DANPY (dimethylaminonaphthylpyridinium): an economical and biocompatible fluorophore

Johnson, Lewis E.; Kingsbury, Jason S.; Elder, Delwin L.; Cattolico, Rose Ann; Latimer, Luke N.; Hardin, William; De Meulenaere, Evelien; Deodato, Chloe; Depotter, Griet; Madabushi, Sowmya; Bigelow, Nicholas W.; Smolarski, Brittany A.; Hougen, Trevor K.; Kaminsky, Werner; Clays, Koen; Robinson, Bruce H.

doi:10.1039/C8OB02536C

Title: DANPY (dimethylaminonaphthylpyridinium): an economical and biocompatible fluorophore

Journal Article · Wed Apr 10 00:00:00 EDT 2019 · Organic and Biomolecular Chemistry

DOI:https://doi.org/10.1039/C8OB02536C· OSTI ID:1501942

^[1]; Kingsbury, Jason S. ^[2];

^[1]; Cattolico, Rose Ann ^[3]; Latimer, Luke N. ^[1]; Hardin, William ^[3]; De Meulenaere, Evelien ^[4];

^[3]; Depotter, Griet ^[4];

^[3];

^[1];

^[2]; Hougen, Trevor K. ^[2];

^[1]; Clays, Koen ^[4];

^[1]

Department of Chemistry, University of Washington, Seattle, USA
Department of Chemistry, Ahmanson Science Center, California Lutheran University, Thousand Oaks, USA
Department of Biology, University of Washington, Seattle, USA
Department of Chemistry, Katholieke Universiteit Leuven, Leuven, Belgium B-3001

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.

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Research Organization:: Donald Danforth Plant Science Center, St. Louis, MO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Bioenergy Technologies Office (BETO); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Sustainable Transportation Office. Bioenergy Technologies Office (BETO)

Grant/Contract Number:: EE0003046

OSTI ID:: 1501942

Alternate ID(s):: OSTI ID: 1613272

Journal Information:: Organic and Biomolecular Chemistry, Journal Name: Organic and Biomolecular Chemistry Vol. 17 Journal Issue: 15; ISSN 1477-0520

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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Cited by: 2 works

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Chemistry

Title: DANPY (dimethylaminonaphthylpyridinium): an economical and biocompatible fluorophore

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