BODIPYs to the rescue: Potential applications in photodynamic inactivation

Durantini, Andrés M.; Heredia, Daniel A.; Durantini, Javier E.; Durantini, Edgardo N.

doi:10.1016/j.ejmech.2017.12.068

Cited by 133 publications

(93 citation statements)

References 90 publications

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“…In recent years, several new photosensitizers have been developed for PDI and many of them proved to be effective for the eradication of microorganisms . In general, these compounds absorb intensely in the visible region and produce triplet excited states with good yields to generate ROS . In addition, the presence of positive charges in the photosensitizer structure allows a better interaction with negative groups in the cell envelope, mainly in Gram‐negative bacteria, which leads to an increased ability to inactivate cells .…”

Section: Introductionmentioning

confidence: 99%

Bacteriochlorin‐bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms

Ballatore

Milanesio

Fujita

et al. 2019

Journal of Biophotonics

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A novel bacteriochlorin bearing two spermine units (BCS) was synthesized from 3, 8,18,13 ). The synthesis involved the Suzuki coupling of BC-Br 3,13 to obtain a bacteriochlorin-dibenzaldehyde (BCA), which was subjected to reductive amination with spermine. The resulting bacteriochlorin BCS presents a strong near-infrared absorption band at 747 nm, emits at 750 nm with fluorescence quantum yield of 0.14, and generates singlet molecular oxygen, O 2 ( 1 Δ g ), with a quantum yield of 0.27. Photokilling capacities mediated by BCS were evaluated in microbial cells. The viability of Staphylococcus aureus decreased 7 logs when cells were incubated with 1 μM BCS and irradiated for 15 minutes. Comparable photocytotoxic effect was obtained with Escherichia coli, when cells were treated for 30 minutes with visible light. BCS was also an effective photosensitizer to inactivate Candida albicans. In addition, this bacteriochlorin was able to eradicate bacteria at short incubation times. The structure of BCS contains eight basic amino groups that, when protonated in water, increase the binding to the cell envelope. In summary, the readily accessible bacteriochlorin BCS was highly effective at low concentrations as a broad-spectrum antimicrobial photosensitizer.

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Section: Introductionmentioning

confidence: 99%

Bacteriochlorin‐bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms

Ballatore

Milanesio

Fujita

et al. 2019

Journal of Biophotonics

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“…These released reactive species react with biological molecules in the cell, resulting in loss of biological functionality and ultimately cell death [32]. Recently, BODIPYs have been suggested as potential PS for the killing of pathogenic microbial cells [1,26,27]. BODIPY dyes 1-3 with different substituents (-NMe2, -NO2 and -Br, respectively) at the meso position were synthesized starting from 2,4-dimethylpyrrole and corresponding aldehydes after oxidation with 2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ) followed by complexation with boron trifluoride etherate (BF3OEt2) (Fig.…”

Section: Discussionmentioning

confidence: 99%

FARKLI BODIPY BOYALARININ METİSİLİN DİRENÇLİ Staphylococcus aureus TEDAVİSİNDE FOTOSENSİTİZER OLARAK ETKİNLİĞİNİN İN VİTRO DEĞERLENDİRİLMESİ

Boran

Algı

Uğur

2018

Mugla Journal of Science and Technology

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The antibiotic period is now ending and the probability of discovering new classes of antibiotics is considerably low. It is required to find out alternative antimicrobial technologies that bacteria will not be able to develop resistance, and that will be equally effective regardless of the current resistance situation. In this regard, we investigated antimicrobial photodynamic inactivation effects of three boradiazaindacenes (BODIPYs) 1-3 against methicillin-resistant Staphylococcus aureus (MRSA). BODIPYs 1-3 with different substituents at the meso position (-NMe2,-NO2 and-Br, respectively) were synthesized. The photodynamic inactivation effects of BODIPYs 1-3 were tested against one broad spectrum antibiotic resistant bacterial model strain, a clinically described MRSA. In particular BODIPY 2 was found more effective when compared to the others at 25, 50 and 100 nM concentrations. BODIPYs 1-3 did not show any toxic effect in the dark at given concentrations. In addition, a high degree of photodynamic inactivation were detected with 2 and 3 by irradiation at 6.66-8.88 J/cm 2 light doses, while the efficiency of 1 was not significantly affected from illumination times. The results indicate that BODIPYs, especially nitro group BODIPY 2, can be used in the photodynamic inactivation of MRSA at nanomolar concentrations and low energy doses.

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“…[18] In this study, we investigate the utility of 2,6-dibrominated BODIPY core dyes and π-extended 3,5-di-carboxystyrylBODIPY dyes (Scheme 1) for photodynamic antimicrobial chemotherapy (PACT) [19][20][21][22][23][24] by studying their PACT activity on both gram-positive (Staphylococcus aureus) and gram-negative (Escherichia coli) bacteria. Although there have been previous studies on BODIPY core dyes, [25][26][27][28] to best of our knowledge, this is the first example of a study of this type with a halogenated 3,5-distyryl-BODIPY dye. These dyes are suitable for use with commercially available 630 nm lasers that are used for photodynamic therapy (PDT), since the main spectral band is red-shifted into the 600−700 nm region.…”

Section: Introductionmentioning

confidence: 94%

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

Kelechi¹,

Bokolombe²,

John³

et al. 2019

MHC

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A 2,6-dibrominated BODIPY core dye with a meso-pyrenyl group has been investigated for use as a photosensitizer dye in photodynamic antimicrobial chemotherapy in the context of both gram-positive (Staphylococcus aureus) and gramnegative (Escherichia coli) bacteria, along with a π-extended 3,5-di-4-carboxystyrylBODIPY dye. The dyes are found to be effective for the treatment of S. aureus, but not in the case of E. coli.

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BODIPYs to the rescue: Potential applications in photodynamic inactivation

Cited by 133 publications

References 90 publications

Bacteriochlorin‐bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms

Bacteriochlorin‐bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms

FARKLI BODIPY BOYALARININ METİSİLİN DİRENÇLİ Staphylococcus aureus TEDAVİSİNDE FOTOSENSİTİZER OLARAK ETKİNLİĞİNİN İN VİTRO DEĞERLENDİRİLMESİ

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

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