Sofía C. Santamarina

Consejo Nacional de Investigaciones Científicas y Técnicas

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Edgardo N. Durantini

National University of Río Cuarto

Daniel A. Heredia

National University of Río Cuarto

Andrés M. Durantini

Southern Illinois University Edwardsville

Edwin J. González López

Consejo Nacional de Investigaciones Científicas y Técnicas

Javier E. Durantini

National University of Río Cuarto

M. Gabriela Alvarez

National University of Río Cuarto

Luís Otero

National University of Río Cuarto

Ana C. Scanone

Consejo Nacional de Investigaciones Científicas y Técnicas

Lorena Macor

Consejo Nacional de Investigaciones Científicas y Técnicas

Melisa Renfige Rodriguez

National University of Río Cuarto

Cooperative Institutions

Consejo Nacional de Investigaciones Científicas y Técnicas

National University of Río Cuarto

Centro Médico Sanitas Córdoba

Fundación Ciencias Exactas y Naturales

Instituto Médico Río Cuarto

Arizona State University

Institute of Information Technologies, Economy and Management

Institute of Molecular Science and Technologies

National Taiwan University

Universidad Nacional de Córdoba

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Functionalized Magnetic Nanoparticles with BODIPYs for Bioimaging and Antimicrobial Therapy Applications

ACS Applied Bio Materials (2020)

Ana C. Scanone Sofía C. Santamarina Daniel A. Heredia Edgardo N. Durantini Andrés M. Durantini

The antimicrobial capability and recyclability of two conjugates that combines the versatility of iron oxide magnetic nanoparticles (MNPs) with the high photosensitizing proficiency of boron-dipyrromethene (BODIPY) dyes are assessed. By a relatively simple synthetic pathway, two conjugates were obtained. The first one, MNP-B1, contains a highly fluorescent dye for bioimaging and suitable inactivating properties. The other one, MNP-B2, is optimized to improve the production of cytotoxic reactive oxygen species (ROS) by incorporating heavy atoms in the BODIPY core. In vitro experiments in bacterial cell suspensions and at the single bacterium level reveal that both conjugates can inactivate either Gram-positive (methicillin-resistant Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. By means of fluorescence microscopy, not only cellular uptake of the conjugates but also recyclability and sustained performance over the cycles of photodynamic inactivation (PDI) are demonstrated. This is the first time that MNPs functionalized with BODIPY dyes are utilized to obtain fluorescent images of bacterial cells and photoinactivate pathogens.

BODIPY

Conjugate

Iron oxide nanoparticles

10.1021/acsabm.9b01035

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Citations (32)

Porphycenes as Broad-Spectrum Antimicrobial Photosensitizers. Potentiation with Potassium Iodide

SSRN Electronic Journal (2022)

Edwin J. González López Sofía C. Santamarina M. Gabriela Alvarez Daniel A. Heredia Edgardo N. Durantini

Two novels meso-tetrasubstituted porphycenes (Pc-Cbz and Pc-NEt2) have been synthesized by palladium-catalyzed Suzuki cross-coupling reactions over 9,10,19,20-tetrakis(4-iodophenyl)porphycene. Pc-Cbz contains four carbazole groups on the periphery of the tetrapyrrolic macrocycle. Instead, Pc-NEt2 presents four basic tertiary amine substituents, which can be protonated at physiological pH, acquiring four positive charges. Both photosensitizers (PSs) were designed to evaluate the effect of different substitution patterns on the photodynamic inactivation of microorganisms. Their absorption and fluorescence properties were almost unmodified regardless of the substituent groups on the periphery. The characteristic red emission makes them promising fluorescent probes for cell imaging. Moreover, both macrocycles were able to generate reactive oxygen species by both photodynamic mechanisms under aerobic light irradiation. The photokilling action of these PSs was assessed in vitro against Candida albicans (yeast), Staphylococcus aureus (Gram-positive bacterium), and Escherichia coli (Gram-negative bacterium). Our results demonstrate that the peripheral substitution significantly affected the photoinactivation performance. Thus, Pc-NEt2 was more effective than Pc-Cbz in killing microorganisms using lower concentrations and shorter irradiation periods, evidencing that external substitution is a main structural feature. Also, the photoinactivation efficiency mediated by these porphycenes was potentiated by adding KI. Under these conditions, a complete eradication of all pathogenic microorganisms was obtained by combining Pc-NEt2 and KI. Therefore, Pc-NEt2 can be used as an effective broad-spectrum antimicrobial PS. Accordingly, this work stands out as a promising starting point for the design of new porphycene-based PSs for photodynamic inactivation (PDI) of microorganisms. Our outcomes also disclose that the combination of these PSs with KI is an important factor in order to improve the PDI treatments and the current antimicrobial therapies.

Broad spectrum

10.2139/ssrn.4082158

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Porphycenes as broad-spectrum antimicrobial photosensitizers. Potentiation with potassium iodide

Journal of Photochemistry and Photobiology A Chemistry (2022)

Edwin J. González López Sofía C. Santamarina M. Gabriela Alvarez Daniel A. Heredia Edgardo N. Durantini

Broad spectrum

10.1016/j.jphotochem.2022.114288

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Antimicrobial Photosensitizing Material Based on Conjugated Zn(II) Porphyrins

Antibiotics (2022)

Sofía C. Santamarina Daniel A. Heredia Andrés M. Durantini Edgardo N. Durantini

The widespread use of antibiotics has led to a considerable increase in the resistance of microorganisms to these agents. Consequently, it is imminent to establish new strategies to combat pathogens. An alternative involves the development of photoactive polymers that represent an interesting strategy to kill microbes and maintain aseptic surfaces. In this sense, a conjugated polymer (PZnTEP) based on Zn(II) 5,10,15,20-tetrakis-[4-(ethynyl)phenyl]porphyrin (ZnTEP) was obtained by the homocoupling reaction of terminal alkyne groups. PZnTEP exhibits a microporous structure with high surface areas allowing better interaction with bacteria. The UV-visible absorption spectra show the Soret and Q bands of PZnTEP red-shifted by about 18 nm compared to those of the monomer. Also, the conjugate presents the two red emission bands, characteristic of porphyrins. This polymer was able to produce singlet molecular oxygen and superoxide radical anion in the presence of NADH. Photocytotoxic activity sensitized by PZnTEP was investigated in bacterial suspensions. No viable Staphylococcus aureus cells were detected using 0.5 µM PZnTEP and 15 min irradiation. Under these conditions, complete photoinactivation of Escherichia coli was observed in the presence of 100 mM KI. Likewise, no survival was detected for E. coli incubated with 1.0 µM PZnTEP after 30 min irradiation. Furthermore, polylactic acid surfaces coated with PZnTEP were able to kill efficiently these bacteria. This surface can be reused for at least three photoinactivation cycles. Therefore, this conjugated photodynamic polymer is an interesting antimicrobial photoactive material for designing and developing self-sterilizing surfaces.

Phototoxicity

10.3390/antibiotics11010091

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Porphyrin Polymers Bearing N,N′-Ethylene Crosslinkers as Photosensitizers against Bacteria

Polymers (2022)

Sofía C. Santamarina Daniel A. Heredia Javier E. Durantini Edgardo N. Durantini

The appearance of microbes resistant to antibiotics requires the development of alternative therapies for the treatment of infectious diseases. In this work two polymers, PTPPF16-EDA and PZnTPPF16-EDA, were synthesized by the nucleophilic aromatic substitution of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin and its Zn(II) complex with ethylenediamine, respectively. In these structures, the tetrapyrrolic macrocycles were N,N'-ethylene crosslinked, which gives them greater mobility. The absorption spectra of the polymers showed a bathochromic shift of the Soret band of ~10 nm with respect to the monomers. This effect was also found in the red fluorescence emission peaks. Furthermore, both polymeric materials produced singlet molecular oxygen with high quantum yields. In addition, they were capable of generating superoxide anion radicals. Photodynamic inactivation sensitized by these polymers was tested in Staphylococcus aureus and Escherichia coli bacteria. A decrease in cell viability greater than 7 log (99.9999%) was observed in S. aureus incubated with 0.5 μM photosensitizer upon 30 min of irradiation. Under these conditions, a low inactivation of E. coli (0.5 log) was found. However, when the cells were treated with KI, the elimination of the Gram-negative bacteria was achieved. Therefore, these polymeric structures are interesting antimicrobial photosensitizing materials for the inactivation of pathogens.

Bathochromic shift

Quantum yield

10.3390/polym14224936

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Tuning the Molecular Structure of Corroles to Enhance the Antibacterial Photosensitizing Activity

Pharmaceutics (2023)

Edwin J. González López Sol R. Martínez Virginia Aiassa Sofía C. Santamarina Rodrigo E. Domínguez

The increase in the antibiotic resistance of bacteria is a serious threat to public health. Photodynamic inactivation (PDI) of micro-organisms is a reliable antimicrobial therapy to treat a broad spectrum of complex infections. The development of new photosensitizers with suitable properties is a key factor to consider in the optimization of this therapy. In this sense, four corroles were designed to study how the number of cationic centers can influence the efficacy of antibacterial photodynamic treatments. First, 5,10,15-Tris(pentafluorophenyl)corrole (Co) and 5,15-bis(pentafluorophenyl)-10-(4-(trifluoromethyl)phenyl)corrole (Co-CF3) were synthesized, and then derivatized by nucleophilic aromatic substitution with 2-dimethylaminoethanol and 2-(dimethylamino)ethylamine, obtaining corroles Co-3NMe2 and Co-CF3-2NMe2, respectively. The straightforward synthetic strategy gave rise to macrocycles with different numbers of tertiary amines that can acquire positive charges in an aqueous medium by protonation at physiological pH. Spectroscopic and photodynamic studies demonstrated that their properties as chromophores and photosensitizers were unaffected, regardless of the substituent groups on the periphery. All tetrapyrrolic macrocycles were able to produce reactive oxygen species (ROS) by both photodynamic mechanisms. Uptake experiments, the level of ROS produced in vitro, and PDI treatments mediated by these compounds were assessed against clinical strains: methicillin-resistant Staphylococcus aureus and Klebsiella pneumoniae. In vitro experiments indicated that the peripheral substitution significantly affected the uptake of the photosensitizers by microbes and, consequently, the photoinactivation performance. Co-3NMe2 was the most effective in killing both Gram-positive and Gram-negative bacteria (inactivation > 99.99%). This work lays the foundations for the development of new corrole derivatives having pH-activable cationic groups and with plausible applications as effective broad-spectrum antimicrobial photosensitizers.

Corrole

Phototoxicity

10.3390/pharmaceutics15020392

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Citations (7)

Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer

The 17th International Electronic Conference on Synthetic Organic Chemistry (2020)

Sofía C. Santamarina Daniel A. Heredia Andrés M. Durantini Edgardo N. Durantini

5,10,15,20-tetrakis-[4-(ethynyl)phenyl]porphyrin (TEP) was synthesized from the condensation of 4-(ethynyl)benzaldehyde and pyrrole catalyzed by boron trifluoride diethyl etherate in dichloromethane (DCM). After oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and purification, TEP was obtained in 34% yield. This porphyrin was metaled with Zn(II) acetate in DCM/methanol to produce the complex ZnTEP in 98% yield. A homocoupling reaction of terminal alkynes of ZnTEP to diynes was used to synthesize conjugated polymer organogel (ZnTEPP). The reaction was co-catalyzed by PdCl2(PPh3)2 and CuI in tetrahydrofuran. The solvent was evaporated to obtain xerogel and the SEM images showed microporous structure. In addition, spectroscopic and photodynamic studies of ZnTEPP indicated that the porphyrin unit retains its properties as a photosensitizer. Thus, this polymer is an interesting material with potential applications in forming photoactive aseptic surfaces.

Tetrahydrofuran

Dichloromethane

Boron trifluoride

Benzaldehyde

Pyrrole

10.3390/ecsoc-24-08317

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Light-Activated Antibacterial Polymeric Surface Based on Porphycene

ACS Applied Polymer Materials (2023)

Edwin J. González López Melisa Renfige Rodriguez Sofía C. Santamarina Lorena Macor Luís Otero

A photoactivatable antimicrobial polymeric surface based on a porphycene derivate was efficiently prepared and evaluated to kill pathogenic microorganisms. The development of this self-sterilizing material consisted in the electrochemical polymerization of a peripherally tetra-substituted porphycene bearing benzyl-carbazole groups (Pc-Cbz). The latter were used as electropolymerizable centers, while the porphycene core triggered the photodynamic action. The electrodeposited photodynamic films (P-Pc-Cbz) were obtained in a reproducible and controllable manner. Electrochemistry studies combined with spectroscopic measurements demonstrated that the porphycene core remains unaffected after the electrodeposition process. Moreover, it retains its spectroscopic and photodynamic properties within the polymeric matrix. The photoactive layers were photostable and able to produce reactive oxygen species (ROS) by both photodynamic mechanisms. Also, the antimicrobial efficiency of P-Pc-Cbz was evaluated against two antibiotic-resistant strains (methicillin-resistant Staphylococcus aureus and Escherichia coli), exhibiting an antimicrobial action higher than 99.998% over these Gram-positive and Gram-negative bacteria. This work represents the first electropolymerization of a porphycene derivative and the first porphycene-based photobiocidal surface. P-Pc-Cbz shows great potential as an efficient self-sterilizing coating activated by visible light.

Carbazole

10.1021/acsapm.2c01890

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Citations (9)

BODIPYs bearing a dimethylaminopropoxy substituent for imaging and photodynamic inactivation of bacteria

Journal of Photochemistry and Photobiology B Biology (2020)

Yohana B. Palacios Sofía C. Santamarina Javier E. Durantini Edgardo N. Durantini Andrés M. Durantini

BODIPY

Cationic polymerization

10.1016/j.jphotobiol.2020.112049

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Citations (16)

Photodynamic Polymers Constituted by Porphyrin Units as Antibacterial Materials

Photochem (2022)

M. Belén Ballatore María E. Pérez Sofía C. Santamarina Javier E. Durantini M. Elisa Milanesio

Photodynamic inactivation of microorganisms has emerged as a promising strategy to kill and eradicate pathogens. In this work, two polymers, TCP-P and ZnTCP-P, were synthesized by oxidative polymerization of 5,10,15,20-tetrakis [3-(N-ethylcarbazoyl)]porphyrin and its complex with Zn(II). Solid polymers consist of rods (diameter 100 nm, length ~100–500 nm) that form microporous structures on a surface. UV-visible absorption spectra in solution showed the Soret and Q bands characteristic of the corresponding constitutional porphyrins. In addition, the polymers presented two red emission bands with quantum yields ΦF = 0.11 for TCP-P and ΦF = 0.050 for ZnTCP-P. These compounds sensitized the production of singlet molecular oxygen with quantum yields of ΦΔ~0.3. Thus, the spectroscopic and photodynamic properties of the porphyrin units were maintained in the conjugates. The photodynamic activity induced by both polymers was tested to inactivate S. aureus. In cell suspensions, TCP-P was more effective than ZnTCP-P in killing bacteria. Viable S. aureus cells were not detected using 4 µM TCP-P after 20 min of irradiation. Moreover, both polymers showed a high photocytotoxic activity to eradicate S. aureus cells attached to a surface. The results indicate that these conjugated polymers can act as effective antimicrobial agents to photoinactivate pathogens.

Conjugated microporous polymer

10.3390/photochem2040057

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Citations (3)