194874-06-1 Usage
Description
Apoptolidin (194874-06-1) is a powerful inducer of apoptosis in a variety of cancer cell lines.1?Is believed to act via inhibition of F0F1-ATPase2?but correlation studies indicate that a second mechanism may be the actual mode of action3.? Cell permeable.
Uses
Apoptolidin, originally isolated from a Nocardiopsis sp., induces apoptotic cell death in rat glial cells transformed with the adenovirus E1A oncogene (IC50 = 11 ng/ml). Apoptolidin is among the most selective cytotoxic agents tested by the NCI in human cancer cell lines. Although the apoptotic activity of apoptolidin correlates with F0F1-ATPase inhibition, recent evidence suggests the existence of a secondary biological target or more complex mode of action.
References
1) Kim et al. (1997), Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp.; J. Antibiot. (Tokyo), 50 628
2) Salomon et al. (2001), Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase; Chem. Biol., 8 71
3) Wender et al. (2006), Correlation of F0F1-ATPase inhibition and antiproliferative activity of apoptolidin analogues; Org. Lett., 8 589
Check Digit Verification of cas no
The CAS Registry Mumber 194874-06-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,4,8,7 and 4 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 194874-06:
(8*1)+(7*9)+(6*4)+(5*8)+(4*7)+(3*4)+(2*0)+(1*6)=181
181 % 10 = 1
So 194874-06-1 is a valid CAS Registry Number.
194874-06-1Relevant articles and documents
Isoapoptolidin: structure and activity of the ring-expanded isomer of apoptolidin.
Wender, Paul A,Gulledge, Aaron V,Jankowski, Orion D,Seto, Haruo
, p. 3819 - 3822 (2002)
[formula: see text] Apoptolidin (1) is a novel oncolytic lead that induces apoptosis in transformed cell lines with exceptional selectivity. We report the isolation and characterization of a ring-expanded macrolide isomer of apoptolidin: isoapoptolidin (2). The solution conformation of isoapoptolidin is described. The rate of isomerization was measured under biologically relevant conditions and found to approach equilibrium within the time frame of most cell-based assays. Isoapoptolidin's ability to inhibit mitochondrial F0F1-ATPase is over 10-fold less than that of apoptolidin.
Total synthesis of apoptolidin: Part 2. Coupling of key building blocks and completion of the synthesis
Nicolaou,Li, Yiwei,Fylaktakidou, Konstantina C.,Mitchell, Helen J.,Sugita, Kazuyuki
, p. 3854 - 3857 (2007/10/03)
No less than 30 stereogenic elements, a highly unsaturated 20-membered macrocyclic system, four carbohydrate units, and unique biological activity, make the natural occurring apoptolidin (1) a challenging synthetic target. The retrosynthetic analysis reve
