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Sibiromycin

Names

[ CAS No. ]:
12684-33-2

[ Name ]:
Sibiromycin

[Synonym ]:
Sibiromycin
C24H31N3O7
Sybiromycin

Biological Activity

[Description]:

Sibiromycin is a naturally produced glycosylated pyrrolobenzodiazepines (PBDs). Sibiromycin is also a potent antitumor antibiotic that binds covalently to DNA in the minor groove at the NH2 of guanine[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> DNA Alkylator/Crosslinker

[In Vitro]

Pyrrolobenzodiazepines (PBDs) are sequence selective DNA alkylating agents with remarkable antineoplastic activity[1]. Alkylation of DNA by anthramycin, sibiromycin and tomaymycin is sequence specific with the following trend for binding preference 5′-Pu-G-Pu>5′-Py-G-Pu>5′-Pu-G-Py>5′-Py-G-Py[1]. Sibiromycin shows cytotoxicity against L1210 (leukemia), ADJ/PC6 (plasmacytoma) and CH1 (ovarian) cells with IC50s of ranging 0.000017 ~0.0029 μM[1].

[References]

[1]. Gerratana B. Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines. Med Res Rev. 2012;32(2):254-293.

[2]. Li W, et al. Biosynthesis of sibiromycin, a potent antitumor antibiotic. Appl Environ Microbiol. 2009;75(9):2869-2878.

Chemical & Physical Properties

[ Density]:
1.41g/cm3

[ Boiling Point ]:
755.7ºC at 760 mmHg

[ Molecular Formula ]:
C24H31N3O7

[ Molecular Weight ]:
473.51900

[ Flash Point ]:
410.8ºC

[ Exact Mass ]:
473.21600

[ PSA ]:
145.44000

[ LogP ]:
1.99250

[ Vapour Pressure ]:
5.32E-24mmHg at 25°C

[ Index of Refraction ]:
1.662

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UY8495000
CHEMICAL NAME :
5H-Pyrrolo(2,1-c)(1,4)benzodiazepin-5-one, 7-((4,6-dideoxy-3-(methyl-4-(methylamino)-beta- D-altropyranosyl)oxy))-10,11-dihydro-9,11-dihydroxy-8 -methyl-2-(1-propenyl )-
CAS REGISTRY NUMBER :
12684-33-2
LAST UPDATED :
199609
DATA ITEMS CITED :
13
MOLECULAR FORMULA :
C24-H31-N3-O7
MOLECULAR WEIGHT :
473.58
WISWESSER LINE NOTATION :
T C576 BVN IM HHJ E1U2 HQ KQ L1 MO- BT6OTJ CQ DQ D1 EM1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
6 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 - rat
DOSE/DURATION :
29 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 :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
459 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 :
32 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 :
84 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 :
58 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD10 - Lethal Dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
5 ug/kg
TOXIC EFFECTS :
Cardiac - pericarditis Cardiac - other changes
TYPE OF TEST :
LD10 - Lethal Dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
12 ug/kg
TOXIC EFFECTS :
Blood - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
98 ug/kg/4D-I
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
22500 ng/kg/30D-I
TOXIC EFFECTS :
Cardiac - cardiomyopathy including infarction Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
30 ug/kg/15D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Rodent - mouse Ascites tumor
DOSE/DURATION :
1 ug/L
REFERENCE :
NEOLA4 Neoplasma. (Karger-Libri, P.O. Box, CH-4009 Basel, Switzerland) V.4- 1957- Volume(issue)/page/year: 22,105,1975

Related Compounds