Header

UZH-Logo

Maintenance Infos

Highly Phototoxic Transplatin‐Modified Distyryl‐BODIPY Photosensitizers for Photodynamic Therapy


Padrutt, Roxane; Babu, Vipin; Klingler, Simon; Kalt, Martina; Schumer, Frank; Anania, Maria I; Schneider, Lukas; Spingler, Bernhard (2021). Highly Phototoxic Transplatin‐Modified Distyryl‐BODIPY Photosensitizers for Photodynamic Therapy. ChemMedChem, 16(4):694-701.

Abstract

We report the synthesis of the first transplatin‐BODIPY conjugates for application in photodynamic therapy (PDT). The distyryl BODIPYs containing two iodine atoms were designed to absorb in the red region, easily undergo intersystem crossing for efficient singlet oxygen generation, and additionally offer the possibility for coordination with mono‐activated transplatin. We were able to demonstrate that coordination of the BODIPYs with a mono‐activated transplatin increases the phototoxic index of the photosensitizers significantly, giving rise to highly phototoxic distyryl BODIPY derivatives, of which one was shown to have the highest ever reported phototoxic index against any cell line. Furthermore, the photophysical mechanism of singlet oxygen generation in distyryl BODIPYs undergoing intramolecular charge transfer was studied experimentally and using time‐dependent density functional theory.

Abstract

We report the synthesis of the first transplatin‐BODIPY conjugates for application in photodynamic therapy (PDT). The distyryl BODIPYs containing two iodine atoms were designed to absorb in the red region, easily undergo intersystem crossing for efficient singlet oxygen generation, and additionally offer the possibility for coordination with mono‐activated transplatin. We were able to demonstrate that coordination of the BODIPYs with a mono‐activated transplatin increases the phototoxic index of the photosensitizers significantly, giving rise to highly phototoxic distyryl BODIPY derivatives, of which one was shown to have the highest ever reported phototoxic index against any cell line. Furthermore, the photophysical mechanism of singlet oxygen generation in distyryl BODIPYs undergoing intramolecular charge transfer was studied experimentally and using time‐dependent density functional theory.

Statistics

Citations

Dimensions.ai Metrics

Altmetrics

Downloads

3 downloads since deposited on 19 Feb 2021
3 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Life Sciences > Molecular Medicine
Life Sciences > Pharmacology
Life Sciences > Drug Discovery
Life Sciences > General Pharmacology, Toxicology and Pharmaceutics
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:General Pharmacology, Toxicology and Pharmaceutics, Organic Chemistry, Molecular Medicine
Language:English
Date:17 February 2021
Deposited On:19 Feb 2021 16:17
Last Modified:20 Feb 2021 21:00
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:1860-7179
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/cmdc.202000702

Download

Closed Access: Download allowed only for UZH members