Structure via PubChem · Public domain (PubChem)
DAPI
Sign in to saveAlso known as 4',6-diamidino-2-phenylindole, antifade, 2-(4-(aminoiminomethyl)phenyl)-1H-indole-6-carboximidamide, 4',6-diamidinophenyl-indole
DAPI (pronounced 'DAPPY', /ˈdæpiː/), or 4′,6-diamidino-2-phenylindole, is a fluorescent stain that binds strongly to adenine–thymine-rich regions in DNA. It is used extensively in fluorescence microscopy. As DAPI can pass through an intact cell membrane, it can be used to stain both live and fixed cells, though it passes through the membrane less efficiently in live cells and therefore provides a marker for membrane viability.
Chemical data
- Formula
- C16H15N5
- Molecular weight
- 277.32 g/mol
- IUPAC name
- 2-(4-carbamimidoylphenyl)-1H-indole-6-carboximidamide
- SMILES
- C1=CC(=CC=C1C2=CC3=C(N2)C=C(C=C3)C(=N)N)C(=N)N
- InChIKey
- FWBHETKCLVMNFS-UHFFFAOYSA-N
- XLogP
- 1.6
- Polar surface area
- 116 Ų
- H-bond donors
- 5
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
10,023 papers- DAPI: a DNA-specific fluorescent probe.Biotechnic & histochemistry : official publication of the Biological Stain Commission · 1995
- Labeling nuclear DNA using DAPI.Cold Spring Harbor protocols · 2011
- DAPI (4',6-diamidino-2-phenylindole) Stains Compact Amyloid Plaques.Journal of Alzheimer's disease : JAD · 2022
- CMA/DAPI Banding of Plant Chromosomes.Methods in molecular biology (Clifton, N.J.) · 2023
- A cautionary (spectral) tail: red-shifted fluorescence by DAPI-DAPI interactions.Biochemical Society transactions · 2016
via PubMed
Wikidata facts
- Mass
- 277.133
- Image
- Indian Muntjac fibroblast cells (24271618921).jpg
Show 3 more facts
- Commons category
- DAPI
- chemical formula
- C₁₆H₁₅N₅
- canonical SMILES
- C1=CC(=CC=C1C2=CC3=C(N2)C=C(C=C3)C(=N)N)C(=N)N
via Wikidata · CC0
Article · 日本語
DAPI（ダピ、ダーピー、4',6-diamidino-2-phenylindole）は染色に用いられる蛍光色素の一種で、DNAに対して強力に結合する物質である。蛍光顕微鏡観察に広く利用されている。
Abstract from DBpedia / Wikipedia · CC BY-SA