121-40-4

121-40-4 structure

Name: (-)-Terreic acid
Chemical Name: Terreic Acid
CAS Number: 121-40-4
Molecular Formula: C₇H₆O₄
Molecular Weight: 154.12000
Catalog: Signaling Pathways Protein Tyrosine Kinase/RTK Btk
Create Date: 2018-03-12 08:00:00
Modify Date: 2024-01-11 12:27:17
Terreic acid, a quinone epoxide antibiotic, acts as an effective Btk inhibitor. Terreic acid blocks the interaction between PKC and the pleckstrin homology domain of Btk. Terreic acid inhibits the binding of GST-BtkPH to PKC in lysates of HMC-1 human mast cells with an IC50 of approximately 100 μM[1].

Name	Terreic Acid
Synonyms	(-)-Terreic acid,(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

Description	Terreic acid, a quinone epoxide antibiotic, acts as an effective Btk inhibitor. Terreic acid blocks the interaction between PKC and the pleckstrin homology domain of Btk. Terreic acid inhibits the binding of GST-BtkPH to PKC in lysates of HMC-1 human mast cells with an IC50 of approximately 100 μM[1].
Related Catalog	Research Areas >> Infection Research Areas >> Inflammation/Immunology Signaling Pathways >> Protein Tyrosine Kinase/RTK >> Btk
Target	Btk; Antibiotic[1]
In Vitro	Terreic acid inhibits the association of Btk with PKCβII in mouse mast cells at lower concentrations (IC50 of ≈30 μM). Terreic acid inhibits the catalytic activity of Btk but not PKC[1]. Terreic acid (pretreatment for 30 min before stimulation by antigen for 3 min) inhibits both the basal and activation levels of Btk autophosphorylating activity with IC50s of 10 μM and 3 μM, respectively[1]. Terreic acid inhibits the autophosphorylating activity of Btk purified partially from recombinant baculovirus-infected Sf9 insect cells in a dose-dependent manner[1]. Western Blot Analysis[1] Cell Line: Mouse bone marrow-derived mast cells Concentration: 0, 5, 10, 20 μM Incubation Time: Pretreated for 30 min Result: Inhibited both the basal and activation levels of Btk autophosphorylating activity in a dose-dependent manner.
In Vivo	Terreic acid inhibits the late-phase response of in vivo allergic cutaneous reactions[1]. Animal Model: BALB/c mice[1] Dosage: 0, 0.15, 1.5, and 15 mg/kg Administration: Injected i.p. 1 hr before antigen challenge. Ear thicknesses were measured at 1 hr and 24 hr Result: The early response, as examined 1 hr after antigen challenge, was not affected by TA. In contrast, TA inhibited the late-phase (24 hr) response in a dose-dependent manner.
References	[1]. Y Kawakami, et al. Terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase. Proc Natl Acad Sci U S A. 1999 Mar 2;96(5):2227-32.

Density	1.613 g/cm3
Boiling Point	333.6ºC at 760 mmHg
Molecular Formula	C₇H₆O₄
Molecular Weight	154.12000
Exact Mass	154.02700
PSA	66.90000
Vapour Pressure	9.63E-06mmHg at 25°C
Index of Refraction	1.618

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RN8925000

CHEMICAL NAME :: 7-Oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, (1R)-

CAS REGISTRY NUMBER :: 121-40-4

LAST UPDATED :: 199409

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C7-H6-O4

MOLECULAR WEIGHT :: 154.13

WISWESSER LINE NOTATION :: T36 BO DV GV EUTJ E1 FQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 75 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

TYPE OF TEST :: DNA adduct

MUTATION DATA

TYPE OF TEST :: DNA adduct

TEST SYSTEM :: Rodent - mouse Liver

DOSE/DURATION :: 200 mg/L

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 10,249,1982

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302 + H312
Precautionary Statements	P280
Hazard Codes	Xi
RIDADR	NONH for all modes of transport

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