Leptomycin

Source: Wikipedia, the free encyclopedia.
Leptomycin B
Names
Preferred IUPAC name
(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-Ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.125.530 Edit this at Wikidata
UNII
  • InChI=1S/C33H48O6/c1-9-28(14-15-29-24(5)13-16-31(36)39-29)19-22(3)12-10-11-21(2)17-25(6)32(37)27(8)33(38)26(7)18-23(4)20-30(34)35/h10-11,13-17,19-20,22,24-27,29,33,38H,9,12,18H2,1-8H3,(H,34,35)/b11-10+,15-14+,21-17+,23-20+,28-19+/t22-,24+,25-,26+,27-,29+,33-/m1/s1 checkY
    Key: YACHGFWEQXFSBS-RJXCBBHPSA-N checkY
  • InChI=1/C33H48O6/c1-9-28(14-15-29-24(5)13-16-31(36)39-29)19-22(3)12-10-11-21(2)17-25(6)32(37)27(8)33(38)26(7)18-23(4)20-30(34)35/h10-11,13-17,19-20,22,24-27,29,33,38H,9,12,18H2,1-8H3,(H,34,35)/b11-10+,15-14+,21-17+,23-20+,28-19+/t22-,24+,25-,26+,27-,29+,33-/m1/s1
    Key: YACHGFWEQXFSBS-RJXCBBHPBE
  • OC(=O)\C=C(/C)C[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)/C=C(\C)/C=C/C[C@@H](C)\C=C(/CC)\C=C\[C@@H]1OC(=O)/C=C\[C@@H]1C
Properties
C33H48O6
Molar mass 540.741 g·mol−1
Density 1.072 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Leptomycins are secondary metabolites produced by Streptomyces spp.

Leptomycin B (LMB) was originally discovered as a potent

antifungal compound. [1] Leptomycin B was found to cause cell elongation of the fission yeast Schizosaccharomyces pombe. Since then this elongation effect has been used for the bioassay of leptomycin. However, recent data shows that leptomycin causes G1 cell cycle arrest in mammalian cells and is a potent anti-tumor agent against murine experimental tumors in combination therapy.[2]

Leptomycin B has been shown to be a potent and specific nuclear export inhibitor in humans

ribonucleoproteins.[citation needed
]

Leptomycin A (LPA) was discovered together with LMB. LMB is twice as potent as LPA.[clarification needed]

See also

References

  1. PMID 6874586
    .
  2. PMID 22412944
    .
  3. PMID 9683540
    .
  4. PMID 8119981
    .
  5. PMID 10430904
    .
  6. PMID 10900010
    .

External links

Original data copied with permission from Leptomycin B manufacturer product page (Fermentek)

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