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Merck

L2913

Leptomycin B

from Streptomyces sp., ≥95% (HPLC), solution, nuclear transport inhibitor

Synonyme(s) :

Antibiotic CI 940, Elactocin, LMB, Mantuamycin

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A propos de cet article

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

Principaux documents

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Nom du produit

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

SMILES string

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

InChI key

YACHGFWEQXFSBS-XYERBDPFSA-N

assay

≥95% (HPLC)

storage condition

protect from light

antibiotic activity spectrum

fungi

mode of action

protein synthesis | interferes

shipped in

dry ice

storage temp.

−20°C

Quality Level

300

Catégories apparentées

Biochem/physiol Actions

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.

General description

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.

signalword

Danger

Hazard Classifications

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

target_organs

Eyes

Classe de stockage

3 - Flammable liquids

wgk

WGK 2

flash_point_f

64.4 °F - closed cup

flash_point_c

18 °C - closed cup

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Certificats d'analyse (COA)

Lot/Batch Number
0000453302
0000453302
0000433139
0000433139
0000368968

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Consulter la Bibliothèque de documents

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
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
N Kudo et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(16), 9112-9117 (1999-08-04)
The cellular target of leptomycin B (LMB), a nuclear export inhibitor, has been identified as CRM1 (exportin 1), an evolutionarily conserved receptor for the nuclear export signal of proteins. However, the mechanism by which LMB inhibits CRM1 still remains unclear.
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
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