Synthesis, structure, photophysical, electrochemical properties and antibacterial activity of brominated BODIPYs

Prasannan, Dijo; Raghav, Darpan; Sujatha, S.; kumar, Haritha Hareendrakrishna; Rathinasamy, Krishnan; Arunkumar, Chellaiah

doi:10.1039/c6ra12258b

Cited by 42 publications

(28 citation statements)

References 57 publications

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“…These results demonstrate that the presence of iodine atoms in 2 and 6 positions of the BODIPY core caused the 30–35‐fold reduction of the fluorescence intensity compared to non‐iodinated analogs. It is the consequence of the heavy atom effect, which leads to enhanced intersystem crossing (S 1 →T 1 transition), and simultaneously decreases the fluorescence (S 1 →S 0 transition) [43,48] . Obtained values correspond well with data for other iodinated BODIPYs and their non‐iodinated analogs [25,33,43,47] …”

Section: Resultssupporting

confidence: 73%

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BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

et al. 2020

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Boron‐dipyrromethene derivatives, including cationic and iodinated analogs, were obtained and subjected to physicochemical and in vitro photodynamic activity studies. Iodinated derivatives revealed a substantial heavy atom effect manifested by a bathochromic shift of the absorption band by about 30 nm and fluorescence intensity reduced by about 30–35 times, compared to that obtained for non‐iodinated ones. In consequence, singlet oxygen generation significantly increased with ΦΔ values in the range 0.69–0.97. The in vitro photodynamic activity was evaluated on Gram‐positive Staphylococcus aureus, Gram‐negative Escherichia coli, and on human androgen‐sensitive prostate adenocarcinoma cells (LNCaP). The novel cationic, iodinated BODIPY, demonstrated the highest activity toward all studied cells. An excellent cytotoxic effect was found against LNCaP cells with an IC50 value of 19.3 nM, whereas the viability of S. aureus was reduced by >5.6 log10 at 0.25 μM concentration and by >5.3 log10 in the case of E. coli at 5 μM. Thus, this analog seems to be a very promising candidate for the application in both anticancer and antimicrobial photodynamic therapy.

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Section: Resultssupporting

confidence: 73%

“…S 0 transition). [43,48] Obtained values correspond well with data for other iodinated BODIPYs and their non-iodinated analogs. [25,33,43,47]…”

Section: Spectroscopic Propertiessupporting

confidence: 77%

BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

et al. 2020

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“…The spectral properties of the products were compared with those of the parent BODIPY. 2‐Bromo‐4,4‐difuoro‐8‐(4‐methylphenyl)‐4‐bora‐3a,4a‐diaza‐ s ‐indacene [17] ( 3 ) was subjected to Pd(0) catalyzed Suzuki cross‐coupling with p ‐formylphenylboronic acid, which give 4 (70 %), providing a β‐substituted phenyl spacer. gem ‐Dibromovinyl product 5 (65 %) was obtained from 4 by adapting the modified Ramirez gem‐ dibromoolefination method [18] using CBr 4 and P(O i −Pr) 3 (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Pd‐Catalyzed Sonogashira Cross‐Coupling Reactions of gem‐Dibromovinyl BODIPY Derivatives

2021

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4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives bearing gem-dibromovinyl moieties at either the βor αpositions of the pyrrole rings, directly or through phenyl spacers, undergo efficiently Sonogashira and Stille Pd-catalyzed cross-coupling. The structures of the resulting 1,1-diynyl-1alkene and 1,1-diphenyl-1-alkene products were assigned using MS, NMR and in some cases X-ray diffraction analysis. 1,1-Diynyl-1-alkene BODIPYs exhibit red shifted absorption maxima, particularly when substituents were introduced at the α-position rather than the β-position of the pyrrole ring. Aromatic compounds showed larger red shifts as compared to the aliphatic substituted analogs. The highest red shifts were observed with compounds featuring electron donating substituents. Spectroscopic properties of α-substituted 1,1-diynyl-p-N,N-dimethylaminophenyl-1-alkenes are sensitive to protonation resulting in remarkable pH-responsive changes in the absorption and fluorescence emission spectra.

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“…Starting BODIPY 1 was prepared according to the literature. 22 All of the reagents were obtained from commercial suppliers and were used without further purification. All of the solvents were freshly distilled from the appropriate drying agents before use.…”

Section: Methodsmentioning

confidence: 99%

Selectfluor-Mediated Benzo[d][1,2,3]Triazole Functionalisation of 4,4-Difluoro-4-Bora-3a,4a-Diaza-s-Indacene

Huang

2018

Journal of Chemical Research

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8-Aryl-1-(1 H-benzo[ d][1,2,3]triazole-yl)-4,4-difluoro-4-bora-3a,4a-diaza- s-indacene and 8-aryl-3,5-di-(1 H-benzo[ d][1,2,3]triazole-yl)-4,4-difluoro-4-bora-3a,4a-diaza- s-indacene derivatives were synthesised by the reaction of 4,4-difluoro-4-bora-3a,4a-diaza- s-indacene with benzo[ d][1,2,3]triazole in the presence of Selectfluor in moderate to good yields. The reaction took placed regioselectively on the 3(5)-position carbon of 4,4-difluoro-4-bora-3a,4a-diaza- s-indacene, which was confirmed by X-ray analysis.

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Synthesis, structure, photophysical, electrochemical properties and antibacterial activity of brominated BODIPYs

Abstract: The unusual di-bromo product, 5b, confirmed by spectral analysis, showed the most potency with the lowest IC50 and MIC values, with excellent activity comparable to the standard antibacterial drug, tetracycline.

Cited by 42 publications

References 57 publications

BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

BODIPY‐Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect

Pd‐Catalyzed Sonogashira Cross‐Coupling Reactions of gem‐Dibromovinyl BODIPY Derivatives

Selectfluor-Mediated Benzo[d][1,2,3]Triazole Functionalisation of 4,4-Difluoro-4-Bora-3a,4a-Diaza-s-Indacene

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