DANPY (dimethylaminonaphthylpyridinium): an economical and biocompatible fluorophore

TitleDANPY (dimethylaminonaphthylpyridinium): an economical and biocompatible fluorophore
Publication TypeJournal Article
Year of Publication2019
AuthorsJohnson L.E, Kingsbury J.S, Elder D.L, Cattolico R.A, Latimer L.N, Hardin W., De Meulenaere E., Deodato C., Depotter G., Madabushi S., Bigelow N.W, Smolarski B.A, Hougen T.K, Kaminsky W., Clays K., Robinson B.H
JournalOrganic & Biomolecular Chemistry
Volume17
Pagination3765-3780
Date Published2019/04
Type of ArticleArticle
ISBN Number1477-0520
Accession NumberWOS:000464584200012
Keywords2-photon fluorescence; absorption; binding; boronic acids; chemistry; ethidium-bromide; excitation cross-sections; hyper-rayleigh scattering; hyperpolarizability; multiphoton fluorescence; prodan
Abstract

Dyes with nonlinear optical (NLO) properties enable new imaging techniques and photonic systems. We have developed a dye (DANPY-1) for photonics applications in biological substrates such as nucleic acids; however, the design specification also enables it to be used for visualizing biomolecules. It is a prototype dye demonstrating a water-soluble, NLO-active fluorophore with high photostability, a large Stokes shift, and a favorable toxicity profile. A practical and scalable synthetic route to DANPY salts has been optimized featuring: (1) convergent Pd-catalyzed Suzuki coupling with pyridine 4-boronic acid, (2) site-selective pyridyl N-methylation, and (3) direct recovery of crystalline intermediates without chromatography. We characterize the optical properties, biocompatibility, and biological staining behavior of DANPY-1. In addition to stability and solubility across a range of polar media, the DANPY-1 chromophore shows a first hyperpolarizability similar to common NLO dyes such as Disperse Red 1 and DAST, a large two-photon absorption cross section for its size, substantial affinity to nucleic acids in vitro, an ability to stain a variety of cellular components, and strong sensitivity of its fluorescence properties to its dielectric environment.

DOI10.1039/c8ob02536c
Short TitleOrg. Biomol. Chem.
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