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
Alteration of binding of the supravital dye Hoechst 33342 to human leukemic cells by adriamycin.	1978 Sep	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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:18:03 UTC 2023` Edited by `admin` on `Fri Dec 15 18:18:03 UTC 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