IsoapoptolidinA ring expanded isomer of apoptolidin

Isoapoptolidin (CAS 476647-30-0)

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Application: A ring expanded isomer of apoptolidin
CAS Number: 476647-30-0
Purity: >90%
Molecular Weight: 1129.4
Molecular Formula: C58H96O21
* Refer to Certificate of Analysis for lot specific data (including water content).
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Isopoptolidin, originally isolated from a Nocardiopsis sp., is a ring expanded isomer of apoptolidin. In water, an equilibrium mixture of apoptolidin:isoapoptolidin (~1.5:1) is formed within hours. In a rapid F0F1-ATPase assay, isoapoptolidin exhibited an IC50 of 17 μM compared to 0.7 μM for apoptolidin. Isoapoptolidin is an inhibitor of ATP5.


References

1. Isoapoptolidin: structure and activity of the ring-expanded isomer of apoptolidin. Wender P.A. et al. Org. Lett. 2002, 4, 3819. 2. Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin. Pennington J. D. et al. Org. Lett. 2002, 4, 3823. 3. Apoptolidin analogs and derivatives for inducing apoptosis in transformed cells. Wender P.A. et al. US Patent Application, 20040180841.

Appearance :
Lyophilized
Physical State :
Solid
Derived From :
Amycolatopsis sp.
Solubility :
Soluble in DMSO, ethanol, methanol, and DMF.
Storage :
Store at -20° C
IC50 :
F0F1-ATPase: IC50 = 17 µM (yeast); apoptolidin: IC50 = 0.7 µM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
16760498
MDL Number :
MFCD11111609
SMILES :
CC1C=C(C=C(C=C(C(=O)OC(C(CC(C(CCC=C(C=CC1OC2C(C(C(C(O2)C)OC)O)O)C)O)OC)O)C3(C(C(C(C(O3)CC(COC)OC4CC(C(C(O4)C)OC5CC(C(C(O5)C)O)OC)(C)O)C)O)C)O)C)C)C

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Certificate of Analysis

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