Near-Infrared-Emitting Hemicyanines and Their Photodynamic Killing of Cancer Cells

Mithun Santra; Matthew Owens; Gavin Birch; Mark Bradley

doi:10.1021/acsabm.1c00996

Near-Infrared-Emitting Hemicyanines and Their Photodynamic Killing of Cancer Cells

Mithun Santra, Matthew Owens, Gavin Birch, Mark Bradley^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

A series of hemicyanine dyes was synthesized starting from the vinyl chloride-based cyanine dye IR-780. The dyes absorbed and emitted in the near-infrared region, while heavy atom (bromo and iodo) substitution promoted the generation of both singlet oxygen (1O2) as well as a range of other reactive oxygen-based species (ROS) upon irradiation at wavelengths greater than 610 nm. One hemicyanine dye displayed an outstanding singlet oxygen quantum efficiency (φΔ = 0.8) and was successfully applied in in vitro studies to mimic photodynamic therapy application.

Original language	English
Journal	ACS Applied Biomaterials
Early online date	29 Nov 2021
DOIs	https://doi.org/10.1021/acsabm.1c00996
Publication status	E-pub ahead of print - 29 Nov 2021

Keywords / Materials (for Non-textual outputs)

fluorescence
heavy atom
hemicyanines
near-infrared emitting
photodynamic therapy

Access to Document

10.1021/acsabm.1c00996

20211222_Bradley_Abm-MS-27-10-21-AAMAccepted author manuscript, 763 KB

https://pubs.acs.org/doi/abs/10.1021/acsabm.1c00996

EPSRC IRC Proteus - Multiplexed 'Touch and Tell' Optical Molecular Sensing and Imaging - Lifetime and Beyond
Bradley, M. (Principal Investigator), Bradley, M. (Principal Investigator), Dhaliwal, K. (Co-investigator), Dhaliwal, K. (Co-investigator), Haslett, C. (Co-investigator), Henderson, R. (Co-investigator), Walsh, T. (Co-investigator) & Walsh, T. (Co-investigator)
Engineering and Physical Sciences Research Council
1/01/19 → 1/06/23
Project: Research
Optimising Innate Host Defence to Combat Antimicrobial Resistance
Dockrell, D. (Principal Investigator), Baillie, K. (Co-investigator), Bradley, M. (Co-investigator), Brown, H. (Co-investigator), Dhaliwal, K. (Co-investigator), Fitzgerald, R. (Co-investigator), Haslett, C. (Co-investigator), Hume, D. (Co-investigator), Rossi, A. (Co-investigator), Walmsley, S. (Co-investigator) & Whyte, M. (Co-investigator)
MRC
1/12/16 → 30/11/22
Project: Research
Multiplexed 'Touch and Tell' Optical Molecular Sensing and Imaging
Bradley, M. (Principal Investigator)
EPSRC
1/10/13 → 31/03/19
Project: Research

Cite this

@article{d4329798b3144dd3949df2cf468ca620,

title = "Near-Infrared-Emitting Hemicyanines and Their Photodynamic Killing of Cancer Cells",

abstract = "A series of hemicyanine dyes was synthesized starting from the vinyl chloride-based cyanine dye IR-780. The dyes absorbed and emitted in the near-infrared region, while heavy atom (bromo and iodo) substitution promoted the generation of both singlet oxygen (1O2) as well as a range of other reactive oxygen-based species (ROS) upon irradiation at wavelengths greater than 610 nm. One hemicyanine dye displayed an outstanding singlet oxygen quantum efficiency (φΔ = 0.8) and was successfully applied in in vitro studies to mimic photodynamic therapy application. ",

keywords = "fluorescence, heavy atom, hemicyanines, near-infrared emitting, photodynamic therapy",

author = "Mithun Santra and Matthew Owens and Gavin Birch and Mark Bradley",

note = "Funding Information: We are thankful for the Medical Research Council grant MR/N02995 X/1 and the Engineering and Physical Sciences Research Council (EPSRC), UK for Interdisciplinary Research Collaboration grants EP/K03197X/1 and EP/R005257/1. We thank the BBSRC/GSK for supporting the Ph.D. studies of Gavin Birch. We thank Dr. Richa Sharma and Paige Shaw for their help in the cell imaging studies. Publisher Copyright: {\textcopyright} ",

year = "2021",

month = nov,

day = "29",

doi = "10.1021/acsabm.1c00996",

language = "English",

journal = "ACS Applied Biomaterials",

issn = "2576-6422",

publisher = "American Chemical Society",

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T1 - Near-Infrared-Emitting Hemicyanines and Their Photodynamic Killing of Cancer Cells

AU - Santra, Mithun

AU - Owens, Matthew

AU - Birch, Gavin

AU - Bradley, Mark

N1 - Funding Information: We are thankful for the Medical Research Council grant MR/N02995 X/1 and the Engineering and Physical Sciences Research Council (EPSRC), UK for Interdisciplinary Research Collaboration grants EP/K03197X/1 and EP/R005257/1. We thank the BBSRC/GSK for supporting the Ph.D. studies of Gavin Birch. We thank Dr. Richa Sharma and Paige Shaw for their help in the cell imaging studies. Publisher Copyright: ©

PY - 2021/11/29

Y1 - 2021/11/29

N2 - A series of hemicyanine dyes was synthesized starting from the vinyl chloride-based cyanine dye IR-780. The dyes absorbed and emitted in the near-infrared region, while heavy atom (bromo and iodo) substitution promoted the generation of both singlet oxygen (1O2) as well as a range of other reactive oxygen-based species (ROS) upon irradiation at wavelengths greater than 610 nm. One hemicyanine dye displayed an outstanding singlet oxygen quantum efficiency (φΔ = 0.8) and was successfully applied in in vitro studies to mimic photodynamic therapy application.

AB - A series of hemicyanine dyes was synthesized starting from the vinyl chloride-based cyanine dye IR-780. The dyes absorbed and emitted in the near-infrared region, while heavy atom (bromo and iodo) substitution promoted the generation of both singlet oxygen (1O2) as well as a range of other reactive oxygen-based species (ROS) upon irradiation at wavelengths greater than 610 nm. One hemicyanine dye displayed an outstanding singlet oxygen quantum efficiency (φΔ = 0.8) and was successfully applied in in vitro studies to mimic photodynamic therapy application.

KW - fluorescence

KW - heavy atom

KW - hemicyanines

KW - near-infrared emitting

KW - photodynamic therapy

U2 - 10.1021/acsabm.1c00996

DO - 10.1021/acsabm.1c00996

M3 - Article

AN - SCOPUS:85120642743

SN - 2576-6422

JO - ACS Applied Biomaterials

JF - ACS Applied Biomaterials

ER -

Near-Infrared-Emitting Hemicyanines and Their Photodynamic Killing of Cancer Cells

Abstract

Keywords / Materials (for Non-textual outputs)

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Projects

EPSRC IRC Proteus - Multiplexed 'Touch and Tell' Optical Molecular Sensing and Imaging - Lifetime and Beyond

Optimising Innate Host Defence to Combat Antimicrobial Resistance

Multiplexed 'Touch and Tell' Optical Molecular Sensing and Imaging

Cite this