Leptomycin B - ≥98% , CAS No.87081-35-4

CAS: 87081-35-4 Cat. No.: L102387 Peso molecular: 540.73 Número EC: 617-954-4

GRADE & PURITY ≥98%

Synonyms

2,10,12,16,18-Nonadecapentaenoic acid, 19-[(2S,3S)-3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl]-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-,(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)- | 2,10,12,16,18-Nonadecapentanoic acid, 19-(3,6-dihydro-3-methyl-6-oxo-2H

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

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, IB, MPF, PKA and MEK.
Leptomycin B is a potent and specific nuclear export inhibitor. Leptomycin B alkylates and inhibits CRM1 (chromosomal region maintenance)/exportin 1, a protein required for nuclear export of proteins containing a nuclear export sequence (NES). In addition to antifungal and antibacterial activities, Leptomycin B blocks the cell cycle and is a potent anti-tumor agent. At low nM concentrations, Leptomycin B blocks the nuclear export of many proteins including HIV-1 Rev, MAPK/ERK, and NF-κB/IκB, and it stabilizes the expression of p53. Leptomycin B also inhibits the export and translation of many RNAs, including COX-2 and c-Fos mRNAs, by inhibiting export of ribonucleoproteins.

Specifications

Sinónimos

2, 10, 12, 16, 18-Nonadecapentaenoic acid, 19-[(2S, 3S)-3, 6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl]-17-ethyl-6-hydroxy-3, 5, 7, 9, 11, 15-hexamethyl-8-oxo-, (2E, 5S, 6R, 7S, 9R, 10E, 12E, 15R, 16Z, 18E)- | 2, 10, 12, 16, 18-Nonadecapentanoic acid, 19-(3, 6-dihydro-3-methyl-6-oxo-2H

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

Leptomycin B is an unsaturated, branched-chain fatty acid, and is an important tool in the study of nuclear export. It is a specific inhibitor of proteins containing nuclear export signal. It inhibits nucleo-cytoplasmic translocation of molecules such as

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nota

Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 6 months. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: CCC(=CC(C)CC=CC(=CC(C)C(=O)C(C)C(C(C)CC(=CC(=O)O)C)O)C)C=CC1C(C=CC(=O)O1)C
• IUPAC Name: (2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-2,3-dihydropyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid
• InChIKey: YACHGFWEQXFSBS-XYERBDPFSA-N
• 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
• Isómeros SMILES: CC/C(=C/[C@H](C)C/C=C/C(=C/[C@@H](C)C(=O)[C@@H](C)[C@@H]([C@@H](C)C/C(=C/C(=O)O)/C)O)/C)/C=C/[C@H]1[C@H](C=CC(=O)O1)C
• WGK Alemania: 1
• Número ONU: 1230
• Peso molecular: 540.73
• Reaxy-Rn: 28552826
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=28552826&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Very long-chain fatty acids
• Alternative Parents: Diterpene lactones Diterpenoids Methyl-branched fatty acids Hydroxy fatty acids Heterocyclic fatty acids Dihydropyranones Unsaturated fatty acids Beta-hydroxy ketones Dicarboxylic acids and derivatives Enoate esters Secondary alcohols Lactones Oxacyclic compounds Carboxylic acids Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Very long-chain fatty acid - Diterpene lactone - Diterpenoid - Branched fatty acid - Dihydropyranone - Methyl-branched fatty acid - Heterocyclic fatty acid - Hydroxy fatty acid - Beta-hydroxy ketone - Dicarboxylic acid or derivatives - Unsaturated fatty acid - Pyran - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Secondary alcohol - Lactone - Ketone - Organoheterocyclic compound - Oxacycle - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Alcohol - Carbonyl group - Organooxygen compound - Organic oxygen compound - Organic oxide - Aliphatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
• External Descriptors: leptomycin

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

XPO1 Tclin Exportin-1 (2 Activities)

Discover Target: XPO1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PC-3 (62116 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

Influenza A virus (11224 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

COS-7 (515 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MDCK (10148 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in ethanol or methanol. Ethanol is recommended. Unstable in DMSO
• Sensibilidad: Moisture sensitive,Light sensitive
• Punto de inflamación (°F): 64.4 °F
• Punto de inflamación (°C): 18 °C
• Peso molecular: 540.700 g/mol
• XLogP3: 7.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 15
• Exact Mass: 540.345 Da
• Monoisotopic Mass: 540.345 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 1020.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 5
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 5
• Covalently-Bonded Unit Count: 1

Referencias

1. Haiping Liu, Haixiang Ma, Xingyue Zeng, Chengyan Wu, Srijan Acharya, Sarabjeet Kour Sudan, Xiaohan Zhang.  (2023)  Ubiquitination of GRK2 Is Required for the β-Arrestin-Biased Signaling Pathway of Dopamine D2 Receptors to Activate ERK Kinases.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  24  (12): (10031).  [PMID:37373182] [10.3390/ijms241210031]

2. Wu Chengyan, Hu Li, Liu Bing, Zeng Xingyue, Ma Haixiang, Cao Yongkai, Li Huijun, Zhang Xiaohan.  (2024)  TRAF6-mediated ubiquitination of AKT in the nucleus is a critical event underlying the desensitization of G protein-coupled receptors.  Cell Communication and Signaling,  22  (1): (1-21).  [PMID:38566235] [10.1186/s12964-024-01592-z]

3. Li Hu, Haiping Liu, Haixiang Ma, Xingyue Zeng, Yongkai Cao, Bing Liu, Huijun Li, Xiaohan Zhang.  (2024)  TRAF6-mediated ubiquitination of AKT1 in the nucleus occurs in a β-arrestin2-dependent manner upon insulin stimulation.  BIOCHEMICAL PHARMACOLOGY,      [PMID:38871335] [10.1016/j.bcp.2024.116362]

4. Fangdi Wang, Li Hu, Xingyue Zeng, Wenbin You, Huijun Li, Bing Liu, Xiaohan Zhang.  (2025)  Nuclear trafficking of PDK1 in importin7-dependent manner is required for insulin-induced AKT ubiquitination.  LIFE SCIENCES,      [PMID:40921246] [10.1016/j.lfs.2025.123934]

5. Lingzhu Zhao, Guoqing Zhao, Jiaxin Fu, Yan Liu, Jinteng Feng, Guangjian Zhang, Feng Xu, Hui Guo, Min Lin.  (2025)  Programmed Cell Death Protein 1 Engagement Impairs Cytoskeletal Forces and Nuclear Mechanotransduction in T Cells.  ACS Nano,      [PMID:41221724] [10.1021/acsnano.5c10650]

6. Shibei Shao, Li Nan, Rui Liu, Yingjie Zhang, Yantong Pan, Kai Wen, Xuezhi Yu, Jianzhong Shen, Zhanhui Wang.  (2026)  High Affinity Antibodies for the Development of a Specific Immunoassay for the Determination of Bongkrekic Acid in Food.  ANALYTICAL LETTERS,      [PMID:] [10.1080/00032719.2026.2615056]