CJ-21058
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| Category | Antibiotics |
| Catalog number | BBF-02784 |
| CAS | 405072-57-3 |
| Molecular Weight | 387.51 |
| Molecular Formula | C23H33NO4 |
| Purity | >98% by HPLC |
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Description
CJ-21058 is a SecA inhibitor originally isolated from CL47745. It shows antiprotozoal effects (IC50 = 7 μM, T. brucei) and inhibits post-translational protein transport into the endoplasmic reticulum. It shows antibacterial and antifungal effects in vivo.
Specification
| Synonyms | CHEMBL565009; (5R,Z)-3-(Hydroxy((1R,2S,6S,8aS)-1,3,6-trimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)methylene)-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione |
| Storage | Store at Store at -20°C |
| IUPAC Name | (3Z)-3-[[(1S,2R,4aS,7R,8aS)-1,3,7-trimethyl-2-[(E)-prop-1-enyl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione |
| Canonical SMILES | CC=CC1C(=CC2CCC(CC2C1(C)C(=C3C(=O)C(N(C3=O)C)CO)O)C)C |
| InChI | InChI=1S/C23H33NO4/c1-6-7-16-14(3)11-15-9-8-13(2)10-17(15)23(16,4)21(27)19-20(26)18(12-25)24(5)22(19)28/h6-7,11,13,15-18,25,27H,8-10,12H2,1-5H3/b7-6+,21-19-/t13-,15+,16-,17+,18?,23-/m1/s1 |
| InChI Key | CNLPKRLJWZPXFN-WITDKLGMSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 562.6±50.0°C at 760 mmHg |
| Density | 1.159±0.06 g/cm3 |
| Solubility | Soluble in DMSO, methanol or methylene chloride |
Reference Reading
1. CJ-21,058, a new SecA inhibitor isolated from a fungus
Yutaka Sugie, Sae Inagaki, Yoshinao Kato, Hiroyuki Nishida, Chang-Hong Pang, Toshiyuki Saito, Shinichi Sakemi, Fadia Dib-Hajj, John P Mueller, Joyce Sutcliffe, Yasuhiro Kojima J Antibiot (Tokyo). 2002 Jan;55(1):25-9. doi: 10.7164/antibiotics.55.25.
A new equisetin derivative, CJ-21,058 (I) was isolated from the fermentation broth of an unidentified fungus CL47745. It shows antibacterial activity against Gram-positive multi-drug resistant bacteria by inhibiting ATP-dependent translocation of precursor proteins across a bacterial cell membrane.
2. Post-translational import of protein into the endoplasmic reticulum of a trypanosome: an in vitro system for discovery of anti-trypanosomal chemical entities
Bhargavi Patham, Josh Duffy, Ariel Lane, Richard C Davis, Peter Wipf, Sheara W Fewell, Jeffrey L Brodsky, Kojo Mensa-Wilmot Biochem J. 2009 Apr 15;419(2):507-17. doi: 10.1042/BJ20081787.
HAT (human African trypanosomiasis), caused by the protozoan parasite Trypanosoma brucei, is an emerging disease for which new drugs are needed. Expression of plasma membrane proteins [e.g. VSG (variant surface glycoprotein)] is crucial for the establishment and maintenance of an infection by T. brucei. Transport of a majority of proteins to the plasma membrane involves their translocation into the ER (endoplasmic reticulum). Thus inhibition of protein import into the ER of T. brucei would be a logical target for discovery of lead compounds against trypanosomes. We have developed a TbRM (T. brucei microsome) system that imports VSG_117 post-translationally. Using this system, MAL3-101, equisetin and CJ-21,058 were discovered to be small molecule inhibitors of VSG_117 translocation into the ER. These agents also killed bloodstream T. brucei in vitro; the concentrations at which 50% of parasites were killed (IC50) were 1.5 microM (MAL3-101), 3.3 microM (equisetin) and 7 microM (CJ-21,058). Thus VSG_117 import into TbRMs is a rapid and novel assay to identify 'new chemical entities' (e.g. MAL3-101, equisetin and CJ-21,058) for anti-trypanosome drug development.
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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 ╳
