Zinc selective chemosensor based on pyridyl-amide fluorescence

Hong Gyu Lee; Ju Hoon Lee; Seung Pyo Jang; Hyun Min Park; Sung Jin Kim; Youngmee Kim; Cheal Kim; Roger G. Harrison

doi:10.1016/j.tet.2011.08.049

Zinc selective chemosensor based on pyridyl-amide fluorescence

Hong Gyu Lee, Ju Hoon Lee, Seung Pyo Jang, Hyun Min Park, Sung Jin Kim, Youngmee Kim, Cheal Kim, Roger G. Harrison

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

72 Scopus citations

Abstract

Chemosensors are developed to image zinc ions. Fluorescence enhancement due to Zn²⁺ binding is an excellent way to detect its presence. A chemosensor for Zn²⁺ based on dipicolylamine (DPA) groups connected by a pyridyl amide backbone has been synthesized. Addition of 2-chloroacetyl chloride to 2,6-diaminopyridine affords 2,6-bis(chloroethylamido)pyridine, which is converted to the sensor BADPA-P by 2,2′-dipicolylamine displacement of chlorine. This compound along with two others, the mono-DPA, ADPA-P and the benzyl in place of pyridyl, BADPA-B, present three potential Zn²⁺ sensors. It was found that BADPA-P in the presence of Zn²⁺ shows a large increase in fluorescence, whether in polar organic or aqueous environments. Its fluorescence in the presence of Cd²⁺, unlike with Zn²⁺, is not enhanced when excited at longer wavelengths. Proton NMR measurements, indicate two Zn²⁺ ions bind to BADPA-P. Also, Zn ²⁺ enhances fluorescence even when other metal ions are present.

Original language	English
Pages (from-to)	8073-8078
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2011.08.049
State	Published - 21 Oct 2011

Bibliographical note

Funding Information:
Financial support from Korean Science & Engineering Foundation (2009-0074066), Converging Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2009-0082832), and Brigham Young University is gratefully acknowledged.

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title = "Zinc selective chemosensor based on pyridyl-amide fluorescence",

abstract = "Chemosensors are developed to image zinc ions. Fluorescence enhancement due to Zn2+ binding is an excellent way to detect its presence. A chemosensor for Zn2+ based on dipicolylamine (DPA) groups connected by a pyridyl amide backbone has been synthesized. Addition of 2-chloroacetyl chloride to 2,6-diaminopyridine affords 2,6-bis(chloroethylamido)pyridine, which is converted to the sensor BADPA-P by 2,2′-dipicolylamine displacement of chlorine. This compound along with two others, the mono-DPA, ADPA-P and the benzyl in place of pyridyl, BADPA-B, present three potential Zn2+ sensors. It was found that BADPA-P in the presence of Zn2+ shows a large increase in fluorescence, whether in polar organic or aqueous environments. Its fluorescence in the presence of Cd2+, unlike with Zn2+, is not enhanced when excited at longer wavelengths. Proton NMR measurements, indicate two Zn2+ ions bind to BADPA-P. Also, Zn 2+ enhances fluorescence even when other metal ions are present.",

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note = "Funding Information: Financial support from Korean Science & Engineering Foundation (2009-0074066), Converging Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2009-0082832), and Brigham Young University is gratefully acknowledged. ",

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AU - Park, Hyun Min

AU - Kim, Sung Jin

AU - Kim, Youngmee

AU - Kim, Cheal

AU - Harrison, Roger G.

N1 - Funding Information: Financial support from Korean Science & Engineering Foundation (2009-0074066), Converging Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2009-0082832), and Brigham Young University is gratefully acknowledged.

PY - 2011/10/21

Y1 - 2011/10/21

N2 - Chemosensors are developed to image zinc ions. Fluorescence enhancement due to Zn2+ binding is an excellent way to detect its presence. A chemosensor for Zn2+ based on dipicolylamine (DPA) groups connected by a pyridyl amide backbone has been synthesized. Addition of 2-chloroacetyl chloride to 2,6-diaminopyridine affords 2,6-bis(chloroethylamido)pyridine, which is converted to the sensor BADPA-P by 2,2′-dipicolylamine displacement of chlorine. This compound along with two others, the mono-DPA, ADPA-P and the benzyl in place of pyridyl, BADPA-B, present three potential Zn2+ sensors. It was found that BADPA-P in the presence of Zn2+ shows a large increase in fluorescence, whether in polar organic or aqueous environments. Its fluorescence in the presence of Cd2+, unlike with Zn2+, is not enhanced when excited at longer wavelengths. Proton NMR measurements, indicate two Zn2+ ions bind to BADPA-P. Also, Zn 2+ enhances fluorescence even when other metal ions are present.

AB - Chemosensors are developed to image zinc ions. Fluorescence enhancement due to Zn2+ binding is an excellent way to detect its presence. A chemosensor for Zn2+ based on dipicolylamine (DPA) groups connected by a pyridyl amide backbone has been synthesized. Addition of 2-chloroacetyl chloride to 2,6-diaminopyridine affords 2,6-bis(chloroethylamido)pyridine, which is converted to the sensor BADPA-P by 2,2′-dipicolylamine displacement of chlorine. This compound along with two others, the mono-DPA, ADPA-P and the benzyl in place of pyridyl, BADPA-B, present three potential Zn2+ sensors. It was found that BADPA-P in the presence of Zn2+ shows a large increase in fluorescence, whether in polar organic or aqueous environments. Its fluorescence in the presence of Cd2+, unlike with Zn2+, is not enhanced when excited at longer wavelengths. Proton NMR measurements, indicate two Zn2+ ions bind to BADPA-P. Also, Zn 2+ enhances fluorescence even when other metal ions are present.

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Zinc selective chemosensor based on pyridyl-amide fluorescence

Abstract

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