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Propidium iodide information


Propidium iodide
Identifiers
CAS Number
  • 25535-16-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:51240 checkY
ChEMBL
  • ChEMBL345124 checkY
ChemSpider
  • 94732 checkY
ECHA InfoCard 100.042.786 Edit this at Wikidata
PubChem CID
  • 104981
UNII
  • TP416O228T checkY
CompTox Dashboard (EPA)
  • DTXSID20894084 Edit this at Wikidata
InChI
  • InChI=1S/C27H33N4.2HI/c1-4-31(3,5-2)17-9-16-30-26-19-22(29)13-15-24(26)23-14-12-21(28)18-25(23)27(30)20-10-7-6-8-11-20;;/h6-8,10-15,18-19,29H,4-5,9,16-17,28H2,1-3H3;2*1H/q+1;;/p-1 checkY
    Key: XJMOSONTPMZWPB-UHFFFAOYSA-M checkY
  • InChI=1/C27H33N4.2HI/c1-4-31(3,5-2)17-9-16-30-26-19-22(29)13-15-24(26)23-14-12-21(28)18-25(23)27(30)20-10-7-6-8-11-20;;/h6-8,10-15,18-19,29H,4-5,9,16-17,28H2,1-3H3;2*1H/q+1;;/p-1
    Key: XJMOSONTPMZWPB-REWHXWOFAB
SMILES
  • CC[N+](C)(CC)CCC[n+]1c2cc(N)ccc2c3ccc(N)cc3c1c4ccccc4.[I-].[I-]
Properties
Chemical formula
C27H34I2N4
Molar mass 668.3946
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Propidium iodide (or PI) is a fluorescent intercalating agent that can be used to stain cells and nucleic acids. PI binds to DNA by intercalating between the bases with little or no sequence preference. When in an aqueous solution, PI has a fluorescent excitation maximum of 493 nm (blue-green), and an emission maximum of 636 nm (red). After binding DNA, the quantum yield of PI is enhanced 20-30 fold, and the excitation/emission maximum of PI is shifted to 535 nm (green) / 617 nm (orange-red).[1] Propidium iodide is used as a DNA stain in flow cytometry to evaluate cell viability or DNA content in cell cycle analysis, [2] or in microscopy to visualize the nucleus and other DNA-containing organelles. Propidium Iodide is not membrane-permeable, making it useful to differentiate necrotic, apoptotic and healthy cells based on membrane integrity.[3][4] PI also binds to RNA, necessitating treatment with nucleases to distinguish between RNA and DNA staining.[5] PI is widely used in fluorescence staining and visualization of the plant cell wall.[6]

  1. ^ "Propidium Iodide". Thermo Fisher Scientific. 2019-11-14. Retrieved 2019-11-14.
  2. ^ "Propidium Iodide Solution - BioLegend". Archived from the original on 10 February 2015. Retrieved 10 January 2015.
  3. ^ Lecoeur H (2002). "Nuclear apoptosis detection by flow cytometry: influence of endogenous endonucleases". Exp. Cell Res. 277 (1): 1–14. doi:10.1006/excr.2002.5537. PMID 12061813.
  4. ^ "Propidium Iodide". ThermoFisher.
  5. ^ Suzuki T, Fujikura K, Higashiyama T, Takata K (1 January 1997). "DNA staining for fluorescence and laser confocal microscopy". J. Histochem. Cytochem. 45 (1): 49–53. doi:10.1177/002215549704500107. PMID 9010468.
  6. ^ Bidhendi, AJ; Chebli, Y; Geitmann, A (May 2020). "Fluorescence Visualization of Cellulose and Pectin in the Primary Plant Cell Wall". Journal of Microscopy. 278 (3): 164–181. doi:10.1111/jmi.12895. PMID 32270489. S2CID 215619998.

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Propidium iodide

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Propidium iodide (or PI) is a fluorescent intercalating agent that can be used to stain cells and nucleic acids. PI binds to DNA by intercalating between...

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Staining

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the already dead cells are called vital stains (e.g. trypan blue or propidium iodide for eukaryotic cells). Those that enter and stain living cells are...

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Cytotoxicity

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compromise cell membrane integrity. Vital dyes, such as trypan blue or propidium iodide are normally excluded from the inside of healthy cells; however, if...

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Supravital staining

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stained positively. (Vital stains include dyes like trypan blue and propidium iodide, which are either too bulky or too charged to cross the cell membrane...

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Cell cycle analysis

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treated with a fluorescent dye that stains DNA quantitatively, such as propidium iodide (PI) or 4,6-diamidino-2-phenylindole (DAPI). The fluorescence intensity...

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Viability assay

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membranes are no longer intact. Examples of this type of assay include propidium iodide, trypan blue, and 7-Aminoactinomycin D (7-AAD). Mitochondrial activity...

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Acrosome reaction

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fluorescences compared). With this technique, a probe for viability such as propidium iodide (PI) could also be included in order to exclude dead cells from the...

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Wood mouse

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of the head adheres to the surface of the head prior to deployment. Propidium iodide staining revealed that only the basal surface of the hook is of nuclear...

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Phenanthridine

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through intercalation. Examples of such dyes are ethidium bromide and propidium iodide. It is an isomer of acridine. Phenanthridine was discovered by Amé...

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Ethidium bromide

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and GelGreen, marketed as safer and more intense DNA stains Propidium iodide and propidium monoazide, related dyes "GESTIS-Stoffdatenbank". gestis.dguv...

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Vital stain

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distinct subsets (e.g. viable, dead, dying etc.). Eosin dye exclusion Propidium iodide, DNA stain that can differentiate necrotic, apoptotic and normal cells...

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Cytogenetics

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probe, and counterstained with 4',6-Diamidino-2-phenylindole (DAPI) or propidium iodide. Analysis of FISH specimens is done by fluorescence microscopy by a...

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Colocalization

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detection of zinc increase and the well accepted cell death indicator propidium iodide also occurred in kidney cells. Using the principles of fluorescent...

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PI

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index, a measure of leanness of a person (similar to body mass index) Propidium iodide, a chemical used as a DNA stain Primary immunodeficiency Protease inhibitor...

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Zeta toxin protein domain

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Zeta toxin induces reversible protective dormancy and permeation to propidium iodide (PI). This protein family entry consists of several bacterial zeta...

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Acridine orange

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Acridine orange can be used in conjunction with ethidium bromide or propidium iodide to differentiate between viable, apoptotic, and necrotic cells. Additionally...

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Fluorophore

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510 530 CyTRAK Orange 520 615 - (Biostatus) (red excitation dark) Propidium Iodide (PI) 536 617 668.4 LDS 751 543;590 712;607 472 DNA (543ex/712em), RNA...

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Flow cytometry

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fish genomes resulted in significantly different genome sizes when propidium iodide (PI) and DAPI were used, respectively. For instance, the genome of...

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Annexin A5

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membrane events with the staining of DNA in the cell nucleus with propidium iodide (PI) or 7-Aminoactinomycin D (AAD-7), distinguishing viable cells from...

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Wheat germ agglutinin

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Arbuscular Mycorrhizal Structures Using Wheat Germ Agglutinin (WGA) and Propidium Iodide". Arbuscular Mycorrhizal Fungi. Methods in Molecular Biology. Vol. 2146...

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Apoptotic DNA fragmentation

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1991). "A rapid and simple method for measuring thymocyte apoptosis by propidium iodide staining and flow cytometry". Journal of Immunological Methods. 139...

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Fluorescein diacetate hydrolysis

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cleave the fluorescein first. It is also used in combination with propidium iodide (PI) to determine viability in eukaryotic cells. Living cells will...

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Cell sorting

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well as surface-expression of proteins. For example, in dead cells, propidium iodide (PI) can penetrate the nucleus where it binds to DNA. The fluorescent...

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Circulating tumor cell

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nuclear staining with propidium iodide the maintrac method can distinguish between dead and living cells. Only vital, propidium excluding EpCAM positive...

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P2X purinoreceptor

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as N-methyl-D-glucamine (NMDG+) and nucleotide binding dyes such as propidium iodide (YO-PRO-1). Whether this change in permeability is due to a widening...

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Ischemic cell death

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stage the membrane becomes abnormally permeable to trypan blue and propidium iodide, indicating membrane compromise. The final stage is cell death and...

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Induced cell cycle arrest

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the more of a particular protein is present. Staining with DNA dyes propidium iodide or 4',6'-diamidino-2-phenylindole (DAPI) allows delineation or sorting...

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Salmon louse

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of salmon louse. Flow cytometry histograms of fluorescent stained (Propidium Iodide, PI) cells of salmon louse mixed with chicken erythrocytes (CEN) and...

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Carbon nanotubes in medicine

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D384-cells and lung carcinoma A549-cells, using the MTT assay and calcein/propidium iodide (PI) staining. Both the as-received and the modified nanotubes were...

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