A new pH fluorescent molecular switch by modulation of twisted intramolecularcharge transfer with protonation

Shen, Ping; Xiao, Shuzhang; Zhan, Xuqin; Zhang, Wei; Chang, Kedi; Yang, Changying

doi:10.1002/poc.3185

Cited by 11 publications

(10 citation statements)

References 24 publications

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“…Currently, it is still a great challenge to develop stable dual‐functional fluorescence sensors for proteins. BOPIM derivatives with electron donor group –PhN(CH 3 ) 2 , BOPIM‐1 and BOPIM‐2 (Scheme ), were previously verified TICT properties and presented pH and polarity‐dependent fluorescence . In the present work, the binding characteristics between BOPIMs and BSA are studied.…”

Section: Introductionmentioning

confidence: 71%

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A Boron 2‐(2′‐pyridyl) Imidazole Fluorescence Probe for Bovine Serum Albumin: Discrimination over Other Proteins and Identification of Its Denaturation

Yang

et al. 2017

Photochem & Photobiology

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Boron 2-(2'-pyridyl) imidazole complex (BOPIM) derivatives, BOPIM-1 and BOPIM-2, involving twisted intra-molecular charge transfer (TICT) characteristic, were investigated to probe bovine serum albumin (BSA). BOPIM-1 was demonstrated to be an efficient fluorescence probe to discriminate BSA from other proteins including human serum albumin (HSA). The encapsulation of BOPIM-1 in the hydrophobic subdomain IIA of BSA inhibited the TICT state and resulted in 70-fold emission enhancement of BOPIM-1. Besides, it was found that BOPIM-1 could distinguish denatured BSA from the native, due to the difference of 15 nm emission wavelength at least. The denaturation of BSA leads to the exposure of binding sites and resulted in an increase in the accessibility of the fluorophore to the BSA cavity, which made a great contribution to the further restraint of TICT state of BOPIM-1. The tracking of BSA denaturizing process was easily achieved, through the change of BOPIM-1 emission wavelength from 485 to 465 nm. Thus, a promising pharmacological dual-functional probe was provided for both the selective recognization of BSA and the identification of denatured BSA from the native.

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Section: Introductionmentioning

confidence: 71%

“…BOPIMs are almost non‐fluorescent in PBS buffer when excited at 365 nm because of TICT effect . For BOPIM‐1 (2.0 μ m ), only a weak emission at 518 nm is observed (Fig.…”

Section: Resultsmentioning

confidence: 94%

A Boron 2‐(2′‐pyridyl) Imidazole Fluorescence Probe for Bovine Serum Albumin: Discrimination over Other Proteins and Identification of Its Denaturation

Yang

et al. 2017

Photochem & Photobiology

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“…[16] Shen et al analyzed BOPIM-DMA and, it was found that the emission of the molecule changed between pH 2.4-4.0 as "on" and "off" and the pKa was calculated as 3.12. [17] While the interaction of BOPIM-dma with many cations in aqueous systems was examined by Ping et al in 2015, [18] Liu et al in 2017 showed that BOPIM-DMA, an innovative fluorophore, was a sensitive probe for bovine serum albumin (BSA). [19] Both in vivo and in vitro studies of BOPIM derivatives were carried out by Chen for the first time, and they showed that the nano form of the BOPIM derivative found in the literature by encapsulating biocompatible poly (PEG/PPG/PLA urethane) has the potential to be used in tumor diagnosis.…”

Section: Introductionmentioning

confidence: 99%

“…Shen et al. analyzed BOPIM‐DMA and, it was found that the emission of the molecule changed between pH 2.4–4.0 as “on” and “off” and the pKa was calculated as 3.12 [17] . While the interaction of BOPIM‐dma with many cations in aqueous systems was examined by Ping et al.…”

Section: Introductionmentioning

confidence: 99%

A New Boron 2‐(2′‐pyridyl) Imidazole Complex as a Candidate Photosensitizer for Photodynamic Therapy

Ekmekci

Eris

2022

ChemistrySelect

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In this work, different from the literature, boron 2-(2'-pyridyl) imidazole complex (BOPIM) was derived from pyridine ring side to extend π conjugation for the first time. In addition, the core of BOPIM was brominated to increase the capacity of singlet oxygen generation via intersystem crossing to function as a photosensitizer. According to photophysical measurements, the new BOPIM derivative had comparatively large Stokes shift as 111 nm among boron-fluorine derivatives in the literature. Its singlet oxygen generation potential and toxic effect in the dark were investigated in the presence of singlet oxygen trap 1,3-Diphenylisobenzofuran (DPBF). According to the obtained results, it was seen that the new BOPIM derivative could be a good photosensitizer for photodynamic therapy.

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“…The π-conjugating system bearing free basic nitrogen atoms can undergo significant change in electronic structure upon protonation, − thus providing a nice strategy to construct fluorescent MOFs for pH detection . However, the strong coordinative ability of the N sites with metal ions imposes a limitation on the strategy.…”

Section: Introductionmentioning

confidence: 99%

A pH-Sensing Fluorescent Metal–Organic Framework: pH-Triggered Fluorescence Transition and Detection of Mycotoxin

Yang

Liu

et al. 2020

Inorg. Chem.

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Due to its great relevance to environmental, biological, and chemical processes, the precise detection of pH or acidic/basic species is an ongoing and imperative need. In this context, pH-sensitive luminescent systems are highly desired. We reported a three-dimensional Zn(II) MOF synthesized from a bipyridyl-tetracarboxylic ligand and composed of 4-fold interpenetrated diamond frameworks. Because the steric hindrance in the ligand prevents metal coordination with the pyridyl group, the MOF features free basic N sites accessible to the small H + ions, which renders pH responsivity. The aqueous dispersion exhibits an abrupt, high-contrast, and reversible on−off fluorescence transition in the narrow pH range of 5.4−6.2. The sensitive bistable system can be used for the precise monitoring of pH within the range and for use as a pH-triggered optical switch. The responsive mechanism through pyridyl protonation is collaboratively supported by data fitting, absorption spectra, and molecular orbital calculations. In particular, spectral and theoretical analyses reveal the destruction of n → π* transitions and the appearance of intramolecular charge-transfer transitions upon pyridyl protonation. Moreover, by virtue of the pH-responsive fluorescence, the MOF shows appealing sensing performance for the detection of 3-nitropropionic acid, a major mycotoxin in moldy sugar cane.

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A new pH fluorescent molecular switch by modulation of twisted intramolecularcharge transfer with protonation

Cited by 11 publications

References 24 publications

A Boron 2‐(2′‐pyridyl) Imidazole Fluorescence Probe for Bovine Serum Albumin: Discrimination over Other Proteins and Identification of Its Denaturation

A Boron 2‐(2′‐pyridyl) Imidazole Fluorescence Probe for Bovine Serum Albumin: Discrimination over Other Proteins and Identification of Its Denaturation

A New Boron 2‐(2′‐pyridyl) Imidazole Complex as a Candidate Photosensitizer for Photodynamic Therapy

A pH-Sensing Fluorescent Metal–Organic Framework: pH-Triggered Fluorescence Transition and Detection of Mycotoxin

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