Application of multifunctional BODIPY in photodynamic therapy

Zhang, Wangquan; Ahmed, Adeel; Cong, Hailin; Wang, Song; Shen, Youqing; Yu, Bing

doi:10.1016/j.dyepig.2020.108937

Cited by 98 publications

(74 citation statements)

References 128 publications

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“…Additionally, the absorption and emission range of BODIPY can be rationally modified by proper substitution at 2, 6 and other positions in the molecular core. Only recently, BODIPYs were successfully applied for bacteria photoinactivation [20][21][22] and as photosensitizers in PDT, modified with a heavy atom (iodine, bromine, metal cation) for efficient triplet state population [4,7,[23][24][25][26][27][28][29]. All of these works appeared in recent years, thus pointing out the possible practical applications of BODIPY in therapy and the need for their advanced developments.…”

Section: Introductionmentioning

confidence: 99%

Photochemical Properties and Stability of BODIPY Dyes

Rybczyński

Smolarkiewicz-Wyczachowski

Piskorz

et al. 2021

IJMS

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The present study is devoted to the combined experimental and theoretical description of the photophysical properties and photodegradation of the new boron-dipyrromethene (BODIPY) derivatives obtained recently for biomedical applications, such as bacteria photoinactivation (Piskorz et al., Dyes and Pigments 2020, 178, 108322). Absorption and emission spectra for a wide group of solvents of different properties for the analyzed BODIPY derivatives were investigated in order to verify their suitability for photopharmacological applications. Additionally, the photostability of the analyzed systems were thoroughly determined. The exposition to the UV light was found first to cause the decrease in the most intensive absorption band and the appearance of the hypsochromically shifted band of similar intensity. On the basis of the chromatographic and computational study, this effect was assigned to the detachment of the iodine atoms from the BODIPY core. After longer exposition to UV light, photodegradation occurred, leading to the disappearance of the intensive absorption bands and the emergence of small intensity signals in the strongly blue-shifted range of the spectrum. Since the most intensive bands in original dyes are ascribed to the molecular core bearing the BF2 moiety, this result can be attributed to the significant cleavage of the BF2 ring. In order to fully characterize the obtained molecules, the comprehensive computational chemistry study was performed. The influence of the intermolecular interactions for their absorption in solution was analyzed. The theoretical data entirely support the experimental outcomes.

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Section: Introductionmentioning

confidence: 99%

Photochemical Properties and Stability of BODIPY Dyes

Rybczyński

Smolarkiewicz-Wyczachowski

Piskorz

et al. 2021

IJMS

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“…In the 1 H-NMR spectrum of (1) the aldehyde proton (=CH) resonated at 9.87 ppm. In the 13 C-NMR spectrum of (1), the C=O group appeared at 191.76 ppm. The molecular ion peak of (1) was shown as 241.46 [M] + .…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY), developed by Treibs and Kreuzer in 1968, displays a wide range of research fields such as material, medical research, diagnosis, and treatment due to their strong absorption, high fluorescence quantum efficiency, and stable chemical structure properties [12][13][14]. They have been used for variety of applications viz.…”

Section: Introductionmentioning

confidence: 99%

Pyridine substituted BODIPYs: synthesis, characterization and cholinesterease, α-glucosidase inhibitory, DNA hydrolytic cleavage effects

Barut¹,

Baş²,

Bıyıklıoğlu³

2021

Turk J Chem

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In this study, the synthesis of new monostyryl (BDPY-2) and distyryl BODIPY dyes (BDPY-4, BDPY-5) containing pyridine groups to has been reported for the first time. The acetylcholinesterase from Electrophorus electricus (AChE), butyrylcholinesterase from equine serum (BuChE), α-glucosidase from Saccharomyces cerevisiae and DNA hydrolytic cleavage actions of BDPY-2, BDPY-4, BDPY-5 were investigated using various techniques.The results indicated that the compounds had varying inhibition properties against AChE, BuChE, and α-glucosidase. BDPY-4 was the most potent compound on AChE with IC 50 of 54.78 ± 4.51 µM and Lineweaver-Burk plots indicated that the compound is bound to a site other than the active site as a noncompetitive inhibitor. The compound-protein binding experiment showed that BDPY-4 changed the microenvironment around AChE. On the other hand, the compounds showed lower α-glucosidase inhibition than the positive control. The DNA hydrolytic cleavage effects were not observed on supercoiled plasmid DNA in the presence of the compounds as compared to negative controls. These findings results suggested that BDPY-4 might be a promising compound to treat Alzheimer's diseases.

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“… 2 For these reasons, boron-dipyrromethane (4,4-difluoro-4-bora-3a,4a-diaza- s -indacene, BODIPY) has been the focus of considerable interest. 3 The structural versatility and spectroscopic properties such as high quantum yields and strong and tunable absorption and emission bands, 4 besides its photostability and solubility in organic solvents, make BODIPY derivatives important tools in a wide range of fields such as biological imaging and labelling, 5 photodynamic therapy agents, 6 chemosensors 3,7 and optoelectronic devices. 8 These properties made BODIPY an important target for synthetic organic chemists.…”

Section: Introductionmentioning

confidence: 99%