Two-Photon Absorption Activity of BOPHY Derivatives: Insights from Theory

Petrusevich, Elizaveta F.; Ośmiałowski, Borys; Zaleśny, Robert; Alam, Md. Mehboob

doi:10.1021/acs.jpca.1c00756

Cited by 7 publications

(4 citation statements)

References 53 publications

(84 reference statements)

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“…This is indeed true for certain polar chromophores, for example the chromophores of various FPs [4,14,16,17,[41][42][43] and some others [44][45][46]. Three-, four-, and generalized few-state models have also been considered [47][48][49][50][51][52][53][54][55].…”

Section: H148 Cromentioning

confidence: 97%

Impact of the Protein Environment on Two-Photon Absorption Cross-Sections of the GFP Chromophore Anion Resolved at the XMCQDPT2 Level of Theory

Aslopovsky

Scherbinin

Kleshchina

et al. 2023

IJMS

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The search for fluorescent proteins with large two-photon absorption (TPA) cross-sections and improved brightness is required for their efficient use in bioimaging. Here, we explored the impact of a single-point mutation close to the anionic form of the GFP chromophore on its TPA activity. We considered the lowest-energy transition of EGFP and its modification EGFP T203I. We focused on a methodology for obtaining reliable TPA cross-sections for mutated proteins, based on conformational sampling using molecular dynamics simulations and a high-level XMCQDPT2-based QM/MM approach. We also studied the numerical convergence of the sum-over-states formalism and provide direct evidence for the applicability of the two-level model for calculating TPA cross-sections in EGFP. The calculated values were found to be very sensitive to changes in the permanent dipole moments between the ground and excited states and highly tunable by internal electric field of the protein environment. In the case of the GFP chromophore anion, even a single hydrogen bond was shown to be capable of drastically increasing the TPA cross-section. Such high tunability of the nonlinear photophysical properties of the chromophore anions can be used for the rational design of brighter fluorescent proteins for bioimaging using two-photon laser scanning microscopy.

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Section: H148 Cromentioning

confidence: 97%

Impact of the Protein Environment on Two-Photon Absorption Cross-Sections of the GFP Chromophore Anion Resolved at the XMCQDPT2 Level of Theory

Aslopovsky

Scherbinin

Kleshchina

et al. 2023

IJMS

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“…Additionally, it is well-known that a long-range exchange (as present in the MN15 functional) is required for a correct description of the charge-transfer process. 60 To pinpoint the factor(s) responsible for the variation in TP activity [61][62][63] among the considered systems a three-state model (3SM) within the generalized few-state models (GFSM) is employed. The parameters such as excitation energy, ground to excited state transition dipole moments, excited-excited state transition moments, and dipole moments of different states are calculated at the RICC2/cc-pVDZ level of theory using the Turbomole7.3 program package.…”

Section: Computational Detailsmentioning

confidence: 99%

Why does the orientation of azulene affect the two-photon activity of a porphyrinoid–azulene system?

Rajput,

Raghuvanshi,

Banana

et al. 2024

Phys. Chem. Chem. Phys.

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“…In addition, probes ANO3', ANO4, and ANO5 exhibit slightly larger δ max compared with their products. It is known that pyrene, fluorene, and boron-dipyrromethene chromophores have high fluorescence quantum yields [38][39][40][52][53][54]. After reaction with NO, the ring and conjugate structure of triazine may inhibit the PeT and thereby strongly emission and increase Φ [14,55].…”

Section: Tpa Propertiesmentioning

confidence: 99%

In silico design of two‐photon fluorescent probes for detecting nitric oxide

Liu

Zhang

2023

Int J of Quantum Chemistry

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With the extensive use of two‐photon fluorescence microscopy in the biology field, the need for developing fluorescent probes with preferred two‐photon absorption (TPA) properties has attracted great interest. Nitric oxide (NO) is a ubiquitous signaling molecule in a variety of physiological and pathological process in living organisms. A two‐photon (TP) probe, that is, 2‐acetyl‐6‐dialkylaminonaphthalene as the reporter and an o‐diaminobenzene as the reaction site for NO, linked by prolinamide (ANO1) has been synthesized. Based on the experimental study, five other TP probes have been theoretically designed by substituting the naphthalene fluorophore with luciferin, pyrene (substitution at 1,6‐position and 2,7‐position), fluorene, and boron‐dipyrromethene units. DFT/TDDFT studies have been conducted one‐photon absorption and emission properties as well as TPA. Our results indicated that both absorption and emission spectra of designed probes show red shifts compared with ANO1. Moreover, the fluorescence intensities are enhanced after reaction with NO. Furthermore, molecular orbitals are analyzed to interpret the photoinduced electron transfer mechanism. Notably, introducing the fluorene moiety can induce the enhancement of μ0n and Δμ0n and thus modulate TPA. Accordingly, ANO4 is thought to be a promising candidate for novel TPA NO probe.

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Two-Photon Absorption Activity of BOPHY Derivatives: Insights from Theory

Cited by 7 publications

References 53 publications

Impact of the Protein Environment on Two-Photon Absorption Cross-Sections of the GFP Chromophore Anion Resolved at the XMCQDPT2 Level of Theory

Impact of the Protein Environment on Two-Photon Absorption Cross-Sections of the GFP Chromophore Anion Resolved at the XMCQDPT2 Level of Theory

Why does the orientation of azulene affect the two-photon activity of a porphyrinoid–azulene system?

In silico design of two‐photon fluorescent probes for detecting nitric oxide

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