Synthesis and photodynamic effects of new porphyrin/4-oxoquinoline derivatives in the inactivation of S. aureus

Sagrillo, Fernanda S.; Dias, Cristina J.; Gomes, Ana T. P. C.; Faustino, Maria A. F.; Almeida, Adelaide; Souza, Alan Gonçalves de; Costa, Amanda Rodrigues Pinto; Boechat, Fernanda da Costa Santos; Souza, Maria Cecília B. V. de; Neves, Maria G. P. M. S.; Cavaleiro, José A. S.

doi:10.1039/c9pp00102f

Cited by 13 publications

(6 citation statements)

References 49 publications

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“…Porphyrins, which are tetrapyrrolic ligands with high chemical stability, unique optical properties and strong redox activity are an example of these compounds [5][6][7]. During the last two decades, such compounds have been extensively studied for use in numerous applications such as solar cells [8][9], chemosensors [10][11][12][13], artificial photosynthesis [14], catalysis [15][16][17][18][19], and biomedical applications [20][21][22]. The absorption spectrum of porphyrins has a typical profile consisting of an intense Soret band at λ = 400-450 nm followed by a weaker quartet of bands at λ = 550-650 nm known as the Q bands.…”

Section: Introductionmentioning

confidence: 99%

New triazine bridged triads based on BODIPY-porphyrin systems: Extended absorption, efficient energy transfer and upconverted emission

Souza

Santos²,

Mariz³

et al. 2021

Dyes and Pigments

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Section: Introductionmentioning

confidence: 99%

New triazine bridged triads based on BODIPY-porphyrin systems: Extended absorption, efficient energy transfer and upconverted emission

Souza

Santos²,

Mariz³

et al. 2021

Dyes and Pigments

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“…For instance, rose bengal and chlorin e6 (20 μM) inactivated only 0.6 and 1.2 log 10 of S. aureus with high light doses of 30 and 20 J/cm 2 , respectively. It is worth noting that the light dose needed to effectively kill S. aureus (>3.0 log 10 ) with CPVBP2 (1.2 J/cm 2 ) is also significantly lower than many reported photosensitizers, including traditional photosensitizers, such as porphyrin, − phthalocyanine, − phenothiazinium, − boron-dipyrromethene, − indocyanine green, − and AIE photosensitizers. ,− …”

Section: Resultsmentioning

confidence: 93%

Restricting Bond Rotations by Ring Fusion: A Novel Molecular Design Strategy to Improve Photodynamic Antibacterial Efficacy of AIE Photosensitizers

Shi

Pan

Wang

et al. 2022

ACS Appl. Mater. Interfaces

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In recent years, aggregation-induced emission photosensitizers (AIE-PSs) for antibacterial photodynamic therapy (aPDT) have received increasing attention because of their ability to increase reactive oxygen species (ROS) generation in the aggregation state. However, their antibacterial effect still has great room for improvement. Herein, we propose that if the rotation of some bonds in AIE-PSs is restricted, the nonradiative decay could be further suppressed to boost the generation of fluorescence and ROS, so as to improve their antibacterial efficacy. Following this molecular design strategy, we developed a new class of carbazole group-based AIE-PSs (CPVBA, CPVBP, CPVBP2, and CPVBP3), in which the rotation of phenyl-N bonds is restricted in the carbazole ring. Compared with diphenylamine group-based AIE-PSs with free rotation of phenyl-N bonds, carbazole group-based AIE-PSs showed stronger fluorescence, ROS generation, and antibacterial abilities, demonstrating the feasibility of this new design strategy. Notably, CPVBP3 can enter the entire cell of E. coli to exert its antibacterial effect, and there are few reports of photosensitizers with similar functions. Furthermore, to the best of our knowledge, the light dose (1.2 J/cm2) we used for CPVBP2 to kill Staphylococcus aureus is much lower than that of many reported photosensitizers, indicating great prospects for AIE antimicrobial photosensitizers.

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“…Due to the π-aromatic ring and stability, various functional groups (-Br, -NO 2 , -COOH, etc. ) , and molecules (glucose, lactose, lysine, oxo-quinoline) − are able to be integrated on the meso -position and β-position of porphyrin rings to achieve optimized physicochemical properties and tailored functionalities. (ii) Interesting optical properties.…”

Section: Introductionmentioning

confidence: 99%

Biomedical Application of Porphyrin-Based Amphiphiles and Their Self-Assembled Nanomaterials

Han,

Liu,

Peng

et al. 2023

Bioconjugate Chem.

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Porphyrins have been vastly explored and applied in many cutting-edge fields with plenty of encouraging achievements because of their excellent properties. As important derivatives of porphyrins, porphyrin-based amphiphiles (PBAs) not only maintain the advanced properties of porphyrins (catalysis, imaging, and energy transfer) but also possess self-assembly and encapsulation capability in aqueous solution. Accordingly, PBAs and their self-assembles have had important roles in diagnosing and treating tumors and inflammation lesions in vivo, but not limited to these. In this article, we introduce the research progress of PBAs, including their constitution, structure design strategies, and performances in tumor and inflammation lesion diagnosis and treatments. On that basis, the defects of synthesized PBAs during their application and the possible effective strategies to overcome the limitations are also proposed. Finally, perspectives on PBAs exploration are updated based on our knowledge. We hope this review will bring researchers from various domains insights about PBAs.

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Synthesis and photodynamic effects of new porphyrin/4-oxoquinoline derivatives in the inactivation of S. aureus

Abstract: New porphyrin/4-oxoquinoline conjugates were synthesized and shown to be excellent photosensitizing agents in the inactivation of S. aureus by the antimicrobial photodynamic therapy protocol.

Cited by 13 publications

References 49 publications

New triazine bridged triads based on BODIPY-porphyrin systems: Extended absorption, efficient energy transfer and upconverted emission

New triazine bridged triads based on BODIPY-porphyrin systems: Extended absorption, efficient energy transfer and upconverted emission

Restricting Bond Rotations by Ring Fusion: A Novel Molecular Design Strategy to Improve Photodynamic Antibacterial Efficacy of AIE Photosensitizers

Biomedical Application of Porphyrin-Based Amphiphiles and Their Self-Assembled Nanomaterials

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