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L2913

Sigma-Aldrich

Leptomycin B

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

Sinonimo/i:

Antibiotic CI 940, Elactocin, LMB, Mantuamycin

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About This Item

Formula empirica (notazione di Hill):
C33H48O6
Numero CAS:
87081-35-4
Peso molecolare:
540.73
Numero MDL:
MFCD06795848
Codice UNSPSC:
12352200
ID PubChem:
24896330
NACRES:
NA.77

product name

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

Livello qualitativo

300

Saggio

≥95% (HPLC)

Condizioni di stoccaggio

protect from light

Spettro attività antibiotica

fungi

Modalità d’azione

protein synthesis | interferes

Condizioni di spedizione

dry ice

Temperatura di conservazione

−20°C

Stringa SMILE

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
YACHGFWEQXFSBS-XYERBDPFSA-N

Descrizione generale

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.

Azioni biochim/fisiol

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.

Avvertenze

Danger

Indicazioni di pericolo

H225,H301 + H311 + H331,H370

Classi di pericolo

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

Organi bersaglio

Eyes

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

64.4 °F - closed cup

Punto d’infiammabilità (°C)

18 °C - closed cup

Certificati d'analisi (COA)

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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
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
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
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
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