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28718-90-3

28718-90-3 Structure

28718-90-3 Structure
IdentificationMore
[Name]

4',6-Diamidino-2-phenylindole dihydrochloride
[CAS]

28718-90-3
[Synonyms]

2-(4-AMIDINOPHENYL)-6-INDOLECARBAMIDINEDIHYDROCHLORIDE
4',6-DIAMIDINE-2'-PHENYLINDOLE DIHYDROCHLORIDE
4',6-DIAMIDINO-2-PHENYLINDOLE, 2HCL
4',6-DIAMIDINO-2-PHENYLINDOLE DIHYDROCHLORIDE
4',6-DIAMIDINO-2-PHENYLINDOLE, HYDROCHLORIDE
DAPI
DAPI, DIHYDROCHLORIDE
2-phenylindole-4',6-dicarboxamidine dihydrohydrochloride (hydrate)
4',6-DIAMIDINO-2-PHENYLINDOLE*DIHYDROCHL ORIDE HYDRA
-Cellstain-Dapi
4',6-DIAMINO-2-PHENYLINDOLE DIHYDROCHLORIDE
DAPI, 2-(4-Amidinophenyl)-6-indolecarbamidine, Dihydrochloride
Diamidino-2-phenylindole-2HCl-H2O
1H-Indole-6-carboximidamide, 2-4-(aminoiminomethyl)phenyl-, dihydrochloride
4'',6-DIAMIDINO-2-PHENYLINDOLE DIHYDROCHLORIDE CRYSTALLINE
2-Phenylindole-4',6-dicarboxamidine dihydrohydrochloride
DAPI (4'',6-DIAMIDINO-2-PHENYLINDOLE DIHYDROCHLORIDE)
[EINECS(EC#)]

249-186-7
[Molecular Formula]

C16H17Cl2N5
[MDL Number]

MFCD00012681
[Molecular Weight]

350.25
[MOL File]

28718-90-3.mol
Chemical PropertiesBack Directory
[Appearance]

Yellow Solid
[Melting point ]

>300°C (dec.)
[storage temp. ]

−20°C
[solubility ]

H2O: 10 mg/mL heat or sonication may be required. Solutions stored in the dark at room temperature or 4 °C should be stable for 2 to 3 weeks.
[form ]

powder
[color ]

Clear
[PH]

4.0-5.0 (10g/l, H2O, 20℃)
[Water Solubility ]

water: soluble
[Usage]

A cell-permeable DNA-binding dye. Binds preferentially to DNA rich in adenine and thymine. Used in flow cytometry for measuring nuclear DNA content or for sorting isolated chromosomes
[ε(extinction coefficient)]

30 at 263nm in H2O at 1mM
[λmax]

358 nm, 342 nm
[BRN ]

4894417
[Stability:]

PROTECT FROM LIGHT! Stable for 2 years as supplied. Solutions in DMSO may be aliquoted and stored at -20°C for up to 3 months.
[Biological Applications]

Nuclear apoptosis assay; targeting drug to cerebral neuron; treating amyloidosis,neurodegenerative diseases,Alzheimer’s disease,Down’s syndrome,type II diabetes; monitoring bioaerosols
[InChI]

InChI=1S/C16H15N5.ClH/c17-15(18)10-3-1-9(2-4-10)13-7-11-5-6-12(16(19)20)8-14(11)21-13;/h1-8,21H,(H3,17,18)(H3,19,20);1H
[InChIKey]

FPNZBYLXNYPRLR-UHFFFAOYSA-N
[SMILES]

C(C1C=CC2C=C(C3C=CC(C(N)=N)=CC=3)NC=2C=1)(N)=N.Cl
[CAS DataBase Reference]

28718-90-3(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H317-H335
[Precautionary statements ]

P261-P264-P271-P272-P280-P302+P352
[Hazard Codes ]

Xi,Xn
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes .
S22:Do not breathe dust .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
[RTECS ]

NL5995050
[F ]

3-8-10-21
[HS Code ]

29339900
Hazard InformationBack Directory
[Description]

DAPI is a fluorescent probe which is commonly used to stain DNA and chromosomes for fluorescent microscopy and flow cytometry applications. It forms a fluorescent complex by attaching in the minor groove of A-T rich sequences of DNA. DAPI is often used as a counterstain, as its ultraviolet (max 358 nm) excitation and blue (max 461 nm) emission wavelengths separate it nicely from many popular primary fluorophores. It can be used on either fixed or live cells, although its low permeability in live cells demands that higher concentrations be used.
[Chemical Properties]

Yellow Solid
[Uses]

4',6-Diamidino-2-phenylindole dihydrochloride is used as a cell-permeable DNA-binding dye. Binds preferentially to DNA rich in adenine and thymine.It is used in flow cytometry for measuring nuclear DNA content or for sorting isolated chromosomes.
[Uses]

DAPI is used for photofootprinting of DNA, to detect annealed probes in blotting applications by specifically visualizing the double-stranded complex and as a cell permeable fluorescent minor groove-binding probe for DNA. For staining DNA in agarose gels
[General Description]

DAPI, 4′,6-diamidino-2-phenylindole, is a blue fluorescent nucleic acid stain that fluoresces brightly upon selectively binding to the minor groove of double stranded DNA. Its selectivity for DNA and high cell permeability allows efficient staining of nuclei with little background from the cytoplasm. The excitation and emission wavelengths of DAPI-DNA complex are 360 nm and 460 nm, respectively.
[Biochem/physiol Actions]

Cell permeable fluorescent minor groove-binding probe for DNA. Binds to the minor groove of double-stranded DNA (preferentially to AT rich DNA), forming a stable complex which fluoresces approximately 20 times greater than DAPI alone.
[storage]

-20°C
[References]

Russell et al. (1975), A simple cytochemical technique for demonstration of DNA in cells infected with mycoplasmas and viruses; Nature, 253 461 Tarnowski et al. (1991), DAPI as a useful stain for nuclear quantitation; Biotech Histochem., 66 297 Estandarte et al. (2016), The use of DAPI fluorescence lifetime imaging for investigating chromatin condensation in human chromosomes; Sci. Rep., 6 31417
[Abs/Em Maxima]

355/460 nm
[Extinction Coefficient]

28800
Spectrum DetailBack Directory
[Spectrum Detail]

4',6-Diamidino-2-phenylindole dihydrochloride(28718-90-3)MS
4',6-Diamidino-2-phenylindole dihydrochloride(28718-90-3)1HNMR
4',6-Diamidino-2-phenylindole dihydrochloride(28718-90-3)FT-IR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

28718-90-3(sigmaaldrich)
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