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AdipoGen Life Sciences
Swinholide A
120
CHF
CHF 120.00
In stock
AG-CN2-0035-C01010 µgCHF 120.00
AG-CN2-0035-C05050 µgCHF 350.00
| 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 |
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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