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Sigma-Aldrich

4′,6-Diamidino-2-phenylindole dihydrochloride

suitable for fluorescence, BioReagent, ≥95.0% (HPLC)

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
Beilstein:
4894417
EC Number:
249-186-7
MDL number:
MFCD00012681
UNSPSC Code:
12171500
PubChem Substance ID:
57648699
NACRES:
NA.32

product line

BioReagent

Assay

≥95.0% (HPLC)

form

powder

solubility

DMF: soluble
H2O: soluble

fluorescence

λex 340 nm; λem 488 nm (nur DAPI)
λex 364 nm; λem 454 nm (DAPI-DNA-Komplex)
λex 374 nm; λem 461 nm in 10 mM Tris; 1 mM EDTA; pH 8.0; DNA

suitability

suitable for fluorescence

storage temp.

room temp

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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Application

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Silvia Pivetti et al.
Science advances, 5(5), eaav1594-eaav1594 (2019-05-21)
Polycomb repressive complexes are evolutionarily conserved complexes that maintain transcriptional repression during development and differentiation to establish and preserve cell identity. We recently described the fundamental role of PRC1 in preserving intestinal stem cell identity through the inhibition of non-lineage-specific
Sanna Koskiniemi et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(17), 7032-7037 (2013-04-11)
Rearrangement hotspot (Rhs) and related YD-peptide repeat proteins are widely distributed in bacteria and eukaryotes, but their functions are poorly understood. Here, we show that Gram-negative Rhs proteins and the distantly related wall-associated protein A (WapA) from Gram-positive bacteria mediate
Minggang Fang et al.
Journal of virology, 83(23), 12569-12578 (2009-09-18)
Autographa californica multiple nucleopolyhedrovirus (AcMNPV) ac96 is a core gene, but its role in virus replication is still unknown. To determine its role in the baculovirus life cycle, we used the AcMNPV bacmid system to generate an ac96-null virus (vAc(96)(null)).
Matteo Bolomini-Vittori et al.
Scientific reports, 9(1), 3556-3556 (2019-03-07)
Local membrane phospholipid enrichment serves as docking platform for signaling proteins involved in many processes including cell adhesion and migration. Tissue-resident dendritic cells (DCs) assemble actomyosin-based structures called podosomes, which mediate adhesion and degradation of extracellular matrix for migration and
Georgia Pennarossa et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(22), 8948-8953 (2013-05-23)
The differentiated state of mature cells of adult organisms is achieved and maintained through the epigenetic regulation of gene expression, which consists of several mechanisms including DNA methylation. The advent of induced pluripotent stem cell technology enabled the conversion of
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