A Dimethylaminophenyl‐Substituted Naphtho[1, 2‐b]quinolizinium as a Multicolor NIR Probe for the Fluorimetric Detection of Intracellular Nucleic Acids and Proteins. Issue 12 (16th September 2021)

• Record Type: Journal Article
• Authors: Wickhorst, Peter Jonas; Druzhinin, Sergey I.; Ihmels, Heiko; Müller, Mareike; Sutera Sardo, Manlio; Schönherr, Holger; Viola, Giampietro
• Is Part Of: ChemPhotoChem. Volume 5:Issue 12(2021)
• Page Start: 1079
• Page End: 1088
• Publication Date: 2021-09-16
• Subjects: bioorganic chemistry -- cell imaging -- fluorescent probes -- intercalation -- nucleic acids; Photochemistry -- Periodicals; Periodicals; Electronic journals; 541.35
• DOI: 10.1002/cptc.202100148
• Languages: English
• ISSNs: 2367-0932

Abstract

Abstract: The dye 3‐(4‐( N, N ‐dimethylamino)phenyl)naphtho[ 1, 2‐b ]quinolizinium was synthesized by means of a Suzuki–Miyaura reaction in good yield, and its binding properties with duplex DNA, quadruplex DNA (G4‐DNA), RNA, and bovine serum albumin (BSA) were investigated by photometric, fluorimetric and polarimetric titrations and DNA denaturation analysis. The compound intercalates into DNA and RNA, associates in binding site I of BSA, and binds to G4‐DNA by terminal π stacking. The ligand exhibits a fluorescence light‐up effect upon complexation to these biomacromolecules, which is more pronounced and blue shifted in the presence of BSA ( Φ fl =0.29, λ fl =627 nm) than with the nucleic acids ( Φ fl =0.01–0.05, λ fl =725–750 nm). Furthermore, the triple‐exponential fluorescence decay of the probe when bound to biomacromolecules in a cell enables their visualization in this medium and the differential labeling of cellular components. Abstract : Light up, light up : The fluorimetric detection of different biomacromolecules is accomplished with 3‐(4‐ N, N ‐dimethylaminophenylnaphtho[1, 2‐ b ]quinolizinium as a fluorescent probe. This molecule shows a light‐up effect in the presence of DNA, RNA and bovine serum albumin (BSA) with different emission energies, intensities, and lifetimes. These effects may be used for the fluorimetric differentiation between different cell compartments.