Chlorobiocin
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| Category | Antibiotics |
| Catalog number | BBF-00636 |
| CAS | 39868-96-7 |
| Molecular Weight | 697.13 |
| Molecular Formula | C35H37ClN2O11 |
| Purity | >98% |
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Description
Chlorobiocin is produced by the strain of Streptomyces hygroscopicus DS 9751 and Novobiocin. Chlorobiocin is found to bind at a second ATP-binding site in the C-terminal domain of Hsp90, thus disrupting the dimerization of the Hsp90 complex. IC50 = 60 μmol/L.
Specification
| Synonyms | Clorobiocin; Antibiotic RP 18,631; NSC 227186 |
| Storage | -20°C |
| IUPAC Name | [(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate |
| Canonical SMILES | CC1=CC=C(N1)C(=O)OC2C(C(OC(C2OC)(C)C)OC3=C(C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CC(=C(C=C5)O)CC=C(C)C)O)Cl)O |
| InChI | InChI=1S/C35H37ClN2O11/c1-16(2)7-9-18-15-19(10-13-22(18)39)31(42)38-25-26(40)20-11-14-23(24(36)28(20)47-33(25)44)46-34-27(41)29(30(45-6)35(4,5)49-34)48-32(43)21-12-8-17(3)37-21/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1 |
| InChI Key | FJAQNRBDVKIIKK-LFLQOBSNSA-N |
Properties
| Appearance | White Crystallineline |
| Antibiotic Activity Spectrum | gram-positive bacteria; gram-negative bacteria |
| Melting Point | 206 °C |
| Solubility | Soluble in DMSO |
Reference Reading
1.Identification of synergists that potentiate the action of polymyxin B against Burkholderia cenocepacia.
Loutet SA;El-Halfawy OM;Jassem AN;López JM;Medarde AF;Speert DP;Davies JE;Valvano MA Int J Antimicrob Agents. 2015 Oct;46(4):376-80. doi: 10.1016/j.ijantimicag.2015.05.010. Epub 2015 Jun 22.
Burkholderia cenocepacia and other members of the Burkholderia cepacia complex (BCC) are highly multidrug-resistant bacteria that cause severe pulmonary infections in patients with cystic fibrosis. A screen of 2686 compounds derived from marine organisms identified molecules that could synergise with polymyxin B (PMB) to inhibit the growth of B. cenocepacia. At 1 μg/mL, five compounds synergised with PMB and inhibited the growth of B. cenocepacia by ≥70% compared with growth in PMB alone. Follow-up testing revealed that one compound from the screen, the aminocoumarin antibiotic novobiocin, synergised with PMB and colistin against tobramycin-resistant clinical isolates of B. cenocepacia and Burkholderia multivorans. In parallel, we show that novobiocin sensitivity is common among BCC species and that these bacteria are even more susceptible to an alternative aminocoumarin, clorobiocin, which also had an additive effect with PMB against B. cenocepacia. These studies support using aminocoumarin antibiotics to treat BCC infections and show that synergisers can be found to increase the efficacy of antimicrobial peptides and polymyxins against BCC bacteria.
2.NovG, a DNA-binding protein acting as a positive regulator of novobiocin biosynthesis.
Eustáquio AS;Li SM;Heide L Microbiology. 2005 Jun;151(Pt 6):1949-61.
The biosynthetic gene cluster of the aminocoumarin antibiotic novobiocin contains two putative regulatory genes, i.e. novE and novG. The predicted gene product of novG shows a putative helix-turn-helix DNA-binding motif and shares sequence similarity with StrR, a well-studied pathway-specific transcriptional activator of streptomycin biosynthesis. Here functional proof is provided, by genetic and biochemical approaches, for the role of NovG as a positive regulator of novobiocin biosynthesis. The entire novobiocin cluster of the producer organism Streptomyces spheroides was expressed in the heterologous host Streptomyces coelicolor M512, and additional strains were produced which lacked the novG gene within the heterologously expressed cluster. These Delta novG strains produced only 2% of the novobiocin formed by the S. coelicolor M512 strains carrying the intact novobiocin cluster. The production could be restored by introducing an intact copy of novG into the mutant. The presence of novG on a multicopy plasmid in the strain containing the intact cluster led to almost threefold overproduction of the antibiotic, suggesting that novobiocin biosynthesis is limited by the availability of NovG protein.
3.Novobiocin antagonism of amastigotes of Trypanosoma cruzi growing in cell-free medium.
Pate PG;Wolfson JS;McHugh GL;Pan SC;Swartz MN Antimicrob Agents Chemother. 1986 Mar;29(3):426-31.
Inhibitors of the enzyme bacterial topoisomerase II (DNA gyrase) were evaluated for activity against Trypanosoma cruzi (Brazil strain), based on the theoretical need for a topoisomerase II in the replication of the kinetoplast DNA network. Novobiocin (500 micrograms/ml) antagonized amastigotes of T. cruzi growing in a cell-free medium at 37 degrees C, as manifested by inhibition of multiplication, abnormal morphology of Giemsa-stained organisms, and delayed or absent growth of cells upon subculturing in a drug-free medium. In contrast, novobiocin (1,000 micrograms/ml) essentially had no effect on the multiplication and motility of epimastigotes growing in a cell-free medium at 27 degrees C. This resistance of epimastigotes represented a difference in the physiology of this morphologic stage and not in the temperature of experimentation, because novobiocin inhibited multiplication of amastigotes at 27 degrees C as well and accelerated transformation to epimastigotes. With T. cruzi growing within cultured human fibroblasts, novobiocin (200 micrograms/ml) markedly inhibited transformation of intracellular amastigotes to trypomastigotes. Clorobiocin, a structural analog of novobiocin and likewise an inhibitor of the B subunit of bacterial topoisomerase II, was five times more potent on a molar basis than novobiocin was in antagonism of amastigotes growing in a cell-free medium and did not antagonize epimastigotes.
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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 ╳
