Merck
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SML0907

Sigma-Aldrich

Apoptolidin A Ready Made Solution

1 mg/mL in DMSO

Synonym(s):
Apoptolidin, FU 40A
Empirical Formula (Hill Notation):
C58H96O21
CAS Number:
Molecular Weight:
1129.37
EC Number:
PubChem Substance ID:

biological source

Amycolatopsis sp.

Quality Level

form

DMSO solution

concentration

1 mg/mL in DMSO

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

shipped in

dry ice

storage temp.

−20°C

SMILES string

CC(/C=C1\C)=C\C(C)=C\[C@@H](C)[C@H](O[C@H]2[C@@H](O)[C@H](O)[C@@H](OC)[C@H](C)O2)/C=C/C(C)=C/CC[C@H](O)[C@@H](OC)CC([C@H]([C@]3([C@H](C)[C@@H](O)[C@@H](C)C(C[C@H](COC)O[C@H]4C[C@@](O)(C)[C@@H](O[C@H]5C[C@@H](OC)[C@H](O)[C@H](C)O5)[C@H](C)O4)O3)O)O)OC1=O

InChI

1S/C58H96O21/c1-29-17-16-18-40(59)43(69-13)25-45(76-55(65)33(5)23-31(3)21-30(2)22-32(4)41(20-19-29)77-56-51(63)50(62)52(71-15)37(9)74-56)53(64)58(67)35(7)48(60)34(6)42(79-58)24-39(28-68-12)75-47-27-57(11,66)54(38(10)73-47)78-46-26-44(70-14)49(61)36(8)72-46/h17,19-23,32,34-54,56,59-64,66-67H,16,18,24-28H2,1-15H3/b20-19+,29-17+,30-22+,31-21+,33-23+/t32-,34+,35-,36+,37+,38+,39-,40+,41-,42?,43+,44-,45?,46+,47+,48+,49-,50+,51+,52+,53-,54+,56+,57+,58-/m1/s1

InChI key

WILMROCKORZEMQ-XIQAQMKHSA-N

General description

Chemical structure: macrolide

Biochem/physiol Actions

Apoptolidin A is a 20-membered macrolide shown to be selectively cytotoxic against several cancer cell lines and noncytotoxic against normal cells. The molecule was originally produced by Nocardiopsis species, and its target site was identified as mitochondrial F0F1-ATPase.
Apoptolidin induces apoptosis selectively in rat glia cells transformed with the adenovirus oncogene E1A. Several minor apoptolidin congeners were isolated, known as Apoptolidins A-D. All apoptolidins were reported to inhibit growth of H292 cancer cells (lung carcinoma) in the submicromolar range. Recently, a stereo-selective synthesis of the Apoptolidin disaccharide was reported.

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

188.6 °F

Flash Point(C)

87 °C

Certificate of Analysis

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Certificate of Origin

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