10-(3-carboxypropyl)-6-(dimethylamino)-N,N-dimethyl-3,10-dihydroacridin-3-iminium perchlorate

• ChemBase ID: 154605
• Molecular Formular: C21H26ClN3O6
• Molecular Mass: 451.90064
• Monoisotopic Mass: 451.15101325
• SMILES: CN(C)c1ccc2cc3ccc(=[N+](C)C)cc3n(c2c1)CCCC(=O)O.[O-][Cl](=O)(=O)=O
• Canonical SMILES: [O-][Cl](=O)(=O)=O.OC(=O)CCCn1c2cc(ccc2cc2c1cc(=[N+](C)C)cc2)N(C)C
• InChI: InChI=1S/C21H25N3O2.ClHO4/c1-22(2)17-9-7-15-12-16-8-10-18(23(3)4)14-20(16)24(19(15)13-17)11-5-6-21(25)26;2-1(3,4)5/h7-10,12-14H,5-6,11H2,1-4H3;(H,2,3,4,5)
• InChIKey: KCYUESOHZRSRGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-(3-carboxypropyl)-6-(dimethylamino)-N,N-dimethyl-3,10-dihydroacridin-3-iminium perchlorate
• IUPAC Traditional name: 10-(3-carboxypropyl)-6-(dimethylamino)-N,N-dimethylacridin-3-iminium perchlorate
• Synonyms: Atto 495

Database IDs

• MDL Number: MFCD07370099
• PubChem SID: 162248743
• PubChem CID: 16212629

CALCULATED PROPERTIES

• Acid pKa: 4.2379174
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.4995612
• LogD (pH = 7.4): -0.18063357
• Log P: -1.0289645
• Molar Refractivity: 121.6212 cm^3
• Polarizability: 39.64209 Å^3
• Polar Surface Area: 46.79 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble; DMF: soluble; DMSO: soluble; H2O: soluble
• Fluorescence: λex 499 nm; λem 535 nm in 0.1 M phosphate pH 7.0

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPCE)
• Suitability: suitable for fluorescence
• Product Line: BioReagent

DETAILS

Sigma Aldrich - 16951

General description
Atto 495 is a new label for proteins and oligo-nucleotides with high molecular absorption (80.000) and quantum yield (0.45) as well as sufficient Stoke′s shift between excitation and emission maximum. Atto 495 is characterized by a high photostability and thermostability. It is slightly hydrophilic, and solubility in polar solvents as DMF or DMSO is high.
Application
Atto 495 is a lipophilic fluorescent compound, which has served as the neutral analyte in the model, along with SDS as the charged micelle acting as a carrier to transport this solute in an electric field1,2. Atto 495 was included as fluorescence EOF marker for chip electrophoresis. This reagent is zwitterionic at pH 8.3 and thus migrates as a neutral substance under the proper conditions3,4.