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(-)-Terreic acid

Names

[ CAS No. ]:
121-40-4

[ Name ]:
(-)-Terreic acid

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

Biological Activity

[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.

Chemical & Physical Properties

[ 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

Toxicological Information

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

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302 + H312

[ Precautionary Statements ]:
P280

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Articles

Studies on terreic acid.

Jpn. J. Antibiot. 33(3) , 320-8, (1980)

It was found that Aspergillus sp. No. Y-8980 which was isolated from a soil sample collected at Yoron Island in Kagoshima Prefecture belonged to Aspergillus terreus group by morphological observation....

An improved mouse model of atopic dermatitis and suppression of skin lesions by an inhibitor of Tec family kinases.

Allergol. Int. 56(4) , 403-9, (2007)

Atopic dermatitis is a chronic or chronically relapsing, pruritic inflammatory skin disease. The incidence of atopic dermatitis has dramatically increased during the past three decades in industrializ...

Characterization of versilin-sensitive sites in self-sensitive producer and sensitive non-producer or unrelated organism.

J. Appl. Bacteriol. 67(2) , 191-200, (1989)

Studies on self-sensitivity of producer mutant vs. sensitivity of non-producer parent and unrelated organism showed that versilin inhibited spore germination and sporulation in the self-sensitive prod...


More Articles

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