Swinholide A
Product Code: AG-CN2-0035
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0035-C010 | 10 ug | £100.00 |
Quantity:
| AG-CN2-0035-C050 | 50 ug | £260.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4deg;C
Documents
Further Information
Appearance:
Colorless oil.
CAS:
95927-67-6
EClass:
32160000
Form (Short):
liquid
InChi:
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
InChiKey:
RJVBVECTCMRNFG-VGHOFLFQSA-N
Long Description:
Chemical. CAS: 95927-67-6. Formula: C78H132O20. MW: 1389.9. Isolated from marine sponge Theonella swinhoei. Cell permeable dimeric dilactone macrolide. Cytotoxic compound. Specific actin filament (F-actin) inhibitor. Disrupts the actin cytoskeleton by sequestering actin dimers and rapidly severing actin filaments (F-actin). Depolymerizes actin filaments (F-actin). Antifungal. Apoptosis inducer. Alterates the actin cytoskeleton of GH4 cells and inhibits insulin-increased prolactin gene transcription.
MDL:
MFCD01861928
Molecular Formula:
C78H132O20
Molecular Weight:
1389.9
Package Type:
Vial
Product 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].
Purity:
>98% (HPLC)
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=CC(C)=CC[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=CC(C)=CC[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
Solubility Chemicals:
Soluble in ethanol, methanol, DMSO, acetone or ethyl acetate.
Source / Host:
Isolated from marine sponge Theonella swinhoei.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
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. Genesca, 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)
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