Publication

Photocontrol of Antibacterial Activity: Shifting from UV to Red Light Activation

Wegener, M., Hansen, M. J., Driessen, A. J. M., Szymanski, W. & Feringa, B. L., 13-Dec-2017, In : Journal of the American Chemical Society. 139, 49, p. 17979-17986 8 p.

Research output: Contribution to journalArticleAcademicpeer-review

APA

Wegener, M., Hansen, M. J., Driessen, A. J. M., Szymanski, W., & Feringa, B. L. (2017). Photocontrol of Antibacterial Activity: Shifting from UV to Red Light Activation. Journal of the American Chemical Society, 139(49), 17979-17986. https://doi.org/10.1021/jacs.7b09281

Author

Wegener, Michael ; Hansen, Mickel J. ; Driessen, Arnold J. M. ; Szymanski, Wiktor ; Feringa, Ben L. / Photocontrol of Antibacterial Activity : Shifting from UV to Red Light Activation. In: Journal of the American Chemical Society. 2017 ; Vol. 139, No. 49. pp. 17979-17986.

Harvard

Wegener, M, Hansen, MJ, Driessen, AJM, Szymanski, W & Feringa, BL 2017, 'Photocontrol of Antibacterial Activity: Shifting from UV to Red Light Activation', Journal of the American Chemical Society, vol. 139, no. 49, pp. 17979-17986. https://doi.org/10.1021/jacs.7b09281

Standard

Photocontrol of Antibacterial Activity : Shifting from UV to Red Light Activation. / Wegener, Michael; Hansen, Mickel J.; Driessen, Arnold J. M.; Szymanski, Wiktor; Feringa, Ben L.

In: Journal of the American Chemical Society, Vol. 139, No. 49, 13.12.2017, p. 17979-17986.

Research output: Contribution to journalArticleAcademicpeer-review

Vancouver

Wegener M, Hansen MJ, Driessen AJM, Szymanski W, Feringa BL. Photocontrol of Antibacterial Activity: Shifting from UV to Red Light Activation. Journal of the American Chemical Society. 2017 Dec 13;139(49):17979-17986. https://doi.org/10.1021/jacs.7b09281


BibTeX

@article{26448b90b50a485996614a7fd5da0726,
title = "Photocontrol of Antibacterial Activity: Shifting from UV to Red Light Activation",
abstract = "The field of photopharmacology aims to introduce smart drugs that, through the incorporation of molecular photoswitches, allow for the remote spatial and temporal control of bioactivity by light. This concept could be particularly beneficial in the treatment of bacterial infections, by reducing the systemic and environmental side effects of antibiotics. A major concern in the realization of such light-responsive drugs is the wavelength of the light that is applied. Studies on the photocontrol of biologically active agents mostly rely on UV light, which is cytotoxic and poorly suited for tissue penetration. In our efforts to develop photoswitchable antibiotics, we introduce here antibacterial agents whose activity can be controlled by visible light, while getting into the therapeutic window. For that purpose, a UV-light-responsive core structure based on diaminopyrimidines with suitable antibacterial properties was identified. Subsequent modification of an azobenzene photoswitch moiety led to structures that allowed us to control their activity against Escherichia coli in both directions with light in the visible region. For the first time, full in situ photocontrol of antibacterial activity in the presence of bacteria was attained with green and violet light. Most remarkably, one of the diaminopyrimidines revealed an at least 8-fold difference in activity before and after irradiation with red light at 652 nm, showcasing the effective {"}activation{"} of a biological agent otherwise inactive within the investigated concentration range, and doing so with red light in the therapeutic window.",
keywords = "PHOTODYNAMIC THERAPY, IN-VIVO, AZOBENZENE PHOTOSWITCHES, VISIBLE-LIGHT, DIHYDROFOLATE REDUCTASES, TRIMETHOPRIM RESISTANCE, ANTIMICROBIAL ACTIVITY, ESCHERICHIA-COLI, OPTICAL CONTROL, BLIND MICE",
author = "Michael Wegener and Hansen, {Mickel J.} and Driessen, {Arnold J. M.} and Wiktor Szymanski and Feringa, {Ben L.}",
year = "2017",
month = "12",
day = "13",
doi = "10.1021/jacs.7b09281",
language = "English",
volume = "139",
pages = "17979--17986",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "AMER CHEMICAL SOC",
number = "49",

}

RIS

TY - JOUR

T1 - Photocontrol of Antibacterial Activity

T2 - Shifting from UV to Red Light Activation

AU - Wegener, Michael

AU - Hansen, Mickel J.

AU - Driessen, Arnold J. M.

AU - Szymanski, Wiktor

AU - Feringa, Ben L.

PY - 2017/12/13

Y1 - 2017/12/13

N2 - The field of photopharmacology aims to introduce smart drugs that, through the incorporation of molecular photoswitches, allow for the remote spatial and temporal control of bioactivity by light. This concept could be particularly beneficial in the treatment of bacterial infections, by reducing the systemic and environmental side effects of antibiotics. A major concern in the realization of such light-responsive drugs is the wavelength of the light that is applied. Studies on the photocontrol of biologically active agents mostly rely on UV light, which is cytotoxic and poorly suited for tissue penetration. In our efforts to develop photoswitchable antibiotics, we introduce here antibacterial agents whose activity can be controlled by visible light, while getting into the therapeutic window. For that purpose, a UV-light-responsive core structure based on diaminopyrimidines with suitable antibacterial properties was identified. Subsequent modification of an azobenzene photoswitch moiety led to structures that allowed us to control their activity against Escherichia coli in both directions with light in the visible region. For the first time, full in situ photocontrol of antibacterial activity in the presence of bacteria was attained with green and violet light. Most remarkably, one of the diaminopyrimidines revealed an at least 8-fold difference in activity before and after irradiation with red light at 652 nm, showcasing the effective "activation" of a biological agent otherwise inactive within the investigated concentration range, and doing so with red light in the therapeutic window.

AB - The field of photopharmacology aims to introduce smart drugs that, through the incorporation of molecular photoswitches, allow for the remote spatial and temporal control of bioactivity by light. This concept could be particularly beneficial in the treatment of bacterial infections, by reducing the systemic and environmental side effects of antibiotics. A major concern in the realization of such light-responsive drugs is the wavelength of the light that is applied. Studies on the photocontrol of biologically active agents mostly rely on UV light, which is cytotoxic and poorly suited for tissue penetration. In our efforts to develop photoswitchable antibiotics, we introduce here antibacterial agents whose activity can be controlled by visible light, while getting into the therapeutic window. For that purpose, a UV-light-responsive core structure based on diaminopyrimidines with suitable antibacterial properties was identified. Subsequent modification of an azobenzene photoswitch moiety led to structures that allowed us to control their activity against Escherichia coli in both directions with light in the visible region. For the first time, full in situ photocontrol of antibacterial activity in the presence of bacteria was attained with green and violet light. Most remarkably, one of the diaminopyrimidines revealed an at least 8-fold difference in activity before and after irradiation with red light at 652 nm, showcasing the effective "activation" of a biological agent otherwise inactive within the investigated concentration range, and doing so with red light in the therapeutic window.

KW - PHOTODYNAMIC THERAPY

KW - IN-VIVO

KW - AZOBENZENE PHOTOSWITCHES

KW - VISIBLE-LIGHT

KW - DIHYDROFOLATE REDUCTASES

KW - TRIMETHOPRIM RESISTANCE

KW - ANTIMICROBIAL ACTIVITY

KW - ESCHERICHIA-COLI

KW - OPTICAL CONTROL

KW - BLIND MICE

U2 - 10.1021/jacs.7b09281

DO - 10.1021/jacs.7b09281

M3 - Article

C2 - 29136373

VL - 139

SP - 17979

EP - 17986

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 49

ER -

ID: 50332534