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Merck

D8417

4′,6-Diamidino-2-phenylindole dihydrochloride

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

Key Documents

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product line

BioReagent

Quality Level

200

assay

≥98% (HPLC)

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

λex 340 nm; λem 488 nm (nur DAPI), λex 364 nm; λem 454 nm (DAPI-DNA-Komplex)

suitability

suitable for fluorescence

storage temp.

2-8°C

SMILES string

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

InChI key

FPNZBYLXNYPRLR-UHFFFAOYSA-N

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General description

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.
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.

Application

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.
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.

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.

Other Notes

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

Disclaimer

Protect from light.

pictograms

Exclamation mark
GHS07

signalword

Warning

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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Certificates of Analysis (COA)

Lot/Batch Number
0000413306
0000413306
0000369266
0000361184
0000355394

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Endogenous Nodal signaling regulates germ cell potency during mammalian testis development
Spiller C M, et al.
Development, 139(22), 4123-4132 (2012)
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)
Chun-Lan Xie et al.
Marine drugs, 17(3) (2019-03-22)
Five new ergostanes, penicisteroids D-H (1-5), were isolated from the liquid culture of the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475, along with 27 known compounds. The structures of the new steroids were established mainly on the basis of extensive analysis
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)
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