Theoretical characterization of two-photon fluorescent probes for nitric oxide detection: sensing mechanism, photophysical properties and protonation effects

Jiao, Yawen; Dong, Xiaowei; Ran, Xin; Deng, Qiyun; Xiao, Haibin; Wang, Zhiming; Zhang, Tian

doi:10.1039/d3cp01091k

Cited by 12 publications

(1 citation statement)

References 75 publications

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“…Although there are numerous effective agents in cancer treatment, the PDT is limited by its poor penetrability upon one-photon excitation and minimal light damage to biological tissues. To overcome the above deficiencies, the two-photon photodynamic therapy (TP-PDT) has attracted great attention with considering its longer excitation wavelength and deeper tissue penetration. ,− Recently, Zn(II) polypyridyl complexes and thionated NpImidazole derivatives have been proposed as effective PSs for TP-PDT . Moreover, Zhou et al demonstrated that the lipid-droplet targeting PS (6DBF2) possesses outstanding therapeutic efficacy in TP-PDT through in vitro cancer cell ablation and in vivo tumor ablation inside mice models.…”

Section: Introductionmentioning

confidence: 99%

Newly Designed Quasi-intrinsic Photosensitizers for Fluorescence Image-Guided Two-Photon Photodynamic Therapy with Type I/II Photoreactions

Cui,

Yuan,

Chen

et al. 2024

J. Med. Chem.

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In this work, a set of quasi-intrinsic photosensitizers are theoretically proposed based on the 2-amino-8-(1′-β-D-2′deoxyribofuranosyl)-imidazo[1,2-α]-1,3,5-triazin-4(8H)-one (P), which could pair with the 6-amino-5-nitro-3-(1′-β-D-2′-deoxyribofuranosyl)-2(1H)-pyridone (Z) and keep the essential structural characters of nucleic acid. It is revealed that the ring expansion and electron-donating/electron-withdrawing substitution bring enhanced two-photon absorption and bright photoluminescence of these monomers, thereby facilitating the selective excitation and tumor localization through fluorescence imaging. However, instead of undergoing radiative transition (S 1 → S 0 ), the base pairing induced fluorescence quenching and rapid intersystem crossing (S 1 → T n ) are observed and characterized by the reduced singlet− triplet energy gaps and large spin−orbit coupling values. To ensure the phototherapeutic properties of the considered base pairs in long-lived T 1 state, we examined the vertical electron affinity as well as vertical ionization potential for production of superoxide anions via Type I photoreaction, and their required T 1 energy (0.98 eV) to generate singlet oxygen 1 O 2 via Type II mechanism.

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Section: Introductionmentioning

confidence: 99%

Newly Designed Quasi-intrinsic Photosensitizers for Fluorescence Image-Guided Two-Photon Photodynamic Therapy with Type I/II Photoreactions

Cui,

Yuan,

Chen

et al. 2024

J. Med. Chem.

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Theoretical study on the luminescent and reaction mechanism of dansyl‐based fluorescence probe for detecting hydrogen sulfide

Li,

Wang,

Pan

et al. 2024

J Comput Chem

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The photophysical and photochemical properties of the sulfonyl azide‐based fluorescent probe DNS–Az and its reduction product DNS by hydrogen sulfide (H2S) have been investigated theoretically. The calculated results indicated the first excited states of DNS–Az was dark state (oscillator strength less than 0.03) and DNS was bright state (oscillator strength more than 0.1), which determined the predicted radiative rate kr of DNS–Az was much smaller than that of DNS, meanwhile, due to more larger reorganization energy of DNS–Az, its predicted internal conversion rate kic was four times larger than that of DNS; moreover, owing to the effect of heavy atom from sulfur atom in DNS–Az, its predicted intersystem crossing rate kisc was seven times larger than that of DNS, thus the calculated fluorescence quantum yield of DNS–Az was only 2.16% and that of DNS was more than 77.2%, the above factors is the basis for DNS–Az molecule to function as a fluorescent probe. Regarding both DNS‐Az and DNS molecules, their maximum Huang‐Rhys factors, which are less than unity, signify the reliability of 0–0 transitions between their S0 and S1 electronic states. In addition, for DNS, our simulated emission peak of the 0–0 transition is 515 nm, a value that exhibits enhanced accuracy and coherence when compared to the experimental datum of 528 nm. The reaction mechanism of DNS‐Az generating DNS by H2S has been investigated too, according to the potential energy profile, we found that the fluorescent probe firstly protonated, then this organic ion broke down into DNS with the aid of a proton.

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Substituent effects on the emission quantum efficiency in pyrene-based luminogens featured two-photon absorption: A theoretical and experimental study

Dong,

Wang,

Ran

et al. 2024

Dyes and Pigments

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Theoretical characterization of two-photon fluorescent probes for nitric oxide detection: sensing mechanism, photophysical properties and protonation effects

Abstract: Nitric oxide (NO) is an important signal molecule in biological systems and correlated with many physiological processes and pathological diseases. To date, numerous fluorescent probes based on o-diamino aromatics have...

Cited by 12 publications

References 75 publications

Newly Designed Quasi-intrinsic Photosensitizers for Fluorescence Image-Guided Two-Photon Photodynamic Therapy with Type I/II Photoreactions

Newly Designed Quasi-intrinsic Photosensitizers for Fluorescence Image-Guided Two-Photon Photodynamic Therapy with Type I/II Photoreactions

Theoretical study on the luminescent and reaction mechanism of dansyl‐based fluorescence probe for detecting hydrogen sulfide

Substituent effects on the emission quantum efficiency in pyrene-based luminogens featured two-photon absorption: A theoretical and experimental study

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