3,8-diamino-5-{3-[diethyl(methyl)azaniumyl]propyl}-6-phenylphenanthridin-5-ium diiodide

• ChemBase ID: 105971
• Molecular Formular: C27H34I2N4
• Molecular Mass: 668.3946
• Monoisotopic Mass: 668.08729311
• SMILES: CC[N+](C)(CC)CCC[n+]1c2cc(ccc2c2ccc(cc2c1c1ccccc1)N)N.[I-].[I-]
• Canonical SMILES: CC[N+](CCC[n+]1c(c2ccccc2)c2cc(N)ccc2c2c1cc(N)cc2)(CC)C.[I-].[I-]
• 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
• InChIKey: XJMOSONTPMZWPB-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,8-diamino-5-{3-[diethyl(methyl)azaniumyl]propyl}-6-phenylphenanthridin-5-ium diiodide
• IUPAC Traditional name: propidium diiodide
• Synonyms: 2,7-Diamino-9-phenyl-10 (diethylaminopropyl)-phenanthridium iodide methiodide; PROPIDIUM IODIDE; 3,8-Diamino-5-[3-(diethylmethylammonio)propyl]-6-phenylphenanthridinium diiodide; Propidium iodide; 3,8-Diamino-5-(3-diethylaminopropyl)-6-phenylphenanthridinium iodide methiodide; 3,8-Diamino-5-[3-(diethylmethylammonio)propyl]-6-phenylphenanthridinium, diiodide; Propidium iodide solution; 3,8-Diamino-5-[3-(diethylmethylammonio)propyl]-6-phenylphenanthridinium Iodide; [3-(3,8-Diamino-6-phenyl-5-phenanthridinio)propyl]diethylmethylammonium Diiodide; 3,8-Diamino-5-(diethylmethylaminopropyl)-6-phenylphenanthridinium Diiodide; Propidium Diiodide

Database IDs

• CAS Number: 25535-16-4
• EC Number: 231-791-2; 247-081-0
• MDL Number: MFCD00011921
• Beilstein Number: 3843838
• PubChem SID: 24898563; 24898510; 162093131
• PubChem CID: 104981
• CHEBI ID: 51240
• CHEMBL: 345124
• Chemspider ID: 94732
• Wikipedia Title: Propidium_iodide

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -4.6443014
• LogD (pH = 7.4): -4.6402345
• Log P: -4.640182
• Molar Refractivity: 145.5442 cm^3
• Polarizability: 54.351612 Å^3
• Polar Surface Area: 55.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Dark Red Solid; solution (1.0 mg/ml in water)
• Melting Point: 220-225 °C (dec.)(lit.); 220-225°C; 224-228°C
• Absorption Wavelength: λmax 493 nm
• Fluorescence: λex 482 nm; λem 608 nm (pH 7.2); λex 530 nm; λem 620 nm in 0.1 M phosphate pH 7.0 (bound to DNA); λex 540 nm; λem 608 nm (bound to DNA)

Safety Information

• Storage Condition: 2-8°C, Desiccate, Protect from light; Refrigerator
• RTECS: SF7949600
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:20/21/22
• Safety Statements: 26; S:26-36-46
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90.0% (HPLC); ≥94% (HPLC); ≥94.0% (HPLC); ≥98%; 95%
• Concentration: 1 mg/mL in H2O
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C27H34I2N4

DETAILS

MP Biomedicals - 02195458

Red powder
Reagent for the fluorescent staining of nucleic acids.
POSSIBLE CARCINOGEN!

Sigma Aldrich - P4170

Application
Fluorescent stain for nucleic acids. Cell membrane integrity excludes propidium iodide from staining viable and apoptotic cells. Propidium iodide may be used in flow cytometry to evaluate cell viability when used with other dyes that stain viable cells or cells that are early in the apoptosis process.

Sigma Aldrich - 70335

Application
Membrane impermeant, phenanthridinium intercalator dye excited by mercury or xenon-arc lamps or argon-ion laser. Suitable for use in fluorescence microscopy, confocal laser scanning microscopy, flow cytometry, and fluorometry. Used as a nuclear counterstain.

Sigma Aldrich - P4864

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Membrane impermeant, phenanthridinium intercalator dye excited by mercury or xenon-arc lamps or argon-ion laser. Suitable for use in fluorescence microscopy, confocal laser scanning microscopy, flow cytometry, and fluorometry. Used as a nuclear counterstain.

Toronto Research Chemicals - P770500

Propidium Iodide is a phenanthridine compound, a class of compounds with reported activity against several species of trypanosomes. Propidium iodide may be used in flow cytometry to evaluate cell viability when used with other dyes that stain viable cells

REFERENCES

• Karlsson, R., et al.: Anal. Biochem., 278, 1 (2000)
• Lundqvist, T., et al.: Curr. Opin Drug Discov. Dev., 8, 513 (2000)
• Elinder, M., et al.: J. Biomol. Screen, 14, 395 (2000)
• Boettcher, A., et al.: J. Biomol. Screen, 2010, 15, 1029 (2000)