bruneomycin

[Description]:

Streptonigrin (Bruneomycin), a natural product produced by Streptomyces flocculus, possesses both anti-tumor and anti-bacterial activity. Streptonigrin acts as a pan-PAD inhibitor with IC50s of 48.3±34.2 µM, 26.1±0.3 µM, 0.43±0.03 µM, and 2.5±0.4 µM for PAD1, PAD2, PAD3, and PAD4, respectively[1].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Epigenetics >> Protein Arginine Deiminase

[Target]

Anti-bacterial[1] IC50: 48.3±34.2 µM (PAD1), 26.1±0.3 µM, (PAD2), 0.43±0.03 µM (PAD3), 2.5±0.4 µM (PAD4)[1]

[References]

[1]. Dreyton CJ, et al. Insights into the mechanism of Streptonigrin-induced protein arginine deiminase inactivation. Bioorg Med Chem. 2014 Feb 15;22(4):1362-9.

[ Density]:
1.54g/cm3

[ Boiling Point ]:
719ºC at 760mmHg

[ Melting Point ]:
301-303℃

[ Molecular Formula ]:
C₂₅H₂₂N₄O₈

[ Molecular Weight ]:
506.46400

[ Flash Point ]:
388.7ºC

[ Exact Mass ]:
506.14400

[ PSA ]:
197.18000

[ LogP ]:
3.59940

[ Index of Refraction ]:
1.716

[ Storage condition ]:
2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TJ7350000

CHEMICAL NAME :: Picolinic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2- quinolyl)-4-(2- hydroxy-3,4-dimethoxyphenyl)-3-methyl-

CAS REGISTRY NUMBER :: 3930-19-6

BEILSTEIN REFERENCE NO. :: 0599390

LAST UPDATED :: 199806

DATA ITEMS CITED :: 64

MOLECULAR FORMULA :: C25-H22-N4-O8

MOLECULAR WEIGHT :: 506.51

WISWESSER LINE NOTATION :: T66 BV EV GNJ CO1 DZ H- BT6NJ CZ DR BQ CO1 DO1& E1 FVQ

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 :: 150 ug/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2330 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 :: 520 ug/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1000 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 :: 865 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 :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 500 ug/kg

TOXIC EFFECTS :: Blood - leukopenia Blood - changes in platelet count

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 600 ug/kg

TOXIC EFFECTS :: Blood - leukopenia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 mg/kg/10D-I

TOXIC EFFECTS :: Blood - other changes Endocrine - changes in spleen weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1710 ug/kg/7D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - urine volume decreased

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 800 ug/kg/10D-I

TOXIC EFFECTS :: Gastrointestinal - other changes Liver - hepatitis (hepatocellular necrosis), zonal Liver - fatty liver degeneration

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 250 ug/kg/10D-I

TOXIC EFFECTS :: Blood - leukopenia Blood - changes in bone marrow (not otherwise specified) Blood - changes in platelet count

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 500 ug/kg/10D-I

TOXIC EFFECTS :: Blood - leukopenia Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 100 ug/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 100 ug/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 200 ug/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 250 ug/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 100 ug/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 100 ug/kg

SEX/DURATION :: female 2 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 90 ug/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sister chromatid exchange

MUTATION DATA

TEST SYSTEM :: Rodent - rabbit

DOSE/DURATION :: 30 ug/kg

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 7(Suppl 3),48,1985 *** REVIEWS *** TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+: Very toxic;

[ Risk Phrases ]:
28

[ Safety Phrases ]:
53-28-36/37/39-45

[ RIDADR ]:
UN 3462 6.1/PG 1

[ WGK Germany ]:
3

[ RTECS ]:
TJ7350000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

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Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

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