66018-38-0

Basic information

• Product Name: LL-Z-1640-2
• Synonyms: LL-Z-1640-2;(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;(5Z)-7-Oxozeaenol;JNK/p38 inhibitor;C292, L 783278
• CAS NO: 66018-38-0
• Molecular Formula: C₁₉H₂₂O₇
• Molecular Weight: 362.37
• Product Categories: antibiotic
• Mol File: 66018-38-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 666.8°C at 760 mmHg
• Flash Point: 240.2°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.09E-18mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Desiccate at -20°C
• Solubility: Soluble in DMSO
• CAS DataBase Reference: LL-Z-1640-2(CAS DataBase Reference)
• NIST Chemistry Reference: LL-Z-1640-2(66018-38-0)
• EPA Substance Registry System: LL-Z-1640-2(66018-38-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 66018-38-0(Hazardous Substances Data)

Usage

Description

LL-Z-1640-2 is a cis-enone resorcylic acid lactone that was first reported in 1978 and later rediscovered as an irreversible and highly selective TAK1 inhibitor. TAK1 is a MAPKKK (Mitogen-Activated Protein Kinase Kinase Kinase) involved in the p38 signaling cascade for pro-inflammatory signals such as cytokines. LL-Z-1640-2 has been shown to effectively prevent inflammation in animal models.

Uses

Used in Pharmaceutical Industry:
LL-Z-1640-2 is used as an anti-inflammatory agent for its ability to effectively prevent inflammation in animal models by inhibiting TAK1, a key enzyme in the p38 signaling cascade for pro-inflammatory signals.
Used in Research Applications:
LL-Z-1640-2 is used as a research tool for studying the role of TAK1 in various cellular processes, particularly those related to inflammation and the immune response. Its irreversible and highly selective nature makes it a valuable compound for investigating the molecular mechanisms underlying these processes.

Biological Activity

Resorcyclic lactone of fungal origin that acts as a potent and selective transforming growth factor- β -activated kinase 1 (TAK1) mitogen-activated protein kinase kinase kinase (MAPKKK) inhibitor (IC 50 = 8 nM). Displays > 33-fold and > 62-fold selectivity over MEKK1 and MEKK4 respectively. Inhibits IL-1-induced activation of NF- κ B (IC 50 = 83 nM) and JNK/p38. Inhibits production of inflammatory mediators, and sensitizes cells to TRAIL- and TNF- α -induced apoptosis in vitro .

InChI:InChI=1/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

Relevant articles and documents

Antifouling and fungicidal resorcylic acid lactones from the sea anemone-derived fungus cochliobolus lunatus

Three new 14-membered resorcylic acid lactones, cochliomycins D-F, 1-3, and eight known analogues, 4-11, were isolated from the sea anemone-derived fungus Cochliobolus lunatus. Compounds 1-4 are diastereomers differing from each other by the absolute configurations of the 4′,5′-diol chiral centers. The absolute configurations of 1-4 were established by the CD exciton chirality method and TDDFT ECD calculations. In antifouling assays, 1, 3-6, and 6a exhibited potent antifouling activities against the larval settlement of the barnacle Balanus amphitrite at nontoxic concentrations, with EC50 values ranging from 1.82 to 22.5 μg/mL. Noticeably, fungicide whole-plant assays indicated that 6 showed excellent activity on the Plasmopara viticola preventative test at 6 ppm and concentration-dependent activity on the Phytophthora infestans preventative application at 200, 60, and 20 ppm. Preliminary structure-activity relationships are also discussed.