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D8417

Sigma-Aldrich

4′,6-Diamidino-2-phenylindole dihydrochloride

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

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Synonym(s):
2-(4-Amidinophenyl)-6-indolecarbamidine dihydrochloride, DAPI dihydrochloride
Empirical Formula (Hill Notation):
C16H15N5 · 2HCl
CAS Number:
28718-90-3
Molecular Weight:
350.25
Beilstein:
4894417
EC Number:
249-186-7
MDL number:
MFCD00012681
PubChem Substance ID:
24894213
NACRES:
NA.75

product line

BioReagent

Quality Level

200

Assay

≥98% (HPLC and TLC)

form

powder

technique(s)

cell culture | mammalian: suitable

solubility

H2O: 20 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.)
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

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

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. 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.

Caution

Protect from light.

Other Notes

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H317 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)
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)
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