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217085

Sigma-Aldrich

4′,6-Diamidino-2-phenylindole dihydrochloride

98%

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:
Molecular Weight:
350.25
Beilstein/REAXYS Number:
4894417
EC Number:
MDL number:
UNSPSC Code:
41116130
PubChem Substance ID:
Pricing and availability is not currently available.

assay

98%

fluorescence

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

storage temp.

−20°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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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.
Forms highly fluorescent complexes with DNA from various sources.

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.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves


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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)).
Angus T Stock et al.
The Journal of experimental medicine, 211(5), 751-759 (2014-04-23)
Infection induces the expression of inflammatory chemokines that recruit immune cells to the site of inflammation. Whereas tissues such as the intestine and skin express unique chemokines during homeostasis, whether different tissues express distinct chemokine profiles during inflammation remains unclear.
Denise M Piscopo et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(11), 4642-4656 (2013-03-15)
The thalamus is crucial in determining the sensory information conveyed to cortex. In the visual system, the thalamic lateral geniculate nucleus (LGN) is generally thought to encode simple center-surround receptive fields, which are combined into more sophisticated features in cortex
Sylvain Bessonnard et al.
Development (Cambridge, England), 141(19), 3637-3648 (2014-09-12)
During blastocyst formation, inner cell mass (ICM) cells differentiate into either epiblast (Epi) or primitive endoderm (PrE) cells, labeled by Nanog and Gata6, respectively, and organized in a salt-and-pepper pattern. Previous work in the mouse has shown that, in absence

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