Hoechst 33258 (trihydrochloride)

Modify Date: 2024-01-02 11:05:59

Hoechst 33258 (trihydrochloride) structure	Common Name	Hoechst 33258 (trihydrochloride)
	CAS Number	23491-45-4	Molecular Weight	533.880
	Density	N/A	Boiling Point	643.1ºC at 760mmHg
	Molecular Formula	C₂₅H₂₇Cl₃N₆O	Melting Point	314 °C
	MSDS	Chinese USA	Flash Point	342.7ºC
	Symbol	GHS07	Signal Word	Warning

Use of Hoechst 33258 (trihydrochloride)

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
Synonym	More Synonyms

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
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

Hoechst 33258 (trihydrochloride) MSDS(Chinese)

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
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

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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)

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Hoechst 33258 (trihydrochloride)

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