Journal of the American Chemical Society, volume 127, issue 48, pages 16812-16823
QZ1 and QZ2: Rapid, Reversible Quinoline-Derivatized Fluoresceins for Sensing Biological Zn(II)
Nolan Elizabeth
1
,
Jaworski Jacek
1
,
Okamoto Ken-ichi
1
,
Hayashi Yasunori
1
,
Sheng Morgan
1
,
Lippard S. J.
1
Publication type: Journal Article
Publication date: 2005-11-10
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
PubMed ID:
16316228
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
QZ1, 2-[2-chloro-6-hydroxy-3-oxo-5-(quinolin-8-ylaminomethyl)-3H-xanthen-9-yl]benzoic acid, and QZ2, 2-[6-hydroxy-3-oxo-4,5-bis-(quinolin-8-ylaminomethyl)-3H-xanthen-9-yl]benzoic acid, two fluorescein-based dyes derivatized with 8-aminoquinoline, have been prepared and their photophysical, thermodynamic, and zinc-binding kinetic properties determined. Because of their low background fluorescence and highly emissive Zn(II) complexes, QZ1 and QZ2 have a large dynamic range, with approximately 42- and approximately 150-fold fluorescence enhancements upon Zn(II) coordination, respectively. These dyes have micromolar K(d) values for Zn(II) and are selective for Zn(II) over biologically relevant concentrations of the alkali and alkaline earth metals. The Zn(II) complexes also fluoresce brightly in the presence of excess Mn(II), Fe(II), Co(II), Cd(II), and Hg(II), offering improved specificity for Zn(II) over di(2-picolyl)amine-based Zn(II) sensors. Stopped-flow kinetic investigations indicate that QZ1 and QZ2 bind Zn(II) with k(on) values of (3-4) x 10(6) M(-1) s(-1), compared to (6-8) x 10(5) M(-1) s(-1) for select ZP (Zinpyr) dyes, at 4.3 degrees C. Dissociation of Zn(II) from QZ1 and QZ2 occurs with k(off) values of 150 and 160 s(-1), over 5 orders of magnitude larger than those for ZP probes, achieving reversibility on the biological (millisecond) time scale. Laser scanning confocal and two-photon microscopy studies reveal that QZ2 is cell-permeable and Zn(II)-responsive in vivo. Because of its weaker affinity for Zn(II), QZ2 responds to higher concentrations of intracellular Zn(II) than members of the ZP family, illustrating that binding affinity is an important parameter for Zn(II) detection in vivo.
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Nolan E. et al. QZ1 and QZ2: Rapid, Reversible Quinoline-Derivatized Fluoresceins for Sensing Biological Zn(II) // Journal of the American Chemical Society. 2005. Vol. 127. No. 48. pp. 16812-16823.
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Nolan E., Jaworski J., Okamoto K., Hayashi Y., Sheng M., Lippard S. J. QZ1 and QZ2: Rapid, Reversible Quinoline-Derivatized Fluoresceins for Sensing Biological Zn(II) // Journal of the American Chemical Society. 2005. Vol. 127. No. 48. pp. 16812-16823.
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TY - JOUR
DO - 10.1021/ja052184t
UR - https://doi.org/10.1021%2Fja052184t
TI - QZ1 and QZ2: Rapid, Reversible Quinoline-Derivatized Fluoresceins for Sensing Biological Zn(II)
T2 - Journal of the American Chemical Society
AU - Okamoto, Ken-ichi
AU - Nolan, Elizabeth
AU - Jaworski, Jacek
AU - Hayashi, Yasunori
AU - Sheng, Morgan
AU - Lippard, S. J.
PY - 2005
DA - 2005/11/10 00:00:00
PB - American Chemical Society (ACS)
SP - 16812-16823
IS - 48
VL - 127
PMID - 16316228
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2005_Nolan
author = {Ken-ichi Okamoto and Elizabeth Nolan and Jacek Jaworski and Yasunori Hayashi and Morgan Sheng and S. J. Lippard},
title = {QZ1 and QZ2: Rapid, Reversible Quinoline-Derivatized Fluoresceins for Sensing Biological Zn(II)},
journal = {Journal of the American Chemical Society},
year = {2005},
volume = {127},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021%2Fja052184t},
number = {48},
pages = {16812--16823},
doi = {10.1021/ja052184t}
}
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MLA
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Nolan, Elizabeth, et al. “QZ1 and QZ2: Rapid, Reversible Quinoline-Derivatized Fluoresceins for Sensing Biological Zn(II).” Journal of the American Chemical Society, vol. 127, no. 48, Nov. 2005, pp. 16812-16823. https://doi.org/10.1021%2Fja052184t.