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 (IC
50s = 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.
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.
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
