The Fluorescence Labelling of Primary Amines with Perylenetetracarboxdiimides

Abstract

The synthesis of perylenetetracarboxdiimide‐labelled aldehydes is described as well as their condensation with primary amines. Thus, a highly fluorescent and light‐fast fluorescence labelling process has been demonstrated. Application of this method to biological targets is also reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Light‐Driven Charge Separation in Isoxazolidine–Perylene Bisimide Dyads

“…Design and synthesis : We started synthesis with the aldehyde12 2 and condensed it to form the nitrone 3 as a key intermediate for the synthesis of isoxazolidines by 1,3‐dipolar cycloaddition 13. However, no reaction of 3 was observed with olefins such as styrene.…”

“…N ‐(1‐Hexylheptyl)‐ N ′‐(4‐ N ′′‐methylcarbaldimin‐ N ′′‐oxidobenzyl)perylene‐3,4:9,10‐tetracarboxylic bisimide (3) : Comopund 2 12 (1.10 g, 1.59 mmol), N ‐methylhydroxylamine hydrochloride (200 mg, 2.39 mmol), and NaHCO 3 (287 mg, 3.31 mmol) were dissolved in CH 2 Cl 2 (50 mL). The resulting solution was treated with MgSO 4 (400 mg), heated under reflux for 5 h, stirred at room temperature for 16 h, filtered and evaporated, and the residue was purified by column separation (silica gel, dichloromethane/methanol 30:1).…”

New RAD51 Inhibitors to Target Homologous Recombination in Human Cells

“…P-formyl-benzyl derivative of B02 ( Figure S1 , compound 10, Figure S3 ) was synthesized from the intermediates 7,8,9 ( Figure S3 ). Intermediate 7 was obtained according to the procedure described in [ 41 ]. Reaction mixtures and isolated compounds were analyzed using reversed-phase HPLC on a Gemini ® 5 µm C18 column (10 × 2 mm, Phenomenex), and elution was performed with a linear gradient of acetonitrile in 0.1% formic acid (for [M + H] + signals) and in 0.1 M ammonium formate (for [M − H] + signals).…”

Angular Benzoperylenetetracarboxylic Bisimides

“…Thus, we protected the aldehyde group as the ethylene acetal according to ref. [9] and prepared either aldehyde 3 e directly by means of the corresponding amino acetals and acidic workup or acetal 3 f if acid was excluded. The former (3 e) is more appropriate for direct labeling such as in the condensations with primary amines, whereas the latter is useful as a protected compound as it allows for the long-term storage of the comparably reactive aldehyde.…”