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C6374

Sigma-Aldrich

Caerulomycin A

from Streptomyces caeruleus, ≥98% (HPLC)

Synonym(s):

Carulomycin A, Cerulomycin

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About This Item

Empirical Formula (Hill Notation):
C12H11N3O2
CAS Number:
21802-37-9
Molecular Weight:
229.23
MDL number:
MFCD03093715
UNSPSC Code:
51111800
PubChem Substance ID:
329775122
NACRES:
NA.77

biological source

Streptomyces caeruleus

Quality Level

200

Assay

≥98% (HPLC)

form

powder

antibiotic activity spectrum

fungi

storage temp.

−20°C

SMILES string

COc1cc(\C=N\O)nc(c1)-c2ccccn2

InChI

1S/C12H11N3O2/c1-17-10-6-9(8-14-16)15-12(7-10)11-4-2-3-5-13-11/h2-8,16H,1H3/b14-8+

InChI key

JCTRJRHLGOKMCF-RIYZIHGNSA-N

Related Categories

Biochem/physiol Actions

Caerulomycins produced by Streptomyces caeruleus are bipyridinic molecules endowed with antibiotic properties. Caerulomycin A was found to have a strong anti-fungal and anti-amoebic activity, and a mild antibacterial activity.

Preparation Note

Caerulomycin A stock solution may be prepared in DMSO or methanol at 1 mg/mL. The stock solution can be further diluted in water to 0.1 mg/mL. Higher concentrations my requrie gentle heating to 40 °C. Dilutions from the stock solution should be freshly prepared.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Qinheng Lin et al.
Wei sheng wu xue bao = Acta microbiologica Sinica, 51(8), 1032-1041 (2011-11-22)
In order to enable the caerulomyicn biosynthetic study by in vivo gene disruptions, it is crucial to develop a genetic modification system for the producer Actinoalloteichus sp. WH1-2216-6. The spore germination timing and the concentration of MgSO4 in the medium
D K Chatterjee et al.
Zeitschrift fur Parasitenkunde (Berlin, Germany), 70(5), 569-573 (1984-01-01)
The anti-amoebic action of the bipyridyl antibiotic caerulomycin was assessed in vitro and in vivo using various strains of Entamoeba histolytica from polyxenic, axenic and monoxenic cultures. Minimum inhibition concentrations of caerulomycin (metronidazole) were 7.5 (5), 15.6(1.95) and 60 (2.5)
Tarek Sammakia et al.
Organic letters, 4(14), 2385-2388 (2002-07-06)
[reaction: see text] The total synthesis of caerulomycin C is described. Key steps in this synthesis utilize 1,2-, 1,3-, and 1,4-halogen dance reactions for the functionalization of the pyridine ring.

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