U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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 of BISBENZIMIDE ETHOXIDE

SMILES

CCOC1=CC=C(C=C1)C2=NC3=CC(=CC=C3N2)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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

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
Record UNII
99KZS6CNZX
Record Status Validated (UNII)
Record Version