ethyl 9-{4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutyl}-6,8,8-trimethyl-2-oxo-2H,6H,7H,8H,9H-chromeno[7,6-b]pyridine-3-carboxylate

• ChemBase ID: 155907
• Molecular Formular: C26H30N2O8
• Molecular Mass: 498.525
• Monoisotopic Mass: 498.20021593
• SMILES: CCOC(=O)c1cc2cc3c(cc2oc1=O)N(C(CC3C)(C)C)CCCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: CCOC(=O)c1cc2cc3C(C)CC(N(c3cc2oc1=O)CCCC(=O)ON1C(=O)CCC1=O)(C)C
• InChI: InChI=1S/C26H30N2O8/c1-5-34-24(32)18-12-16-11-17-15(2)14-26(3,4)27(19(17)13-20(16)35-25(18)33)10-6-7-23(31)36-28-21(29)8-9-22(28)30/h11-13,15H,5-10,14H2,1-4H3
• InChIKey: PUEQEMDTFPYCDY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 9-{4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutyl}-6,8,8-trimethyl-2-oxo-2H,6H,7H,8H,9H-chromeno[7,6-b]pyridine-3-carboxylate
• IUPAC Traditional name: atto 425 nhs-ester
• Synonyms: Atto 425-N-hydroxysuccinimide ester; Atto 425 NHS ester

Database IDs

• CAS Number: 892156-28-4
• MDL Number: MFCD04974819
• PubChem SID: 162250045; 24850231
• PubChem CID: 16211368

CALCULATED PROPERTIES

• Acid pKa: 17.709116
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.0455227
• LogD (pH = 7.4): 3.056412
• Log P: 3.0565524
• Molar Refractivity: 129.1782 cm^3
• Polarizability: 49.536854 Å^3
• Polar Surface Area: 119.52 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; H2O: soluble
• Fluorescence: λex 437 nm; λem 483 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

• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C26H30N2O8

DETAILS

Sigma Aldrich - 16805

Application
Atto fluorescent labels are designed for high sensitivity applications, including single molecule detection. Atto labels have rigid structures that do not show any cis-trans-isomerization. Thus these labels display exceptional intensity with minimal spectral shift on conjugation.
Atto 425 NHS ester is used in the development of bifunctional fluorescent, inorganic micro-partices (Zeolite L crystals) designed for targeting or imaging mutliple components 1. Reacts with amino groups or amine modified oliognucleotides to form a stable amine bond. Utilized as an essential component of molecular beacons, which were designed for use in real-time PCR assays to allow for rapid and accurate identification of gram-negative bacteria 2. When conjugated with benzylguanine, the fluorescence of Atto 425-NHS is quenched but becomes fluorescent upon labeling of the SNAP-tag fusion protein, making this conjugate an ideal candidate for experiments in living cells 3. Used as one of the donor probes in three-color FRET experiments designed to investigate the kinetics of RNA-protein complex formation 4.
Other Notes
Study of stability during one- and two-photon excitation in fluorescence correlation spectroscopy, FCS5; employed in triple-color coincidence analysis6.