5Z-7-Oxozeaenol
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 562434

CAS#: 253863-19-3

Description: 5Z-7-Oxozeaenol is a covalent inhibitor that acts against the several protein kinases (e.g. ERK2 and TAK1) that possess a free cysteine at the gatekeeper-2 position.

Chemical Structure

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5Z-7-Oxozeaenol
CAS# 253863-19-3
Instruction

Theoretical Analysis

MedKoo Cat#: 562434
Name: 5Z-7-Oxozeaenol
CAS#: 253863-19-3
Chemical Formula: C19H22O7
Exact Mass: 362.14
Molecular Weight: 362.370
Elemental Analysis: C, 62.98; H, 6.12; O, 30.91

Price and Availability

Size Price Availability Quantity
1mg USD 275 2 Weeks
5mg USD 665 2 Weeks
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Synonym: 5Z-7-Oxozeaenol; 5Z 7 Oxozeaenol; 5Z7Oxozeaenol; 5-Z-7-Oxozeaenol; 5 Z 7 Oxozeaenol; 5Z7O; L-783279; 5 Z 7 O; L 783279; 5-Z-7-O; L783279; (5Z)-7-Oxozeaenol;

IUPAC/Chemical Name: (3S,5Z,8S,9S,11E)-3,4,9,10-Tetrahydro-8,9,16-trihydroxy-14-methoxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione

InChi Key: NEQZWEXWOFPKOT-BYRRXHGESA-N

InChi Code: InChI=1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3-/t11-,15-,18+/m0/s1

SMILES Code: 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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 362.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Fan Z, Xu X, Qi X, Wu Y. Role of TGF-β activated kinase-1 inhibitor on the interaction between macrophages and mesangial cells on the condition of high glucose. Immunol Invest. 2018 Jan 26:1-12. doi: 10.1080/08820139.2018.1428199. [Epub ahead of print] PubMed PMID: 29373048.

2: Lu L, Zhang X, Tong H, Zhang W, Xu P, Qu S. Central Administration of 5Z-7-Oxozeaenol Protects Experimental Autoimmune Encephalomyelitis Mice by Inhibiting Microglia Activation. Front Pharmacol. 2017 Nov 3;8:789. doi: 10.3389/fphar.2017.00789. eCollection 2017. PubMed PMID: 29163172; PubMed Central PMCID: PMC5675872.

3: Kobayashi A, Kobayashi S, Miyai K, Osawa Y, Horiuchi T, Kato S, Maekawa T, Yamamura T, Watanabe J, Sato K, Tsuda H, Kimura F. TAK1 inhibition ameliorates survival from graft-versus-host disease in an allogeneic murine marrow transplantation model. Int J Hematol. 2018 Feb;107(2):222-229. doi: 10.1007/s12185-017-2345-7. Epub 2017 Oct 12. PubMed PMID: 29027124.

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5: Uchida K, Takano S, Matsumoto T, Nagura N, Inoue G, Itakura M, Miyagi M, Aikawa J, Iwase D, Minatani A, Fujimaki H, Takaso M. Transforming growth factor activating kinase 1 regulates extracellular matrix degrading enzymes and pain-related molecule expression following tumor necrosis factor-α stimulation of synovial cells: an in vitro study. BMC Musculoskelet Disord. 2017 Jul 1;18(1):283. doi: 10.1186/s12891-017-1648-4. PubMed PMID: 28668088; PubMed Central PMCID: PMC5493881.

6: van Caam A, Madej W, Garcia de Vinuesa A, Goumans MJ, Ten Dijke P, Blaney Davidson E, van der Kraan P. TGFβ1-induced SMAD2/3 and SMAD1/5 phosphorylation are both ALK5-kinase-dependent in primary chondrocytes and mediated by TAK1 kinase activity. Arthritis Res Ther. 2017 May 31;19(1):112. doi: 10.1186/s13075-017-1302-4. PubMed PMID: 28569204; PubMed Central PMCID: PMC5452635.

7: Nakajima M, Kawaguchi M, Ota K, Fujita J, Matsukura S, Huang SK, Morishima Y, Ishii Y, Satoh H, Sakamoto T, Hizawa N. IL-17F induces IL-6 via TAK1-NFκB pathway in airway smooth muscle cells. Immun Inflamm Dis. 2017 Jun;5(2):124-131. doi: 10.1002/iid3.149. Epub 2017 Mar 3. PubMed PMID: 28474507; PubMed Central PMCID: PMC5418132.

8: Guan S, Lu J, Zhao Y, Woodfield SE, Zhang H, Xu X, Yu Y, Zhao J, Bieerkehazhi S, Liang H, Yang J, Zhang F, Sun S. TAK1 inhibitor 5Z-7-oxozeaenol sensitizes cervical cancer to doxorubicin-induced apoptosis. Oncotarget. 2017 May 16;8(20):33666-33675. doi: 10.18632/oncotarget.16895. PubMed PMID: 28430599; PubMed Central PMCID: PMC5464900.

9: Xu X, Sun J, Song R, Doscas ME, Williamson AJ, Zhou J, Sun J, Jiao X, Liu X, Li Y. Inhibition of p70 S6 kinase (S6K1) activity by A77 1726, the active metabolite of leflunomide, induces autophagy through TAK1-mediated AMPK and JNK activation. Oncotarget. 2017 May 2;8(18):30438-30454. doi: 10.18632/oncotarget.16737. PubMed PMID: 28389629; PubMed Central PMCID: PMC5444754.

10: Liu Z, Kong F, Vallance JE, Harmel-Laws E, Amarachintha S, Steinbrecher KA, Rosen MJ, Bhattacharyya S. Activation of TGF-β activated kinase 1 promotes colon mucosal pathogenesis in inflammatory bowel disease. Physiol Rep. 2017 Apr;5(7). pii: e13181. doi: 10.14814/phy2.13181. PubMed PMID: 28373409; PubMed Central PMCID: PMC5392505.

11: Zhang L, Fu Z, Li X, Tang H, Luo J, Zhang D, Zhuang Y, Han Z, Yin M. Transforming growth factor β-activated kinase 1 inhibitor suppresses the proliferation in triple-negative breast cancer through TGF-β/TGFR pathway. Chem Biol Drug Des. 2017 Sep;90(3):450-455. doi: 10.1111/cbdd.12965. Epub 2017 Apr 11. PubMed PMID: 28224764.

12: Li P, Zhao QL, Jawaid P, Rehman MU, Ahmed K, Sakurai H, Kondo T. Enhancement of hyperthermia-induced apoptosis by 5Z-7-oxozeaenol, a TAK1 inhibitor, in Molt-4 cells. Int J Hyperthermia. 2017 Jan 22:1-11. doi: 10.1080/02656736.2017.1278629. [Epub ahead of print] PubMed PMID: 28111999.

13: Ren K, Mo ZC, Liu X, Tang ZL, Jiang Y, Peng XS, Zhang QH, Shi JF, Yi GH. TGF-β Down-regulates Apolipoprotein M Expression through the TAK-1-JNK-c-Jun Pathway in HepG2 Cells. Lipids. 2017 Feb;52(2):109-117. doi: 10.1007/s11745-016-4227-9. Epub 2016 Dec 30. PubMed PMID: 28039587.

14: Olianas MC, Dedoni S, Onali P. The GABA(B) positive allosteric modulators CGP7930 and GS39783 stimulate ERK1/2 signalling in cells lacking functional GABA(B) receptors. Eur J Pharmacol. 2017 Jan 5;794:135-146. doi: 10.1016/j.ejphar.2016.11.030. Epub 2016 Nov 19. PubMed PMID: 27876620.

15: Jones DS, Jenney AP, Swantek JL, Burke JM, Lauffenburger DA, Sorger PK. Profiling drugs for rheumatoid arthritis that inhibit synovial fibroblast activation. Nat Chem Biol. 2017 Jan;13(1):38-45. doi: 10.1038/nchembio.2211. Epub 2016 Oct 31. PubMed PMID: 27820799; PubMed Central PMCID: PMC5372219.

16: Bo L, Cui H, Fang Z, Qun T, Xia C. Inactivation of transforming growth factor-β-activated kinase 1 promotes taxol efficacy in ovarian cancer cells. Biomed Pharmacother. 2016 Dec;84:917-924. doi: 10.1016/j.biopha.2016.09.105. Epub 2016 Oct 17. PubMed PMID: 27764753.

17: Chang MC, Chang HH, Lin PS, Huang YA, Chan CP, Tsai YL, Lee SY, Jeng PY, Kuo HY, Yeung SY, Jeng JH. Effects of TGF-β1 on plasminogen activation in human dental pulp cells: Role of ALK5/Smad2, TAK1 and MEK/ERK signalling. J Tissue Eng Regen Med. 2016 Oct 9. doi: 10.1002/term.2339. [Epub ahead of print] PubMed PMID: 27723266.

18: Ying X, Zhao Y, Yao T, Yuan A, Xu L, Gao L, Ding S, Ding H, Pu J, He B. Novel Protective Role for Ubiquitin-Specific Protease 18 in Pathological Cardiac Remodeling. Hypertension. 2016 Nov;68(5):1160-1170. Epub 2016 Aug 29. PubMed PMID: 27572150.

19: Li P, Zhao QL, Jawaid P, Rehman MU, Sakurai H, Kondo T. Enhancement of hyperthermia-induced apoptosis by 5Z-7-oxozeaenol, a TAK1 inhibitor, in A549 cells. Cell Stress Chaperones. 2016 Sep;21(5):873-81. doi: 10.1007/s12192-016-0712-6. Epub 2016 Jul 22. PubMed PMID: 27448221; PubMed Central PMCID: PMC5003804.

20: Xu X, Fan Z, Qi X, Shao Y, Wu Y. The role of TGF-β-activated kinase 1 in db/db mice and high glucose-induced macrophage. Int Immunopharmacol. 2016 Sep;38:120-31. doi: 10.1016/j.intimp.2016.05.021. Epub 2016 Jun 3. PubMed PMID: 27268284.