Cytogenin
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| Category | Antibiotics |
| Catalog number | BBF-01138 |
| CAS | 132971-59-6 |
| Molecular Weight | 222.19 |
| Molecular Formula | C11H10O5 |
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Description
It is produced by the strain of Streptoverticillium eurocidicum. It has weak cytotoxicity.
Specification
| Synonyms | Antibiotic MI 43-37F 11; 8-Hydroxy-3-(hydroxymethyl)-6-methoxy-1H-2-benzopyran-1-one; 1H-2-Benzopyran-1-one,8-hydroxy-3-(hydroxymethyl)-6-methoxy- |
| IUPAC Name | 8-hydroxy-3-(hydroxymethyl)-6-methoxyisochromen-1-one |
| Canonical SMILES | COC1=CC(=C2C(=C1)C=C(OC2=O)CO)O |
| InChI | InChI=1S/C11H10O5/c1-15-7-2-6-3-8(5-12)16-11(14)10(6)9(13)4-7/h2-4,12-13H,5H2,1H3 |
| InChI Key | CAWNOJXNAUEIGB-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 482.1 °C at 760 mmHg |
| Melting Point | 148.5-149.5 °C |
| Density | 1.423 g/cm3 |
| Solubility | Soluble in Methanol, Acetonitrile |
Reference Reading
1. Synthesis and biological evaluation of cytogenin derivatives
N Matsumoto, T Nakashima, K Isshiki, H Kuboki, S I Hirano, H Kumagai, T Yoshioka, M Ishizuka, T Takeuchi J Antibiot (Tokyo). 2001 Mar;54(3):285-96. doi: 10.7164/antibiotics.54.285.
To enhance the stability in vivo, new derivatives of cytogenin were synthesized, and their biological activity and stability in mice were estimated. 2-(8-Hydroxy-6-methoxy-1-oxo-1H-2-benzopyran-3-yl)propionic acid (NM-3) was found to be the most stable among them. It modified collagen-induced arthritis in mice. It also showed potent anti-angiogenic activity in a mouse dorsal air sac assay.
2. Effect of cytogenin, a novel immunomodulator, on streptozotocin-induced diabetes in mice
Hiroyuki Kumagai, Kuniko Wakazono, Naoki Agata, Kunio Isshiki, Masaaki Ishizuka, Daishiro Ikeda J Antibiot (Tokyo). 2005 Mar;58(3):202-5. doi: 10.1038/ja.2005.24.
The anti-diabetic effect of cytogenin was examined using streptozotocin-induced diabetes in mice. Cytogenin suppressed not only the increase of plasma glucose level but also the body weight reduction in diabetic mice. Histological examination of the pancreas taken from diabetic mice given cytogenin showed that cytogenin decreased the number of macrophages infiltrated into islet of pancreas. Further, cytogenin suppressed the nitric oxide generation by macrophages treated with lipopolysaccharide through decreasing of inducible nitric oxide synthase expression. Cytogenin suppressed interleukin-6 expression by macrophage treated with LPS, suggesting that the anti-diabetic activity of cytogenin might be partly attributed to the suppressive activity against nitric oxide generation.
3. Effects of cytogenin, a novel microbial product, on embryonic and tumor cell-induced angiogenic responses in vivo
T Oikawa, M Sasaki, M Inose, M Shimamura, H Kuboki, S Hirano, H Kumagai, M Ishizuka, T Takeuchi Anticancer Res. 1997 May-Jun;17(3C):1881-6.
Cytogenin (8-hydroxy-3-hydroxymethyl-6-methoxyisocoumarin) is a new microbial product with antitumor and antirheumatoid arthritis effects in vivo when administered orally, although its mechanism(s) of action is not known well. Both neoplasia and rheumatoid arthritis are referred to as angiogenesis-dependent diseases. The aim of the present study was to investigate the effects of cytogenin on both physiological and pathological angiogenesis, using the growing chick embryo chorioallantoic membrane and mouse dorsal air sac assay systems, respectively. The microbial product at doses up to 100 micrograms/egg did not significantly affect embryonic angiogenesis when topically placed on the surface of the chorioallantoic membrane, suggesting that it has no effect on the physiological (or normal) angiogenic response. By contrast, systemic administration of cytogenin (100 mg/kg p.o., for 5 consecutive days) significantly suppressed angiogenesis induced by malignant tumor cells (S-180), one of pathological neovascularization, in a mouse dorsal air sac assay system. Pharmacokinetic studies in mice revealed that the maximal concentration of cytogenin in plasma after a single 100 mg/kg oral dose of the compound was 32 microM. In vitro experiments involving cultured vascular endothelial cells showed that cytogenin at concentrations determined by pharmacokinetic study, had little effect on plasminogen activator secretion, tube formation and the proliferation of endothelial cells. These results suggest that cytogenin is a novel oral antiangiogenic agent, that the mechanism of its antiangiogenic action contributes to its suppressive effects on both tumor growth and rheumatoid arthritis that we previously found, and that it could be developed as a potential therapeutic agent for cancer, rheumatoid arthritis and other angiogenesis-dependent disorders such as diabetic retinopathy.
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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 ╳
