New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling

Shyamala Pillai; Laura Wirpsza; Maxim Kozlov; Salvatore A.E. Marras; Lev N. Krasnoperov; Arkady Mustaev

doi:10.1117/12.921056

New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling

Shyamala Pillai, Laura Wirpsza, Maxim Kozlov, Salvatore A.E. Marras, Lev N. Krasnoperov, Arkady Mustaev

Chemistry and Environmental Science

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

1 Scopus citations

Abstract

New luminescent lanthanide chelates containing thiol-, amine-, and click-reactive groups in antenna-fluorophore moieties were synthesized. The chelates include diethylenetriaminepentaacetic acid (DTPA) coupled to two types of chromophores: 7-amino-4-trifluoromethyl-2(1H) quinolinone, and 7-amino-4-trifluoromethyl-2-alkoxyquinoline. The synthesized compounds were characterized using NMR, light absorption, steady-state and time-resolved fluorescent spectroscopy. Some of the compounds displayed high brightness with Tb3+, Eu3+, and Dy3+. Obtained reactive lanthanide chelates can be easily attached to biological molecules. The probes demonstrated high performance in molecular beaconbased DNA hybridization assays (sub-pico molar detection limit), in bacterial proteome labeling, and in live cell imaging.

Original language	English (US)
Title of host publication	Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV
DOIs	https://doi.org/10.1117/12.921056
State	Published - 2012
Event	Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV - San Francisco, CA, United States Duration: Jan 23 2012 → Jan 25 2012

Publication series

Name	Progress in Biomedical Optics and Imaging - Proceedings of SPIE
Volume	8233
ISSN (Print)	1605-7422

Other

Other	Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV
Country/Territory	United States
City	San Francisco, CA
Period	1/23/12 → 1/25/12

All Science Journal Classification (ASJC) codes

Electronic, Optical and Magnetic Materials
Biomaterials
Atomic and Molecular Physics, and Optics
Radiology Nuclear Medicine and imaging

Keywords

Lanthanide ion probes
click reaction
molecular beacons
time-resolved detection

Access to Document

10.1117/12.921056

Cite this

Pillai, S., Wirpsza, L., Kozlov, M., Marras, S. A. E., Krasnoperov, L. N., & Mustaev, A. (2012). New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling. In Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV Article 82331C (Progress in Biomedical Optics and Imaging - Proceedings of SPIE; Vol. 8233). https://doi.org/10.1117/12.921056

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title = "New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling",

abstract = "New luminescent lanthanide chelates containing thiol-, amine-, and click-reactive groups in antenna-fluorophore moieties were synthesized. The chelates include diethylenetriaminepentaacetic acid (DTPA) coupled to two types of chromophores: 7-amino-4-trifluoromethyl-2(1H) quinolinone, and 7-amino-4-trifluoromethyl-2-alkoxyquinoline. The synthesized compounds were characterized using NMR, light absorption, steady-state and time-resolved fluorescent spectroscopy. Some of the compounds displayed high brightness with Tb3+, Eu3+, and Dy3+. Obtained reactive lanthanide chelates can be easily attached to biological molecules. The probes demonstrated high performance in molecular beaconbased DNA hybridization assays (sub-pico molar detection limit), in bacterial proteome labeling, and in live cell imaging.",

keywords = "Lanthanide ion probes, click reaction, molecular beacons, time-resolved detection",

author = "Shyamala Pillai and Laura Wirpsza and Maxim Kozlov and Marras, {Salvatore A.E.} and Krasnoperov, {Lev N.} and Arkady Mustaev",

year = "2012",

doi = "10.1117/12.921056",

language = "English (US)",

isbn = "9780819488763",

series = "Progress in Biomedical Optics and Imaging - Proceedings of SPIE",

booktitle = "Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV",

note = "Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV ; Conference date: 23-01-2012 Through 25-01-2012",

}

Pillai, S, Wirpsza, L, Kozlov, M, Marras, SAE, Krasnoperov, LN & Mustaev, A 2012, New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling. in Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV., 82331C, Progress in Biomedical Optics and Imaging - Proceedings of SPIE, vol. 8233, Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV, San Francisco, CA, United States, 1/23/12. https://doi.org/10.1117/12.921056

New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling. / Pillai, Shyamala; Wirpsza, Laura; Kozlov, Maxim et al.
Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV. 2012. 82331C (Progress in Biomedical Optics and Imaging - Proceedings of SPIE; Vol. 8233).

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

TY - GEN

T1 - New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling

AU - Pillai, Shyamala

AU - Wirpsza, Laura

AU - Kozlov, Maxim

AU - Marras, Salvatore A.E.

AU - Krasnoperov, Lev N.

AU - Mustaev, Arkady

PY - 2012

Y1 - 2012

N2 - New luminescent lanthanide chelates containing thiol-, amine-, and click-reactive groups in antenna-fluorophore moieties were synthesized. The chelates include diethylenetriaminepentaacetic acid (DTPA) coupled to two types of chromophores: 7-amino-4-trifluoromethyl-2(1H) quinolinone, and 7-amino-4-trifluoromethyl-2-alkoxyquinoline. The synthesized compounds were characterized using NMR, light absorption, steady-state and time-resolved fluorescent spectroscopy. Some of the compounds displayed high brightness with Tb3+, Eu3+, and Dy3+. Obtained reactive lanthanide chelates can be easily attached to biological molecules. The probes demonstrated high performance in molecular beaconbased DNA hybridization assays (sub-pico molar detection limit), in bacterial proteome labeling, and in live cell imaging.

AB - New luminescent lanthanide chelates containing thiol-, amine-, and click-reactive groups in antenna-fluorophore moieties were synthesized. The chelates include diethylenetriaminepentaacetic acid (DTPA) coupled to two types of chromophores: 7-amino-4-trifluoromethyl-2(1H) quinolinone, and 7-amino-4-trifluoromethyl-2-alkoxyquinoline. The synthesized compounds were characterized using NMR, light absorption, steady-state and time-resolved fluorescent spectroscopy. Some of the compounds displayed high brightness with Tb3+, Eu3+, and Dy3+. Obtained reactive lanthanide chelates can be easily attached to biological molecules. The probes demonstrated high performance in molecular beaconbased DNA hybridization assays (sub-pico molar detection limit), in bacterial proteome labeling, and in live cell imaging.

KW - Lanthanide ion probes

KW - click reaction

KW - molecular beacons

KW - time-resolved detection

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T3 - Progress in Biomedical Optics and Imaging - Proceedings of SPIE

BT - Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV

T2 - Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV

Y2 - 23 January 2012 through 25 January 2012

ER -

Pillai S, Wirpsza L, Kozlov M, Marras SAE, Krasnoperov LN, Mustaev A. New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling. In Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications IV. 2012. 82331C. (Progress in Biomedical Optics and Imaging - Proceedings of SPIE). doi: 10.1117/12.921056

New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling

Abstract

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All Science Journal Classification (ASJC) codes

Keywords

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