21-hydroxyoligomycin A
21-hydroxyoligomycin A Basic information
- Product Name:
- 21-hydroxyoligomycin A
- Synonyms:
-
- 21-hydroxyoligomycin A
- HydroxyoligoMycin A, 21-
- NeMadectin oMega, LL-F28249 oMega
- Spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-[2H]pyran]-3,9,13-trione,22-ethyl-3',4',5',6'-tetrahydro-7,11,14,15,23-pentahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-,(1R,2'S,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,28S,29R)-
- CAS:
- 102042-09-1
- MF:
- C45H74O12
- MW:
- 807.06
- Product Categories:
-
- Antibiotic
- Mol File:
- 102042-09-1.mol
21-hydroxyoligomycin A Chemical Properties
- Boiling point:
- 916.6±65.0 °C(Predicted)
- Density
- 1.17±0.1 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- Soluble in DMSO
- form
- White to off-white powder.
- pka
- 12.52±0.70(Predicted)
21-hydroxyoligomycin A Usage And Synthesis
Uses
21-Hydroxyoligomycin A is a rare member of the oligomycin class isolated as a co-metabolite of nemadectin, hence its original naming as nemadectin omega. Only limited literature references to this metabolite are available. However, in-house testing suggests that 21-hydroxyoligomycin has a more selective action against mammalian tumour cell lines than oligomycin A, exhibiting only weak antifungal and nematocidal activity.
Uses
21-Hydroxyoligomycin A is an oligomycin antibiotic coisolated with nemadectins.
Biological Activity
21-hydroxy oligomycin a is an antibiotic which was first isolated from s. cyaneogriseus ssp.noncyanogenus [1]. 21-hydroxy oligomycin a functions as μm inhibitor of the multidrug efflux pump p-gp, and low nm inhibitors of k-ras pm localization [1].cancer cell viability screening confirmed that 21-hydroxy oligomycin a was cytotoxic to human colorectal carcinoma cells (ic50 > 3 μm), and was inhibitor of the abc transporter efflux pump p-glyco-protein (p-gp). significantly, 21-hydroxy oligomycin a was exceptionally potent inhibitor of k-ras pm localisation with emax of 0.67–0.75 and an ic50 of 1.5–14 nm [1]. 21-hydroxy oligomycin a was inhibitor of k-ras pm localisation in mdck cell with an ic50 of 4.82 ± 0.70 nm. 21-hydroxy oligomycin a was moderately cytotoxic towards both sw620 and sw620 ad300 cells with the ic50 of 14.4 ± 0.6 and 11.8 ± 3.1 μm, respectively. in the flow cytometry assay, 21-hydroxy oligomycin a (20 μm) increased intracellular calcein fluorescence significantly when compared with the negative control [1].
References
[1] salim a a, tan l, huang x c, et al. oligomycins as inhibitors of k-ras plasma membrane localisation[j]. organic & biomolecular chemistry, 2016, 14(2): 711-715.
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