Synthesis, spectroscopic properties and photodynamic activity of two cationic BODIPY derivatives with application in the photoinactivation of microorganisms

Agazzi, Maximiliano L.; Ballatore, M. Belén; Reynoso, Eugenia; Quiroga, Ezequiel D.; Durantini, Edgardo N.

doi:10.1016/j.ejmech.2016.10.001

Cited by 54 publications

(64 citation statements)

References 55 publications

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“…In addition, BODIPYs 2 and 4 exhibited very low intensity, broad and flat band in the range of 310–410 nm, which in the case of 3 and 5 was more intensive, better developed, and found between 330 nm and 430 nm. This low‐wavelength band corresponds with the S 0 →S 2 transition [24,46] . The bathochromic shift of absorption bands for iodinated compounds 3 and 5 , in comparison to non‐iodinated 2 and 4 , results from the heavy atom effect caused by the introduction of iodine atoms to the BODIPY core [25,33,42,47] …”

Section: Resultsmentioning

confidence: 96%

“…Not many reports concerning cationic BODIPY derivatives with photodynamic activity have been published so far. Cationic BODIPYs with trimethylammonium and pyridinium substituents have revealed promising photoinactivation activity against both Gram‐positive and Gram‐negative bacteria [24–26] . Noteworthy, BODIPY dye possessing a positively charged, quaternized 1,3‐thiazole ring, and galactose moiety has shown high effectivity and selectivity toward bacterial biofilm over mammalian cells [27] .…”

Section: Introductionmentioning

confidence: 99%

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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: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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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“…These studies revealed that high rates of reduction in the cell survivals. However, the main advantages of BODIPYs 1-3 are able to kill microbial cells at relatively low concentrations (nM) and low energy doses (2.22 J/cm 2 to 8.88 J/cm 2 ) when compared to the other studies [12,21,26,27]. In a study, Orlandi et al [26] reported that PDI combines the use of 2,6-diiodo-1,3,5,7-tetramethyl-8-(N-benzyl-4pyridyl)-4,4′-difluoroboradiazaindacene PS against Pseudomonas aeruginosa.…”

Section: Discussionmentioning

confidence: 99%

“…singlet oxygen) and used as photodynamic therapy agents [23,25]. In recent years, 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives have been proposed as phototherapeutic agents for the photodynamic inactivation of pathogenic microorganisms [21,26,27]. In line with the explanations above, we investigated the in vitro antimicrobial effect of BODIPY dyes 1-3 against MRSA.…”

Section: Introductionmentioning

confidence: 96%

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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Synthesis, spectroscopic properties and photodynamic activity of two cationic BODIPY derivatives with application in the photoinactivation of microorganisms

Cited by 54 publications

References 55 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

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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