Triphenylphosphonium cation: A valuable functional group for antimicrobial photodynamic therapy

Bresolí‐Obach, Roger; Gispert, Ignacio; Peña, Diego G.; Boga, Sonia; Gulías, Òscar; Agut, Montserrat; Vázquez, M. Eugenio; Nonell, Santi

doi:10.1002/jbio.201800054

Cited by 24 publications

(31 citation statements)

References 35 publications

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“…The perylenequinone derivative hypericin-glucamine is another example of a synthetic PS derivative that promotes periodontal repair [ 132 ]. Bresolí-Obach et al [ 133 ] reported that a phenalenone PS showed significant photostability and phototoxicity against Gram-positive bacteria. Additionally, in that study, a triphenylphosphonium derivative PS selectively killed Gram-positive bacteria.…”

Section: Synthetic Derivatives Of Natural Pssmentioning

confidence: 99%

Natural Photosensitizers in Antimicrobial Photodynamic Therapy

2021

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Health problems and reduced treatment effectiveness due to antimicrobial resistance have become important global problems and are important factors that negatively affect life expectancy. Antimicrobial photodynamic therapy (APDT) is constantly evolving and can minimize this antimicrobial resistance problem. Reactive oxygen species produced when nontoxic photosensitizers are exposed to light are the main functional components of APDT responsible for microbial destruction; therefore, APDT has a broad spectrum of target pathogens, such as bacteria, fungi, and viruses. Various photosensitizers, including natural extracts, compounds, and their synthetic derivatives, are being investigated. The main limitations, such as weak antimicrobial activity against Gram-negative bacteria, solubility, specificity, and cost, encourage the exploration of new photosensitizer candidates. Many additional methods, such as cell surface engineering, cotreatment with membrane-damaging agents, nanotechnology, computational simulation, and sonodynamic therapy, are also being investigated to develop novel APDT methods with improved properties. In this review, we summarize APDT research, focusing on natural photosensitizers used in in vitro and in vivo experimental models. In addition, we describe the limitations observed for natural photosensitizers and the methods developed to counter those limitations with emerging technologies.

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Section: Synthetic Derivatives Of Natural Pssmentioning

confidence: 99%

Natural Photosensitizers in Antimicrobial Photodynamic Therapy

2021

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“…In particular, following the major concerns around MDR bacteria, several new PS have been tested, adapted or developed for aPDT [30]. In this sense, positively charged PS appear promising for aPDT as they can interact electrostatically with the negatively charged bacterial membrane, and the synthesis of several PS functionalised with small cationic functional groups has been reported [31][32][33][34][35]. Nonetheless, two main concerns can arise from this strategy: (i) a poor target selectivity since such cationic species, due to electrostatic interactions with mammalian cells, lead to off-target damage, and (ii) the poor efficiency of aPDT against a certain type of pathogens, in particular Gram− bacteria and biofilms.…”

Section: Introductionmentioning

confidence: 99%

Design of Photosensitizing Agents for Targeted Antimicrobial Photodynamic Therapy

2020

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Photodynamic inactivation of microorganisms has gained substantial attention due to its unique mode of action, in which pathogens are unable to generate resistance, and due to the fact that it can be applied in a minimally invasive manner. In photodynamic therapy (PDT), a non-toxic photosensitizer (PS) is activated by a specific wavelength of light and generates highly cytotoxic reactive oxygen species (ROS) such as superoxide (O2−, type-I mechanism) or singlet oxygen (1O2*, type-II mechanism). Although it offers many advantages over conventional treatment methods, ROS-mediated microbial killing is often faced with the issues of accessibility, poor selectivity and off-target damage. Thus, several strategies have been employed to develop target-specific antimicrobial PDT (aPDT). This includes conjugation of known PS building-blocks to either non-specific cationic moieties or target-specific antibiotics and antimicrobial peptides, or combining them with targeting nanomaterials. In this review, we summarise these general strategies and related challenges, and highlight recent developments in targeted aPDT.

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“…It is well-established that some lipophilic cations, for example of the triphenylphosphonium class 96 can enter bacterial cells in a process driven by the cytoplasmic membrane potential (negative inside) and have even been conjugated to photosensitisers to increase their antibacterial effect in the cytoplasm. 97 Multiple active transporters may also exist for many large cationic lipophilic molecules. 98 The very small degrees of dark toxicity of 1 towards S. aureus and E. coli (Fig.…”

Section: Resultsmentioning

confidence: 99%