Photoactive antimicrobial coating based on a PEDOT-fullerene C<sub>60</sub> polymeric dyad

Reynoso, Eugenia; Durantini, Andrés M.; Solis, Claudia Alejandra; Macor, Lorena; Otero, Luís; Gervaldo, Miguel; Durantini, Edgardo N.; Heredia, Daniel A.

doi:10.1039/d1ra03417k

Cited by 24 publications

(24 citation statements)

References 84 publications

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“…Also, two small peaks, located at 437 and 705 nm, can be observed for P‐C 60 . These ones are distinctive and diagnostic of N ‐methylfulleropyrrolidines [17,47] . Furthermore, P‐C 60 has high absorption in the UV‐region corresponding to π‐π* transitions of the fullerene moiety [17,37] …”

Section: Resultsmentioning

confidence: 99%

“…These ones are distinctive and diagnostic of N-methylfulleropyrrolidines. [17,47] Furthermore, P-C 60 has high absorption in the UV-region corresponding to π-π* transitions of the fullerene moiety. [17,37] Regarding the dyad BP-C 60 , it is easily observed that the absorption spectrum of BP-C 60 corresponds to a linear combination of the two constitutional components BP and P-C 60 .…”

Section: Absorption and Fluorescence Spectroscopic Characterizationmentioning

confidence: 99%

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BOPHY‐Fullerene C₆₀ Dyad as a Photosensitizer for Antimicrobial Photodynamic Therapy

Lopez

Sarotti

Martínez

et al. 2021

Chemistry A European J

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A novel BOPHY–fullerene C60 dyad (BP‐C60) was designed as a heavy‐atom‐free photosensitizer (PS) with potential uses in photodynamic treatment and reactive oxygen species (ROS)‐mediated applications. BP‐C60 consists of a BOPHY fluorophore covalently attached to a C60 moiety through a pyrrolidine ring. The BOPHY core works as a visible‐light‐harvesting antenna, while the fullerene C60 subunit elicits the photodynamic action. This fluorophore–fullerene cycloadduct, obtained by a straightforward synthetic route, was fully characterized and compared with its individual counterparts. The restricted rotation around the single bond connecting the BOPHY and pyrrolidine moieties led to the formation of two atropisomers. Spectroscopic, electrochemical, and computational studies disclose an efficient photoinduced energy/electron transfer process from BOPHY to fullerene C60. Photodynamic studies indicate that BP‐C60 produces ROS by both photomechanisms (type I and type II). Moreover, the dyad exhibits higher ROS production efficiency than its individual constitutional components. Preliminary screening of photodynamic inactivation on bacteria models (Staphylococcus aureus and Escherichia coli) demonstrated the ability of this dyad to be used as a heavy‐atom‐free PS. To the best of our knowledge, this is the first time that not only a BOPHY–fullerene C60 dyad is reported, but also that a BOPHY derivative is applied to photoinactivate microorganisms. This study lays the foundations for the development of new BOPHY‐based PSs with plausible applications in the medical field.

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Section: Resultsmentioning

confidence: 99%

Section: Absorption and Fluorescence Spectroscopic Characterizationmentioning

confidence: 99%

BOPHY‐Fullerene C₆₀ Dyad as a Photosensitizer for Antimicrobial Photodynamic Therapy

Lopez

Sarotti

Martínez

et al. 2021

Chemistry A European J

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“…It was observed that the inactivation was accomplished after 30 min of irradiation using the same light dose as reported here for ZnPc-PEDOT (3.6 J/cm 2 ). 18 Until now, the improvement of self-sterilizing surfaces by the addition of KI in PDI treatments was never reported. Our results provide evidence on how a relatively weak antimicrobial material can be significantly improved by simply aerosolizing a low-cost inorganic salt on the material.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The generation of photoactive polymers by electrochemical procedures is a reliable way to obtain antimicrobial surfaces. − Exploiting electrochemical procedures it is possible to generate polymeric films controlling their morphology and thickness. − To this end, tetrapyrrolic derivatives bearing amino, diethyl aniline, and thiophene , have been synthesized. However, there are only a few reports about the use of ethylenedioxythiophene (EDOT), a monomer that polymerizes to form polyethylenedioxythiophene (PEDOT), one of the most versatile and conductive materials .…”

Section: Introductionmentioning

confidence: 99%

Potentiation Effect of Iodine Species on the Antimicrobial Capability of Surfaces Coated with Electroactive Phthalocyanines

Baigorria

Durantini

Martínez

et al. 2021

ACS Appl. Bio Mater.

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The spreading of different infections can occur through direct contact with glass surfaces in commonly used areas. Incorporating the use of alternative therapies in these materials seems essential to reduce and also avoid bacterial resistance. In this work, the capability to kill microbes of glass surfaces coated with two electroactive metalated phthalocyanines (ZnPc-EDOT and CuPc-EDOT) is assessed. The results show that both of these materials are capable of producing reactive oxygen species; however, the polymer with Zn(II) (ZnPc-PEDOT) has a singlet oxygen quantum yield 8-fold higher than that of the Cu(II) containing analogue. This was reflected in the in vitro experiments where the effectiveness of the surfaces was tested in bacterial suspensions, monitoring single microbe inactivation upon attachment to the polymers, and eliminating mature biofilms. Furthermore, we evaluated the use of an inorganic salt (KI) to potentiate the photodynamic inactivation mediated by an electropolymerized surface. The addition of the salt improved the efficiency of phototherapy at least two times for both polymers; nevertheless, the material coated with ZnPc-PEDOT was the only one capable of eliminating >99.98% of the initial microbes loading under different circumstances.

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“…Antibacterial properties are also found in carbon nanomaterials, which include graphene, carbon nanotubes, fullerenes, and various forms of diamonds [4][5][6][7][8][9][10]. Moreover, it was shown that the antibacterial properties of C 60 fullerenes are not associated with the production of reactive oxygen species (ROS), and materials based on them exert oxidative stress independent of ROS [11][12][13][14], thereby significantly reducing cytotoxicity. The ability of fullerene to photocatalyze in a nanocomposite can be used to create self-cleaning materials [15].…”

Section: Introductionmentioning

confidence: 99%

Novel Biocompatible with Animal Cells Composite Material Based on Organosilicon Polymers and Fullerenes with Light-Induced Bacteriostatic Properties

et al. 2021

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A technology for producing a nanocomposite based on the borsiloxane polymer and chemically unmodified fullerenes has been developed. Nanocomposites containing 0.001, 0.01, and 0.1 wt% fullerene molecules have been created. It has been shown that the nanocomposite with any content of fullerene molecules did not lose the main rheological properties of borsiloxane and is capable of structural self-healing. The resulting nanomaterial is capable of generating reactive oxygen species (ROS) such as hydrogen peroxide and hydroxyl radicals in light. The rate of ROS generation increases with an increase in the concentration of fullerene molecules. In the absence of light, the nanocomposite exhibits antioxidant properties. The severity of antioxidant properties is also associated with the concentration of fullerene molecules in the polymer. It has been shown that the nanocomposite upon exposure to visible light leads to the formation of long-lived reactive protein species, and is also the reason for the appearance of such a key biomarker of oxidative stress as 8-oxoguanine in DNA. The intensity of the process increases with an increase in the concentration of fullerene molecules. In the dark, the polymer exhibits weak protective properties. It was found that under the action of light, the nanocomposite exhibits significant bacteriostatic properties, and the severity of these properties depends on the concentration of fullerene molecules. Moreover, it was found that bacterial cells adhere to the surfaces of the nanocomposite, and the nanocomposite can detach bacterial cells not only from the surfaces, but also from wetted substrates. The ability to capture bacterial cells is primarily associated with the properties of the polymer; they are weakly affected by both visible light and fullerene molecules. The nanocomposite is non-toxic to eukaryotic cells, the surface of the nanocomposite is suitable for eukaryotic cells for colonization. Due to the combination of self-healing properties, low cytotoxicity, and the presence of bacteriostatic properties, the nanocomposite can be used as a reusable dry disinfectant, as well as a material used in prosthetics.

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Photoactive antimicrobial coating based on a PEDOT-fullerene C₆₀ polymeric dyad

Abstract: A photostable and photodynamic antimicrobial surface was developed. The antimicrobial activity of the material reached outstanding levels of inactivation under different conditions: planktonic suspensions, adhered cells to the surface, and biofilms.

Cited by 24 publications

References 84 publications

BOPHY‐Fullerene C₆₀ Dyad as a Photosensitizer for Antimicrobial Photodynamic Therapy

BOPHY‐Fullerene C₆₀ Dyad as a Photosensitizer for Antimicrobial Photodynamic Therapy

Potentiation Effect of Iodine Species on the Antimicrobial Capability of Surfaces Coated with Electroactive Phthalocyanines

Novel Biocompatible with Animal Cells Composite Material Based on Organosilicon Polymers and Fullerenes with Light-Induced Bacteriostatic Properties

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Photoactive antimicrobial coating based on a PEDOT-fullerene C60 polymeric dyad

Abstract: A photostable and photodynamic antimicrobial surface was developed. The antimicrobial activity of the material reached outstanding levels of inactivation under different conditions: planktonic suspensions, adhered cells to the surface, and biofilms.

Cited by 24 publications

References 84 publications

BOPHY‐Fullerene C60 Dyad as a Photosensitizer for Antimicrobial Photodynamic Therapy

BOPHY‐Fullerene C60 Dyad as a Photosensitizer for Antimicrobial Photodynamic Therapy

Potentiation Effect of Iodine Species on the Antimicrobial Capability of Surfaces Coated with Electroactive Phthalocyanines

Novel Biocompatible with Animal Cells Composite Material Based on Organosilicon Polymers and Fullerenes with Light-Induced Bacteriostatic Properties

Contact Info

Product

Resources

About

Photoactive antimicrobial coating based on a PEDOT-fullerene C₆₀ polymeric dyad

BOPHY‐Fullerene C₆₀ Dyad as a Photosensitizer for Antimicrobial Photodynamic Therapy

BOPHY‐Fullerene C₆₀ Dyad as a Photosensitizer for Antimicrobial Photodynamic Therapy