5Z-7-Oxozeaenol (Synonyms: FR148083; L783279; LL-Z 1640-2)

Name: 5Z-7-Oxozeaenol
Brand: MedChemExpress
SKU: HY-12686
Rating: 5.0 (18 reviews)

Cat. No.: HY-12686 Purity: 99.30%: FAQs
Data Sheet SDS COA Handling Instructions

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5Z-7-Oxozeaenol is a natural anti-protozoan compound from fungal origin, acting as a potent irreversible and selective inhibitor of TAK1 and VEGF-R2, with IC₅₀s of 8 nM and 52 nM, respectively.

For research use only. We do not sell to patients.

5Z-7-Oxozeaenol Chemical Structure

CAS No. : 253863-19-3

Size	Price	Stock	Quantity
1 mg	USD 250	In-stock	Estimated Time of Arrival: December 31
5 mg	USD 950	In-stock	Estimated Time of Arrival: December 31
10 mg	USD 1650	In-stock	Estimated Time of Arrival: December 31
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Based on 18 publication(s) in Google Scholar

17 Publications Citing Use of MCE 5Z-7-Oxozeaenol

: 5Z-7-Oxozeaenol purchased from MedChemExpress. Usage Cited in: Neurosci Lett. 2022 Oct 18;136914. [Abstract]; 5Z-7-oxozeaenol (10 nM) significantly inhibits LPS-induced high expression of NF-κB and TAK1 in microglial.

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Biological Activity
Protocol
Purity & Documentation
References
Customer Review

Description

IC₅₀ & Target^[1]^[2]

TAK1

8.1 nM (IC₅₀)

MEK1

411 nM (IC₅₀)

VEGFR-2

52 nM (IC₅₀)

VEGFR-3

110 nM (IC₅₀)

FLT3

170 nM (IC₅₀)

PDGFR-β

340 nM (IC₅₀)

B-RAF VE

6300 nM (IC₅₀)

SRC

6600 nM (IC₅₀)

Cellular Effect

Cell Line	Type	Value	Description	References
ASPC1	IC₅₀	6020 nM Compound: 5Z7	Antiproliferative activity against human AsPC1 cells harboring KRAS G12D mutant after 72 hrs by CellTiter-Glo assay Antiproliferative activity against human AsPC1 cells harboring KRAS G12D mutant after 72 hrs by CellTiter-Glo assay	[PMID: 28038940]
BaF3	IC₅₀	12 nM Compound: 5Z7	Antiproliferative activity against mouse BA/F3 cells harboring KRAS G12D mutant after 72 hrs in presence of IL-3 by CellTiter-Glo assay Antiproliferative activity against mouse BA/F3 cells harboring KRAS G12D mutant after 72 hrs in presence of IL-3 by CellTiter-Glo assay	[PMID: 28038940]
BaF3	IC₅₀	4 nM Compound: 5Z7	Antiproliferative activity against mouse BA/F3 cells harboring KRAS G12D mutant after 72 hrs by CellTiter-Glo assay Antiproliferative activity against mouse BA/F3 cells harboring KRAS G12D mutant after 72 hrs by CellTiter-Glo assay	[PMID: 28038940]
HCT-15	EC₅₀	2 nM Compound: 1	Cytotoxicity against TNFalpha-induced human HCT-15 cells assessed as reduction in cell viability preincubated for 2 hrs followed by TNFalpha stimulation and measured after 72 hrs by celltiter-glo assay Cytotoxicity against TNFalpha-induced human HCT-15 cells assessed as reduction in cell viability preincubated for 2 hrs followed by TNFalpha stimulation and measured after 72 hrs by celltiter-glo assay	[PMID: 33859795]
HeLa	IC₅₀	0.25 μM Compound: 5	Inhibition of NFkappa p65 isolated from nuclear extract of human HeLa cells by ELISA Inhibition of NFkappa p65 isolated from nuclear extract of human HeLa cells by ELISA	[PMID: 21513293]
HT-29	IC₅₀	3.6 μM Compound: 5	Cytotoxicity against human HT-29 cells after 72 hrs by MTS assay Cytotoxicity against human HT-29 cells after 72 hrs by MTS assay	[PMID: 21513293]
MCF7	IC₅₀	3.8 μM Compound: 5	Cytotoxicity against human MCF7 cells after 72 hrs by MTS assay Cytotoxicity against human MCF7 cells after 72 hrs by MTS assay	[PMID: 21513293]
MDA-MB-435	IC₅₀	3.3 μM Compound: 5	Cytotoxicity against human MDA-MB-435 cells after 72 hrs by MTS assay Cytotoxicity against human MDA-MB-435 cells after 72 hrs by MTS assay	[PMID: 21513293]
NCI-H23	IC₅₀	1 μM Compound: 5Z7	Antiproliferative activity against human NCI-H23 cells harboring KRAS G12C mutant after 72 hrs by CellTiter-Glo assay Antiproliferative activity against human NCI-H23 cells harboring KRAS G12C mutant after 72 hrs by CellTiter-Glo assay	[PMID: 28038940]
NCI-H460	IC₅₀	1.2 μM Compound: 5	Cytotoxicity against human H460 cells after 72 hrs by MTS assay Cytotoxicity against human H460 cells after 72 hrs by MTS assay	[PMID: 21513293]
PANC-1	IC₅₀	2500 nM Compound: 5Z7	Antiproliferative activity against human PANC1 cells harboring KRAS G12D mutant after 72 hrs by CellTiter-Glo assay Antiproliferative activity against human PANC1 cells harboring KRAS G12D mutant after 72 hrs by CellTiter-Glo assay	[PMID: 28038940]
SF-268	IC₅₀	5.1 μM Compound: 5	Cytotoxicity against human SF268 cells after 72 hrs by MTS assay Cytotoxicity against human SF268 cells after 72 hrs by MTS assay	[PMID: 21513293]
Sf9	IC₅₀	8.1 nM Compound: 1	Inhibition of TAK1 (unknown origin) expressed in sf9 cells assessed as 32P level incorporation into myelin basic protein incubated for 5 mins at 30 degC by immunoprecipitation method Inhibition of TAK1 (unknown origin) expressed in sf9 cells assessed as 32P level incorporation into myelin basic protein incubated for 5 mins at 30 degC by immunoprecipitation method	[PMID: 26481152]
SK-CO-1	IC₅₀	250 nM Compound: 5Z7	Antiproliferative activity against human SKCO1 cells harboring KRAS G12V mutant after 72 hrs by CellTiter-Glo assay Antiproliferative activity against human SKCO1 cells harboring KRAS G12V mutant after 72 hrs by CellTiter-Glo assay	[PMID: 28038940]
SW-620	IC₅₀	2540 nM Compound: 5Z7	Antiproliferative activity against human SW620 cells harboring KRAS G12V mutant after 72 hrs by CellTiter-Glo assay Antiproliferative activity against human SW620 cells harboring KRAS G12V mutant after 72 hrs by CellTiter-Glo assay	[PMID: 28038940]
THP-1	IC₅₀	11 nM Compound: 1, f152A1	Antiinflammatory activity in human THP1 cells assessed as inhibition of LPS-induced TNFalpha production by PLAP reporter assay Antiinflammatory activity in human THP1 cells assessed as inhibition of LPS-induced TNFalpha production by PLAP reporter assay	[PMID: 19783437]

In Vitro

5Z-7-Oxozeaenol is a potent irreversible and selective inhibitor of transforming growth factor (TGF)-β-activated kinase 1 (TAK1, IC₅₀, 8.1 nM), less active on MEK1 (IC₅₀, 411 nM). 5Z-7-Oxozeaenol prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase^[1]. 5Z-7-Oxozeaenol is also an inhibitor of VEGF-R2, with an IC₅₀ of 52 nM. 5Z-7-Oxozeaenol has inhibitory activity against VEGF-R3, FLT3, PDGFR-β, B-RAF VE and SRC, with IC₅₀s of 110, 170, 340, 6300 and 6600 nM, respectively^[2]. 5Z-7-Oxozeaenol inhibits JNK/p38 paythway, but it is not a direct inhibitor and is signal specific. 5Z-7-Oxozeaenol suppresses the PMA-induced AP-1 activity almost to the basal level in the KT cells, but has no effects on IL-1-induced NF-kB activity in the KK cells^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

362.37

Formula

C₁₉H₂₂O₇

CAS No.

253863-19-3

Appearance

Solid

Color

White to off-white

SMILES

O=C(O[C@@H](C)C/C=C\1)C2=C(O)C=C(OC)C=C2/C=C/C[C@H](O)[C@H](O)C1=O

Structure Classification

Others

Initial Source

Microorganisms

Cochliobolus lunatus

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 30 mg/mL (82.79 mM; Need ultrasonic and warming; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.7596 mL	13.7981 mL	27.5961 mL
5 mM	0.5519 mL	2.7596 mL	5.5192 mL
10 mM	0.2760 mL	1.3798 mL	2.7596 mL

View the 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.

Molarity Calculator
Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

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.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (6.90 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.
Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (6.90 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.
Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 2.5 mg/mL (6.90 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

DMSO +

Tween-80 +

Saline

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.

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).

Calculation results:

Working solution concentration: mg/mL

Method for preparing stock solution: mg drug dissolved in μL DMSO (Stock solution concentration: mg/mL).

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).

Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.

If the continuous dosing period exceeds half a month, please choose this protocol carefully.

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.

Purity & Documentation

Purity: 99.60%

Select Batch:

Data Sheet (282 KB) SDS (479 KB)

COA (256 KB) HNMR (289 KB) LCMS (268 KB)

Handling Instructions (2659 KB)

References

[1]. Ninomiya-Tsuji J, et al. A resorcylic acid lactone, 5Z-7-oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase. J Biol Chem. 2003 May 16;278(20):18485-90. [Content Brief]

[2]. Dakas PY, et al. Modular synthesis of radicicol A and related resorcylic acid lactones, potent kinase inhibitors. Angew Chem Int Ed Engl. 2007;46(36):6899-902. [Content Brief]

[3]. Takehana K, et al. A radicicol-related macrocyclic nonaketide compound, antibiotic LL-Z1640-2, inhibits the JNK/p38 pathways in signal-specific manner. Biochem Biophys Res Commun. 1999 Apr 2;257(1):19-23. [Content Brief]

Kinase Assay
^[1]

For screening TAK1 inhibitors, insect expression vectors for TAK1 and TAB1 are co-infected into Sf9 cells. After 2 days of incubation, cell lysates are immunoprecipitated with anti-TAK1 antibody (M-17). The immunoprecipitates are incubated with various compounds (5Z-7-Oxozeaenol, etc.) and subsequently incubated with 2 μg of myelin basic protein and 10 μCi of [γ-³²P]ATP (3,000 Ci/mmol) in 10 μL of the kinase buffer containing 10 mM HEPES (pH 7.4), 1 mM dithiothreitol, 5 mM MgCl₂ at 30°C for 5 min. Samples are separated by 10% SDS-PAGE, and ³²P incorporated into myelin basic protein is quantified with a bioimage analyzer. The catalytic activity of MEK1 is determined by activation of ERK2 to phosphorylate dure. The catalytic activity of MEKK1 is measured with 2 μg of myelin basic protein as a substrate in the kinase buffer. For subsequent kinase assays, immunoprecipitates are incubated with 5 μCi of [γ-³²P]ATP (3,000 Ci/mmol) and 1 μg of bacterially expressed MKK6 or GST-IκBα-(1-72) in 10 μL of the kinase buffer at 25°C for 2 min. Samples are separated by 10% SDS-PAGE and visualized by autoradiography^[1].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

References

[1]. Ninomiya-Tsuji J, et al. A resorcylic acid lactone, 5Z-7-oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase. J Biol Chem. 2003 May 16;278(20):18485-90. [Content Brief]

[2]. Dakas PY, et al. Modular synthesis of radicicol A and related resorcylic acid lactones, potent kinase inhibitors. Angew Chem Int Ed Engl. 2007;46(36):6899-902. [Content Brief]

[3]. Takehana K, et al. A radicicol-related macrocyclic nonaketide compound, antibiotic LL-Z1640-2, inhibits the JNK/p38 pathways in signal-specific manner. Biochem Biophys Res Commun. 1999 Apr 2;257(1):19-23. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO	1 mM	2.7596 mL	13.7981 mL	27.5961 mL	68.9903 mL
	5 mM	0.5519 mL	2.7596 mL	5.5192 mL	13.7981 mL
	10 mM	0.2760 mL	1.3798 mL	2.7596 mL	6.8990 mL
	15 mM	0.1840 mL	0.9199 mL	1.8397 mL	4.5994 mL
	20 mM	0.1380 mL	0.6899 mL	1.3798 mL	3.4495 mL
	25 mM	0.1104 mL	0.5519 mL	1.1038 mL	2.7596 mL
	30 mM	0.0920 mL	0.4599 mL	0.9199 mL	2.2997 mL
	40 mM	0.0690 mL	0.3450 mL	0.6899 mL	1.7248 mL
	50 mM	0.0552 mL	0.2760 mL	0.5519 mL	1.3798 mL
	60 mM	0.0460 mL	0.2300 mL	0.4599 mL	1.1498 mL
	80 mM	0.0345 mL	0.1725 mL	0.3450 mL	0.8624 mL

5Z-7-Oxozeaenol Related Classifications

Inflammation/Immunology Infection

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

5Z-7-Oxozeaenol253863-19-3FR148083 L783279 LL-Z 1640-2FR 148083FR-148083L783279L 783279L-783279MAP3KVEGFRAntibioticMAP kinase kinase kinase, MEKK, MAPKKKVascular endothelial growth factor receptorInhibitorinhibitorinhibit

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5Z-7-Oxozeaenol (Synonyms: FR148083; L783279; LL-Z 1640-2)

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17 Publications Citing Use of MCE 5Z-7-Oxozeaenol

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Complete Stock Solution Preparation Table

5Z-7-Oxozeaenol Related Classifications

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