| Identification | Back Directory | [Name]
1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate | [CAS]
241127-58-2 | [Synonyms]
Adaphostin
1-Adamantyl 4-((2
5-Dihydroxybenzyl)Amino)Benzoate
1-Adamantyl 4-((2,5-Dihydroxybenzyl)Amino)Benzoate
1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate
4-[[(2,5-Dihydroxyphenyl)methyl]amino]benzoicacidtricyclo[3.3.1.13,7]dec-1-ylester
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, tricyclo[3.3.1.13,7]dec-1-yl ester
Apoptosis,tyrosine kinase,inhibit,Bcr-Abl,Adaphostin,chronic myelogenous leukemia,myeloid,Inhibitor,ROS,NSC-680410,p210Bcr/abl,NSC680410,CML | [Molecular Formula]
C24H27NO4 | [MDL Number]
MFCD06411386 | [MOL File]
241127-58-2.mol | [Molecular Weight]
393.48 |
| Chemical Properties | Back Directory | [storage temp. ]
Desiccate at +4°C | [solubility ]
DMSO: soluble20mg/mL, clear | [form ]
powder | [color ]
white to beige | [InChI]
1S/C24H27NO4/c26-21-5-6-22(27)19(10-21)14-25-20-3-1-18(2-4-20)23(28)29-24-11-15-7-16(12-24)9-17(8-15)13-24/h1-6,10,15-17,25-27H,7-9,11-14H2/t15-,16+,17-,24- | [InChIKey]
YJZSUCFGHXQWDM-ONHXBKDTSA-N | [SMILES]
O=C(C1=CC=C(NCC2=CC(O)=CC=C2O)C=C1)OC34C[C@@]5([H])C[C@@](C[C@@](C5)([H])C4)([H])C3 |
| Hazard Information | Back Directory | [Uses]
Novel antitumor agent that induces apoptosis in tumor cells through inhibition of the tyrosine kinase BCR/ABL. | [Biological Functions]
Adaphostin is a p210bcr/abl tyrosine kinase inhibitor and a potent inducer of myeloid cell death.
Adaphostin is a p210bcr/abl tyrosine kinase inhibitor displaying anti-proliferative activity in leukemia models, human prostate cancer cell line PC-3 and other cancer cell lines. Adaphostin is a potent inducer of myeloid cell death. Similarly to AG957, adaphostin appears to induce a degradation of WT and mutated Bcr/Abl. | [Biological Activity]
p210 bcr/abl tyrosine kinase inhibitor (IC 50 = 14 μ M). Induces apoptosis in T-lymphoblastic human leukemia cell lines (IC 50 values range from 16.8 to 216.3 nM) in vitro . Displays selectivity for chronic myelogenous leukemia (CML) myeloid progenitors in vitro . | [References]
[1] P A SVINGEN. Effects of the bcr/abl kinase inhibitors AG957 and NSC 680410 on chronic myelogenous leukemia cells in vitro.[J]. Clinical Cancer Research, 2000, 6 1: 237-249.
[2] IOANNIS A AVRAMIS. In vitro and in vivo evaluations of the tyrosine kinase inhibitor NSC 680410 against human leukemia and glioblastoma cell lines.[J]. Cancer Chemotherapy and Pharmacology, 2002, 50 6: 479-489. DOI:10.1007/s00280-002-0507-6.
[3] NADA ORSOLIC. Adaphostin has significant and selective activity against chronic and acute myeloid leukemia cells[J]. Cancer Science, 2006, 97 9: 952-960. DOI:10.1111/j.1349-7006.2006.00269.x.
[4] JOYA CHANDRA. Involvement of reactive oxygen species in adaphostin-induced cytotoxicity in human leukemia cells.[J]. Blood, 2003, 102 13: 4512-4519. DOI:10.1182/blood-2003-02-0562.
[5] KOUTAROH OKADA. Prediction of ALK mutations mediating ALK-TKIs resistance and drug re-purposing to overcome the resistance.[J]. ACS Catalysis , 2019: 105-119. DOI:10.1016/j.ebiom.2019.01.019. |
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