CJ-12372
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03728 |
| CAS | 157110-17-3 |
| Molecular Weight | 336.34 |
| Molecular Formula | C20H16O5 |
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Description
CJ-12372 is an inhibitor of DNAgyrase produced by an unidentified fungus N 983-46. It has anti-Gram-positive bacteria, including Staphylococcus, Streptococcus, Enterococcus and Ciprofloxacin (Ciprofloxacin) drug-resistant bacteria activity, with MIC of 25-100 μg/mL.
Specification
| IUPAC Name | spiro[2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-3,8'-6,7-dihydro-5H-naphthalene]-1',4',5'-triol |
| Canonical SMILES | C1CC2(C3=C(C=CC(=C3C1O)O)O)OC4=CC=CC5=C4C(=CC=C5)O2 |
| InChI | InChI=1S/C20H16O5/c21-12-7-8-14(23)19-18(12)13(22)9-10-20(19)24-15-5-1-3-11-4-2-6-16(25-20)17(11)15/h1-8,13,21-23H,9-10H2 |
| InChI Key | ALYLMNAEGJISEJ-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 238°C(dec.) |
Reference Reading
1. Molecular data indicate that Rhytidhysteron rufulum (ascomycetes, Patellariales) in Costa Rica consists of four distinct lineages corroborated by morphological and chemical characters
Catalina Murillo, Federico J Albertazzi, Julieta Carranza, H Thorsten Lumbsch, Giselle Tamayo Mycol Res. 2009 Apr;113(Pt 4):405-16. doi: 10.1016/j.mycres.2008.09.003. Epub 2008 Sep 30.
Rhytidhysteron rufulum is a poorly known, common, pantropical species, capable of utilizing different substrata and occupying diverse habitats, and is the only species of its genus in Costa Rica. We have employed molecular, morphological, and chemical data to assess the variability and differentiation of R. rufulum in Costa Rica, including sites from the Pacific and Atlantic coast. Phylogenetic analyses of nuclear ITS rDNA sequences revealed the presence of four distinct lineages in the R. rufulum complex. Re-examination of the morphology and anatomy showed differences between these lineages in ascomatal, ascal, and ascospore size that have previously been regarded as intraspecific variations. In addition, there was a correlation between molecular phylogenies and chemical components as determined by hplc and nuclear magnetic resonance (NMR). Two lineages (clades I and II) produced the palmarumycins MK-3018, CJ-12372, and CR(1), whereas clade III produced dehydrocurvularin, and clade IV unidentified compounds. Our results based on a polyphasic approach contradict previous taxonomic interpretations of one morphologically variable species.
2. CJ-12,371 and CJ-12,372, two novel DNA gyrase inhibitors. Fermentation,isolation, structural elucidation and biological activities
S Sakemi, T Inagaki, K Kaneda, H Hirai, E Iwata, T Sakakibara, Y Yamauchi, M Norcia, L M Wondrack, J A Sutcliffe, et al. J Antibiot (Tokyo). 1995 Feb;48(2):134-42. doi: 10.7164/antibiotics.48.134.
A fermentation broth of an unidentified fungus (N983-46) was found to produce DNA gyrase inhibitors, CJ-12,371 (1) and CJ-12,372 (2). Following isolation by solvent extraction and silica gel and ODS (reverse phase) chromatographies, the structures were determined to be novel spiro-ketal compounds with S-configuration at position C-1. CJ-12,371 and CJ-12,372 inhibit both DNA supercoiling and relaxation mediated by Escherichia coli DNA gyrase. The interaction of these compounds with DNA gyrase appears to be novel in that the compounds inhibit supercoiling and relaxation without blocking religation; thus, no cleavage intermediate of double strand DNA is observed. Both compounds have antibacterial activity against several species of pathogenic Gram-positive bacteria, with MICs between 25 and 100 micrograms/ml. These results suggest that the antibacterial potency of CJ-12,371 and CJ-12,372 is attributed to the inhibition of DNA gyrase. However, the compounds did not inhibit DNA gyrase selectively, as they also inhibited eukaryotic topoisomerase II-mediated relaxation. Semi-synthetic modifications to the dihydroxy motif in CJ-12,371 altered both gyrase- and topoisomerase II-inhibitory activities, but did not enhance selectivity.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
