574776

Swinholide A, Theonella swinhoei

A dimeric dilactone macrolide that is cytotoxic to a variety of cancer cell lines in vitro.

• Synonym(s): Swinholide A, Theonella swinhoei
• Empirical Formula (Hill Notation): C₇₈H₁₃₂O₂₀
• CAS Number: 95927-67-6
• Molecular Weight: 1389.87
• MDL number: MFCD01861928
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: oil
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: colorless
• solubility: acetone: soluble; ethanol: soluble
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: O1[C@H](C[C@@H](C[C@@H]1C)OC)CC[C@@H]([C@H](O)[C@@H]([C@H]2OC(=O)\C=C\C(=C\C[C@@H](C[C@H]3O[C@H](C[C@@H]([C@H]([C@H](C[C@H]([C@@H]([C@H](OC(=O)\C=C\C(=C\C[C@@H](C[C@H]5O[C@H](C[C@@H]([C@H]([C@H](C[C@H]([C@@H]2C)O)O)C)OC)CC=C5)O)\C)[C@H]([C@@H](O)[C@H](CC[
• InChI: 1S/C78H132O20/c1-45-23-29-57(79)37-59-19-17-21-61(95-59)41-71(91-15)52(8)68(82)44-70(84)54(10)78(56(12)76(88)48(4)28-32-64-40-66(90-14)36-50(6)94-64)98-74(86)34-26-46(2)24-30-58(80)38-60-20-18-22-62(96-60)42-72(92-16)51(7)67(81)43-69(83)53(9)77(97-73(85)3

Description

General description

A dimeric dilactone macrolide isolated from the marine sponge Theonella swinhoei. Cytotoxic to a variety of cancer cell lines in vitro. Disrupts the actin cytoskeleton by sequestering actin dimers with a binding stoichiometry of 1:1, and rapidly severing F-actin. Also possesses antifungal activity.

A dimeric dilactone macrolide that is cytotoxic to a variety of cancer cell lines in vitro. Disrupts the actin cytoskeleton by sequestering actin dimers with a binding stoichiometry of 1:1, and rapidly severing F-actin. Also possesses antifungal properties.

Biochem/physiol Actions

Cell permeable: no

Primary Target
Disrupts the actin cytoskeleton

Product does not compete with ATP.

Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Saito, S.Y., et al. 1998. J. Biochem. (Tokyo) 123, 571.
Bubb, M.R., et al. 1995. J. Biol. Chem. 270, 3463.
Kobayashi, M., et al. 1994. Chem. Pharm. Bull. 42, 19.
Doi, M., et al. 1991. J. Org. Chem. 56, 3629.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Hazard Statements: H413
• Precautionary Statements: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable