Swinholide A

Specifications / Handling

More Information
Product Details
Product Type	Chemical
Properties
Formula	C₇₈H₁₃₂O₂₀
MW	1389.9
CAS	95927-67-6
Source/Host Chemicals	Isolated from marine sponge Theonella swinhoei.
Purity Chemicals	≥98% (HPLC)
Appearance	Colorless oil.
Solubility	Soluble in ethanol, methanol, DMSO, acetone or ethyl acetate.
InChi Key	RJVBVECTCMRNFG-VGHOFLFQSA-N
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
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

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].

Product 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. Genescà, 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)
Pointed-end processive elongation of actin filaments by Vibrio effectors VopF and VopL: E. Kudryashova, et al.; Sci. Adv. 8, eadc9239 (2022)

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