A benzothiazolium-based fluorescent probe with ideal p: K afor mitochondrial pH imaging and cancer cell differentiation

Bo Lin; Li Fan; Ying Zhou; Jinyin Ge; Xueli Wang; Chuan Dong; Shaomin Shuang; Man Shing Wong

doi:10.1039/D0TB01253J

A benzothiazolium-based fluorescent probe with ideal p: K _afor mitochondrial pH imaging and cancer cell differentiation

Bo Lin, Li Fan, Ying Zhou, Jinyin Ge, Xueli Wang, Chuan Dong, Shaomin Shuang^*, Man Shing Wong^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

14 Citations (Scopus)

Abstract

A mitochondrial pH sensing fluorescent probe namely 2-(2-(6-hydroxynaphthalen-2-yl)vinyl)-3-(6-(triphenyl-phosphonio)hexyl)benzothiazol-3-ium bromide (HTBT2) was designed and facilely synthesized via the Knoevenagel condensation reaction. HTBT2 displayed a linear fluorescence enhancement at 612 nm in response to pH changes between 8.70 and 7.20. The pKa value was determined to be 8.04 ± 0.02, which might be ideal for mitochondrial pH (pHmito ∼8.0) detection. HTBT2 also exhibited a remarkable large Stokes shift of 176 nm, which could diminish the interference of excitation light. The results of live cell imaging studies suggested that HTBT2 showed excellent targeting ability for mitochondria. Importantly, it was successfully applied to visualize mitochondrial pH changes in live cells and differentiate the pHmito difference between cancer cell lines and normal cell lines. Our results consistently supported that HTBT2 held practical promise for the investigation of physiological processes related to pHmito changes and clinical potential for cancer cell differentiation. This journal is

Original language	English
Pages (from-to)	10586-10592
Number of pages	7
Journal	Journal of Materials Chemistry B
Volume	8
Issue number	46
Early online date	28 Sept 2020
DOIs	https://doi.org/10.1039/D0TB01253J
Publication status	Published - 14 Dec 2020

Scopus Subject Areas

General Chemistry
Biomedical Engineering
General Materials Science

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1039/D0TB01253J

Cite this

@article{84c39c13d5f2459ca1900627c419ec46,

title = "A benzothiazolium-based fluorescent probe with ideal p: K afor mitochondrial pH imaging and cancer cell differentiation",

abstract = "A mitochondrial pH sensing fluorescent probe namely 2-(2-(6-hydroxynaphthalen-2-yl)vinyl)-3-(6-(triphenyl-phosphonio)hexyl)benzothiazol-3-ium bromide (HTBT2) was designed and facilely synthesized via the Knoevenagel condensation reaction. HTBT2 displayed a linear fluorescence enhancement at 612 nm in response to pH changes between 8.70 and 7.20. The pKa value was determined to be 8.04 ± 0.02, which might be ideal for mitochondrial pH (pHmito ∼8.0) detection. HTBT2 also exhibited a remarkable large Stokes shift of 176 nm, which could diminish the interference of excitation light. The results of live cell imaging studies suggested that HTBT2 showed excellent targeting ability for mitochondria. Importantly, it was successfully applied to visualize mitochondrial pH changes in live cells and differentiate the pHmito difference between cancer cell lines and normal cell lines. Our results consistently supported that HTBT2 held practical promise for the investigation of physiological processes related to pHmito changes and clinical potential for cancer cell differentiation. This journal is ",

author = "Bo Lin and Li Fan and Ying Zhou and Jinyin Ge and Xueli Wang and Chuan Dong and Shaomin Shuang and Wong, {Man Shing}",

note = "Funding Information: The work was supported by the National Natural Science Foundation of China (No. 91843301, 21874087 and 81901814), the Key R&D project of Shanxi Province (201803D421031), Talents Project and General Research Fund (GRF) (HKBU 12301317) from the Research Grant Council of Hong Kong. We also appreciate Lanqi Huang, Di Xu, Tongxin Zhang and Wu Chun from Hong Kong Baptist University, Hong Kong for assisting with experiments. Publisher copyright: {\textcopyright} The Royal Society of Chemistry 2020",

year = "2020",

month = dec,

day = "14",

doi = "10.1039/D0TB01253J",

language = "English",

volume = "8",

pages = "10586--10592",

journal = "Journal of Materials Chemistry B",

issn = "2050-750X",

publisher = "Royal Society of Chemistry",

number = "46",

}

TY - JOUR

T1 - A benzothiazolium-based fluorescent probe with ideal p

T2 - K afor mitochondrial pH imaging and cancer cell differentiation

AU - Lin, Bo

AU - Fan, Li

AU - Zhou, Ying

AU - Ge, Jinyin

AU - Wang, Xueli

AU - Dong, Chuan

AU - Shuang, Shaomin

AU - Wong, Man Shing

N1 - Funding Information: The work was supported by the National Natural Science Foundation of China (No. 91843301, 21874087 and 81901814), the Key R&D project of Shanxi Province (201803D421031), Talents Project and General Research Fund (GRF) (HKBU 12301317) from the Research Grant Council of Hong Kong. We also appreciate Lanqi Huang, Di Xu, Tongxin Zhang and Wu Chun from Hong Kong Baptist University, Hong Kong for assisting with experiments. Publisher copyright: © The Royal Society of Chemistry 2020

PY - 2020/12/14

Y1 - 2020/12/14

N2 - A mitochondrial pH sensing fluorescent probe namely 2-(2-(6-hydroxynaphthalen-2-yl)vinyl)-3-(6-(triphenyl-phosphonio)hexyl)benzothiazol-3-ium bromide (HTBT2) was designed and facilely synthesized via the Knoevenagel condensation reaction. HTBT2 displayed a linear fluorescence enhancement at 612 nm in response to pH changes between 8.70 and 7.20. The pKa value was determined to be 8.04 ± 0.02, which might be ideal for mitochondrial pH (pHmito ∼8.0) detection. HTBT2 also exhibited a remarkable large Stokes shift of 176 nm, which could diminish the interference of excitation light. The results of live cell imaging studies suggested that HTBT2 showed excellent targeting ability for mitochondria. Importantly, it was successfully applied to visualize mitochondrial pH changes in live cells and differentiate the pHmito difference between cancer cell lines and normal cell lines. Our results consistently supported that HTBT2 held practical promise for the investigation of physiological processes related to pHmito changes and clinical potential for cancer cell differentiation. This journal is

AB - A mitochondrial pH sensing fluorescent probe namely 2-(2-(6-hydroxynaphthalen-2-yl)vinyl)-3-(6-(triphenyl-phosphonio)hexyl)benzothiazol-3-ium bromide (HTBT2) was designed and facilely synthesized via the Knoevenagel condensation reaction. HTBT2 displayed a linear fluorescence enhancement at 612 nm in response to pH changes between 8.70 and 7.20. The pKa value was determined to be 8.04 ± 0.02, which might be ideal for mitochondrial pH (pHmito ∼8.0) detection. HTBT2 also exhibited a remarkable large Stokes shift of 176 nm, which could diminish the interference of excitation light. The results of live cell imaging studies suggested that HTBT2 showed excellent targeting ability for mitochondria. Importantly, it was successfully applied to visualize mitochondrial pH changes in live cells and differentiate the pHmito difference between cancer cell lines and normal cell lines. Our results consistently supported that HTBT2 held practical promise for the investigation of physiological processes related to pHmito changes and clinical potential for cancer cell differentiation. This journal is

UR - http://www.scopus.com/inward/record.url?scp=85097580159&partnerID=8YFLogxK

U2 - 10.1039/D0TB01253J

DO - 10.1039/D0TB01253J

M3 - Journal article

C2 - 33125023

AN - SCOPUS:85097580159

SN - 2050-750X

VL - 8

SP - 10586

EP - 10592

JO - Journal of Materials Chemistry B

JF - Journal of Materials Chemistry B

IS - 46

ER -