D8417

4′,6-Diamidino-2-phenylindole dihydrochloride

Name: 4′,6-Diamidino-2-phenylindole dihydrochloride
Brand: SIGMA

powder, BioReagent, suitable for cell culture, ≥98% (HPLC), suitable for fluorescence

Synonym(s):

2-(4-Amidinophenyl)-6-indolecarbamidine dihydrochloride, DAPI dihydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₁₅N₅ · 2HCl

CAS Number:

28718-90-3

Molecular Weight:

350.25

UNSPSC Code:

41116130

NACRES:

NA.75

PubChem Substance ID:

24894213

EC Number:

249-186-7

Beilstein/REAXYS Number:

4894417

MDL number:

MFCD00012681

Product Name

4′,6-Diamidino-2-phenylindole dihydrochloride, powder, BioReagent, suitable for cell culture, ≥98% (HPLC), suitable for fluorescence

InChI key

FPNZBYLXNYPRLR-UHFFFAOYSA-N

InChI

1S/C16H15N5.2ClH/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);2*1H

SMILES string

Cl.Cl.NC(=N)c1ccc(cc1)-c2cc3ccc(cc3[nH]2)C(N)=N

product line

BioReagent

form

powder

technique(s)

cell culture | mammalian: suitable

solubility

H₂O: 20 mg/mL
PBS: insoluble

ε (extinction coefficient)

30 at 263 nm in H₂O

fluorescence

λ_ex 340 nm; λ_em 488 nm (nur DAPI)
λ_ex 364 nm; λ_em 454 nm (DAPI-DNA-Komplex)

suitability

suitable for fluorescence

storage temp.

2-8°C

Quality Level

200

assay

≥98% (HPLC)

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Application

4′,6-Diamidino-2-phenylindole dihydrochloride has been used in staining of various cells in immunocytochemistry and cytochemistry, human subcutaneous adipose tissues for fluorescence imaging, embryo sections for immunofluorescence.

DAPI is several times more sensitive than ethidium bromide for staining DNA in agarose gels.

DAPI is several times more sensitive than ethidium bromide for staining DNA in agarose gels. It may be used for photofootprinting of DNA, to detect annealed probes in blotting applications by specifically visualizing the double-stranded complex, and to study the changes in DNA and analyze DNA content during apoptosis using flow cytometry. DAPI staining has also been shown to be a sensitive and specific detection method for mycoplasma.

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.

Disclaimer

Protect from light.

General description

4′,6-Diamidino-2-phenylindole dihydrochloride is a fluorescent dye for staining DNA. It strongly interacts with the dAT-rich (deoxy adenine-thymine) regions of the DNA.

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.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

pictograms

GHS07

signalword

Warning

hcodes

H315,H317,H335

pcodes

P261 - P264 - P271 - P272 - P280 - P302 + P352

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1A - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Behavior of mesenchymal stem cells stained with 4', 6-diamidino-2-phenylindole dihydrochloride (DAPI) in osteogenic and non osteogenic cultures

Ocarino N M, et al.

Biocell, 32(2), 175-183 (2008)

Endogenous Nodal signaling regulates germ cell potency during mammalian testis development

Spiller C M, et al.

Development, 139(22), 4123-4132 (2012)

Interaction of 4?-6-diamidino-2-phenylindole to nucleic acids, and its implication to their template activity in RNA-polymerase reaction of E. coli bacteria and of friend-virus infected mouse spleen

Mildner B, et al.

Cancer letters, 4(2), 89-98 (1978)

IFATS collection: Human adipose tissue-derived stem cells induce angiogenesis and nerve sprouting following myocardial infarction, in conjunction with potent preservation of cardiac function

Cai L, et al.

Stem Cells, 27(1), 230-237 (2009)

Flavivirus NS4A-induced autophagy protects cells against death and enhances virus replication

McLean J E, et al.

Test, 286(25), 22147-22159 (2011)

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