543-21-5 Usage
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 543-21-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 3 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 543-21:
(5*5)+(4*4)+(3*3)+(2*2)+(1*1)=55
55 % 10 = 5
So 543-21-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H4N2O2/c5-3(7)1-2-4(6)8/h(H2,5,7)(H2,6,8)
543-21-5Relevant articles and documents
From Linear Molecular Chains to Extended Polycyclic Networks: Polymerization of Dicyanoacetylene
Gou, Huiyang,Zhu, Li,Huang, Haw-Tyng,Biswas, Arani,Keefer, Derek W.,Chaloux, Brian L.,Prescher, Clemens,Yang, Liuxiang,Kim, Duck Young,Ward, Matthew D.,Lerach, Jordan,Wang, Shengnan,Oganov, Artem R.,Epshteyn, Albert,Badding, John V.,Strobel, Timothy A.
, p. 6706 - 6718 (2017/08/29)
Dicyanoacetylene (C4N2) is an unusual energetic molecule with alternating triple and single bonds (think miniature, nitrogen-capped carbyne), which represents an interesting starting point for the transformation into extended carbon-nitrogen solids. While pressure-induced polymerization has been documented for a wide variety of related molecular solids, precise mechanistic details of reaction pathways are often poorly understood and the characterization of recovered products is typically incomplete. Here, we study the high-pressure behavior of C4N2 and demonstrate polymerization into a disordered carbon-nitrogen network that is recoverable to ambient conditions. The reaction proceeds via activation of linear molecules into buckled molecular chains, which spontaneously assemble into a polycyclic network that lacks long-range order. The recovered product was characterized using a variety of optical spectroscopies, X-ray methods, and theoretical simulations and is described as a predominately sp2 network comprising "pyrrolic" and "pyridinic" rings with an overall tendency toward a two-dimensional structure. This understanding offers valuable mechanistic insights into design guidelines for next-generation carbon nitride materials with unique structures and compositions.
The infrared and Raman spectrum of dicyanoacetylene. The ν9 fundamental
Winther, F.,Ketelsen, M.,Guarnieri, A.
, p. 65 - 74 (2007/10/02)
The Raman spectrum of liquid dicyanoacetylene, NC-CC-CN, was reinvestigated and ν3 found at 617 cm-1.The Fermi resonance between ν1 and 2ν5 is explained, considering the isotopic species NC-13CC-CN.The high resolution infrared spectrum of the lowest frequency fundamental ν9 has been recorded for the first time, and the rotational constants for several states with v9 /= 9 have been determied.
