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Bruceantin

Names

[ CAS No. ]:
41451-75-6

[ Name ]:
Bruceantin

[Synonym ]:
[11b,12a,15b(E)]-15-[(3,4-Dimethyl-1-oxo-2-pentenyl)oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxopicras-3-en-21-oic Acid Methyl Ester
Methyl (11β,12α,15β)-15-{[(2E)-3,4-dimethyl-2-pentenoyl]oxy}-3,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate
Methyl (11β,12α,15β)-15-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-3,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate
Picras-3-en-21-oic acid, 15-[[(2E)-3,4-dimethyl-1-oxo-2-penten-1-yl]oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, (11β,12α,15β)-

Biological Activity

[Description]:

Bruceantin(NSC165563) is first isolated from Brucea antidysenterica, a tree used in Ethiopia for the treatment of cancer, and activity was observed against B16 melanoma, colon 38, and L1210 and P388 leukemia in mice.IC50 value:Target: anticancerCell differentiation was induced and c-MYC was down-regulated, suggesting a mechanistic correlation between c-MYC down-regulation and induction of cell differentiation or cell death. Treatment of HL-60 and RPMI 8226 cell lines induced apoptosis, and this involved the caspase and mitochondrial pathways. Moreover, an in vivo study using RPMI 8226 human-SCID xenografts demonstrated that bruceantin induced regression in early as well as advanced tumors, and these significant antitumor responses were facilitated in the absence of overt toxicity.

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Cancer
Natural Products >> Others

[References]

[1]. Cuendet M, et al. Multiple myeloma regression mediated by bruceantin. Clin Cancer Res. 2004 Feb 1;10(3):1170-9.

[2]. Cuendet M, et al. Antitumor activity of bruceantin: an old drug with new promise. J Nat Prod. 2004 Feb;67(2):269-72.


[Related Small Molecules]

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Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
731.0±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C28H36O11

[ Molecular Weight ]:
548.579

[ Flash Point ]:
239.4±26.4 °C

[ Exact Mass ]:
548.225769

[ PSA ]:
165.89000

[ LogP ]:
2.96

[ Vapour Pressure ]:
0.0±5.4 mmHg at 25°C

[ Index of Refraction ]:
1.598

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EH8798000
CHEMICAL NAME :
Bruceantin
CAS REGISTRY NUMBER :
41451-75-6
LAST UPDATED :
198605
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C28-H36-O11
MOLECULAR WEIGHT :
548.64

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
7027 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2727 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3359 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1950 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
500 ug/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - other changes Blood - hemorrhage

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Rodent - mouse Lymphocyte
DOSE/DURATION :
15 umol/L
REFERENCE :
JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,883,1979

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds