BISBENZIMIDE ETHOXIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H28N6O
Molecular Weight	452.5508
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=CC=C(C=C1)C2=NC3=C(N2)C=CC(=C3)C4=NC5=C(N4)C=CC(=C5)N6CCN(C)CC6

InChI

InChIKey=PRDFBSVERLRRMY-UHFFFAOYSA-N

InChI=1S/C27H28N6O/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)

HIDE SMILES / InChI

Molecular Formula	C27H28N6O
Molecular Weight	452.5508
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2449244	Binding Agent 1064
DNA topoisomerase I 59 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10506445 \| https://www.ncbi.nlm.nih.gov/pubmed/9675078	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: http://adisinsight.springer.com/drugs/800001915	Primary		Not Provided 504	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 Sep	7028425

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:18:03 GMT 2023` Edited by `admin` on `Fri Dec 15 18:18:03 GMT 2023`
Record UNII	99KZS6CNZX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BISBENZIMIDE ETHOXIDE

Common Name

English

2,5'-BIBENZIMIDAZOLE, 2'-(P-ETHOXYPHENYL)-5-(4-METHYL-1-PIPERAZINYL)-

Common Name

English

HO-342

Code

English

2-(2-(4-ETHOXYPHENYL)-6-BENZIMIDAZOLYL)-6-(1-METHYL-4-PIPERAZINYL)BENZIMIDAZOLE

Systematic Name

English

BISBENZIMIDE ETHOXIDE [MI]

Common Name

English

NSC-334072

Code

English

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

Systematic Name

English

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

Systematic Name

English

Code System Code Type Description

FDA UNII

99KZS6CNZX