Mechanistic aspects in the photodynamic inactivation of Candida albicans sensitized by a dimethylaminopropoxy porphyrin and its equivalent with cationic intrinsic charges

Quiroga, Ezequiel D.; Cordero, Paula; Mora, Sabrina; Alvarez, M. Gabriela; Durantini, Edgardo N.

doi:10.1016/j.pdpdt.2020.101877

Cited by 12 publications

(14 citation statements)

References 37 publications

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“…Additionally, these amino units are separated from the porphyrin macrocycle by an aliphatic spacer that affords a higher mobility. The presence of positive charges with appropriate flexibility of movements can allow for better interactions with microorganisms [7,16]. To evaluate this effect, porphyrins 6 and 7 were optimized to a stationary point on the Born-Oppenheimer potential energy surface of the molecular structures [27].…”

Section: Synthesis Of Porphyrin-schiff Base Conjugatesmentioning

confidence: 99%

“…Porphyrins substituted in the meso position by basic amino groups through Schiff base functions are capable of acquiring positive charges at physiological pH [ 14 ]. Thus, the presence of cationic groups from protonation can allow for better interactions with the cell wall of microbial cells [ 7 , 15 , 16 ]. In this study, the spectroscopic characteristics of porphyrins 6 and 7 were determined in solution, and their photodynamic properties were investigated in the presence of different photo-oxidizable substrates.…”

Section: Introductionmentioning

confidence: 99%

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Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents

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New porphyrin–Schiff base conjugates bearing one (6) and two (7) basic amino groups were synthesized by condensation between tetrapyrrolic macrocycle-containing amine functions and 4-(3-(N,N-dimethylamino)propoxy)benzaldehyde. This approach allowed us to easily obtain porphyrins substituted by positive charge precursor groups in aqueous media. These compounds showed the typical Soret and four Q absorption bands with red fluorescence emission (ΦF ~ 0.12) in N,N-dimethylformamide. Porphyrins 6 and 7 photosensitized the generation of O2(1Δg) (ΦΔ ~ 0.44) and the photo-oxidation of L-tryptophan. The decomposition of this amino acid was mainly mediated by a type II photoprocess. Moreover, the addition of KI strongly quenched the photodynamic action through a reaction with O2(1Δg) to produce iodine. The photodynamic inactivation capacity induced by porphyrins 6 and 7 was evaluated in Staphylococcus aureus, Escherichia coli, and Candida albicans. Furthermore, the photoinactivation of these microorganisms was improved using potentiation with iodide anions. These porphyrins containing basic aliphatic amino groups can be protonated in biological systems, which provides an amphiphilic character to the tetrapyrrolic macrocycle. This effect allows one to increase the interaction with the cell wall, thus improving photocytotoxic activity against microorganisms.

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Section: Synthesis Of Porphyrin-schiff Base Conjugatesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents

et al. 2021

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“…Differences between means were tested for significance by one-way ANOVA. Results were considered statistically significant with a confidence level of 95% (p < 0.05) [18]. Data were represented as the mean ± standard deviation.…”

Section: Controls and Statistical Analysismentioning

confidence: 98%

“…The maximum amount of DMF used was 1% v/v and this amount of organic solvent was not toxic to C. albicans. Each sample was incubated with TAPC for 30 min in the dark at 37 • C. Sodium azide (50 mM) and D-mannitol (100 mM) were added to C. albicans suspensions from stock solutions 1 M and 2 M in water, respectively [18]. Additionally, cultures were treated with 100 mM DMSO.…”

Section: Pdi Of C Albicans Planktonic Cellsmentioning

confidence: 99%

Photodynamic Effect of 5,10,15,20-Tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]chlorin towards the Human Pathogen Candida albicans under Different Culture Conditions

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Photocytotoxic activity sensitized by 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]chlorin (TAPC) was investigated in Candida albicans under different culture conditions. Planktonic cells incubated with 2.5 μM TAPC were eradicated after 5 min irradiation with white light. Studies in the presence of reactive oxygen species scavengers indicated the involvement of mainly a type II mechanism. Furthermore, cell growth of C. albicans was suppressed in the presence of 5 μM TAPC. A decrease in pseudohyphae survival of 5 log was found after 30 min irradiation. However, the photokilling of this virulence factor reached a 1.5 log reduction in human serum. The uptake of TAPC by pseudohyphae decreased in serum due to the interaction of TAPC with albumin. The binding constant of the TAPC-albumin complex was ~104 M−1, while the bimolecular quenching rate constant was ~1012 s−1 M−1, indicating that this process occurred through a static process. Thus, the photoinactivation of C. albicans was considerably decreased in the presence of albumin. A reduction of 2 log in cell survival was observed using 4.5% albumin and 30 min irradiation. The results allow optimizing the best conditions to inactivate C. albicans under different culture conditions.

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“…It was even more effective than a bacteriochlorin substituted by eight aliphatic amine groups [34]. In addition, it was established that a porphyrin substituted by dimethylaminopropoxy groups without intrinsic charges was equally active as its analogous cationic porphyrin in photo-inactivating microorganisms [37,38]. Therefore, the presence of a precursor group of positive charge should be considered to design effective brominated BODIPYs to kill bacteria.…”

Section: J O U R N a L P R E -P R O O Fmentioning

confidence: 99%

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

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et al. 2020

Journal of Photochemistry and Photobiology B: Biology

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Mechanistic aspects in the photodynamic inactivation of Candida albicans sensitized by a dimethylaminopropoxy porphyrin and its equivalent with cationic intrinsic charges

Abstract: Mechanistic aspects in the photodynamic inactivation of Candida albicans sensitized by a dimethylaminopropoxy porphyrin and its equivalent with cationic intrinsic charges,

Cited by 12 publications

References 37 publications

Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents

Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents

Photodynamic Effect of 5,10,15,20-Tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]chlorin towards the Human Pathogen Candida albicans under Different Culture Conditions

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

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