Fluorescent sensors based on [12]aneN3-modified BODIPY: Discrimination of different biological thiols in aqueous solution and living cells

Yong Guang Gao; Ying Zhang; You Di Shi; Hu Jun Hao; Bing Gong; Zhong Lin Lu

doi:10.1016/j.bmc.2016.02.024

Fluorescent sensors based on [12]aneN₃-modified BODIPY: Discrimination of different biological thiols in aqueous solution and living cells

Yong Guang Gao
, Ying Zhang
, You Di Shi
, Hu Jun Hao
, Bing Gong
, Zhong Lin Lu

Chemistry

Beijing Normal University

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

19 Scopus citations

Abstract

Two fluorescent probes, 1 and 2, derived from borondipyrromethene (BODIPY) modified with macrocyclic polyamine [12]aneN₃, were synthesized and applied in the discrimination of cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) with absorption and fluorescent spectroscopy in comparison. It was found that Boc-protected 1 showed highly sensitive and selective recognition of GSH over Cys and Hcy; while probe 2 was able to distinguish the three different thiols due to their different reactivities. With its water-solubility, rapid responsiveness, high sensitivity and low cytotoxicity, probe 2 was successfully applied in the fast detection of three biothiols in living cells.

Original language	English
Pages (from-to)	1550-1559
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	24
Issue number	7
DOIs	https://doi.org/10.1016/j.bmc.2016.02.024
State	Published - Apr 1 2016

Keywords

BODIPY
Sensor
Thiols
[12]aneN

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10.1016/j.bmc.2016.02.024

Cite this

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title = "Fluorescent sensors based on [12]aneN3-modified BODIPY: Discrimination of different biological thiols in aqueous solution and living cells",

abstract = "Two fluorescent probes, 1 and 2, derived from borondipyrromethene (BODIPY) modified with macrocyclic polyamine [12]aneN3, were synthesized and applied in the discrimination of cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) with absorption and fluorescent spectroscopy in comparison. It was found that Boc-protected 1 showed highly sensitive and selective recognition of GSH over Cys and Hcy; while probe 2 was able to distinguish the three different thiols due to their different reactivities. With its water-solubility, rapid responsiveness, high sensitivity and low cytotoxicity, probe 2 was successfully applied in the fast detection of three biothiols in living cells.",

keywords = "BODIPY, Sensor, Thiols, [12]aneN",

author = "Gao, \{Yong Guang\} and Ying Zhang and Shi, \{You Di\} and Hao, \{Hu Jun\} and Bing Gong and Lu, \{Zhong Lin\}",

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doi = "10.1016/j.bmc.2016.02.024",

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TY - JOUR

T1 - Fluorescent sensors based on [12]aneN3-modified BODIPY

T2 - Discrimination of different biological thiols in aqueous solution and living cells

AU - Gao, Yong Guang

AU - Zhang, Ying

AU - Shi, You Di

AU - Hao, Hu Jun

AU - Gong, Bing

AU - Lu, Zhong Lin

PY - 2016/4/1

Y1 - 2016/4/1

N2 - Two fluorescent probes, 1 and 2, derived from borondipyrromethene (BODIPY) modified with macrocyclic polyamine [12]aneN3, were synthesized and applied in the discrimination of cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) with absorption and fluorescent spectroscopy in comparison. It was found that Boc-protected 1 showed highly sensitive and selective recognition of GSH over Cys and Hcy; while probe 2 was able to distinguish the three different thiols due to their different reactivities. With its water-solubility, rapid responsiveness, high sensitivity and low cytotoxicity, probe 2 was successfully applied in the fast detection of three biothiols in living cells.

AB - Two fluorescent probes, 1 and 2, derived from borondipyrromethene (BODIPY) modified with macrocyclic polyamine [12]aneN3, were synthesized and applied in the discrimination of cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) with absorption and fluorescent spectroscopy in comparison. It was found that Boc-protected 1 showed highly sensitive and selective recognition of GSH over Cys and Hcy; while probe 2 was able to distinguish the three different thiols due to their different reactivities. With its water-solubility, rapid responsiveness, high sensitivity and low cytotoxicity, probe 2 was successfully applied in the fast detection of three biothiols in living cells.

KW - BODIPY

KW - Sensor

KW - Thiols

KW - [12]aneN

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DO - 10.1016/j.bmc.2016.02.024

M3 - Article

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AN - SCOPUS:84960113349

SN - 0968-0896

VL - 24

SP - 1550

EP - 1559

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 7

ER -

Fluorescent sensors based on [12]aneN₃-modified BODIPY: Discrimination of different biological thiols in aqueous solution and living cells

Abstract

Keywords

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