SML0907

Apoptolidin A Ready Made Solution

1 mg/mL in DMSO

• Synonym(s): Apoptolidin, FU 40A
• Empirical Formula (Hill Notation): C₅₈H₉₆O₂₁
• CAS Number: 194874-06-1
• Molecular Weight: 1129.37
• EC Number: 200-664-3
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825615
• NACRES: NA.77

Properties

• biological source: Amycolatopsis sp.
• Quality Level: 200
• 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

Description

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.

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 2
• flash_point_f: 188.6 °F
• flash_point_c: 87 °C