Photoinactivation of Planktonic and Biofilm Forms of Escherichia coli through the Action of Cationic Zinc(II) Phthalocyanines

Lourenço, Leandro M. O.; Rocha, Deisy M. G. C.; Ramos, Catarina I. V.; Gomes, Maria C.; Almeida, Adelaide; Faustino, Maria A. F.; Almeida Paz, Filipe A.; Neves, Maria G. P. M. S.; Cunha, Ângela; Tomé, João P. C.

doi:10.1002/cptc.201900020

Title: Photoinactivation of Planktonic and Biofilm Forms of Escherichia coli through the Action of Cationic Zinc(II) Phthalocyanines

Abstract

Abstract Novel water‐soluble zinc(II) phthalocyanines (ZnPc) peripherally substituted with 4‐dimethylaminopyridine (DMAP) units (ZnPc 1 – 2 ) and the corresponding quaternized derivatives (ZnPc 1 a – 2 a ) were synthesized and their photodynamic inactivation (PDI) efficiency against a Gram‐negative bacterium, a recombinant bioluminescent Escherichia coli strain either in planktonic or biofilm form, was investigated. The analysis of the photophysical properties revealed that the increase in the number of DMAP units on ZnPc shifted the absorption and emission band in aqueous media to the red region. The presence of multi‐positive charges on ZnPc derivatives prevented aggregation and enhances the solubility in aqueous media. The quaternized derivatives ZnPc 1 a and 2 a displayed good stability and promising efficacy to generate singlet oxygen ( ¹ O ₂ ). The affinity of the amphiphilic ZnPc 1 – 2 and quaternized ZnPc 1 a – 2 a to planktonic bacterial cells corresponded to an average uptake of ∼10 ⁶ PS molecules.CFU ⁻¹ . The PDI assays conducted with planktonic cells and biofilms of E. coli show that irradiation with red or white light (150 mW.cm ⁻² ) in the presence of 20 μM of ZnPc derivatives caused an effective inactivation. ZnPc 1 a and ZnPc 2 a exhibited the highest inactivation efficiency, particularlymore »« less

Authors:

Lourenço, Leandro M. O. ^[1]; Rocha, Deisy M. G. C. ^[2]; Ramos, Catarina I. V. ^[3]; Gomes, Maria C. ^[2]; Almeida, Adelaide ^[4]; Faustino, Maria A. F. ^[1]; Almeida Paz, Filipe A. ^[5]; Neves, Maria G. P. M. S. ^[1]; Cunha, Ângela ^[4]; Tomé, João P. C. ^[6]

QOPNA-LAQV-REQUINTE and Department of Chemistry University of Aveiro Campus Universitário de Santiago 3810-193 Aveiro Portugal
QOPNA-LAQV-REQUINTE and Department of Chemistry University of Aveiro Campus Universitário de Santiago 3810-193 Aveiro Portugal, CESAM and Department of Biology University of Aveiro Campus Universitário de Santiago 3810-193 Aveiro Portugal
Mass Spectrometry Laboratory and Department of Chemistry University of Aveiro Campus Universitário de Santiago 3810-193 Aveiro Portugal
CESAM and Department of Biology University of Aveiro Campus Universitário de Santiago 3810-193 Aveiro Portugal
CICECO-Aveiro Institute of Materials and Department of Chemistry University of Aveiro Campus Universitário de Santiago 3810-193 Aveiro Portugal
CQE and Departamento de Engenharia Química Instituto Superior Técnico, Universidade de Lisboa Av. Rovisco Pais, n°1 1049-001 Lisboa Portugal

Publication Date:: Fri Feb 22 00:00:00 EST 2019

Sponsoring Org.:: USDOE

OSTI Identifier:: 1511867

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: ChemPhotoChem

Additional Journal Information:: Journal Name: ChemPhotoChem Journal Volume: 3 Journal Issue: 5; Journal ID: ISSN 2367-0932

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Lourenço, Leandro M. O., Rocha, Deisy M. G. C., Ramos, Catarina I. V., Gomes, Maria C., Almeida, Adelaide, Faustino, Maria A. F., Almeida Paz, Filipe A., Neves, Maria G. P. M. S., Cunha, Ângela, and Tomé, João P. C. Photoinactivation of Planktonic and Biofilm Forms of Escherichia coli through the Action of Cationic Zinc(II) Phthalocyanines.  Germany: N. p., 2019. 
Web.  doi:10.1002/cptc.201900020.

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                    Lourenço, Leandro M. O., Rocha, Deisy M. G. C., Ramos, Catarina I. V., Gomes, Maria C., Almeida, Adelaide, Faustino, Maria A. F., Almeida Paz, Filipe A., Neves, Maria G. P. M. S., Cunha, Ângela, & Tomé, João P. C. Photoinactivation of Planktonic and Biofilm Forms of Escherichia coli through the Action of Cationic Zinc(II) Phthalocyanines.  Germany.  https://doi.org/10.1002/cptc.201900020

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                    Lourenço, Leandro M. O., Rocha, Deisy M. G. C., Ramos, Catarina I. V., Gomes, Maria C., Almeida, Adelaide, Faustino, Maria A. F., Almeida Paz, Filipe A., Neves, Maria G. P. M. S., Cunha, Ângela, and Tomé, João P. C. Fri .  
"Photoinactivation of Planktonic and Biofilm Forms of Escherichia coli through the Action of Cationic Zinc(II) Phthalocyanines".  Germany.  https://doi.org/10.1002/cptc.201900020.

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@article{osti_1511867,

  title        = {Photoinactivation of Planktonic and Biofilm Forms of Escherichia coli through the Action of Cationic Zinc(II) Phthalocyanines},

  author       = {Lourenço, Leandro M. O. and Rocha, Deisy M. G. C. and Ramos, Catarina I. V. and Gomes, Maria C. and Almeida, Adelaide and Faustino, Maria A. F. and Almeida Paz, Filipe A. and Neves, Maria G. P. M. S. and Cunha, Ângela and Tomé, João P. C.},

  abstractNote = {Abstract Novel water‐soluble zinc(II) phthalocyanines (ZnPc) peripherally substituted with 4‐dimethylaminopyridine (DMAP) units (ZnPc 1 – 2 ) and the corresponding quaternized derivatives (ZnPc 1 a – 2 a ) were synthesized and their photodynamic inactivation (PDI) efficiency against a Gram‐negative bacterium, a recombinant bioluminescent Escherichia coli strain either in planktonic or biofilm form, was investigated. The analysis of the photophysical properties revealed that the increase in the number of DMAP units on ZnPc shifted the absorption and emission band in aqueous media to the red region. The presence of multi‐positive charges on ZnPc derivatives prevented aggregation and enhances the solubility in aqueous media. The quaternized derivatives ZnPc 1 a and 2 a displayed good stability and promising efficacy to generate singlet oxygen ( 1 O 2 ). The affinity of the amphiphilic ZnPc 1 – 2 and quaternized ZnPc 1 a – 2 a to planktonic bacterial cells corresponded to an average uptake of ∼10 6  PS molecules.CFU −1 . The PDI assays conducted with planktonic cells and biofilms of E. coli show that irradiation with red or white light (150 mW.cm −2 ) in the presence of 20 μM of ZnPc derivatives caused an effective inactivation. ZnPc 1 a and ZnPc 2 a exhibited the highest inactivation efficiency, particularly of the planktonic form, causing a 5 log‐scale (99.99 %) reduction in bioluminescence. The inactivation factor for biofilms was 99 % (2 log). ZnPc 1 a and ZnPc 2 a can be regarded as promising photosensitizers for the photodynamic inactivation of Gram‐negative bacteria.},

  doi          = {10.1002/cptc.201900020},

  journal      = {ChemPhotoChem},

  number       = 5,

  volume       = 3,

  place        = {Germany},

  year         = {Fri Feb 22 00:00:00 EST 2019},

  month        = {Fri Feb 22 00:00:00 EST 2019}

}

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https://doi.org/10.1002/cpmc.130

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Title: Photoinactivation of Planktonic and Biofilm Forms of Escherichia coli through the Action of Cationic Zinc(II) Phthalocyanines

Abstract

Citation Formats

Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines journal, July 2007

Escherichia coli Biofilms Have an Organized and Complex Extracellular Matrix Structure journal, September 2013

Photodynamic antimicrobial chemotherapy with cationic phthalocyanines against Escherichia coli planktonic and biofilm cultures journal, January 2017

Photodynamic oxidation of Escherichia coli membrane phospholipids: new insights based on lipidomics : Photodynamic oxidation of journal, October 2013

Biofilms: Survival Mechanisms of Clinically Relevant Microorganisms journal, April 2002

Control of Listeria innocua biofilms by biocompatible photodynamic antifouling chitosan based materials journal, February 2017

Use of Merocyanine 540 for Photodynamic Inactivation of Staphylococcus aureus Planktonic and Biofilm Cells journal, November 2004

Synthetic approaches to glycophthalocyanines journal, April 2014

Inverted methoxypyridinium phthalocyanines for PDI of pathogenic bacteria journal, January 2015

Physicochemical and photodynamic antimicrobial chemotherapy studies of mono- and tetra-pyridyloxy substituted indium(III) phthalocyanines journal, March 2015

Molecular mechanisms of antimicrobial tolerance and resistance in bacterial and fungal biofilms journal, June 2014

The antibacterial effect of photodynamic therapy in dental plaque-derived biofilms journal, December 2009

Light parameters influence cell viability in antifungal photodynamic therapy in a fluence and rate fluence-dependent manner journal, May 2009

Synthesis and photophysical characterization of dimethylamine-derived Zn( ii )phthalocyanines: exploring their potential as selective chemosensors for trinitrophenol journal, January 2015

Use of Photosensitizers in Semisolid Formulations for Microbial Photodynamic Inactivation: Miniperspective journal, December 2015

Mono- and tetra-substituted zinc(II) phthalocyanines containing morpholinyl moieties: Synthesis, antifungal photodynamic activities, and structure-activity relationships journal, May 2016

Photosensitized oxidation of phosphatidylethanolamines monitored by electrospray tandem mass spectrometry: ESI-MS of photosensitized phosphatidylethanolamines journal, December 2013

Photodynamic inactivation of bioluminescent Escherichia coli by neutral and cationic pyrrolidine-fused chlorins and isobacteriochlorins journal, February 2014

Photophysical and photochemical studies of sulphonated non-transition metal phthalocyanines in aqueous and non-aqueous media journal, July 2005

Photodynamic inactivation of Penicillium chrysogenum conidia by cationic porphyrins journal, January 2011

An insight on bacterial cellular targets of photodynamic inactivation journal, February 2014

Non-invasive determination of conjugative transfer of plasmids bearing antibiotic-resistance genes in biofilm-bound bacteria: effects of substrate loading and antibiotic selection journal, June 2012

1,3-Dipolar cycloadditions with meso-tetraarylchlorins – site selectivity and mixed bisadducts journal, January 2017

A new hexadeca substituted non-aggregating zinc phthalocyanine journal, January 2014

Solutions to the Public Goods Dilemma in Bacterial Biofilms journal, January 2014

Survival strategies of infectious biofilms journal, January 2005

Biofouling in water systems – cases, causes and countermeasures journal, July 2002

A comparative study of irradiation systems for photoinactivation of microorganisms journal, January 2010

The Extracellular Matrix Component Psl Provides Fast-Acting Antibiotic Defense in Pseudomonas aeruginosa Biofilms journal, August 2013

Photodynamic inactivation of Escherichia coli with cationic ammonium Zn( ii ) phthalocyanines journal, January 2015

Effects of Growth Phase and Extracellular Slime on Photodynamic Inactivation of Gram-Positive Pathogenic Bacteria journal, May 2004

Bioluminescence and its application in the monitoring of antimicrobial photodynamic therapy journal, October 2011

Antimicrobial Photodynamic Therapy against Endodontic Enterococcus faecalis and Candida albicans Mono and Mixed Biofilms in the Presence of Photosensitizers: A Comparative Study with Classical Endodontic Irrigants journal, March 2017

Single-species microbial biofilm screening for industrial applications journal, July 2007

The photochemistry and photophysics of a series of alpha octa(alkyl-substituted) silicon, zinc and palladium phthalocyanines journal, January 2014

Molecular Mechanism of Uptake of Cationic Photoantimicrobial Phthalocyanine across Bacterial Membranes Revealed by Molecular Dynamics Simulations journal, March 2018

Photodynamic inactivation of bacteria: finding the effective targets journal, July 2015

Direct measurement of chlorine penetration into biofilms during disinfection. journal, January 1994

Photodynamic Inactivation of Bacterial and Yeast Biofilms With a Cationic Porphyrin journal, September 2014

Potential applications of porphyrins in photodynamic inactivation beyond the medical scope journal, March 2015

Potential of photodynamic therapy in treatment of fungal infections of the mouth. Design and characterisation of a mucoadhesive patch containing toluidine blue O journal, January 2007

Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers journal, February 2017

Highly positive-charged zinc(II) phthalocyanine as non-aggregated and efficient antifungal photosensitizer journal, June 2015

Photosensitising agents—circumventing resistance and breaking down biofilms: a review journal, March 2004

Silicon(IV) Phthalocyanine-Decorated Cyclodextrin Vesicles as a Self-Assembled Phototherapeutic Agent against MRSA journal, May 2016

Sewage bacteriophage inactivation by cationic porphyrins: influence of light parameters journal, January 2010

Photodynamic inactivation of bacteria and viruses using two monosubstituted zinc(II) phthalocyanines journal, September 2014

Photodynamic therapy: a new antimicrobial approach to infectious disease? journal, January 2004

Nucleic acid changes during photodynamic inactivation of bacteria by cationic porphyrins journal, July 2013

Phthalocyanine Thio-Pyridinium Derivatives as Antibacterial Photosensitizers† journal, April 2012

Evaluation of antibacterial properties of novel phthalocyanines against Escherichia coli – Comparison of analytical methods journal, September 2014

Ultrafast intramolecular charge transfer in tetrapyrazinoporphyrazines controls the quantum yields of fluorescence and singlet oxygen journal, January 2010

Evolving perspectives of biofilm structure journal, June 1999

Peripheral substitution as a tool for tuning electron-accepting properties of phthalocyanine analogs in intramolecular charge transfer journal, January 2015

Toluidine Blue-Mediated Photodynamic Effects on Staphylococcal Biofilms journal, October 2007

Susceptibility of non-enveloped DNA- and RNA-type viruses to photodynamic inactivation journal, January 2012

Mechanism of Uptake of a Cationic Water-Soluble Pyridinium Zinc Phthalocyanine across the Outer Membrane of Escherichia coli journal, March 2000

Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines
journal, July 2007

Escherichia coli Biofilms Have an Organized and Complex Extracellular Matrix Structure
journal, September 2013

Photodynamic antimicrobial chemotherapy with cationic phthalocyanines against Escherichia coli planktonic and biofilm cultures
journal, January 2017

Photodynamic oxidation of Escherichia coli membrane phospholipids: new insights based on lipidomics : Photodynamic oxidation of
journal, October 2013

Biofilms: Survival Mechanisms of Clinically Relevant Microorganisms
journal, April 2002

Control of Listeria innocua biofilms by biocompatible photodynamic antifouling chitosan based materials
journal, February 2017

Use of Merocyanine 540 for Photodynamic Inactivation of Staphylococcus aureus Planktonic and Biofilm Cells
journal, November 2004

Synthetic approaches to glycophthalocyanines
journal, April 2014

Inverted methoxypyridinium phthalocyanines for PDI of pathogenic bacteria
journal, January 2015

Physicochemical and photodynamic antimicrobial chemotherapy studies of mono- and tetra-pyridyloxy substituted indium(III) phthalocyanines
journal, March 2015

Molecular mechanisms of antimicrobial tolerance and resistance in bacterial and fungal biofilms
journal, June 2014

The antibacterial effect of photodynamic therapy in dental plaque-derived biofilms
journal, December 2009

Light parameters influence cell viability in antifungal photodynamic therapy in a fluence and rate fluence-dependent manner
journal, May 2009

Synthesis and photophysical characterization of dimethylamine-derived Zn( ii )phthalocyanines: exploring their potential as selective chemosensors for trinitrophenol
journal, January 2015

Use of Photosensitizers in Semisolid Formulations for Microbial Photodynamic Inactivation: Miniperspective
journal, December 2015

Mono- and tetra-substituted zinc(II) phthalocyanines containing morpholinyl moieties: Synthesis, antifungal photodynamic activities, and structure-activity relationships
journal, May 2016

Photosensitized oxidation of phosphatidylethanolamines monitored by electrospray tandem mass spectrometry: ESI-MS of photosensitized phosphatidylethanolamines
journal, December 2013

Photodynamic inactivation of bioluminescent Escherichia coli by neutral and cationic pyrrolidine-fused chlorins and isobacteriochlorins
journal, February 2014

Photophysical and photochemical studies of sulphonated non-transition metal phthalocyanines in aqueous and non-aqueous media
journal, July 2005

Photodynamic inactivation of Penicillium chrysogenum conidia by cationic porphyrins
journal, January 2011

An insight on bacterial cellular targets of photodynamic inactivation
journal, February 2014

Non-invasive determination of conjugative transfer of plasmids bearing antibiotic-resistance genes in biofilm-bound bacteria: effects of substrate loading and antibiotic selection
journal, June 2012

1,3-Dipolar cycloadditions with meso-tetraarylchlorins – site selectivity and mixed bisadducts
journal, January 2017

A new hexadeca substituted non-aggregating zinc phthalocyanine
journal, January 2014

Solutions to the Public Goods Dilemma in Bacterial Biofilms
journal, January 2014

Survival strategies of infectious biofilms
journal, January 2005

Biofouling in water systems – cases, causes and countermeasures
journal, July 2002

A comparative study of irradiation systems for photoinactivation of microorganisms
journal, January 2010

The Extracellular Matrix Component Psl Provides Fast-Acting Antibiotic Defense in Pseudomonas aeruginosa Biofilms
journal, August 2013

Photodynamic inactivation of Escherichia coli with cationic ammonium Zn( ii ) phthalocyanines
journal, January 2015

Effects of Growth Phase and Extracellular Slime on Photodynamic Inactivation of Gram-Positive Pathogenic Bacteria
journal, May 2004

Bioluminescence and its application in the monitoring of antimicrobial photodynamic therapy
journal, October 2011

Antimicrobial Photodynamic Therapy against Endodontic Enterococcus faecalis and Candida albicans Mono and Mixed Biofilms in the Presence of Photosensitizers: A Comparative Study with Classical Endodontic Irrigants
journal, March 2017

Single-species microbial biofilm screening for industrial applications
journal, July 2007

The photochemistry and photophysics of a series of alpha octa(alkyl-substituted) silicon, zinc and palladium phthalocyanines
journal, January 2014

Molecular Mechanism of Uptake of Cationic Photoantimicrobial Phthalocyanine across Bacterial Membranes Revealed by Molecular Dynamics Simulations
journal, March 2018

Photodynamic inactivation of bacteria: finding the effective targets
journal, July 2015

Direct measurement of chlorine penetration into biofilms during disinfection.
journal, January 1994

Photodynamic Inactivation of Bacterial and Yeast Biofilms With a Cationic Porphyrin
journal, September 2014

Potential applications of porphyrins in photodynamic inactivation beyond the medical scope
journal, March 2015

Potential of photodynamic therapy in treatment of fungal infections of the mouth. Design and characterisation of a mucoadhesive patch containing toluidine blue O
journal, January 2007

Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers
journal, February 2017

Highly positive-charged zinc(II) phthalocyanine as non-aggregated and efficient antifungal photosensitizer
journal, June 2015

Photosensitising agents—circumventing resistance and breaking down biofilms: a review
journal, March 2004

Silicon(IV) Phthalocyanine-Decorated Cyclodextrin Vesicles as a Self-Assembled Phototherapeutic Agent against MRSA
journal, May 2016

Sewage bacteriophage inactivation by cationic porphyrins: influence of light parameters
journal, January 2010

Photodynamic inactivation of bacteria and viruses using two monosubstituted zinc(II) phthalocyanines
journal, September 2014

Photodynamic therapy: a new antimicrobial approach to infectious disease?
journal, January 2004

Nucleic acid changes during photodynamic inactivation of bacteria by cationic porphyrins
journal, July 2013

Phthalocyanine Thio-Pyridinium Derivatives as Antibacterial Photosensitizers†
journal, April 2012

Evaluation of antibacterial properties of novel phthalocyanines against Escherichia coli – Comparison of analytical methods
journal, September 2014

Ultrafast intramolecular charge transfer in tetrapyrazinoporphyrazines controls the quantum yields of fluorescence and singlet oxygen
journal, January 2010

Evolving perspectives of biofilm structure
journal, June 1999

Peripheral substitution as a tool for tuning electron-accepting properties of phthalocyanine analogs in intramolecular charge transfer
journal, January 2015

Toluidine Blue-Mediated Photodynamic Effects on Staphylococcal Biofilms
journal, October 2007

Susceptibility of non-enveloped DNA- and RNA-type viruses to photodynamic inactivation
journal, January 2012

Mechanism of Uptake of a Cationic Water-Soluble Pyridinium Zinc Phthalocyanine across the Outer Membrane of Escherichia coli
journal, March 2000