosin (5 mg/kg; intraperitoneal injection; twice weekly; for 3 weeks). Ki-67, a marker of proliferation, can be expressed less frequently in tumor cells when treated with prodigiosin [1].
|
| Cell Assay |
Cell proliferation assay[1]
Cell Types: MDA-MB-231 and MDA-MB-468 Cell Tested Concentrations: 10 nM, 25 nM, 50 nM, 100 nM, 250 nM, 500 nM, 1000 nM, 2500 nM, 5000 nM Incubation Duration: 24 hrs (hours), 48 hrs (hours). Experimental Results: Reduce the viability of breast cancer cells. The IC50 value of MDA-MB-231 cells at 48 hrs (hours) was 62.52 nM, and the IC50 value of MDA-MB-468 cells was 261.2 nM. Western Blot Analysis[1] Cell Types: HEK293T Cell Tested Concentrations: 50 nM, 100 nM, 250 nM, 500 nM Incubation Duration: 24 hrs (hours) Experimental Results: Dramatically diminished levels of phosphorylated LRP6 and DVL2, active β-catenin and total β- Catenin. |
| Animal Protocol |
Animal/Disease Models: Female BALB/c nude mice were injected with MDA-MB-231 cells [1].
Doses: 5 mg/kg. Route of Administration: intraperitoneal (ip) injection; twice a week; for 3 consecutive weeks. Experimental Results: Dramatically inhibited mouse tumor growth. |
| References |
|
| Additional Infomation |
Prodigiosin is a member of the class of tripyrroles that is a red-coloured pigment with antibiotic properties produced by Serratia marcescens. It has a role as an antimicrobial agent, a biological pigment, a bacterial metabolite, an apoptosis inducer and an antineoplastic agent. It is a tripyrrole, an aromatic ether and a ring assembly.
Prodigiosine has been reported in Serratia marcescens and Vibrio gazogenes with data available. 4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)- 2,2'-bi-1H-pyrrole. A toxic, bright red tripyrrole pigment from Serratia marcescens and others. It has antibacterial, anticoccidial, antimalarial, and antifungal activities, but is used mainly as a biochemical tool. See also: Prodigiosin (annotation moved to). |
| Molecular Formula |
C20H25N3O
|
|---|---|
| Molecular Weight |
323.44
|
| Exact Mass |
323.2
|
| CAS # |
82-89-3
|
| Related CAS # |
Prodigiosin hydrochloride;56144-17-3
|
| PubChem CID |
135455579
|
| Appearance |
Brown to red solid powder
|
| Density |
1.12g/cm3
|
| Boiling Point |
542.4ºC at 760 mmHg
|
| Flash Point |
281.8ºC
|
| Index of Refraction |
1.591
|
| LogP |
4.776
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
24
|
| Complexity |
523
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CCCCCC1=C(NC(=C1)/C=C\2/C(=CC(=N2)C3=CC=CN3)OC)C
|
| InChi Key |
SHUNBVWMKSXXOM-UNOMPAQXSA-N
|
| InChi Code |
InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21-22H,4-6,8H2,1-3H3/b19-12-
|
| Chemical Name |
(2Z,5Z)-4-methoxy-5-((5-methyl-4-pentyl-1H-pyrrol-2-yl)methylene)-1,5-dihydro-2,2'-bipyrrolylidene
|
| Synonyms |
Prodigiosine BRN 4526727 NSC 47147
|
| 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 (In Vitro) |
DMSO : ~25 mg/mL (~77.30 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
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 | 3.0918 mL | 15.4588 mL | 30.9176 mL | |
| 5 mM | 0.6184 mL | 3.0918 mL | 6.1835 mL | |
| 10 mM | 0.3092 mL | 1.5459 mL | 3.0918 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT06502249 | NOT YET RECRUITING | Lung Cancer NSCLC |
Ain Shams University | 2026-06 |
|
|
|
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
COA
