BISBENZIMIDE ETHOXIDE TRIHYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H28N6O.3ClH
Molecular Weight	561.934
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of BISBENZIMIDE ETHOXIDE TRIHYDROCHLORIDE

Structure Search

SMILES

Cl.Cl.Cl.CCOC1=CC=C(C=C1)C2=NC3=CC(=CC=C3N2)C4=NC5=C(N4)C=CC(=C5)N6CCN(C)CC6

InChI

InChIKey=JABNPSKWVNCGMX-UHFFFAOYSA-N

InChI=1S/C27H28N6O.3ClH/c1-3-34-21-8-4-18(5-9-21)26-28-22-10-6-19(16-24(22)30-26)27-29-23-11-7-20(17-25(23)31-27)33-14-12-32(2)13-15-33;;;/h4-11,16-17H,3,12-15H2,1-2H3,(H,28,30)(H,29,31);3*1H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2449244 | https://www.ncbi.nlm.nih.gov/pubmed/10506445 | http://adisinsight.springer.com/drugs/800001915

Bisbenzimide ethoxide is a fluorescent nucleic acid stain useful for DNA labeling in fluorescence microscopy and flow cytometry. It appears to bind to AT-rich regions containing at least four such basepairs. Bisbenzimide ethoxide seems to bind relatively poorly to nucleotide sequences containing the alternating step TpA. Bisbenzimide ethoxide induced apoptosis in the HL-60 cells in a time- and dose-dependent manner. Endogenous nuclear topoisomerase I activity in HL-60 cells was inhibited by treatment with Bisbenzimide ethoxide.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2449244	Binding Agent 1076
DNA topoisomerase I 60 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10506445 \| https://www.ncbi.nlm.nih.gov/pubmed/9675078	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: http://adisinsight.springer.com/drugs/800001915	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Simultaneous quantitation of Hoechst 33342 and immunofluorescence on viable cells using a fluorescence activated cell sorter.	1980-09	7028425
Separation of viable T and B lymphocytes using a cytochemical stain, Hoechst 33342.	1980-01	6153191
Fluorescence flow analysis of lymphocyte activation using Hoechst 33342 dye.	1979-01	86569
Alteration of binding of the supravital dye Hoechst 33342 to human leukemic cells by adriamycin.	1978-09	688284

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Cultures of Chinese hamster ovary (CHO) cells were presynchronized in early S phase by sequential treatment with isoleucine deficiency and hydroxyurea blockades; then they were switched to medium supplemented with Bisbenzimide ethoxide at 7.5 ug/ml for 12 hr. Up to 95% of the cells accumulated in G2 phase under those conditions.

Name

Type

Language

HOECHST-33342

Preferred Name

English

BISBENZIMIDE ETHOXIDE TRIHYDROCHLORIDE

Common Name

English

2,5'-BI-1H-BENZIMIDAZOLE, 2'-(4-ETHOXYPHENYL)-5-(4-METHYL-1-PIPERAZINYL)-, TRIHYDROCHLORIDE

Common Name

English

BISBENZIMIDE H 33342

Common Name

English

BISBENZIMIDE ETHOXIDE TRIHYDROCHLORIDE [MI]

Common Name

English

HOE-33342

Code

English

Code System Code Type Description

CAS

875756-97-1