2,6-Dibrominated 3,5-DistyrylBODIPYs as Photosensitizer Dyes for Photodynamic Antimicrobial Chemotherapy

Kelechi, A Lebechi; Bokolombe, P Ngoy; John, Mack; Nyokong, Tebello

doi:10.6060/mhc190662m

Cited by 4 publications

(1 citation statement)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The photophysicochemical properties of 1 – 4 have been analyzed in CHCl 3 , ethanol, THF, DMSO and their photodynamic antimicrobial activities (PACT) were examined against Staphylococcus aureus ( S. aureus ) as a representative gram‐(+) bacteria. Although brominated 3,5‐distyrylBODIPY dyes have previously been reported for PACT studies (18–20), to the best of our knowledge, this is the first example of a diiodinated diarylvinylBODIPY derivative in this context.…”

Section: Introductionmentioning

confidence: 93%

Diiodinated Mono‐ and Dipyridylvinyl BODIPY Dyes: Photophysicochemical Properties, in vitro Antibacterial Studies, Molecular Docking and Theoretical Calculations

Şen

Sindelo

Nnaji

et al. 2022

Photochem & Photobiology

Self Cite

View full text Add to dashboard Cite

In this study, novel mono-and dipyridylvinyl boron dipyrromethene dyes are prepared to compare their photodynamic antimicrobial chemotherapy (PACT) activities against Staphylococcus aureus to the corresponding core dyes. Pyridylvinyl substitution at the 3-or 3,5-positions of a meso-4-bromophenylBODIPY core dye via a Knoevenagel reaction with an aromatic 2-bromopyridinecarboxaldehyde shifts the major BODIPY spectral band to longer wavelength. The extended π-conjugation red shifts the main spectral band into the 602-618 nm region in CHCl 3 , THF, ethanol and DMSO after monopyridylvinyl substitution and to 685-704 nm after dipyridylvinyl substitution. An enhancement of the population of the T 1 state through the incorporation of iodine atoms at the 2,6-positions results in moderately high singlet oxygen quantum yields in DMSO. The π-extended dyes were found to have significantly lower PACT activities than the diiodinated core dye.

show abstract

Section: Introductionmentioning

confidence: 93%

Diiodinated Mono‐ and Dipyridylvinyl BODIPY Dyes: Photophysicochemical Properties, in vitro Antibacterial Studies, Molecular Docking and Theoretical Calculations

Şen

Sindelo

Nnaji

et al. 2022

Photochem & Photobiology

Self Cite

View full text Add to dashboard Cite

show abstract

Porphyrinoid macrocycles as potential photosensitizers for photodynamic inhibition of biofilm formation in household water storage systems

Malomane,

Mlambo,

Kuvarega

et al. 2024

Int. J. Environ. Sci. Technol.

View full text Add to dashboard Cite

The issue of biofilm formation by microorganisms in household water storage systems is a problem that lowers the efficiency of disinfectants. Antimicrobial photodynamic inactivation (aPDI) is a potential alternative to the current water disinfection methods. It employs a photosensitizer agent that inactivates microbes by absorbing light of a specific wavelength in the presence of molecular oxygen. Although aPDI has been proven in literature to have a wide spectrum of action, effective against resistant microbes and biofilms, it has not been approved for real-life applications yet. Therefore, there is an ongoing search for ideal photosensitizers that can produce sufficient reactive oxygen species for efficient inactivation of microbes and disruption of biofilms in household water storage systems. This review summarises the developments that have been made so far with porphyrin-, expanded porphyrin-, corrole-, and boron dipyrromethene-based photosensitizers. First, the issues with the current water disinfection methods are described, and then aPDI is also described as a possible alternative to the current methods. Emphasis is put on the antimicrobial activities and the solid support materials that the porphyrinoid family members have been incorporated into for potential application in the disinfection of household water and limitation of biofilm formation in water storage systems.

show abstract

Photodynamic antimicrobial activities of halogenated 3,5-dimethyl- and 1,3,5,7-tetramethyl-meso-pentafluorophenyl BODIPY dyes

May¹,

Chiyumba²,

Harris³

et al. 2022

J. Porphyrins Phthalocyanines

View full text Add to dashboard Cite

The photodynamic antimicrobial chemotherapy (PACT) activities of four meso-pentafluorophenylBODIPY dyes were studied against Staphylococcus aureus to identify structure-property relationships related to the introduction of different substituents on the BODIPY core. 1,3,5,7-Tetramethyl dyes with bromine and iodine atoms at the 2,6-positions (2a and 3a) were synthesized and characterized along with 3,5-dimethyl dyes that were either tetrabrominated at the 1,2,6,7-positions (2b) or diiodinated (3b) at the 2,6-positions. The incorporation of iodine atoms on the BODIPY core at the 2,6-positions enhanced the PACT activity relative to those of the di- and tetrabrominated dyes. Replacing the methyl groups at the 1,7-positions with protons to form 3b results in greater PACT activity than is the case with 3a since the absence of steric hindrance related to methyl groups at the 1,7-positions allows the meso-aryl ring to rotate closer to the plane of the [Formula: see text]-system of the BODIPY core. The tetrabrominated dye was found to have the lowest PACT activity due to a lack of stability in solution and poor uptake by the bacteria being studied. The electron-withdrawing pentafluorophenyl group was selected to lower the dipole moment of the BODIPY core dye since poor PACT activity was observed when a 2,6-dibromo-1,3,5,7-tetramethyl BODIPY dye was prepared with a thiomethylphenyl group (2c).

show abstract

2,6-Dibrominated 3,5-DistyrylBODIPYs as Photosensitizer Dyes for Photodynamic Antimicrobial Chemotherapy

Cited by 4 publications

References 56 publications

Diiodinated Mono‐ and Dipyridylvinyl BODIPY Dyes: Photophysicochemical Properties, in vitro Antibacterial Studies, Molecular Docking and Theoretical Calculations

Diiodinated Mono‐ and Dipyridylvinyl BODIPY Dyes: Photophysicochemical Properties, in vitro Antibacterial Studies, Molecular Docking and Theoretical Calculations

Porphyrinoid macrocycles as potential photosensitizers for photodynamic inhibition of biofilm formation in household water storage systems

Photodynamic antimicrobial activities of halogenated 3,5-dimethyl- and 1,3,5,7-tetramethyl-meso-pentafluorophenyl BODIPY dyes

Contact Info

Product

Resources

About