HYPOTHEMYCIN

Product Name: HYPOTHEMYCIN
CAS No.: 76958-67-3
Chemical Name: HYPOTHEMYCIN
Synonyms: f 152 D2;Nsc354462;HYPOTHEMYCIN;Hypothemicin;Hypothemycin, MEK inhibitor;Hypothemycin - CAS 76958-67-3 - Calbiochem;(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-Tetrahydro-3,4,12-trihydroxy-14-methoxy-9-methyl-3H-oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione;(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-Tetrahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione;(1aR,3S,4S,6Z,9S,15bR)-1a,2,4,5,11,8,9,15b-Octahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11-dione;3H-Oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione,1a,8,9,15b-tetrahydro-3,4,12-trihydroxy-14-methoxy-9-methyl-,(1aR,3S,4S,6Z,9S,15bR)-
CBNumber: CB3229169
Molecular Formula: C19H22O8
Formula Weight: 378.37
MOL File: 76958-67-3.mol

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HYPOTHEMYCIN Property

Melting point:: 170-172℃
storage temp.: -20°C
solubility: DMSO: soluble
form: Lyophilized solid
color: White
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

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Safety

Hazard Codes: Xn
Risk Statements: 22
WGK Germany: 3
HS Code: 29419000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning
Hazard statements: H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: H1667
Product name: Hypothemycin
Purity: from Hypomyces trichothecoides, ≥98% (HPLC)
Packaging: 250μg
Price: $221
Updated: 2024/03/01

Sigma-Aldrich

Product number: H1667
Product name: Hypothemycin
Purity: from
Packaging: 1mg
Price: $679
Updated: 2024/03/01

Cayman Chemical

Product number: 27913
Product name: Hypothemycin
Packaging: 1mg
Price: $199
Updated: 2024/03/01

TRC

Product number: H998480
Product name: Hypothemycin
Packaging: 5mg
Price: $1620
Updated: 2021/12/16

Usbiological

Product number: 207223
Product name: Hypothemycin
Packaging: 250ug
Price: $342
Updated: 2021/12/16

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HYPOTHEMYCIN Chemical Properties,Usage,Production

Description

Hypothemycin (76958-67-3) is a potent and selective inhibitor of MEK.1-3?Acts via covalent binding to Cys residue.2?In cells, hypothemycin inhibits the MEK-ERK axis with sufficient selectivity to normalize transformed phenotypes3. Inhibits TNFα production in LPS-stimulated macrophages.4

Uses

Hypothemycin is a potent and selective inhibitor of threonine/tyrosine-specific kinase, MEK, and other protein kinases that contain a conserved cysteine residue in the ATP-binding site in in vitro studies.

General Description

A cell-permeable cis-enone resorlic acid lactone (RAL) and (5Z)-7-Oxozeaenol (Cat. No. 499610) analog that inhibits several kinases via an initial affinity binding to the ATP pocket, followed by a covalent adduct formation with a conserved ATP site cysteine residue of the targeted enzymes, including, but not limited to, Flt1/VEGFR-1, Flt3, cKit(D816V), MAPK1, MAPK2, MEK1, MKK6, PKCμ, PKD2, PRAK, and Tak1 (≥90% inhibition at 2 μM). Hypothemycin is also reported to inhibit two non-RAL targets (99% and 82% inhibition of TrkA and TrkB, respectively, at 2 μM), while one of the 46 putative cis-enone RALs targets, namely GSK-3α, is shown not to be affected. Hypothemycin inhibits multiple kinases involved in MAP kinase pathways and is therefore particularly effective in inhibiting BRAF(V600E)-dependent tumor growth. (5Z)-Zeaenol (Cat. No. 499609) may serve as a negative control.

Biochem/physiol Actions

Hypothemycin, one of the highly oxygenated analogues in the group of 14-membered resorcylic acid lactones (RAL), has minor antifungal and cytotoxic activity and exhibits an in vitro anti-malarial activity with an IC50 of 2.2 μg/mL. Hypothemycin is also reported to selectively and irreversibly inhibit protein kinases that contain a conserved cysteine residue (Cys166) that is located within the ATP-binding domain. Though this group accounts for less then 10% of all identified kinases, there are several targets implicated in aberrant cellular proliferation such as ERKs, MEK, FMS-like tyrosine kinase protein (FLT), and platelet-derived growth factor receptors (PDGFR). In cell culture, hypothemycin displays potent cytotoxicity against cancer cell lines that are dependent on certain activating kinase mutations. Additionally, hypothemycin demonstrates significant tumor growth inhibition in at least three separate murine xenograft models. Hypothemycin also inhibits the production of several cytokines such as IL2, IL6, IFNγ, and TNFα.

References

1) Zhou et al. (1999), Resorcylic acid lactones: naturally occurring potent and selective inhibitors of MEK; J. Antibiot., 52 1086 2) Schirmer et al. (2006), Targeted covalent inactivation of protein kinases by resorcylic acid lactone polyketides; Proc. Natl. Acad. Sci. USA, 103 4234 3) Fukazawa et al. (2010), The resorcylic acid lactone hypothemycin selectively inhibits the mitogen-activated protein kinase kinase-extracellular signal-regulated kinase pathway in cells; Biol. Pharm. Bull., 33 168 4) Park et al. (2015), Hypothemycin inhibits tumor necrosis factor-α production by tristetraprolin-dependent down-regulation of mRNA stability in lipopolysaccharide-stimulated macrophages; Int. Immunopharmacol., 29 863

HYPOTHEMYCIN Preparation Products And Raw materials

Raw materials

Preparation Products

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HYPOTHEMYCIN Suppliers

China 18 Germany 1 United Kingdom 2 United States 11 Global 32

Shanghai Tauto Biotech Co., Ltd.

Tel: 021-51320588
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AdooQ BioScience, LLC

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Sigma-Aldrich

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Shanghai EFE Biological Technology Co., Ltd.

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Lynnchem

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Novachemistry

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Shenzhen Regent Biochemical Technology Co., Ltd.

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Shanghai Hongye Biotechnology Co. Ltd

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TargetMol Chemicals Inc.

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ChemeGen(Shanghai) Biotechnology Co.,Ltd.

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76958-67-3, HYPOTHEMYCINRelated Search:

Troglitazone ZM 336372 LFM-A13 17-AAG HYPOTHEMYCIN 1-(EPOXYETHYL)-3-METHOXYBENZENE CIS-3-HEXENYL SALICYLATE (1R,2R)-(+)-1-PHENYLPROPYLENE OXIDE

HYPOTHEMYCIN

(1aR,3S,4S,6Z,9S,15bR)-1a,2,4,5,11,8,9,15b-Octahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11-dione

(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-Tetrahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione

Hypothemicin

Nsc354462

3H-Oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione,1a,8,9,15b-tetrahydro-3,4,12-trihydroxy-14-methoxy-9-methyl-,(1aR,3S,4S,6Z,9S,15bR)-

(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-Tetrahydro-3,4,12-trihydroxy-14-methoxy-9-methyl-3H-oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione

f 152 D2

Hypothemycin - CAS 76958-67-3 - Calbiochem

Hypothemycin, MEK inhibitor

76958-67-3

Antibiotic