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Swinholide A, Theonella swinhoei

Name: Swinholide A, <i>Theonella swinhoei</i>
Brand: MM

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

Synonym(s):

Swinholide A, Theonella swinhoei

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About This Item

Empirical Formula (Hill Notation):

C₇₈H₁₃₂O₂₀

CAS Number:

95927-67-6

Molecular Weight:

1389.87

MDL number:

MFCD01861928

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

oil

Quality level:

100

Storage condition:

OK to freeze, protect from light

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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

InChI key

RJVBVECTCMRNFG-ANKJNSLFSA-N

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

Preparation Note

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

Disclaimer

Toxicity: Standard Handling (A)

hcodes

H413

pcodes

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class

10 - Combustible liquids

flash_point_f

Not applicable

flash_point_c