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Streptonigrin

HCID 5298
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Basic information

CAS
3930-19-6
Standard SMILES
COC1=C(N)C(=O)c2nc(-c3nc(C(=O)O)c(C)c(-c4ccc(OC)c(OC)c4O)c3N)ccc2C1=O
InChIKey
PVYJZLYGTZKPJE-UHFFFAOYSA-N
Molecular formula
C25H22N4O8
Average molar mass
506.5 g/mol
Monoisotopic mass
506.14376367

Overview

Streptonigrin is complex cytotoxic antibiotic obtained from Streptomyces flocculus or S. rufochronmogenus. It is used in advanced carcinoma and causes leukopenia. It has a role as an antimicrobial agent and an antineoplastic agent. It is a quinolone and a member of pyridines.

Names & identifiers

Preferred name
Streptonigrin
IUPAC
5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid
English name
Streptonigrin
Molecular formula
C25H22N4O8
Molecular weight
506.46

Names & synonyms

streptonigrinBruneomycin3930-19-6RufocromomycinNigrinRufocromomycineStreptonigranValacidinRufocromomicinaNSC-45383RufocromomycinumNSC 45383
Show more names
5278r.p.NSC 83950NSC 56748phaeomycinAO 50165L302
NSC45383NSC83950NSC-839502-Pyridinecarboxylic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acidCHEBI:9287DTXSID00960034261Q3JB310

Database identifiers

CAS
3930-19-6
PubChem CID
5298
DTXSID
DTXSID00960034
ChEMBL
CHEMBL11417
ChEBI
CHEBI:9287
UNII
261Q3JB310
EC Number
223-501-8
Nikkaji
J2.203I、J2.999.943K、J2.999.944I

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
197 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
12
Rotatable bonds
6
Heavy atoms
37
Formal charge
0
Complexity
944

Experimental & physicochemical properties

DrugsPharmaceuticals -> Antibiotics
Solubility74.9 [ug/mL] (The mean of the results at pH 7.4)

Physicochemical properties

Melting point
301 · 301-303℃
Boiling point
595.12 °C · 595.12°C (rough estimate)
Density
1.413 · 1.4130 (rough estimate)
refractive index
1.6 · 1.6000 (estimate)
storage temp.
2 · 2-8°C
solubility
Chloroform:Methanol (1:1): 2 mg/ml
form
A solid
pka
6.2 · 6.2-6.4 (1:1 aq dioxane)
color
Light brown to brown
Merck
13 · 13,8907
BRN
599390 · 599390
InChI
1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 1 (100%)

Safety data

F
10-18
PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
TJ7350000
ridadr
UN 3462 6.1/PG 1
Toxicity
LD50 oral in mouse: 2330ug/kg
risk_code
28
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T+
safety_code
53-28-36/37/39-45
hazard_class
6.1(a)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
II
Hazard statements
H300
Hazard Classifications
Acute Tox. 1 Oral

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationChemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Applications · 3 items

DescriptionStreptonigrin is a phenylpyridylquinoline originally isolated from S. flocculus with diverse biological activities. Streptonigrin (2.5-12.5 μM) induces DNA cleavage by calf thymus topoisomerase II in a concentration-dependent manner. It induces phage production in S. typhimurium when used at concentrations ranging from 1 to 10 μg/ml. Streptonigrin (10 μg/ml) inhibits DNA synthesis in and reduces survival of S. typhimurium bacteria. Streptonigrin is bactericidal against E. coli in an iron-dependent manner, an effect that is blocked by the iron chelators deferoxamine and orthophenanthroline. Streptonigrin (40 nM) is cytotoxic to human HT-29 colon carcinoma cells but not to BE colon carcinoma cells in which NAD(P)H:quinone oxidoreductase is not expressed. Streptonigrin (0.001-0.1 μg/ml) inhibits mitosis and induces chromatin breaks in human leukocytes in a concentration-dependent manner. In vivo, streptonigrin (0.05 mg/kg, i.p.) increases the mean survival time in rats infected with Rauscher virus.

UsesStreptonigrin is an aminoquinone antitumour antibiotic. Its antineoplastic activity requires reductive activation by Xanthine-converting enzymes. It induces apoptosis by a mechanism involving NF-κB. DNA cleavage reaction and chromosome damage by Streptonigrin are influenced by the nature of the metal ion present and dependent on the production of free radicals. Its antibiotic activity is iron-activated. Streptonigrin from Streptomyces flocculus

UsesStreptonigrin is an unusual aminoquinone with broad biological activity against bacteria, fungi, nematodes, viruses and tumour cells. Streptonigrin acts as a bioreductive agent, highly dependent on interactions with metal ions, notably iron, and plays an important role in free radical production through redox cycling of NAD(P)H:quinone oxidoreductase (NQO1).

Additional notes

DefinitionChEBI: Complex cytotoxic antibiotic obtained from Streptomyces flocculus or S. rufochronmogenus. It is used in advanced carcinoma and causes leukopenia.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
InChIKey
PVYJZLYGTZKPJE-UHFFFAOYSA-N
SMILES
COc1ccc(c(O)c1OC)-c2c(C)c(nc(c2N)-c3ccc4C(=O)C(OC)=C(N)C(=O)c4n3)C(O)=O
FDA UNII
261 Q3JB310 · 261Q3JB310
NCI Drug Dictionary
streptonigrin
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
300 · H300
Precautionary statements
264 · P264-P270-P301+P310-P405-P501
PPE
3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
T+
Risk Statements
28 · 28
Safety Statements
53 · 53-28-36/37/39-45
RIDADR
3462 · UN 3462 6.1/PG 1
WGK Germany
3 · 3
RTECS
7350000 · TJ7350000
F
10 · 10-18
HazardClass
6.1 · 6.1(a)
PackingGroup
II
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
1 Oral · Acute Tox. 1 Oral
Toxicity
50 oral · LD50 oral in mouse: 2330ug/kg
Precautionary statements
P264-P270-P301+P310-P405-P501