Curcumin derivatives as photosensitizers in photodynamic therapy: Photophysical properties and: In vitro studies with prostate cancer cells

K. T. Kazantzis; K. Koutsonikoli; B. Mavroidi; M. Zachariadis; P. Alexiou; M. Pelecanou; K. Politopoulos; E. Alexandratou; M. Sagnou

doi:10.1039/c9pp00375d

Curcumin derivatives as photosensitizers in photodynamic therapy: Photophysical properties and: In vitro studies with prostate cancer cells

K. T. Kazantzis, K. Koutsonikoli, B. Mavroidi, M. Zachariadis, P. Alexiou, M. Pelecanou, K. Politopoulos, E. Alexandratou, M. Sagnou

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

91 Citations (SciVal)

Abstract

Photodynamic therapy (PDT) is a minimally invasive approach to treat various forms of cancer, based on the ability of certain non-toxic molecules (photosensitizers) to generate reactive oxygen species (ROS) after excitation by light of a certain wavelength and eventually induce strong phototoxic reactions against malignant cells and other pathogens. Curcumin is one of the most extensively investigated phytochemicals with a wide range of therapeutic properties and has been shown to induce strong photocytotoxic effects in micromolar concentrations against a variety of cancer cell lines. Curcumin (1) is comparatively evaluated with the naturally occurring bisdemethoxy Curcumin (2), which lacks the two methoxy groups, as well as two newly synthesized curcuminoids, the cinnamaldehyde derivative (3) and the dimethylamino one (4), designed to increase the absorption maximum and hence the tissue penetration. The synthetic curcuminoids were successfully synthesized in sufficient amounts and their photophysical properties such as absorption, fluorescence, photobleaching and free radical generation were investigated. Compound 4 exhibited a significant increase in peak absorption (497 nm) and strong fluorescent emission signals were recorded for all curcuminoids. Photobleaching of 4 was comparable to 1 whereas 2 and 3 showed more extended photobleaching but much higher ROS production in very short irradiation times. Compounds 2 and 4 exhibited specific intracellular localization. After dark and light cytotoxicity experiments against LNCaP prostate cancer cell line for all curcuminoids, concentration of 3 μM and irradiance of 6 mW cm^-2 were selected for the PDT application which resulted in remarkable results with very short LD₅₀. Curcuminoids 2 and 4 exhibited a significant dose-dependent PDT effect. The biphasic dose-response photodynamic effect observed for 1 and 3 may provide a strategy against prolonged and sustained photosensitivity.

Original language	English
Pages (from-to)	193-206
Number of pages	14
Journal	Photochemical and Photobiological Sciences
Volume	19
Issue number	2
DOIs	https://doi.org/10.1039/c9pp00375d
Publication status	Published - 29 Feb 2020

Bibliographical note

Funding Information:
The authors acknowledge support of this work by the projects “Target Identification and Development of Novel Approaches for Health and Environmental Applications” (MIS 5002514) which is implemented under the Action for the Strategic Development on the Research and Technological Sectors, and “A Greek Research Infrastructure for Visualizing and Monitoring Fundamental Biological Processes (BioImaging-GR)” (MIS 5002755) which is implemented under the Action “Reinforcement of the Research and Innovation Infrastructure”. Both projects are funded by the Operational Programme “Competitiveness, Entrepreneurship and Innovation” (NSRF 2014–2020) and co-financed by Greece and the European Union (European Regional Development Fund). B. Mavroidi gratefully acknowledges financial support by Stavros Niarchos Foundation (SNF) through implementation of the program of Industrial Fellowships at NCSR “Demokritos”.

Publisher Copyright:
This journal is © The Royal Society of Chemistry and Owner Societies.

ASJC Scopus subject areas

Physical and Theoretical Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1039/c9pp00375dLicence: CC BY

Cite this

Kazantzis, K. T., Koutsonikoli, K., Mavroidi, B., Zachariadis, M., Alexiou, P., Pelecanou, M., Politopoulos, K., Alexandratou, E., & Sagnou, M. (2020). Curcumin derivatives as photosensitizers in photodynamic therapy: Photophysical properties and: In vitro studies with prostate cancer cells. Photochemical and Photobiological Sciences, 19(2), 193-206. https://doi.org/10.1039/c9pp00375d

Kazantzis, KT, Koutsonikoli, K, Mavroidi, B, Zachariadis, M, Alexiou, P, Pelecanou, M, Politopoulos, K, Alexandratou, E & Sagnou, M 2020, 'Curcumin derivatives as photosensitizers in photodynamic therapy: Photophysical properties and: In vitro studies with prostate cancer cells', Photochemical and Photobiological Sciences, vol. 19, no. 2, pp. 193-206. https://doi.org/10.1039/c9pp00375d

@article{b0ddd0b115564b4ba71da62e5dd7111d,

title = "Curcumin derivatives as photosensitizers in photodynamic therapy: Photophysical properties and: In vitro studies with prostate cancer cells",

abstract = "Photodynamic therapy (PDT) is a minimally invasive approach to treat various forms of cancer, based on the ability of certain non-toxic molecules (photosensitizers) to generate reactive oxygen species (ROS) after excitation by light of a certain wavelength and eventually induce strong phototoxic reactions against malignant cells and other pathogens. Curcumin is one of the most extensively investigated phytochemicals with a wide range of therapeutic properties and has been shown to induce strong photocytotoxic effects in micromolar concentrations against a variety of cancer cell lines. Curcumin (1) is comparatively evaluated with the naturally occurring bisdemethoxy Curcumin (2), which lacks the two methoxy groups, as well as two newly synthesized curcuminoids, the cinnamaldehyde derivative (3) and the dimethylamino one (4), designed to increase the absorption maximum and hence the tissue penetration. The synthetic curcuminoids were successfully synthesized in sufficient amounts and their photophysical properties such as absorption, fluorescence, photobleaching and free radical generation were investigated. Compound 4 exhibited a significant increase in peak absorption (497 nm) and strong fluorescent emission signals were recorded for all curcuminoids. Photobleaching of 4 was comparable to 1 whereas 2 and 3 showed more extended photobleaching but much higher ROS production in very short irradiation times. Compounds 2 and 4 exhibited specific intracellular localization. After dark and light cytotoxicity experiments against LNCaP prostate cancer cell line for all curcuminoids, concentration of 3 μM and irradiance of 6 mW cm-2 were selected for the PDT application which resulted in remarkable results with very short LD50. Curcuminoids 2 and 4 exhibited a significant dose-dependent PDT effect. The biphasic dose-response photodynamic effect observed for 1 and 3 may provide a strategy against prolonged and sustained photosensitivity.",

author = "Kazantzis, {K. T.} and K. Koutsonikoli and B. Mavroidi and M. Zachariadis and P. Alexiou and M. Pelecanou and K. Politopoulos and E. Alexandratou and M. Sagnou",

note = "Funding Information: The authors acknowledge support of this work by the projects “Target Identification and Development of Novel Approaches for Health and Environmental Applications” (MIS 5002514) which is implemented under the Action for the Strategic Development on the Research and Technological Sectors, and “A Greek Research Infrastructure for Visualizing and Monitoring Fundamental Biological Processes (BioImaging-GR)” (MIS 5002755) which is implemented under the Action “Reinforcement of the Research and Innovation Infrastructure”. Both projects are funded by the Operational Programme “Competitiveness, Entrepreneurship and Innovation” (NSRF 2014–2020) and co-financed by Greece and the European Union (European Regional Development Fund). B. Mavroidi gratefully acknowledges financial support by Stavros Niarchos Foundation (SNF) through implementation of the program of Industrial Fellowships at NCSR “Demokritos”. Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry and Owner Societies.",

year = "2020",

month = feb,

day = "29",

doi = "10.1039/c9pp00375d",

language = "English",

volume = "19",

pages = "193--206",

journal = "Photochemical and Photobiological Sciences",

issn = "1474-905X",

publisher = "Royal Society of Chemistry",

number = "2",

}

TY - JOUR

T1 - Curcumin derivatives as photosensitizers in photodynamic therapy

T2 - Photophysical properties and: In vitro studies with prostate cancer cells

AU - Kazantzis, K. T.

AU - Koutsonikoli, K.

AU - Mavroidi, B.

AU - Zachariadis, M.

AU - Alexiou, P.

AU - Pelecanou, M.

AU - Politopoulos, K.

AU - Alexandratou, E.

AU - Sagnou, M.

N1 - Funding Information: The authors acknowledge support of this work by the projects “Target Identification and Development of Novel Approaches for Health and Environmental Applications” (MIS 5002514) which is implemented under the Action for the Strategic Development on the Research and Technological Sectors, and “A Greek Research Infrastructure for Visualizing and Monitoring Fundamental Biological Processes (BioImaging-GR)” (MIS 5002755) which is implemented under the Action “Reinforcement of the Research and Innovation Infrastructure”. Both projects are funded by the Operational Programme “Competitiveness, Entrepreneurship and Innovation” (NSRF 2014–2020) and co-financed by Greece and the European Union (European Regional Development Fund). B. Mavroidi gratefully acknowledges financial support by Stavros Niarchos Foundation (SNF) through implementation of the program of Industrial Fellowships at NCSR “Demokritos”. Publisher Copyright: This journal is © The Royal Society of Chemistry and Owner Societies.

PY - 2020/2/29

Y1 - 2020/2/29

N2 - Photodynamic therapy (PDT) is a minimally invasive approach to treat various forms of cancer, based on the ability of certain non-toxic molecules (photosensitizers) to generate reactive oxygen species (ROS) after excitation by light of a certain wavelength and eventually induce strong phototoxic reactions against malignant cells and other pathogens. Curcumin is one of the most extensively investigated phytochemicals with a wide range of therapeutic properties and has been shown to induce strong photocytotoxic effects in micromolar concentrations against a variety of cancer cell lines. Curcumin (1) is comparatively evaluated with the naturally occurring bisdemethoxy Curcumin (2), which lacks the two methoxy groups, as well as two newly synthesized curcuminoids, the cinnamaldehyde derivative (3) and the dimethylamino one (4), designed to increase the absorption maximum and hence the tissue penetration. The synthetic curcuminoids were successfully synthesized in sufficient amounts and their photophysical properties such as absorption, fluorescence, photobleaching and free radical generation were investigated. Compound 4 exhibited a significant increase in peak absorption (497 nm) and strong fluorescent emission signals were recorded for all curcuminoids. Photobleaching of 4 was comparable to 1 whereas 2 and 3 showed more extended photobleaching but much higher ROS production in very short irradiation times. Compounds 2 and 4 exhibited specific intracellular localization. After dark and light cytotoxicity experiments against LNCaP prostate cancer cell line for all curcuminoids, concentration of 3 μM and irradiance of 6 mW cm-2 were selected for the PDT application which resulted in remarkable results with very short LD50. Curcuminoids 2 and 4 exhibited a significant dose-dependent PDT effect. The biphasic dose-response photodynamic effect observed for 1 and 3 may provide a strategy against prolonged and sustained photosensitivity.

AB - Photodynamic therapy (PDT) is a minimally invasive approach to treat various forms of cancer, based on the ability of certain non-toxic molecules (photosensitizers) to generate reactive oxygen species (ROS) after excitation by light of a certain wavelength and eventually induce strong phototoxic reactions against malignant cells and other pathogens. Curcumin is one of the most extensively investigated phytochemicals with a wide range of therapeutic properties and has been shown to induce strong photocytotoxic effects in micromolar concentrations against a variety of cancer cell lines. Curcumin (1) is comparatively evaluated with the naturally occurring bisdemethoxy Curcumin (2), which lacks the two methoxy groups, as well as two newly synthesized curcuminoids, the cinnamaldehyde derivative (3) and the dimethylamino one (4), designed to increase the absorption maximum and hence the tissue penetration. The synthetic curcuminoids were successfully synthesized in sufficient amounts and their photophysical properties such as absorption, fluorescence, photobleaching and free radical generation were investigated. Compound 4 exhibited a significant increase in peak absorption (497 nm) and strong fluorescent emission signals were recorded for all curcuminoids. Photobleaching of 4 was comparable to 1 whereas 2 and 3 showed more extended photobleaching but much higher ROS production in very short irradiation times. Compounds 2 and 4 exhibited specific intracellular localization. After dark and light cytotoxicity experiments against LNCaP prostate cancer cell line for all curcuminoids, concentration of 3 μM and irradiance of 6 mW cm-2 were selected for the PDT application which resulted in remarkable results with very short LD50. Curcuminoids 2 and 4 exhibited a significant dose-dependent PDT effect. The biphasic dose-response photodynamic effect observed for 1 and 3 may provide a strategy against prolonged and sustained photosensitivity.

UR - http://www.scopus.com/inward/record.url?scp=85081945518&partnerID=8YFLogxK

U2 - 10.1039/c9pp00375d

DO - 10.1039/c9pp00375d

M3 - Article

C2 - 31956888

AN - SCOPUS:85081945518

SN - 1474-905X

VL - 19

SP - 193

EP - 206

JO - Photochemical and Photobiological Sciences

JF - Photochemical and Photobiological Sciences

IS - 2

ER -

Curcumin derivatives as photosensitizers in photodynamic therapy: Photophysical properties and: In vitro studies with prostate cancer cells

Abstract

Bibliographical note

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this