2-(4-carbamimidoylphenyl)-1H-indole-6-carboximidamide dihydrochloride

• ChemBase ID: 104891
• Molecular Formular: C16H17Cl2N5
• Molecular Mass: 350.24568
• Monoisotopic Mass: 349.08610093
• SMILES: Cl.Cl.NC(=N)c1ccc(cc1)c1cc2c([nH]1)cc(cc2)C(=N)N
• Canonical SMILES: NC(=N)c1ccc(cc1)c1cc2c([nH]1)cc(cc2)C(=N)N.Cl.Cl
• InChI: 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
• InChIKey: FPNZBYLXNYPRLR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-carbamimidoylphenyl)-1H-indole-6-carboximidamide dihydrochloride
• IUPAC Traditional name: DAPI dihydrochloride
• Synonyms: DAPI; 4',6-DIAMIDINO-2-PHENYLINDOLE DIHYDROCHLORIDE; 2-(4-Amidinophenyl)-6-indolecarbamidine dihydrochloride; DAPI dihydrochloride; 4′,6-Diamidino-2-phenylindole dihydrochloride

Database IDs

• CAS Number: 28718-90-3
• EC Number: 249-186-7
• MDL Number: MFCD00012681
• Beilstein Number: 4894417
• PubChem SID: 24894305; 24859612; 162091779; 24894213
• PubChem CID: 160166

CALCULATED PROPERTIES

• Acid pKa: 14.501453
• H Acceptors: 4
• H Donor: 5
• LogD (pH = 5.5): -3.3503847
• LogD (pH = 7.4): -3.3225315
• Log P: 1.4801712
• Molar Refractivity: 105.5032 cm^3
• Polarizability: 33.95792 Å^3
• Polar Surface Area: 115.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; H2O: soluble; H2O: soluble20 mg/mL (heat or sonication may be required. Solutions stored in the dark at room temperature or 4 °C should be stable for 2 to 3 weeks.); H2O: soluble20 mg/mL (Heat or sonication may be required. Solutions stored in the dark at room temperature or 4 °C should be stable for 2 to 3 weeks.); PBS: insoluble
• Apperance: powder
• Absorption Wavelength: ε/263 nm, H2O 30; ε1mM/263 nm, H2O 30
• 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

Safety Information

• Storage Condition: 0°C, Desiccate, Store Under Nitrogen, Protect from light
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); ≥98% (HPLC and TLC)
• Suitability: suitable for cell culture; suitable for fluorescence
• Quality Level: PREMIUM
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C16H15N5 · 2HCl

DETAILS

MP Biomedicals - 02157574

Dihydrochloride
Crystalline

Sigma Aldrich - D9542

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
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.
Caution
Protect from light.
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.

Sigma Aldrich - D8417

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.
Caution
Protect from light.
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.

Sigma Aldrich - 32670

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
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.
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.