Chaetoglobosin A

Names

[ Name ]:
Chaetoglobosin A

[Synonym ]:
chaetoglobosins
Chaetoglobosin A
CHAETOGLOBOSIN A
CHAETOGLOBOSIN
CHAETOGLOBOSINB
18-dimethyl-,(7s,13e,16s,17e,19r,21e)-ol-3-yl)-1
CHAETOGLOBOSINE
(13)cytochalasa-13,17,21-triene-1,20,23-trione,6,7-epoxy-19-hydroxy-10-(1h-ind
CHAETOGLOBOSINM
CHAETOGLOBOSINL

Biological Activity

[Description]:

Chaetoglobosin A, the active principle within the extract of Penicillium aquamarinium, is a member of the cytochalasan family. Chaetoglobosin A preferentially induces apoptosis. Chaetoglobosin A targets filamentous actin in CLL cells and thereby induces cell-cycle arrest and inhibits membrane ruffling and cell migration[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Others

[Target]

Filamentous actin[1]

[References]

[1]. Knudsen PB, et al. Chaetoglobosin A preferentially induces apoptosis in chronic lymphocytic leukemia cells by targeting the cytoskeleton. Leukemia. 2014 Jun;28(6):1289-98.

Chemical & Physical Properties

[ Density]:
1.3 g/cm3

[ Boiling Point ]:
789.7ºC at 760 mmHg

[ Molecular Formula ]:
C₃₂H₃₆N₂O₅

[ Molecular Weight ]:
528.63900

[ Flash Point ]:
431.4ºC

[ Exact Mass ]:
528.26200

[ PSA ]:
111.79000

[ LogP ]:
4.16120

[ Index of Refraction ]:
1.651

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HA5305000

CHEMICAL NAME :: (13)Cytochalasa-13,17,21-triene-1,20,23-trione, 6,7-epoxy-19-hydroxy-10-(1H-indol-3-yl)- 16,18-dimethyl-, (7S,13E,16S,17E,19R,21E)-

CAS REGISTRY NUMBER :: 50335-03-0

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C32-H36-N2-O5

MOLECULAR WEIGHT :: 528.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJEMAG Japanese Journal of Experimental Medicine. (Kinokuniya Book-Stores of America Co., Ltd., West Bldg., Japan Cultural and Trade Center, 1581 Webster St., San Francisco, CA 94115) V.7- 1928- Volume(issue)/page/year: 48,105,1978

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes Gastrointestinal - other changes Liver - other changes

REFERENCE :: JJEMAG Japanese Journal of Experimental Medicine. (Kinokuniya Book-Stores of America Co., Ltd., West Bldg., Japan Cultural and Trade Center, 1581 Webster St., San Francisco, CA 94115) V.7- 1928- Volume(issue)/page/year: 48,105,1978

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJEMAG Japanese Journal of Experimental Medicine. (Kinokuniya Book-Stores of America Co., Ltd., West Bldg., Japan Cultural and Trade Center, 1581 Webster St., San Francisco, CA 94115) V.7- 1928- Volume(issue)/page/year: 48,105,1978

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6500 ug/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Lungs, Thorax, or Respiration - chronic pulmonary edema

REFERENCE :: JJEMAG Japanese Journal of Experimental Medicine. (Kinokuniya Book-Stores of America Co., Ltd., West Bldg., Japan Cultural and Trade Center, 1581 Webster St., San Francisco, CA 94115) V.7- 1928- Volume(issue)/page/year: 48,105,1978 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 700 ug/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: MAIKD3 Maikotokishin (Tokyo). Mycotoxin. (Maikotokishin Kenkyukai, c/o Tokyo Rika Daigaku Yakugakubu, 12 Funagawara-machi, Ichigaya, Shinjuku-ku, Tokyo 162, Japan) No.1- 1975- Volume(issue)/page/year: (10),17,1980

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Exploiting the cytoskeletal filaments of neoplastic cells to potentiate a novel therapeutic approach.

Biochim. Biophys. Acta 1846(2) , 599-616, (2014)

Although cytoskeletal-directed agents have been a mainstay in chemotherapeutic protocols due to their ability to readily interfere with the rapid mitotic progression of neoplastic cells, they are all ...

Chaetoglobosin K induces apoptosis and G2 cell cycle arrest through p53-dependent pathway in cisplatin-resistant ovarian cancer cells.

Cancer Lett. 356(2 Pt B) , 418-33, (2015)

Adverse side effects and acquired resistance to conventional platinum based chemotherapy have become major impediments in ovarian cancer treatment, and drive the development of more selective anticanc...

Chaetoglobosin F, a small molecule compound, possesses immunomodulatory properties on bone marrow-derived dendritic cells via TLR9 signaling pathway.

Immunobiology 218(3) , 292-302, (2013)

Chaetoglobosin F (Cha F), a cytochalasan-based alkaloid, was obtained from the EtOAc extract of a solid culture of Chaetomium globosum IFB-E019. Dendritic cells (DCs), the most potent antigen presenti...