Diazaquinomycin A
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| Category | Antibiotics |
| Catalog number | BBF-01382 |
| CAS | 87614-40-2 |
| Molecular Weight | 354.41 |
| Molecular Formula | C20H22N2O4 |
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Description
Diazaquinomycin A is produced by the strain of Streptomyces sp.OM-704-KA333. It has anti-gram-positive bacterial activity and has antagonistic effect with metabolism of folic acid.
Specification
| Synonyms | Antibiotic OM 704A; NSC626554; 2,8-Dihydroxy-3,7-dimethyl-4,6-dipropylpyrido[3,2-g]quinoline-5,10-dione |
| IUPAC Name | 3,7-dimethyl-4,6-dipropyl-1,9-dihydropyrido[3,2-g]quinoline-2,5,8,10-tetrone |
| Canonical SMILES | CCCC1=C(C(=O)NC2=C1C(=O)C3=C(C2=O)NC(=O)C(=C3CCC)C)C |
| InChI | InChI=1S/C20H22N2O4/c1-5-7-11-9(3)19(25)21-15-13(11)17(23)14-12(8-6-2)10(4)20(26)22-16(14)18(15)24/h5-8H2,1-4H3,(H,21,25)(H,22,26) |
| InChI Key | WZZGVUSWZMBPPL-UHFFFAOYSA-N |
Properties
| Appearance | Red Acicular Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 291-295°C |
Reference Reading
1. Diazaquinomycins E-G, novel diaza-anthracene analogs from a marine-derived Streptomyces sp
Michael W Mullowney, Eoghainín Ó hAinmhire, Anam Shaikh, Xiaomei Wei, Urszula Tanouye, Bernard D Santarsiero, Joanna E Burdette, Brian T Murphy Mar Drugs. 2014 Jun 11;12(6):3574-86. doi: 10.3390/md12063574.
As part of our program to identify novel secondary metabolites that target drug-resistant ovarian cancers, a screening of our aquatic-derived actinomycete fraction library against a cisplatin-resistant ovarian cancer cell line (OVCAR5) led to the isolation of novel diaza-anthracene antibiotic diazaquinomycin E (DAQE; 1), the isomeric mixture of diazaquinomycin F (DAQF; 2) and diazaquinomycin G (DAQG; 3), and known analog diazaquinomycin A (DAQA; 4). The structures of DAQF and DAQG were solved through deconvolution of X-Ray diffraction data of their corresponding co-crystal. DAQE and DAQA exhibited moderate LC50 values against OVCAR5 of 9.0 and 8.8 μM, respectively. At lethal concentrations of DAQA, evidence of DNA damage was observed via induction of apoptosis through cleaved-PARP. Herein, we will discuss the isolation, structure elucidation, and biological activity of these secondary metabolites.
2. Mitogen-activated protein kinase routes as targets in the action of diaza-anthracene compounds with a potent growth-inhibitory effect on cancer cells
Carlos Pipaón, Pilar Gutierrez, Juan Carlos Montero, Mariluz Lorenzo, Ana Eguiraun, Jesús A De la Fuente, Atanasio Pandiella, Javier León, José M Ortiz Mol Cancer Ther. 2002 Aug;1(10):811-9.
1,8-Diaza-anthracene-tetraones are novel intermediates in the synthesis of the antifolate antibiotic diazaquinomycin A that was found before to have potent antitumor activity. Three of them (CV65, CV66, and CV70) were found to inhibit growth of a panel of several human tumor cell lines. The IC50s ranged from 0.05 to 1.5 microM and are comparable with that of doxorubicin. Among the three drugs, CV70 showed the highest cytotoxic activity. The growth-inhibitory action of these compounds was unrelated to the p53 status of the cells. At micromolar concentrations, all three compounds induced apoptosis, CV70 being the most proapoptotic. The incubation of HeLa cells with CV65, CV66, and CV70, at concentrations between 10 and 20 microM, inhibited the activation of c-Jun NH2-terminal kinase by various stimuli and prevented growth factor-induced extracellular signal-regulated kinase (ERK) 5 activation. At least one drug, CV65, also inhibited p38. This was surprising because proapoptotic antitumor drugs activate stress signaling pathways. Activation of ERK1/ 2 by growth factors or phorbol esters was unaffected by preincubation of cells with CV compounds. In vitro, CV compounds inhibit the enzyme quinone reductase but not c-Jun NH2-terminal kinase or ERK5. Because doxorubicin also inhibits quinone reductase, we conclude that the inhibitory effect of CV compounds on stress signaling kinases is not a direct effect on the kinases and is likely attributable to upstream elements of the activation cascades.
3. Isolation and structure elucidation of diazaquinomycin C from a terrestrial Streptomyces sp. and confirmation of the akashin structure
R P Maskey, I Grün-Wollny, H Laatsch Nat Prod Res. 2005 Feb;19(2):137-42. doi: 10.1080/14786410410001704741.
In the screening of terrestrial Streptomycetes for bioactive components, a new antibiotic designated as diazaquinomycin C (2b) was isolated. The new antibiotic was found to be a homologue of diazaquinomycin A (2a) by spectroscopic methods and by comparison of the NMR data with those of 2a. The same strain additionally produced the akashins 1a-1c. The configuration of the N-O acetale bond in these rare glycosylated dichloroindigo derivatives was confirmed to be beta.
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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 ╳
