Leptomycin A

Names

[ Name ]:
Leptomycin A

[Synonym ]:
(2E,10E,12E,16E,18E)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-19-(3-methyl-6-oxo-2,3-dihydropyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid
2,10,12,16,18-Nonadecapentaenoic acid,19-(3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl)-3,5,7,9,11,15,17-heptamethyl-6-hydroxy-8-oxo
C32H46O6
2,10,12,16,18-Nonadecapentaenoic acid,19-(3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo
Leptomycin A
Jildamycin

Biological Activity

[Description]:

Leptomycin A, a Streptomyces metabolite, 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. Leptomycin A suppresses HIV-1 replication. Less potent than Leptomycin B[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

Signaling Pathways >> Membrane Transporter/Ion Channel >> CRM1

[Target]

CRM1[1][2].

[References]

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

[2]. Wolff B, et al. Leptomycin B is an inhibitor of nuclear export: inhibition of nucleo-cytoplasmic translocation of the human immunodeficiency virus type 1 (HIV-1) Rev protein and Rev-dependent mRNA. Chem Biol. 1997 Feb;4(2):139-47.

Chemical & Physical Properties

[ Density]:
1.079g/cm3

[ Boiling Point ]:
717.7ºC at 760 mmHg

[ Molecular Formula ]:
C₃₂H₄₆O₆

[ Molecular Weight ]:
526.70400

[ Flash Point ]:
224.2ºC

[ Exact Mass ]:
526.32900

[ PSA ]:
100.90000

[ LogP ]:
6.39460

[ Index of Refraction ]:
1.544

[ Storage condition ]:
?20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RA5391000

CHEMICAL NAME :: 2,10,12,16,18-Nonadecapentaenoic acid, 19-(3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl)- 3,5,7,9,11,15,17-heptamethyl-6-hydroxy-8-oxo-

CAS REGISTRY NUMBER :: 87081-36-5

LAST UPDATED :: 199401

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C32-H46-O6

MOLECULAR WEIGHT :: 526.78

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Yeast - Schizosaccharomyces pombe

DOSE/DURATION :: 10 ug/L

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 38,1573,1985

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Hazard Codes ]:
F,T

[ Risk Phrases ]:
11-23/24/25-39/23/24/25

[ Safety Phrases ]:
16-36/37-45

[ RIDADR ]:
UN 1230 3/PG 2

Articles

Serine residue 115 of MAPK-activated protein kinase MK5 is crucial for its PKA-regulated nuclear export and biological function.

Cell. Mol. Life Sci. 68 , 847-62, (2011)

The mitogen-activated protein kinase-activated protein kinase-5 (MK5) resides predominantly in the nucleus of resting cells, but p38(MAPK), extracellular signal-regulated kinases-3 and -4 (ERK3 and ER...

Leptomycins A and B, new antifungal antibiotics. I. Taxonomy of the producing strain and their fermentation, purification and characterization.

J. Antibiot. 36(6) , 639-45, (1983)

A strain of Streptomyces was found to produce new antifungal antibiotics. The active compounds were purified and separated into two substances named leptomycin A and B by high performance liquid chrom...

Leptomycins A and B, new antifungal antibiotics. II. Structure elucidation.

J. Antibiot. 36(6) , 646-50, (1983)

The structures of new antifungal antibiotics, leptomycins A and B produced by Streptomyces sp. ATS1287 were determined as described below (Fig. 1) on the basis of their spectral and chemical character...

Related Compounds

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