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S9810

Sigma-Aldrich

Swinholide A from Theonella swinhoei

≥80% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C78H132O20
Molecular Weight:
1389.87
UNSPSC Code:
12352204
PubChem Substance ID:
329824634
NACRES:
NA.83

assay

≥80% (HPLC)

storage temp.

−20°C

SMILES string

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]4O[C@@H](CC=C4)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]5C[C@@H](C[C@H](C)O5)OC)C1

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)33-25-45)55(11)75(87)47(3)27-31-63-39-65(89-13)35-49(5)93-63/h17-20,23-26,33-34,47-72,75-84,87-88H,21-22,27-32,35-44H2,1-16H3/b33-25+,34-26+,45-23+,46-24+/t47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65+,66+,67-,68-,69+,70+,71-,72-,75-,76-,77-,78-/m0/s1

InChI key

RJVBVECTCMRNFG-ANKJNSLFSA-N

Application

A valuable molecular probe that sequesters actin dimers in vitro in both polymerizing and non-polymerizing buffers with a binding stoichiometry of 1:1. It also rapidly severs F-actin.

Packaging

Packaged under argon.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLBT3629
SLBQ7007V
SLBP9596V
SLBN9672V
SLBN7654V

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S Y Saito et al.
Journal of biochemistry, 123(4), 571-578 (1998-05-21)
We compared the effects of dimeric marine toxins, bistheonellide A, and swinholide A, on actin polymerization. Bistheonellide A and swinholide A possess two identical side chains with similar structures to those of other marine toxins, mycalolide B, and aplyronine A.
M R Bubb et al.
The Journal of biological chemistry, 270(8), 3463-3466 (1995-02-24)
Swinholide A, isolated from the marien sponge Theonella swinhoei, is a 44-carbon ring dimeric dilactone macrolide with a 2-fold axis of symmetry. Recent studies have elucidated its unusual structure and shown that it has potent cytotoxic activity. We now report
Stéphane Vassilopoulos et al.
Nature communications, 10(1), 5803-5803 (2019-12-22)
Recent super-resolution microscopy studies have unveiled a periodic scaffold of actin rings regularly spaced by spectrins under the plasma membrane of axons. However, ultrastructural details are unknown, limiting a molecular and mechanistic understanding of these enigmatic structures. Here, we combine

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