Top Suppliers:I want be here




23491-45-4

23491-45-4 structure
23491-45-4 structure
  • Name: Hoechst 33258 (trihydrochloride)
  • Chemical Name: p-[5-(4-methyl-1-piperazinyl)(2,5'-bi-1H-benzimidazol)-2'-yl]phenol trihydrochloride
  • CAS Number: 23491-45-4
  • Molecular Formula: C25H27Cl3N6O
  • Molecular Weight: 533.880
  • Catalog: Dye Reagents
  • Create Date: 2018-05-30 08:00:00
  • Modify Date: 2024-01-02 11:05:59
  • Hoechst 33258 trihydrochloride is a fluorescent dyes, which can be used as a cell dye for DNA.

Name p-[5-(4-methyl-1-piperazinyl)(2,5'-bi-1H-benzimidazol)-2'-yl]phenol trihydrochloride
Synonyms BBIH
BISBENZIMIDE H 33258
Hoechst33258
Hoechst Stain
4-[5-(4-Methylpiperazin-1-yl)-1H,1'H-2,5'-bibenzimidazol-2'-yl]phenol trihydrochloride
BISBENZIMIDE
Phenol, 4-[5-(4-methyl-1-piperazinyl)[2,5'-bi-1H-benzimidazol]-2'-yl]-, trihydrochloride
Bisbenzimide H 33258 trihydrochloride
2'-(4-Hydroxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole Trihydrochloride
Phenol, 4-[5- (4-methyl-1-piperazinyl)(2,5'-bi-1H-benzimidazol)- 2'-yl]-, trihydrochloride
Bisbenzimide H 33258 Hydrate
MFCD00012679
4-[5-(4-Methyl-1-piperazinyl)-1H,1'H-2,5'-bibenzimidazol-2'-yl]phenol trihydrochloride
Hoechst 33258
2'-(4-hydroxyphenyl)-5-(4-methylpiperazin-4-ium-1-yl)-3H,3'H-2,6'-bi-3,1-benzimidazol-1-ium trichloride
Phenol, p-[5-[5- (4-methyl-1-piperazinyl)-2-benzimidazolyl]-2- benzimidazolyl]-, trihydrochloride
Pibenzimol HCl
Phenol, 4-(5-(4-methyl-1-piperazinyl)(2,5'-bi-1H-benzimidazol)-2'-yl)-, trihydrochloride
phenol, 4-[6-(4-methyl-1-piperazinyl)[2,5'-bi-1H-benzimidazol]-2'-yl]-, hydrochloride (1:3)
phenol, 4-[5-(4-methyl-1-piperazinyl)[2,6'-bi-1H-benzimidazol]-2'-yl]-, hydrochloride (1:3)
EINECS 245-690-6
Phenol, 4-[5-(4-methyl-1-piperazinyl)[2,5'-bi-1H-benzimidazol]-2'-yl]-, hydrochloride (1:3)
Hoechst 33258 (trihydrochloride)
Description Hoechst 33258 trihydrochloride is a fluorescent dyes, which can be used as a cell dye for DNA.
Related Catalog
Target

IC50: 51.31±4.56 μM (HeLa cell), 32.43±3.27 μM (HL60 cell), 15.42±2.16 μM (U937 cell)[1]

In Vitro Hoechst 33258, a fluorescent compound with a head-to-tail bis-benzimidazole structure, is initially found to be cytotoxic against L1210 murine leukemia. Hoechst 33258 is evaluated for their cytotoxicity against human tumor cell lines, which are cervix carcinoma cell line (HeLa), Human promyelocytic leukemia cell (HL60) and U937 cell Line. The IC50 determined in the case of HeLa, HL60 and U937 is 51.31±4.56, 32.43±3.27 and 15.42±2.16 μM for Hoechst 33258, respectively[1]. The cytotoxic property of Hoechst 33258 is investigated on a panel of seven tumour cell lines of different histological origin and Madine-Darby canine kidney (MDCK) normal cells. All cell lines, except MCF-7, exposed to Hoechst 33258 exhibit GI50 from 84×10-6 to 191.5×10-6 mol/dm3. Under the same experimental conditions, Hoechst 33258, used as a binder reference compound, stops the cell cycle in S phase and G0/G1[2].
Cell Assay Hoechst 33258 is prepared as stock solutions in highly pure water. Working solutions in a concentration range of 10-3-10-6 mol/dm3 are prepared prior to testing. Cytotoxic effects of Hoechst 33258 on tested cell lines are determined by the MTT assay. Cells are seeded in 96 micro well flat bottom plates at a concentration of 2×104 cells/mL and left overnight in the CO2 incubator allowing them to attach to the plate surface. Growing medium is replaced with compound supplemented or control medium and incubated for 72 h. Fresh medium with 5 mg/mL of MTT is added onto cells and incubated for 4 h at 37°C. Upon media removal, water insoluble MTT-formazan crystals formed inside the living cells are dissolved in DMSO and the absorbance at 570 nm proportional to the number of living cells is measured on an Elisa Microplate Reader. All experiments are performed at least three times in triplicates.The GI50 value, defined as the compound concentration (μM) leading to cellular growth inhibition by 50%, is calculated and used as a parameter to compare cytotoxicity among the compounds[2].
References

[1]. Wang XJ, et al. Newly synthesized bis-benzimidazole derivatives exerting anti-tumor activity through inductionof apoptosis and autophagy. Bioorg Med Chem Lett. 2012 Oct 1;22(19):6297-300.

[2]. Stolić I, et al. Synthesis, DNA/RNA affinity and antitumour activity of new aromatic diamidines linked by 3,4-ethylenedioxythiophene. Eur J Med Chem. 2011 Feb;46(2):743-55.

Boiling Point 643.1ºC at 760mmHg
Melting Point 314 °C
Molecular Formula C25H27Cl3N6O
Molecular Weight 533.880
Flash Point 342.7ºC
Exact Mass 532.131165
PSA 84.07000
LogP 6.63950
Storage condition 2-8°C
Water Solubility SOLUBLE

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SM1140500
CHEMICAL NAME :
Phenol, p-(5-(5-(4-methyl-1-piperazinyl)-2-benzimidazolyl)-2- benzimidazolyl)-, trihydrochloride
CAS REGISTRY NUMBER :
23491-45-4
LAST UPDATED :
199709
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C25-H24-N6-O.3Cl-H
MOLECULAR WEIGHT :
533.93
WISWESSER LINE NOTATION :
T56 BM DNJ CR DQ& G- CT56 BM DNJ G- AT6N DNTJ D1 &GH 3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
32200 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
36900 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea Skin and Appendages - hair

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Mammal - species unspecified Lymphocyte
DOSE/DURATION :
1600 nmol/L
REFERENCE :
CHROAU Chromosoma. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1939- Volume(issue)/page/year: 52,297,1975
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H315-H319
Precautionary Statements P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn: Harmful;
Risk Phrases R22
Safety Phrases S26-S36-S24/25-S23
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS SM1140500