Adaphostin

Names

[ Name ]:
Adaphostin

[Synonym ]:
tyrphostin AG957 adamantyl ester
4'-adamantylbenzoate-1'-N-1,4-dihydroxybenzylamine
AG 957,Adamantyl Ester
Adaphostin

Biological Activity

[Description]:

Adaphostin (NSC 680410), the adamantyl ester of AG957, is a potent p210bcr/abl inhibitor (IC50=14 μM). Adaphostin induces apoptosis in T-lymphoblastic human leukemia cell lines (IC50 ranging from 17 to 216 nM). Adaphostin has significant and selective activity against chronic and acute myeloid leukemia cells. Adaphostin increased the level of reactive oxygen species (ROS) within CLL B cells[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> Bcr-Abl

[In Vitro]

Adaphostin down-regulates p210bcr/abl in K562 cells and inhibits granulocyte colony formation in chronic myelogenous leukemia (CML) specimens at lower concentrations without enhanced toxicity in normal progenitors[1]. Adaphostin-induced p53 up-regulation, DNA strand breaks, and ROS production in ML-1 cells is inhibited by N-acetylcysteine (NAC)[4].

[References]

[1]. Svingen PA, et al. Effects of the bcr/abl kinase inhibitors AG957 and NSC 680410 on chronic myelogenous leukemia cells in vitro. Clin Cancer Res. 2000;6(1):237-249.

[2]. Avramis IA, et al. In vitro and in vivo evaluations of the tyrosine kinase inhibitor NSC 680410 against human leukemia and glioblastoma cell lines. Cancer Chemother Pharmacol. 2002;50(6):479-489.

[3]. Orsolic N, et al. Adaphostin has significant and selective activity against chronic and acute myeloid leukemia cells. Cancer Sci. 2006;97(9):952-960.

[4]. Chandra J, et al. Involvement of reactive oxygen species in adaphostin-induced cytotoxicity in human leukemia cells. Blood. 2003;102(13):4512-4519.

Chemical & Physical Properties

[ Density]:
1.33g/cm3

[ Boiling Point ]:
606.2ºC at 760mmHg

[ Molecular Formula ]:
C₂₄H₂₇NO₄

[ Molecular Weight ]:
393.47500

[ Flash Point ]:
320.4ºC

[ Exact Mass ]:
393.19400

[ PSA ]:
70.00000

[ LogP ]:
4.99130

[ Vapour Pressure ]:
2.73E-15mmHg at 25°C

[ Index of Refraction ]:
1.661

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Adaphostin

Names

Biological Activity

Chemical & Physical Properties

Safety Information

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream