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Details

Stereochemistry ACHIRAL
Molecular Formula C27H28N6O
Molecular Weight 452.5518
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BISBENZIMIDE ETHOXIDE

SMILES

CCOc1ccc(cc1)-c2[nH]c3ccc(cc3n2)-c4nc5ccc(cc5[nH]4)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 452.5518
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Alteration of binding of the supravital dye Hoechst 33342 to human leukemic cells by adriamycin.
1978 Sep
Fluorescence flow analysis of lymphocyte activation using Hoechst 33342 dye.
1979 Jan
Separation of viable T and B lymphocytes using a cytochemical stain, Hoechst 33342.
1980 Jan
Simultaneous quantitation of Hoechst 33342 and immunofluorescence on viable cells using a fluorescence activated cell sorter.
1980 Sep
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 Sat Jun 26 05:33:51 UTC 2021
Edited
by admin
on Sat Jun 26 05:33:51 UTC 2021
Record UNII
99KZS6CNZX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BISBENZIMIDE ETHOXIDE
MI  
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
Created by admin on Sat Jun 26 05:33:51 UTC 2021 , Edited by admin on Sat Jun 26 05:33:51 UTC 2021
PRIMARY
PUBCHEM
1464
Created by admin on Sat Jun 26 05:33:51 UTC 2021 , Edited by admin on Sat Jun 26 05:33:51 UTC 2021
PRIMARY
EPA CompTox
23491-52-3
Created by admin on Sat Jun 26 05:33:51 UTC 2021 , Edited by admin on Sat Jun 26 05:33:51 UTC 2021
PRIMARY
ECHA (EC/EINECS)
245-691-1
Created by admin on Sat Jun 26 05:33:51 UTC 2021 , Edited by admin on Sat Jun 26 05:33:51 UTC 2021
PRIMARY
MERCK INDEX
M2520
Created by admin on Sat Jun 26 05:33:51 UTC 2021 , Edited by admin on Sat Jun 26 05:33:51 UTC 2021
PRIMARY Merck Index
CAS
23491-52-3
Created by admin on Sat Jun 26 05:33:51 UTC 2021 , Edited by admin on Sat Jun 26 05:33:51 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE