Apoptolidin

Apoptolidin is a polyketide isolated from Nocardiopsis bacteria[1]. Apoptolidin is a selective mitochondrial F1FO ATPase inhibitor. Apoptolidin is an apoptosis inducer and induces apoptotic cell death in cells transformed with the adenovirus type 12 oncogenes including ElA (IC50=10-17 ng/ml) but not in normal cells.

Product information

CAS Number: 194874-06-1

Molecular Weight: 1129.37

Formula: C58H96O21

Chemical Name: (9R, 10R, 17S, 18S, 20S)-10-{[(2R, 3S, 4S, 5R, 6S)-3, 4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}-20-[(R)-[(2R, 3R, 4S, 5R, 6R)-2, 4-dihydroxy-6-[(2R)-2-{[(2R, 4S, 5S, 6S)-4-hydroxy-5-{[(2S, 4R, 5R, 6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4, 6-dimethyloxan-2-yl]oxy}-3-methoxypropyl]-3, 5-dimethyloxan-2-yl](hydroxy)methyl]-17-hydroxy-18-methoxy-3, 5, 7, 9, 13-pentamethyl-1-oxacycloicosa-3, 5, 7, 11, 13-pentaen-2-one

Smiles: C[C@]1(O)C[C@H](O[C@@H](COC)C[C@H]2O[C@@](O)([C@H](O)[C@@H]3C[C@H](OC)[C@@H](O)CCC=C(C)C=C[C@@H](O[C@@H]4O[C@@H](C)[C@H](OC)[C@@H](O)[C@@H]4O)[C@H](C)C=C(C)C=C(C)C=C(C)C(=O)O3)[C@H](C)[C@@H](O)[C@H]2C)O[C@@H](C)[C@@H]1O[C@H]1C[C@@H](OC)[C@H](O)[C@@H](C)O1 |c:26,47,50,53,t:29|

InChiKey: WILMROCKORZEMQ-XMRJXNIMSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Apoptolidin has cytotoxicity against normal and transformed cells, it against RG-E1A-7, RG-E1A19K-2, RG-E1A54K-9, RG-E1-4 and Adl2-3Y1 with IC50 values of 11 ng/ml, 10 ng/ml, 13 ng/ml, 10 ng/ml and 17 ng/ml, respectively.

References:

1. J W Kim, et al. Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp. J Antibiot (Tokyo). 1997 Jul;50(7):628-30.
2. A R Salomon, et al. Understanding and exploiting the mechanistic basis for selectivity of polyketide inhibitors of F(0)F(1)-ATPase. Proc Natl Acad Sci U S A. 2000 Dec 19;97(26):14766-71.

Products are for research use only. Not for human use.