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ProductsBack/Swinholide A [95927-67-6]
Chemical Structure
Chemical Structure
Chemical Structure

Swinholide A [95927-67-6]

Research Use Only
AG-CN2-0035
AdipoGen Life Sciences
CAS Number95927-67-6
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Product group Chemicals
Estimated Purity>97% (HPLC)
Molecular Weight1389.9
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Swinholide A [95927-67-6]
  • Delivery Days Customer
    10
  • CAS Number
    95927-67-6
  • Certification
    Research Use Only
  • Estimated Purity
    >97% (HPLC)
  • Hazard Information
    Non-hazardous
  • Molecular Formula
    C78H132O20
  • Molecular Weight
    1389.9
  • Scientific Description
    Cell permeable dimeric dilactone macrolide [1]. Cytotoxic compound [1, 2, 7]. Specific actin filament (F-actin) inhibitor. Disrupts the actin cytoskeleton by sequestering actin dimers and rapidly severing actin filaments (F-actin) [3, 5, 7, 8]. Depolymerizes actin filaments (F-actin) [6]. Antifungal [4]. Apoptosis inducer [9]. Alterates the actin cytoskeleton of GH4 cells and inhibits insulin-increased prolactin gene transcription [10]. - Chemical. CAS: 95927-67-6. Formula: C78H132O20. MW: 1389.9. Isolated from marine sponge Theonella swinhoei. Cell permeable dimeric dilactone macrolide. Cytotoxic compound. Specific actin filament (F-actin) inhibitor. Disrupts the actin cytoskeleton by sequestering actin dimers and rapidly severing actin filaments (F-actin). Depolymerizes actin filaments (F-actin). Antifungal. Apoptosis inducer. Alterates the actin cytoskeleton of GH4 cells and inhibits insulin-increased prolactin gene transcription.
  • SMILES
    CO[C@@H]1C[C@H](C)O[C@@H](CC[C@H](C)[C@H](O)[C@H](C)[C@H]2OC(=O)\C=C\C(\C)=C\C[C@H](O)C[C@@H]3O[C@@H](CC=C3)C[C@H](OC)[C@@H](C)[C@@H](O)C[C@@H](O)[C@H](C)[C@H](OC(=O)\C=C\C(\C)=C\C[C@H](O)C[C@H]3O[C@@H](CC=C3)C[C@H](OC)[C@@H](C)[C@@H](O)C[C@@H](O)[C@@H]2C)[C@@H](C)[C@@H](O)[C@@H](C)CC[C@H]2C[C@@H](C[C@H](C)O2)OC)C1
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

References

  • Marine natural products. XXIII. Three new cytotoxic dimeric macrolides, swinholides B and C and isoswinholide A, congeners of swinholide A, from the Okinawan marine sponge Theonella swinhoei: M. Kobayashi, et al.; Chem. Pharm. Bull. (Tokyo) 38, 2960 (1990)
  • Marine natural products. XXXI. Structure-activity correlation of a potent cytotoxic dimeric macrolide swinholide A, from the Okinawan marine sponge Theonella swinhoei, and its isomers: M. Kobayashi, et al.; Chem. Pharm. Bull. (Tokyo) 42, 19 (1994)
  • Swinholide A is a microfilament disrupting marine toxin that stabilizes actin dimers and severs actin filaments: M.R. Bubb, et al.; J. Biol. Chem. 270, 3463 (1995)
  • Two classes of metabolites from Theonella swinhoei are localized in distinct populations of bacterial symbionts: C.A. Bewley, et al.; Experientia 52, 716 (1996)
  • Use of the F-actin-binding drugs, misakinolide A and swinholide A: M.R. Bubb & I. Spector; Methods Enzymol. 298, 26 (1998)
  • Actin-depolymerizing effect of dimeric macrolides, bistheonellide A and swinholide A: S.Y. Saito, et al.; J. Biochem. 123, 571 (1998)
  • Actin-binding marine macrolides: total synthesis and biological importance: K.S. Yeung & I. Paterson; Angew. Chem. Int. Ed. Engl. 41, 4632 (2002) (Review)
  • Structural basis of swinholide A binding to actin: V.A. Klenchin, et al.; Chem. Biol. 12, 287 (2005)
  • Actin cytoskeleton derangement induces apoptosis in renal ischemia/reperfusion: M. Genesca, et al.; Apoptosis 11, 563 (2006)
  • Insulin-increased prolactin gene expression requires actin treadmilling: potential role for p21 activated kinase: F.M. Stanley; Endocrinol. 148, 5874 (2007)