Anchoring BODIPY photosensitizers enable pan-microbial photoinactivation

Gu, Kedan; Lin, Guangyu; Zhu, Yuan-Xing; Ji, Xin; Li, Jiyang; Dong, Xiaochun; Zhao, Weili

doi:10.1016/j.ejmech.2020.112361

Cited by 16 publications

(15 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In our recent publication, we have optimized BODIPY PSs with anchoring bis-cationic moieties linked to the boron center to reach the goal of pan-inactivation of microbials. 45 In the present work, we could achieve more potent pan-activation by aPDT with 3c elected through structure modification of BODIPY mesopyridinium species.…”

Section: Resultsmentioning

confidence: 89%

“…47 In our recent report, we found that the modification of BODIPY PS on boron atom to install bis-cationic propargylic ammonium portion enables efficient aPDT over various microbials and may reach favorable panmicrobial photoinactivation. 45 In our continuing interest in the discovery of efficient BODPY-type PS, we are looking forward to develop monocationic BODIPY PSs with pan-microbial eradication capabilities. Although various monocationic BODIPY PSs shown in Figure 1 have been presented, the effects of cationic species on the aPDT activities have not been well studied.…”

Section: Resultsmentioning

confidence: 99%

“…The damage to mammalian cells is expected to be minimized by incubation time as well since BODIPY PSs were taken up rapidly by microbial cells. 45 2.9. Mechanism Studies.…”

Section: Resultsmentioning

confidence: 99%

“…41−44 Our group recently documented that BODIPY PSs carrying bis-cationic moieties on boron atom (VIII) possessed powerful pan-microbial photodynamic activities. 45 One of our recent approaches in this area is to develop compact BODIPY anchoring type PS with high aPDT activities against various pathogenic species. In this study, we evaluated the effects of pyridinium on the aPDT activities against microbials and provided clear evidence that meso-pyridinium BODIPY PSs are promising to combat pathogenic microorganism infections.…”

Section: Introductionmentioning

confidence: 99%

“…Iodinated BODIPY IV carrying a cationic head revealed a high photoinactivation rate against bacteria. , Zinc(II)-dipicolylamine (ZnDPA) coordination complex ( V ) can also selectively associate with the anionic surfaces of bacteria and inactivated 99–99.99% of bacterial samples. Meso -( para -pyridinium) BODIPY PSs VI and VII have been reported to effectively photodamage pathogenic microorganisms. − Our group recently documented that BODIPY PSs carrying bis-cationic moieties on boron atom ( VIII ) possessed powerful pan-microbial photodynamic activities . One of our recent approaches in this area is to develop compact BODIPY anchoring type PS with high aPDT activities against various pathogenic species.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Discovery of Meso-(meta-Pyridinium) BODIPY Photosensitizers: In Vitro and In Vivo Evaluations for Antimicrobial Photodynamic Therapy

Lin

Zhang

et al. 2021

J. Med. Chem.

Self Cite

View full text Add to dashboard Cite

Antimicrobial photodynamic therapy (aPDT) has emerged as a novel and promising approach for the treatment of pathogenic microorganism infections. The efficacy of aPDT depends greatly on the behavior of the photosensitizer. Herein, we report the design, preparation, antimicrobial photodynamic activities, as well as structure–activity relationships of a series of photosensitizers modified at the meso position of a 1,3,5,7-tetramethyl BODIPY scaffold with various pyridinyl and pyridinium moieties. The photodynamic antimicrobial activities of all photosensitizers have been tested against Staphylococcus aureus, Escherichia coli, Candida albicans, and Methicillin-resistant S. aureus (MRSA). The methyl meso-(meta-pyridinium) BODIPY photosensitizer (3c) possessed the highest phototoxicity against these pathogens at minimal inhibitory concentrations (MIC) ranging from 0.63 to 1.25 μM with a light dose of 81 J/cm2. Furthermore, 3c exhibited an impressive antimicrobial efficacy in S. aureus-infected mice wounds. Taken together, these findings suggest that 3c is a promising candidate as the antimicrobial photosensitizer for combating pathogenic microorganism infections.

show abstract

Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

“…The damage to mammalian cells is expected to be minimized by incubation time as well since BODIPY PSs were taken up rapidly by microbial cells. 45 2.9. Mechanism Studies.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Discovery of Meso-(meta-Pyridinium) BODIPY Photosensitizers: In Vitro and In Vivo Evaluations for Antimicrobial Photodynamic Therapy

Lin

Zhang

et al. 2021

J. Med. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

One‐Pot Synthesis of a Cyclic Antimicrobial Peptide‐Conjugated Phthalocyanine for Synergistic Chemo‐Photodynamic Killing of Multidrug‐Resistant Bacteria

Chu

Chin

Wong

et al. 2020

Advanced Therapeutics

View full text Add to dashboard Cite

Multidrug-resistant (MDR) bacteria pose a serious threat to public health globally. Among the various antimicrobial modalities that have recently emerged, photodynamic therapy has received considerable attention because of its various potential advantages, including the unlikelihood of inducing drug resistance. A facile synthetic approach is reported to prepare a phthalocyanine-based photosensitizer conjugated with a cyclic bactenecin peptide. This one-pot procedure that involves site-selective alkylation of the two cysteine residues of a linear bactenecin peptide followed by Diels-Alder reaction leads to the formation of the conjugate labeled as cBac-Pc in 27% isolated yield. As shown by confocal fluorescence microscopy, this conjugate shows selective affinity toward bacterial over mammalian cells. It can also induce synergistic cytotoxic effects due to the cyclic peptide and phthalocyanine against a spectrum of Gram-positive and Gram-negative bacterial strains, including two ATCC-type strains and two clinical isolates of MDR bacterial strains. It is believed that the inhibition mechanism is based on the physical destruction of the cell membrane due to the cyclic peptide followed by photodynamic action induced by the phthalocyanine unit. Multidrug-resistant (MDR) bacteria have become a serious threat to public health that is accounting for at least 700 000 deaths

show abstract

Access to Pyridinyl or Pyridinium Aza‐BODIPYs with Tunable Near‐Infrared Fluorescence through ICT from 4‐Pyridinyl Pyrroles**

Liu

Yue

et al. 2022

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Aza-dipyrromethene boron difluoride (Aza-BODIPY) dyes have attracted much interest in recent decades. In this manuscript, we provide a facile way to access pyridinesubstituted pyrroles. A series of 1/7-pyridinyl and pyridinium near-infrared (NIR) Aza-BODIPYs with/without rigidity were constructed and their spectroscopic properties were extensively investigated. These pyridinyl Aza-BOIDIPYs displayed slight bathochromic shifts and maintained bright NIR emission. Pyridinium Aza-BODIPYs showed increased bathochromic shift, however, the molar extinction coefficients and fluorescence quantum yields were decreased owing to ICT effect. The impacts followed the order of pyridin-4-ium > pyridin-2-ium > pyridin-3-ium, which was in consistence with their ICT strength. MO calculation was performed to provide possible explanation to the red-shifted absorption/emission, and apparent charge separation in pyridin-4-ium Aza-BODI-PYs. The pyridinium Aza-BODIPY localized in lysosome and potentially avoided harmful ''alkalinizing effects'' of traditional lysosome-targeting fluorescent dyes containing amine moiety. We are working on construction of pyridinyl and pyridinium Aza-BODIPY photosensitizers against microbials or tumors.

show abstract

Anchoring BODIPY photosensitizers enable pan-microbial photoinactivation

Cited by 16 publications

References 44 publications

Discovery of Meso-(meta-Pyridinium) BODIPY Photosensitizers: In Vitro and In Vivo Evaluations for Antimicrobial Photodynamic Therapy

Discovery of Meso-(meta-Pyridinium) BODIPY Photosensitizers: In Vitro and In Vivo Evaluations for Antimicrobial Photodynamic Therapy

One‐Pot Synthesis of a Cyclic Antimicrobial Peptide‐Conjugated Phthalocyanine for Synergistic Chemo‐Photodynamic Killing of Multidrug‐Resistant Bacteria

Access to Pyridinyl or Pyridinium Aza‐BODIPYs with Tunable Near‐Infrared Fluorescence through ICT from 4‐Pyridinyl Pyrroles**

Contact Info

Product

Resources

About