Curvularol
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01098 |
| CAS | 339293-67-3 |
| Molecular Weight | 266.33 |
| Molecular Formula | C15H22O4 |
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Description
It is produced by the strain of Curvularia sp. RK97-F166. It has weak anti-fungal activity and no anti-bacterial effect. Curvularol of 150 ng/mL inhibits the cell cycle progression of NRK in normal rats at G1 stage. Curvularol of 100 ng/mL can restore the morphology of SRC TS-deformed NRK cells. Like Cycloheximide, it inhibits protein synthesis.
Specification
| Synonyms | (2S,4S,5S,5aR,9aS,10S)-5,5a,8-trimethyl-5a,6,7,9a-tetrahydro-5H-spiro[2,5-methano[1]benzoxepine-4,2'-oxirane]-2,10(3H)-diol |
| IUPAC Name | (1S,2R,7S,9S,11S)-1,2,5-trimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-11,2'-oxirane]-9,12-diol |
| Canonical SMILES | CC1=CC2C(CC1)(C3(C(C(O2)(CC34CO4)O)O)C)C |
| InChI | InChI=1S/C15H22O4/c1-9-4-5-12(2)10(6-9)19-15(17)7-14(8-18-14)13(12,3)11(15)16/h6,10-11,16-17H,4-5,7-8H2,1-3H3/t10-,11?,12-,13+,14+,15-/m0/s1 |
| InChI Key | SSTQGEBHEZQSQQ-HCKLQLJTSA-N |
Properties
| Antibiotic Activity Spectrum | Fungi |
Reference Reading
1. Identification of Saccharomyces cerevisiae ribosomal protein L3 as a target of curvularol, a G1-specific inhibitor of mammalian cells
Yoshifumi Kobayashi, Masaki Mizunuma, Hiroyuki Osada, Tokichi Miyakawa Biosci Biotechnol Biochem. 2006 Oct;70(10):2451-9. doi: 10.1271/bbb.60186. Epub 2006 Oct 7.
The cellular target of curvularol, a G1-specific cell-cycle inhibitor of mammalian cells, was identified by a genetic approach in Saccharomyces cerevisiae. Since the wild-type W303 strain was highly resistant to curvularol, a drug hypersensitive parental strain was constructed in which various genes implicated in general drug resistance had been disrupted. Curvularol resistant mutants were isolated, and strains that exhibited a semi-dominant, curvularol-specific resistance phenotype were selected. All five strains examined were classified into a single genetic complementation group designated YCR1. A mutant gene responsible for curvularol resistance was identified as an allele of the RPL3 gene encoding the ribosomal protein L3. Sequence analysis of the mutant genes revealed that Trp255Cys and Trp255Leu substitutions of Rpl3p are responsible for curvularol resistance. Rpl3p mutants in which Trp255 residue was replaced by other amino acids were constructed. All of these replacements led to varying degrees of increased resistance to curvularol and growth defects.
2. Isolation, and biological properties of a new cell cycle inhibitor, curvularol, isolated from Curvularia sp. RK97-F166
Y Honda, M Ueki, G Okada, R Onose, R Usami, K Horikoshi, H Osada J Antibiot (Tokyo). 2001 Jan;54(1):10-6. doi: 10.7164/antibiotics.54.10.
A new cell growth inhibitor, curvularol, was isolated from the fermentation broth of Curvularia sp. RK97-F166. Curvularol showed no antibacterial activity, and very weak antifungal activity. However, curvularol inhibited the cell cycle progression of normal rat kidney (NRK) cells in G1 phase at 150 ng/ml. Curvularol induced the morphological reversion of srcts-transformed NRK cells at 100 ng/ml, and inhibited protein synthesis same as cycloheximide.
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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 ╳
