H1667

Hypothemycin

from Hypomyces trichothecoides, ≥98% (HPLC)

• Synonyme(s) : 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)-, NSC354462
• Formule empirique (notation de Hill): C₁₉H₂₂O₈
• Numéro CAS: 76958-67-3
• Poids moléculaire : 378.37
• Numéro MDL: MFCD08457932
• Code UNSPSC : 51111800
• ID de substance PubChem : 329815176
• Nomenclature NACRES : NA.77

Propriétés

• Source biologique: Hypomyces trichothecoides
• Niveau de qualité: 200
• Pureté: ≥98% (HPLC)
• Solubilité: DMSO: soluble; acetone: soluble; deionized water: insoluble
• Température de stockage: −20°C
• Chaîne SMILES: COc1cc(O)c2C(=O)O[C@@H](C)CC=CC(=O)[C@@H](O)[C@@H](O)CC3OC3c2c1
• InChI: 1S/C19H22O8/c1-9-4-3-5-12(20)17(23)14(22)8-15-18(27-15)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,14-15,17-18,21-23H,4,8H2,1-2H3/b5-3-/t9-,14-,15+,17+,18+/m0/s1
• Clé InChI: SSNQAUBBJYCSMY-KNTMUCJRSA-N

Description

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H302
• Conseils de prudence: P301 + P312 + P330
• Classification des risques: Acute Tox. 4 Oral
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable