APHE-3

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APHE-3
Category Antibiotics
Catalog number BBF-03524
CAS 13640-26-1
Molecular Weight 198.22
Molecular Formula C12H10N2O
Purity >95% by HPLC

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Description

APHE-3 is a pyrazoloisoquinolinone antibiotic produced by Streptoverticillium griseocarneum. It has weak anti-Gram-positive bacteria activity. APHE-3 can also inhibit lymphocyte proliferation in the presence of Phytohemagglutinin, with IC50 of about 0.1 mmol/L.

Specification

Synonyms Pimprinine; WS 30581C
Storage -20°C
IUPAC Name 5-(1H-indol-3-yl)-2-methyl-1,3-oxazole
Canonical SMILES CC1=NC=C(O1)C2=CNC3=CC=CC=C32
InChI InChI=1S/C12H10N2O/c1-8-13-7-12(15-8)10-6-14-11-5-3-2-4-9(10)11/h2-7,14H,1H3
InChI Key WZJPGCHCOHYLMB-UHFFFAOYSA-N
Source Streptomyces sp.

Properties

Appearance Tan Powder
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 369.5±45.0°C at 760 mmHg
Density 1.3±0.1 g/cm3
Solubility Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility.

Reference Reading

1. APHE-3, a spore-associated antibiotic of Streptomyces griseocarneus NCIMB 40447
M E Arias, R Cruz, J Soliveri Appl Microbiol Biotechnol . 2000 Apr;53(4):480-3. doi: 10.1007/s002530051645.
Solid cultures of the producing strain grown on Bennett medium develop abundant mycelium and intense sporulation. Under these conditions biosynthesis of APHE antibiotics (APHE-1 to -3) is accomplished. Further studies show that APHE-3 is basically produced during spore formation and mostly present in spores, while APHE-1 and APHE-2 are the predominant antibiotics in the mycelium. APHE compounds are present in almost all streptomycetes tested, indicating a possible role in the life cycle of these microorganisms.

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