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Hoechst 33258 structure, CAS 23491-45-4

Hoechst 33258

CAS Number23491-45-4

SynonymsBBIH; 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; 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'-y

Molecular FormulaC25H27Cl3N6O

Molecular Weight533.88

Purity≥98.0 (HPLC)%

Density

Boiling Point643.1ºC at 760mmHg

Melting Point314 °C

Flash Point

Appearanceliquid

EINECS

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Signal WordWarning

Cat. No.: 2A-9039264 Purity: ≥98.0 (HPLC)%
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Quality Control of [ 23491-45-4 ] Purity: ≥98.0 (HPLC)% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number23491-45-4
Catalog No.2A-9039264
Chinese Name赫斯特荧光燃料,33258
SynonymsBBIH; 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; 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'-y
Molecular FormulaC25H27Cl3N6O
Molecular Weight533.88
Purity≥98.0 (HPLC)
Boiling Point643.1ºC at 760mmHg
Melting Point314 °C
Appearanceliquid
Water SolubilitySOLUBLE
Storage Condition2-8℃
ApplicationHoechst 33258 trihydrochloride is a fluorescent dye used for DNA staining.
PubChem ID329770334
MDL NumberMFCD29074011
SMILESCl.Cl.Cl.CN1CCN(CC1)c2ccc3[nH]c(nc3c2)-c4ccc5nc([nH]c5c4)-c6ccc(O)cc6
InChI1S/C25H24N6O.3ClH/c1-30-10-12-31(13-11-30)18-5-9-21-23(15-18)29-25(27-21)17-4-8-20-22(14-17)28-24(26-20)16-2-6-19(32)7-3-16;;;/h2-9,14-15,32H,10-13H2,1H3,(H,26,28)(H,27,29);3*1H
InChI KeySMNPLAKEGAEPJD-UHFFFAOYSA-N
NACRES CodeNA.32
UNSPSC12171500
Hazard Symbolstransportation
MSDSmsds/39264_1_23491_45_4.pdf
BioactivityHoechst 33258 trihydrochloride is a fluorescent dyes, which can be used as a cell dye for DNA. Related Catalog Signaling Pathways >> Others >> Others Dye Reagents Research Areas >> Cancer 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. Chemical & Physical Properties 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 InChIKey SMNPLAKEGAEPJD-UHFFFAOYSA-N SMILES CN1CCN(c2ccc3nc(-c4ccc5nc(-c6ccc(O)cc6)[nH]c5c4)[nH]c3c2)CC1.Cl.Cl.Cl Storage condition 2-8°C Water Solubility SOLUBLE
Use ofHoechst 33258 trihydrochloride is a fluorescent dyes, which can be used as a cell dye for DNA. Properties Articles60 Name p-[5-(4-methyl-1-piperazinyl)(2,5'-bi-1H-benzimidazol)-2'-yl]phenol trihydrochloride Synonym More Synonyms Hoechst 33258 (trihydrochloride) Biological Activity Description Hoechst 33258 trihydrochloride is a fluorescent dyes, which can be used as a cell dye for DNA. Related Catalog Signaling Pathways >> Others >> Others Dye Reagents Research Areas >> Cancer 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. Chemical & Physical Properties Exact Mass 532.131165 PSA 84.07000 LogP 6.63950 InChIKey SMNPLAKEGAEPJD-UHFFFAOYSA-N Water Solubility SOLUBLE
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MSDS Transport InfoModule 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available
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