| Identification | Back Directory | [Name]
ACETYLENEDICARBOXAMIDE | [CAS]
543-21-5 | [Synonyms]
Aquamycin
Lenamycin
Renamycin
2-BUTYNEDIAMIDE
but-2-ynediaMide
ACETYLENEDICARBOXAMIDE
1,2-Ethynedicarboxamide
Acetylendicarbonsaeureamid
acetylenedicarboxylicaciddiamide
Acetylenedicarboxamide,95%,pract.
Acetylenedicarboxylic acid diamide
ACETYLENEDICARBOXAMIDE (PRACT), 95%
AquaMycin, ButynesiaMide, LenaMycin
Acetylenedicarboxamide2-Butynediamide | [EINECS(EC#)]
200-816-9 | [Molecular Formula]
C4H4N2O2 | [MDL Number]
MFCD00017146 | [MOL File]
543-21-5.mol | [Molecular Weight]
112.09 |
| Chemical Properties | Back Directory | [Appearance]
CREAM TO BEIGE FINE CRYSTALLINE POWDER | [Melting point ]
179 °C
| [Boiling point ]
209.98°C (rough estimate) | [density ]
1.4421 (rough estimate) | [refractive index ]
1.4610 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml | [form ]
Fine Crystalline Powder | [pka]
13.01±0.50(Predicted) | [color ]
Cream to beige | [EPA Substance Registry System]
2-Butynediamide (543-21-5) |
| Hazard Information | Back Directory | [Chemical Properties]
CREAM TO BEIGE FINE CRYSTALLINE POWDER | [Uses]
Cellocidin is a small neutral alkyne produced by a number of Streptomyces species, first discovered by Suzuki and colleagues in 1958. Cellocidin has a broad antibacterial, antifungal and antitumor profile due to its ability to react with endogenous thiols like cysteine and glutathione. Cellocidin occurs as a weak active in many bioassays using actinomycete crude extracts and is thus a useful standard for chemical and bioassay dereplication. | [Definition]
ChEBI: A dicarboxylic acid diamide resulting from the formal condensation of both of the carboxy groups of butynedioic acid with ammonia. An antibacterial agent produced by Streptomyces chibaensis. | [Description]
Cellocidin is an antibiotic originally isolated from S. chibaensis. It is active against various bacterial strains including M. tuberculosis and against the trypanosomes T. brucei and T. rhodesiense (IC50s = 150 and 30 ng/ml, respectively). It inhibits proliferation of LCL1 and LCL2 cells transformed by Epstein-Barr virus (EBV), activates the c-Myc and NF-κB pathways in BC3 and LCL1 cells, and induces necrotic cell death in B cells infected with gammaherpes virus. Cellocidin (100-200 ppm) is protective against bacterial leaf blight in rice plants and inhibits α-ketoglutarate oxidation in X. oryzae, the bacterium that causes leaf blight, when used at a concentration of 1 ppm, suggesting that it inhibits the citric acid cycle. Formulations containing cellocidin have been used as agricultural pesticides. | [Purification Methods]
Acetylenedicarboxamide crystallises from MeOH and H2O [m 190-192o(dec) as hemihydrate]. When prepared from the ester + NH3 it has m 213o(dec). Also a melting point of 290-292o(dec) has been reported. [Saggimo J Org Chem 22 1171 1857, Kharash et al. J Org Chem 10 392 1945, Blomquist & Winslow J Org Chem 10 156 1945, Beilstein 2 I 317, 2 III 1995, 2 IV 2295.] | [References]
[1] S SUZUKI. Cellocidin, a new antibiotic.[J]. Journal of Antibiotics, 1958, 11 3: 81-83.
[2] KAZUHIKO OTOGURO. Selective and Potent in Vitro Antitrypanosomal Activities of Ten Microbial Metabolites[J]. Journal of Antibiotics, 2008, 61 6: 372-378. DOI: 10.1038/ja.2008.52
[3] RICHARD K. DZENG . Small molecule growth inhibitors of human oncogenic gammaherpesvirus infected B-cells[J]. Molecular Oncology, 2015, 9 2: Pages 365-376. DOI: 10.1016/j.molonc.2014.09.006
[4] MISATO T. Mode of action of agricultural antibiotics developed in Japan.[J]. Residue reviews, 1969, 25: 93-106. DOI: 10.1007/978-1-4615-8443-8_8 |
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