Frenolicin B
Frenolicin B is a covalent enzyme inhibitor and an orally active antiparasitic agent, with an IC50 of 0.2 μM against human Prx1. Frenolicin B selectively inhibits Glutaredoxin 3 via covalent modification of the active-site cysteines Cys159/Cys261. Frenolicin B selectively inhibits Peroxiredoxin 1 via covalent modification of the active-site cysteines Cys83/Cys173. Frenolicin B can be used in research related to colon cancer, breast cancer, lung cancer and malaria.
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- CAS No.: 68930-68-7
- 화학식: C18H16O6
- 분자량:328.32
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보관:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
- 순도&문서
- References
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Biological Activity
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| A549 | IC50 |
0.28 μM
Compound: 7
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Cytotoxicity against human A549 cells after 2 days by MTT assay
Cytotoxicity against human A549 cells after 2 days by MTT assay
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[PMID: 23944931] |
| MDA-MB-468 | IC50 |
0.06 μM
Compound: 3, frenolicin
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Cytotoxicity against human MDA468 cells expressing AKT
Cytotoxicity against human MDA468 cells expressing AKT
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[PMID: 19309081] |
Frenolicin B (0.032-30 μM; 15 min room temperature incubation) is a potent, selective inhibitor of purified recombinant human Prx1, with an apparent IC50 of 0.2 μM, inhibition kinetics parameters kᵢ = 0.65 μM and kᵢₙₐcₜ = 0.02 min-1, and ~20-fold higher potency against Prx1 than Prx2[1].
Frenolicin B (1-10 μM; 1 h pre-incubation) directly engages Prx1 and Grx3 in HCT116 colon cancer cell lysates and with purified recombinant proteins, as demonstrated by competitive binding with an active biotinylated probe[1].
Frenolicin B (200 μM; 2 h 37 °C incubation) covalently modifies the active site cysteines Cys83/Cys173 of purified recombinant human Prx1 and Cys159/Cys261 of purified recombinant human Grx3, which are essential for ligand binding[1].
Frenolicin B (2 μM; 12 h post-transfection incubation) inhibits cap-dependent translation in a 4E-BP1-dependent manner in HCT116 human colon cancer cells[1].
Frenolicin B (72 h incubation) exhibits preferential cytotoxicity against human cancer cell lines (colon, breast, lung) with IC50 values ranging from 50 nM to 130 nM after 72 h incubation, compared to non-malignant cells with higher IC50 values[1].
Frenolicin B (2 μM; 3 h incubation) increases extracellular H2O2 levels and at 2 μM for 1 h increases intracellular ROS levels in HCT116 human colon cancer cells, with ROS induction reversible by NAC pre-treatment[1].
Frenolicin B (0.2-2 μM; 12 h incubation) dose-dependently inhibits mTORC1-mediated 4E-BP1 phosphorylation at T37/46, S65, and T70, and induces apoptosis (cleaved PARP) in HCT116 human colon cancer cells, with these effects reversed by NAC pre-treatment[1].
Frenolicin B (0.002-80 μM; 72 h) inhibits in vitro growth of Plasmodium falciparum HB3, Dd2, and 7G8 strains with IC50 values of 600 ± 100 nM, 800 ± 200 nM, and 800 ± 150 nM, respectively, and incubation with selected human cytochrome P450 enzymes either maintains or improves its antiparasitic potency[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:HCT116 human colon cancer cell; purified recombinant human Prx1/Grx3 proteins
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Concentration:1-10 μM (Frenolicin B, HCT116 lysate pre-incubation); 1-2 μM (probe 1)
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Incubation Time:1 h (Frenolicin B pre-incubation with HCT116 lysates); 1 h (probe 1 incubation)
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Result:Competed with active probe 1 for binding to Prx1 and Grx3 in HCT116 lysates.
Confirmed direct binding to pure recombinant Prx1 and Grx3 via probe 1 labeling.
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Cell Line:HCT116 human colon cancer cells
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Concentration:0.2-2 μM; 400 μM (NAC pre-treatment)
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Incubation Time:12 h (phosphorylation analysis); 6 h (NAC reversal analysis); 1 h (NAC pre-treatment)
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Result:Dose-dependently inhibited phosphorylation of 4E-BP1 at T37/46, S65, and T70.
Induced cleaved PARP (apoptotic marker).
Had inhibition of 4E-BP1 phosphorylation and induction of cleaved PARP reversed by pre-treatment with NAC.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:CD1 mice (8-week-old)[2]
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Dosage:10 mg/kg; 20 mg/kg; 40 mg/kg; 63 mg/kg
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Administration:p.o.; daily; 4 days
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Result:Reduced mean parasitemia to 39 % and cured 0/5 mice at 10 mg/kg.
Reduced mean parasitemia to 37 % and cured 0/5 mice at 20 mg/kg.
Reduced mean parasitemia to 33 % and cured 1/5 mice at 40 mg/kg.
Reduced mean parasitemia to 15% (a >50% reduction relative to vehicle control) and cured 2/5 mice at 63 mg/kg.
Chemical Information
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CAS No. 68930-68-7
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분자량 328.32
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화학식 C18H16O6
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SMILES
O=C1C2=C(C(C3=C(O)C=CC=C31)=O)[C@H](O[C@@]4([H])[C@]2([H])OC(C4)=O)CCC
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Structure Classification
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Initial Source
S. roseofulvus.
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선적
Room temperature in continental US; may vary elsewhere.
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보관
Please store the product under the recommended conditions in the Certificate of Analysis.
순도&문서
References
[1]. Ye Q, et al. Frenolicin B Targets Peroxiredoxin 1 and Glutaredoxin 3 to Trigger ROS/4E-BP1-Mediated Antitumor Effects. Cell Chem Biol. 2019 Mar 21;26(3):366-377.e12. [Content Brief]
[2]. Fitzgerald JT, et al. In vitro and in vivo activity of frenolicin B against Plasmodium falciparum and P berghei. J Antibiot (Tokyo). 2011 Dec;64(12):799-801. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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