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L2913

Sigma-Aldrich

Leptomycin B

from Streptomyces sp., ≥95% (HPLC), solution, anti-fungal antibiotic

Synonyme(s) :

Antibiotic CI 940, Elactocin, LMB, Mantuamycin

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About This Item

Formule empirique (notation de Hill):
C33H48O6
Numéro CAS:
87081-35-4
Poids moléculaire :
540.73
Numéro MDL:
MFCD06795848
Code UNSPSC :
12352200
ID de substance PubChem :
24896330
Nomenclature NACRES :
NA.77

product name

Leptomycin B solution from Streptomyces sp., ≥95% (HPLC), Supplied in methanol: water (7:3)

Niveau de qualité

300

Pureté

≥95% (HPLC)

Conditions de stockage

protect from light

Spectre d'activité de l'antibiotique

fungi

Mode d’action

protein synthesis | interferes

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

CCC(\C=C\[C@@H]1OC(=O)C=C[C@@H]1C)=C\[C@H](C)C\C=C\C(C)=C\[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C\C(C)=C\C(O)=O

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

Clé InChI

YACHGFWEQXFSBS-XYERBDPFSA-N

Description générale

Leptomycin B is an anti-fungal antibiotic, anti-tumor cytotoxin that inhibits CRM1-dependent, NES-dependent nucleo-cytoplasmic translocation (nuclear export inhibitor). NES containing proteins include HIV-1 REV; actin, c-Abl, cyclin B1, MDM2/p53, I?B, MPF, PKA and MEK.

Actions biochimiques/physiologiques

Leptomycin B is an unsaturated, branched-chain fatty acid, and is an important tool in the study of nuclear export. Leptomycin B is a specific inhibitor of proteins containing nuclear export signal. Leptomycin B inhibits nucleo-cytoplasmic translocation of molecules such as the HIV-1 Rev protein and Rev-dependent export of mRNA. The addition of very small amounts to fibroblasts causes accumulation of MEK in the nucleus. Other proteins that are influenced by leptomycin B are actin, c-Abl, cyclin B1, MDM2/p53, IκB, MPF, and PKA. The suggested inhibition mechanism involves the direct binding of leptomycin B to CRM1, which blocks the binding of CRM1 to proteins containing the nuclear export signal, via the interaction with cysteine residue in CRM1 control conserved region.

Pictogrammes

FlameSkull and crossbonesHealth hazard
GHS02,GHS06,GHS08

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

Organes cibles

Eyes

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

64.4 °F - closed cup

Point d'éclair (°C)

18 °C - closed cup

Certificats d'analyse (COA)

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K Nishi et al.
The Journal of biological chemistry, 269(9), 6320-6324 (1994-03-04)
The molecular action of leptomycin B (LMB), an agent inducing arrest of the eukaryotic cell cycle at G1 and G2 phases, was investigated by analyzing an LMB resistance gene of Schizosaccharomyces pombe. A genomic library of an LMB-resistant mutant was
D A Freedman et al.
Molecular and cellular biology, 18(12), 7288-7293 (1998-11-20)
The MDM2 oncoprotein targets the p53 tumor suppressor protein for degradation when the two proteins are expressed in cells. The regulation of p53 levels by MDM2 requires the ability of MDM2 to be exported from the nucleus by utilizing its
A Wada et al.
The EMBO journal, 17(6), 1635-1641 (1998-05-02)
Actin is a highly conserved, ubiquitous cytoskeletal protein, which is essential for multiple cellular functions. Despite its small size (Mr = 42 000), unpolymerized forms of actin, as well as polymerized forms, exist primarily in the cytoplasm, excluded from the
M Fukuda et al.
Nature, 390(6657), 308-311 (1997-12-31)
The discovery of nuclear export signals (NESs) in a number of proteins revealed the occurrence of signal-dependent transport of proteins from the nucleus to the cytoplasm. Although the consensus motif of the NESs has been shown to be a leucine-rich
Daisuke Kaida et al.
Nature chemical biology, 3(9), 576-583 (2007-07-24)
The removal of intervening sequences from transcripts is catalyzed by the spliceosome, a multicomponent complex that assembles on the newly synthesized pre-mRNA. Pre-mRNA translation in the cytoplasm leads to the generation of aberrant proteins that are potentially harmful. Therefore, tight
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