Synthesis, and Evaluation of Photophysical Properties of a Potential DPP-derived Photosensitizer for Photodynamic Therapy with D-A-D Architecture

Overview

Journal J Mater Sci Mater Med

Publisher Springer

Specialty Biomedical Engineering

Date 2024 Feb 1

PMID 38300359

Authors

Vanessa Escalona Hernandez

Itzia Irene Padilla-Martinez

Rosa Angeles Vazquez Garcia

Maria Aurora Veloz Rodriguez

Oscar Javier Hernandez-Ortiz

Affiliations

Soon will be listed here.

Abstract

The study of a macromolecule derived from DPP and triphenylamine, (DPP-BisTPA) by computational chemistry, its synthesis by direct arylation, optical characterization (UV-Vis and fluorescence) and electrochemistry (cyclic voltammetry), as well as its evaluation as a generator of reactive oxygen species indirectly, through the degradation of uric acid. The results obtained by DFT using B3LYP/6-31G (d, p) and TD-DFT using CAM-B3LYP/6-31G (d, p) reveal values of energy levels of the first singlet and triplet excited state that indicate a possible intersystem crossover and the possible generation of reactive oxygen species by a type I mechanism. The compound presents an absorption region within the phototherapeutic window. The electrochemical bandgap is 1.64 eV which suggests a behavior as a semiconductor. DPP-BisTPa were processed as hemispherical nanoparticles with a size around 100 nm, and NPOs were evaluated as a photosensitizer with a ROS generation yield of 4% using a photodynamic therapy flashlight as the light source.

References

Dinu A, Apetrei C . A Review of Sensors and Biosensors Modified with Conducting Polymers and Molecularly Imprinted Polymers Used in Electrochemical Detection of Amino Acids: Phenylalanine, Tyrosine, and Tryptophan. Int J Mol Sci. 2022; 23(3). PMC: 8835779. DOI: 10.3390/ijms23031218. View

Ho-Wu R, Yau S, Goodson 3rd T . Efficient Singlet Oxygen Generation in Metal Nanoclusters for Two-Photon Photodynamic Therapy Applications. J Phys Chem B. 2017; 121(43):10073-10080. DOI: 10.1021/acs.jpcb.7b09442. View

Yang Z, Fan X, Li H, Li X, Li S, Zhang Z . A Small-Molecule Diketopyrrolopyrrole-Based Dye for in vivo NIR-IIa Fluorescence Bioimaging. Chemistry. 2021; 27(57):14240-14249. DOI: 10.1002/chem.202102312. View

Schmitt J, Heitz V, Sour A, Bolze F, Ftouni H, Nicoud J . Diketopyrrolopyrrole-porphyrin conjugates with high two-photon absorption and singlet oxygen generation for two-photon photodynamic therapy. Angew Chem Int Ed Engl. 2014; 54(1):169-73. DOI: 10.1002/anie.201407537. View

Asgher M, Qamar S, Sadaf M, Iqbal H . Multifunctional materials conjugated with near-infrared fluorescent organic molecules and their targeted cancer bioimaging potentialities. Biomed Phys Eng Express. 2021; 6(1):012003. DOI: 10.1088/2057-1976/ab6e1d. View

Zahid S, Rasool A, Shehzad R, Bhatti I, Iqbal J . Tuning the optoelectronic properties of triphenylamine (TPA) based small molecules by modifying central core for photovoltaic applications. J Mol Model. 2021; 27(9):237. DOI: 10.1007/s00894-021-04867-1. View

Wang Z, Zheng X, Chen P, Li D, Zhang Q, Liu H . Synchronous construction of a porous intramolecular D-A conjugated polymer via electron donors for superior photocatalytic decontamination. J Hazard Mater. 2021; 424(Pt B):127379. DOI: 10.1016/j.jhazmat.2021.127379. View

Cardona C, Li W, Kaifer A, Stockdale D, Bazan G . Electrochemical considerations for determining absolute frontier orbital energy levels of conjugated polymers for solar cell applications. Adv Mater. 2011; 23(20):2367-71. DOI: 10.1002/adma.201004554. View

Beaujuge P, Amb C, Reynolds J . Spectral engineering in π-conjugated polymers with intramolecular donor-acceptor interactions. Acc Chem Res. 2010; 43(11):1396-407. DOI: 10.1021/ar100043u. View

10.

Afolabi S, Semire B, Idowu M . Electronic and optical properties' tuning of phenoxazine-based D-A-π-A organic dyes for dye-sensitized solar cells. DFT/TDDFT investigations. Heliyon. 2021; 7(4):e06827. PMC: 8082551. DOI: 10.1016/j.heliyon.2021.e06827. View

11.

Sarcan E, Silindir-Gunay M, Ozer A . Theranostic polymeric nanoparticles for NIR imaging and photodynamic therapy. Int J Pharm. 2018; 551(1-2):329-338. DOI: 10.1016/j.ijpharm.2018.09.019. View

12.

Qi S, Kwon N, Yim Y, Nguyen V, Yoon J . Fine-tuning the electronic structure of heavy-atom-free photosensitizers for fluorescence imaging and mitochondria-targeted photodynamic therapy. Chem Sci. 2021; 11(25):6479-6484. PMC: 8152625. DOI: 10.1039/d0sc01171a. View

13.

Khalid M, Ali A, Jawaria R, Asghar M, Asim S, Khan M . First principles study of electronic and nonlinear optical properties of A-D-π-A and D-A-D-π-A configured compounds containing novel quinoline-carbazole derivatives. RSC Adv. 2022; 10(37):22273-22283. PMC: 9054527. DOI: 10.1039/d0ra02857f. View

14.

Fusco S, Barra M, Gontrani L, Bonomo M, Chianese F, Galliano S . Novel Thienyl DPP derivatives Functionalized with Terminal Electron-Acceptor Groups: Synthesis, Optical Properties and OFET Performance. Chemistry. 2022; 28(25):e202104552. PMC: 9314809. DOI: 10.1002/chem.202104552. View

15.

Kitisriworaphan W, Chawanpunyawat T, Manyum T, Chasing P, Namuangruk S, Sudyoadsuk T . The improvement in hole-transporting and electroluminescent properties of diketopyrrolopyrrole pigment by grafting with carbazole dendrons. RSC Adv. 2022; 11(21):12710-12719. PMC: 8696974. DOI: 10.1039/d1ra00805f. View

16.

He H, Zheng X, Liu S, Zheng M, Xie Z, Wang Y . Diketopyrrolopyrrole-based carbon dots for photodynamic therapy. Nanoscale. 2018; 10(23):10991-10998. DOI: 10.1039/c8nr02643b. View

17.

Chen J, Liu Q, Li H, Zhao Z, Lu Z, Huang Y . Density Functional Theory Investigations of D-A-D' Structural Molecules as Donor Materials in Organic Solar Cell. Front Chem. 2018; 6:200. PMC: 5994543. DOI: 10.3389/fchem.2018.00200. View

18.

Zou J, Yin Z, Wang P, Chen D, Shao J, Zhang Q . Photosensitizer synergistic effects: D-A-D structured organic molecule with enhanced fluorescence and singlet oxygen quantum yield for photodynamic therapy. Chem Sci. 2018; 9(8):2188-2194. PMC: 5903368. DOI: 10.1039/c7sc04694d. View

19.

Montaseri H, Kruger C, Abrahamse H . Review: Organic nanoparticle based active targeting for photodynamic therapy treatment of breast cancer cells. Oncotarget. 2020; 11(22):2120-2136. PMC: 7275783. DOI: 10.18632/oncotarget.27596. View

20.

Cai Y, Liang P, Tang Q, Yang X, Si W, Huang W . Diketopyrrolopyrrole-Triphenylamine Organic Nanoparticles as Multifunctional Reagents for Photoacoustic Imaging-Guided Photodynamic/Photothermal Synergistic Tumor Therapy. ACS Nano. 2016; 11(1):1054-1063. DOI: 10.1021/acsnano.6b07927. View