3-(3-Phenoxybenzyl)amino-β-carboline

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3-(3-Phenoxybenzyl)amino-β-carboline is a potent tubulin inhibitor. 3-(3-Phenoxybenzyl)amino-β-carboline promotes selective degradation of αβ-tubulin heterodimers. 3-(3-Phenoxybenzyl)amino-β-carboline induces G2/M phase cell cycle arrest and apoptosis. 3-(3-Phenoxybenzyl)amino-β-carboline exhibits anticancer activity.

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3-(3-Phenoxybenzyl)amino-β-carboline Chemical Structure

CAS No. : 1327080-54-5

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Biological Activity
Purity & Documentation
References
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Description

Cellular Effect

Cell Line	Type	Value	Description	References
A2780S	IC₅₀	45 nM Compound: 2	Antiproliferative activity against human A2780S cells assessed as reduction in cell viability measured after 24 hrs by MTT assay Antiproliferative activity against human A2780S cells assessed as reduction in cell viability measured after 24 hrs by MTT assay	[PMID: 35084853]
HeLa	IC₅₀	51 nM Compound: 2	Antiproliferative activity against human HeLa cells assessed as reduction in cell viability measured after 24 hrs by MTT assay Antiproliferative activity against human HeLa cells assessed as reduction in cell viability measured after 24 hrs by MTT assay	[PMID: 35084853]
HeLa S3	IC₅₀	0.074 μM Compound: 10e	Cytotoxicity against human HeLaS3 cells after 24 to 72 hrs by MTT assay Cytotoxicity against human HeLaS3 cells after 24 to 72 hrs by MTT assay	[PMID: 22520257]
HeLa S3	IC₅₀	0.074 μM Compound: 2h	Cytotoxicity against human HeLaS3 cells after 24 to 72 hrs by MTT assay Cytotoxicity against human HeLaS3 cells after 24 to 72 hrs by MTT assay	[PMID: 21752645]
MCF7	IC₅₀	49 nM Compound: 2	Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability measured after 24 hrs by MTT assay Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability measured after 24 hrs by MTT assay	[PMID: 35084853]
NCI-H460	IC₅₀	62 nM Compound: 2	Antiproliferative activity against human NCI-H460 cells assessed as reduction in cell viability measured after 24 hrs by MTT assay Antiproliferative activity against human NCI-H460 cells assessed as reduction in cell viability measured after 24 hrs by MTT assay	[PMID: 35084853]
Raji	IC₅₀	31 nM Compound: 2	Antiproliferative activity against human Raji cells assessed as reduction in cell viability measured after 24 hrs by MTT assay Antiproliferative activity against human Raji cells assessed as reduction in cell viability measured after 24 hrs by MTT assay	[PMID: 35084853]
Sarcoma-180	IC₅₀	0.03 μM Compound: 10e	Cytotoxicity against mouse Sarcoma 180 cells after 24 to 72 hrs by MTT assay Cytotoxicity against mouse Sarcoma 180 cells after 24 to 72 hrs by MTT assay	[PMID: 22520257]

In Vitro

3-(3-Phenoxybenzyl)amino-β-carboline specifically denatures tubulin, making it prone to aggregation that predisposes it to ubiquitinylation and then degradation^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

365.43

Formula

C₂₄H₁₉N₃O

CAS No.

1327080-54-5

SMILES

C(N1)(C=NC(NCC2=CC=CC(OC3=CC=CC=C3)=C2)=C4)=C4C5=C1C=CC=C5

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Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Yang J, et al. Small Molecules Promote Selective Denaturation and Degradation of Tubulin Heterodimers through a Low-Barrier Hydrogen Bond. J Med Chem. 2022 Jun 28. [Content Brief]