Synthetic access to tetracationic benzoporphyrins and their role as photosensitizers towards gram-negative escherichia coli

Filipe M. P. Morais; Cátia Vieira; Ana T. P. C. Gomes; Maria A. F. Faustino; Adelaide Almeida; Maria G. P. M. S. Neves; Nuno M. M. Moura

doi:10.3390/ecsoc-26-13587

Synthetic access to tetracationic benzoporphyrins and their role as photosensitizers towards gram-negative escherichia coli

Filipe M. P. Morais, Cátia Vieira, Ana T. P. C. Gomes, Maria A. F. Faustino, Adelaide Almeida, Maria G. P. M. S. Neves, Nuno M. M. Moura

Research output: Contribution to journal › Conference article › peer-review

Abstract

Currently, world population faces an episode where bacteria are becoming resistant to antibiotics, and it is crucial to find alternatives and new molecules to fight these microorganisms. Photodynamic inactivation of microorganisms has been pointed out as an alternative to conventional therapies. This work describes the synthesis of benzoporphyrins derivatives bearing triazolyl groups and of the analogues with pyridyl units under Heck coupling conditions. The benzoporphyrin derivatives containing pyridyl groups were further quaternized with iodomethane and 1-iodopentane to evaluate the influence of alkyl chain size on their photoinactivation ability. The biological studies towards Gram-negative Escherichia coli showed that the tetracationic benzoporphyrins can efficiently inactivate this bacterium.

Original language	English
Number of pages	7
Journal	Chemistry Proceedings
Volume	12
Issue number	1
DOIs	https://doi.org/10.3390/ecsoc-26-13587
Publication status	Published - 15 Nov 2022
Externally published	Yes

Keywords

Tetracationic benzoporphyrins
Heck coupling reaction
Antimicrobial photodynamic therapy
Bioluminescent E. coli

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title = "Synthetic access to tetracationic benzoporphyrins and their role as photosensitizers towards gram-negative escherichia coli",

abstract = "Currently, world population faces an episode where bacteria are becoming resistant to antibiotics, and it is crucial to find alternatives and new molecules to fight these microorganisms. Photodynamic inactivation of microorganisms has been pointed out as an alternative to conventional therapies. This work describes the synthesis of benzoporphyrins derivatives bearing triazolyl groups and of the analogues with pyridyl units under Heck coupling conditions. The benzoporphyrin derivatives containing pyridyl groups were further quaternized with iodomethane and 1-iodopentane to evaluate the influence of alkyl chain size on their photoinactivation ability. The biological studies towards Gram-negative Escherichia coli showed that the tetracationic benzoporphyrins can efficiently inactivate this bacterium.",

keywords = "Tetracationic benzoporphyrins, Heck coupling reaction, Antimicrobial photodynamic therapy, Bioluminescent E. coli",

author = "Morais, {Filipe M. P.} and C{\'a}tia Vieira and Gomes, {Ana T. P. C.} and Faustino, {Maria A. F.} and Adelaide Almeida and Neves, {Maria G. P. M. S.} and Moura, {Nuno M. M.}",

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month = nov,

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doi = "10.3390/ecsoc-26-13587",

language = "English",

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journal = "Chemistry Proceedings",

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T1 - Synthetic access to tetracationic benzoporphyrins and their role as photosensitizers towards gram-negative escherichia coli

AU - Morais, Filipe M. P.

AU - Vieira, Cátia

AU - Gomes, Ana T. P. C.

AU - Faustino, Maria A. F.

AU - Almeida, Adelaide

AU - Neves, Maria G. P. M. S.

AU - Moura, Nuno M. M.

PY - 2022/11/15

Y1 - 2022/11/15

N2 - Currently, world population faces an episode where bacteria are becoming resistant to antibiotics, and it is crucial to find alternatives and new molecules to fight these microorganisms. Photodynamic inactivation of microorganisms has been pointed out as an alternative to conventional therapies. This work describes the synthesis of benzoporphyrins derivatives bearing triazolyl groups and of the analogues with pyridyl units under Heck coupling conditions. The benzoporphyrin derivatives containing pyridyl groups were further quaternized with iodomethane and 1-iodopentane to evaluate the influence of alkyl chain size on their photoinactivation ability. The biological studies towards Gram-negative Escherichia coli showed that the tetracationic benzoporphyrins can efficiently inactivate this bacterium.

AB - Currently, world population faces an episode where bacteria are becoming resistant to antibiotics, and it is crucial to find alternatives and new molecules to fight these microorganisms. Photodynamic inactivation of microorganisms has been pointed out as an alternative to conventional therapies. This work describes the synthesis of benzoporphyrins derivatives bearing triazolyl groups and of the analogues with pyridyl units under Heck coupling conditions. The benzoporphyrin derivatives containing pyridyl groups were further quaternized with iodomethane and 1-iodopentane to evaluate the influence of alkyl chain size on their photoinactivation ability. The biological studies towards Gram-negative Escherichia coli showed that the tetracationic benzoporphyrins can efficiently inactivate this bacterium.

KW - Tetracationic benzoporphyrins

KW - Heck coupling reaction

KW - Antimicrobial photodynamic therapy

KW - Bioluminescent E. coli

U2 - 10.3390/ecsoc-26-13587

DO - 10.3390/ecsoc-26-13587

M3 - Conference article

SN - 2673-4583

VL - 12

JO - Chemistry Proceedings

JF - Chemistry Proceedings

IS - 1

ER -

Synthetic access to tetracationic benzoporphyrins and their role as photosensitizers towards gram-negative escherichia coli

Abstract

Keywords

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