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L2913

Sigma-Aldrich

Leptomycin B

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

Sinónimos:

Antibiotic CI 940, Elactocin, LMB, Mantuamycin

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About This Item

Fórmula empírica (notación de Hill):
C33H48O6
Número de CAS:
87081-35-4
Peso molecular:
540.73
Número MDL:
MFCD06795848
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24896330
NACRES:
NA.77

product name

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

Nivel de calidad

300

Análisis

≥95% (HPLC)

condiciones de almacenamiento

protect from light

espectro de actividad antibiótica

fungi

Modo de acción

protein synthesis | interferes

Condiciones de envío

dry ice

temp. de almacenamiento

−20°C

cadena 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

Clave InChI

YACHGFWEQXFSBS-XYERBDPFSA-N

Descripción general

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.

Acciones bioquímicas o fisiológicas

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.

Palabra de señalización

Danger

Clasificaciones de peligro

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

Órganos de actuación

Eyes

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

64.4 °F - closed cup

Punto de inflamabilidad (°C)

18 °C - closed cup

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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
Marise R Heerma van Voss et al.
OncoTargets and therapy, 10, 3501-3513 (2017-08-02)
DEAD box protein 3 (DDX3) is an RNA helicase with oncogenic properties that shuttles between the cytoplasm and nucleus. The majority of DDX3 is found in the cytoplasm, but a subset of tumors has distinct nuclear DDX3 localization of yet
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