An inhibitor of nuclear transport
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Leptomycin A

Item No. 21762

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E,6R)-19-[(2S,3S)-3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl]-6-hydroxy-3,5S,7S,9R,11,15R,17-heptamethyl-8-oxo-2,10E,12E,16Z,18E-nonadecapentaenoic acid
CAS Number
87081-36-5
Synonyms
  • NSC 369326
Molecular Formula
C32H46O6
Formula Weight
526.7
Purity
≥99%
Formulation (Request formulation change)
A solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: SolubleMethanol: Soluble
SMILES
O=C1O[C@@H](/C=C/C(C)=C\[C@H](C)C/C=C/C(C)=C/[C@H](C([C@H]([C@@H]([C@H](C/C(C)=C/C(O)=O)C)O)C)=O)C)[C@@H](C)C=C1
InChi Code
InChI=1S/C32H46O6/c1-20(16-22(3)12-14-28-24(5)13-15-30(35)38-28)10-9-11-21(2)17-25(6)31(36)27(8)32(37)26(7)18-23(4)19-29(33)34/h9,11-17,19-20,24-28,32,37H,10,18H2,1-8H3,(H,33,34)/b11-9+,14-12+,21-17+,22-16-,23-19+/t20-,24+,25-,26+,27-,28+,32-/m1/s1
InChi Key
QECBVZBMGUAZDL-WRDLAOIUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Leptomycin A is an inhibitor of CRM1 (exportin 1) that blocks CRM1 interaction with nuclear export signals, preventing the nuclear export of a broad range of proteins.1 Leptomycin A inhibits Rev translocation, though less potently than leptomycin B (Item No. 10004976) with IC50 values of 0.8 and 0.1 nM, respectively after 7 hours.2 Rev export to the cytoplasm is required for HIV-1 replication. Leptomycin A was originally identified as an antifungal agent.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kudo, N., Wolff, B., Sekimoto, T., et al. Leptomycin B inhibition of signal-mediated nuclear export by direct binding to CRM1. Exp. Cell Res. 242(2), 540-547 (1998).

    2. Wang, Y., Ponelle, M., Sanglier, J.-J., et al. Novel leptomycins from a Streptomyces strain A92-308902: Inhibitors of the nucleo-cytoplasmic translocation of the HIV-1 regulatory protein rev. Helv. Chim. Acta. 80(7), 2157-2167 (1997).