A quantitative structure–property relationship (QSPR) study of singlet oxygen generation by pteridines

2016 ◽  
Vol 15 (6) ◽  
pp. 801-811 ◽  
Author(s):  
Andrey A. Buglak ◽  
Taisiya A. Telegina ◽  
Mikhail S. Kritsky
Keyword(s):  
Dipole Moment ◽  
Singlet Oxygen ◽  
Quantum Yields ◽  
Quantitative Structure ◽  
Oxygen Production ◽  
Structure Property ◽  
Oxygen Generation ◽  
Singlet Oxygen Generation ◽  
Structure Property Relationship ◽  
Qspr Study

Singlet oxygen production quantum yields of pteridine photosensitizers were analyzed with the QSPR method. The ability of pterins and flavins to generate1O2in D2O correlated withEHOMOand electronegativity, as well as with the dipole moment and some other parameters.

scholarly journals Quantitative Structure–property Relationship Modelling for the Prediction of Singlet Oxygen Generation by Heavy-Atom-Free BODIPY Photosensitizers

2021 ◽  
Author(s):  
Andrey A. Buglak ◽  
Asterios Charisiadis ◽  
Aimee Sheehan ◽  
Christopher J. Kingsbury ◽  
Mathias O.. Senge ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Quantum Chemical ◽  
Heavy Atom ◽  
Quantum Yields ◽  
Structure Property ◽  
Quantum Chemical Descriptors ◽  
Oxygen Generation ◽  
Singlet Oxygen Generation ◽  
Structure Property Relationship ◽  
Chemical Descriptors

Heavy-atom-free sensitizers forming long-living triplet excited states via the spin-orbit charge transfer intersystem crossing (SOCT-ISC) process have recently attracted attention due to their potential to replace costly transition metal complexes in photonic applications. The efficiency of SOCT-ISC in BODIPY donor-acceptor dyads, so far the most thoroughly investigated class of such sensitizers, can be finely tuned by structural modification. However, predicting the triplet state yields and reactive oxygen species (ROS) generation quantum yields for such compounds in a particular solvent is still very challenging due to a lack of established quantitative structure-property relationship (QSPR) models. Herein, we analyzed the available data on singlet oxygen generation quantum yields (F?) for a dataset containing > 70 heavy-atom-free BODIPY in three different solvents (toluene, acetonitrile, and tetrahydrofuran). In order to build reliable QSPR model, we synthesized a series of new BODIPYs containing different electron donating aryl groups in the meso position, studied their optical and structural properties along with the solvent dependence of singlet oxygen generation, which confirmed the formation of triplet states via the SOCT-ISC mechanism. For the combined dataset of BODIPY structures, a total of more than 5000 quantum-chemical descriptors was calculated including quantum-chemical descriptors using Density Functional Theory (DFT), namely M06-2X functional. QSPR models predicting F? values were developed using multiple linear regression (MLR), which perform significantly better than other machine learning methods and show sufficient statistical parameters (R = 0.88 ? 0.91 and q2 = 0.62 ? 0.69) for all three solvents. A small root mean squared error of 8.2% was obtained for F? values predicted using MLR model in toluene. As a result, we proved that QSPR and machine learning techniques can be useful for predicting F? values in different media and virtual screening of new heavy-atom-free BODIPYs with improved photosensitizing ability.<br>

scholarly journals Quantitative Structure–property Relationship Modelling for the Prediction of Singlet Oxygen Generation by Heavy-Atom-Free BODIPY Photosensitizers

2021 ◽  
Author(s):  
Andrey A. Buglak ◽  
Asterios Charisiadis ◽  
Aimee Sheehan ◽  
Christopher J. Kingsbury ◽  
Mathias O.. Senge ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Quantum Chemical ◽  
Heavy Atom ◽  
Quantum Yields ◽  
Structure Property ◽  
Quantum Chemical Descriptors ◽  
Oxygen Generation ◽  
Singlet Oxygen Generation ◽  
Structure Property Relationship ◽  
Chemical Descriptors

Heavy-atom-free sensitizers forming long-living triplet excited states via the spin-orbit charge transfer intersystem crossing (SOCT-ISC) process have recently attracted attention due to their potential to replace costly transition metal complexes in photonic applications. The efficiency of SOCT-ISC in BODIPY donor-acceptor dyads, so far the most thoroughly investigated class of such sensitizers, can be finely tuned by structural modification. However, predicting the triplet state yields and reactive oxygen species (ROS) generation quantum yields for such compounds in a particular solvent is still very challenging due to a lack of established quantitative structure-property relationship (QSPR) models. Herein, we analyzed the available data on singlet oxygen generation quantum yields (F?) for a dataset containing > 70 heavy-atom-free BODIPY in three different solvents (toluene, acetonitrile, and tetrahydrofuran). In order to build reliable QSPR model, we synthesized a series of new BODIPYs containing different electron donating aryl groups in the meso position, studied their optical and structural properties along with the solvent dependence of singlet oxygen generation, which confirmed the formation of triplet states via the SOCT-ISC mechanism. For the combined dataset of BODIPY structures, a total of more than 5000 quantum-chemical descriptors was calculated including quantum-chemical descriptors using Density Functional Theory (DFT), namely M06-2X functional. QSPR models predicting F? values were developed using multiple linear regression (MLR), which perform significantly better than other machine learning methods and show sufficient statistical parameters (R = 0.88 ? 0.91 and q2 = 0.62 ? 0.69) for all three solvents. A small root mean squared error of 8.2% was obtained for F? values predicted using MLR model in toluene. As a result, we proved that QSPR and machine learning techniques can be useful for predicting F? values in different media and virtual screening of new heavy-atom-free BODIPYs with improved photosensitizing ability.<br>

Singlet oxygen generation of subphthalocyanine-fused dimer and trimer

2020 ◽  
Vol 24 (01n03) ◽  
pp. 211-219
Author(s):  
Rei Fujishiro ◽  
Hayato Sonoyama ◽  
Yuki Ide ◽  
Takuya Fujimura ◽  
Ryo Sasai ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Quantum Yields ◽  
Absorption Bands ◽  
Low Light ◽  
Oxygen Generation ◽  
Singlet Oxygen Generation ◽  
Near Ir ◽  
Interesting Class ◽  
High Fluorescence ◽  
Significant Wavelength

Subphthalocyanine (SubPc) macrocycles are known as an interesting class of nonplanar aromatic dyes. Despite documented high fluorescence and singlet oxygen quantum yields, the properties of SubPcs in photodynamic therapy (PDT) are underestimated, because their absorption bands do not reach a significant wavelength range. With this in mind, we combined a SubPc ring and a SubPc ring by introducing a common benzene ring and obtained a SubPc dimer (2) and trimer (3) with the Q-band at the near-IR region, owing to the expansion of the [Formula: see text] electron conjugated system. In this study, we reported 1O2 generation abilities of 2 and 3based on the applied absolute singlet oxygen quantum yields ([Formula: see text]absolute). Subsequent research revealed that 2 and 3 showed the potential to generate 1O2 to not only in toluene but also in DMSO. Although the photocytotoxicity of 2 and 3 were investigated upon photo-irradiation with a low light dose of approximately 1.5 J/cm2, 2 and 3 showed almost negligible toxic properties toward HEp2 cells.

New heterogeneous photosensitizers with phthalocyanine molecules covalently linked to aminopropyl silica gel

2011 ◽  
Vol 15 (07n08) ◽  
pp. 718-726 ◽  
Author(s):  
Nina A. Kuznetsova ◽  
Olga A. Yuzhakova ◽  
Marina G. Strakhovskaya ◽  
Anna O. Shumarina ◽  
Anton S. Kozlov ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Silica Gel ◽  
Fluorescence Spectra ◽  
Quantum Yields ◽  
Absorption And Fluorescence Spectra ◽  
Oxygen Generation ◽  
E Coli ◽  
Singlet Oxygen Generation ◽  
Aqueous Suspensions ◽  
Covalently Linked

New heterogeneous photosensitizers were synthesized, in which phthalocyanines of zinc and aluminum, tetrasubstituted at non-peripheral positions with modified thiophenyl groups, were grafted to aminopropyl silica gel. The absorption and fluorescence spectra, and the quantum yields of fluorescence and photosensitized singlet oxygen generation were estimated for aqueous suspensions of these sensitizers. It is shown that upon photoexcitation, silica gel-bound phthalocyanines produce singlet oxygen and display photobactericidal activity against bacteria E. coli.

scholarly journals Absorption Characteristics and Quantum Yields of Singlet Oxygen Generation of Thioguanosine Derivatives

2018 ◽  
Vol 94 (4) ◽  
pp. 677-684 ◽  
Author(s):  
Shoma Miyata ◽  
Takeshi Yamada ◽  
Tasuku Isozaki ◽  
Hideyuki Sugimura ◽  
Yao-Zhong Xu ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Quantum Yields ◽  
Oxygen Generation ◽  
Singlet Oxygen Generation ◽  
Absorption Characteristics
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