title: Diketopyrrolopyrrole-Triphenylamine Organic Nanoparticles as Multifunctional Reagents for Photoacoustic Imaging-Guided Photodynamic/Photothermal Synergistic Tumor Therapy.
abstract: Herein, a donor-acceptor-donor (D-A-D) structured small molecule (DPP-TPA) is designed and synthesized for photoacoustic imaging (PAI) guided photodynamic/photothermal synergistic therapy. In the diketopyrrolopyrrole (DPP) molecule, a thiophene group is contained to increase the intersystem crossing (ISC) ability through the heavy atom effect. Simultaneously, triphenylamine (TPA) is introduced for bathochromic shift absorption as well as charge transport capacity enhancement. After formation of nanoparticles (NPs, ∼76 nm) by reprecipitation, the absorption of DPP-TPA NPs further displays obvious bathochromic-shift with the maximum absorption peak at 660 nm. What's more, the NPs architecture enhances the D-A-D structure, which greatly increases the charge transport capacity and impels the charge to generate heat by light. DPP-TPA NPs present high photothermal conversion efficiency (η = 34.5%) and excellent singlet oxygen (1O2) generation (ΦΔ= 33.6%) under 660 nm laser irradiation. PAI, with high spatial resolution and deep biotissue penetration, indicates DPP-TPA NPs can rapidly target the tumor sites within 2 h by the enhanced permeability and retention (EPR) effect. Importantly, DPP-TPA NPs could effectively hinder the tumor growth by photodynamic/photothermal synergistic therapy in vivo even at a low dosage (0.2 mg/kg) upon laser irradiation (660 nm 1.0 W/cm2). This study illuminates the photothermal conversion mechanism of small organic NPs and demonstrates the promising application of DPP-TPA NPs in PAI guided phototherapy.
authors.affiliation: Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and ‡School of Pharmaceutical Sciences, Nanjing Tech University (NanjingTech) , 30 South Puzhu Road, Nanjing 211816, China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Cai
authors.affiliation: Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and ‡School of Pharmaceutical Sciences, Nanjing Tech University (NanjingTech) , 30 South Puzhu Road, Nanjing 211816, China.
authors.forename: Pingping
authors.initials: P
authors.lastname: Liang
authors.affiliation: Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and ‡School of Pharmaceutical Sciences, Nanjing Tech University (NanjingTech) , 30 South Puzhu Road, Nanjing 211816, China.
authors.forename: Qianyun
authors.initials: Q
authors.lastname: Tang
authors.affiliation: Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and ‡School of Pharmaceutical Sciences, Nanjing Tech University (NanjingTech) , 30 South Puzhu Road, Nanjing 211816, China.
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Yang
authors.affiliation: Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and ‡School of Pharmaceutical Sciences, Nanjing Tech University (NanjingTech) , 30 South Puzhu Road, Nanjing 211816, China.
authors.forename: Weili
authors.initials: W
authors.lastname: Si
authors.affiliation: Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and ‡School of Pharmaceutical Sciences, Nanjing Tech University (NanjingTech) , 30 South Puzhu Road, Nanjing 211816, China.
authors.forename: Wei
authors.identifier: 0000-0001-7004-6408
authors.initials: W
authors.lastname: Huang
authors.affiliation: Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and ‡School of Pharmaceutical Sciences, Nanjing Tech University (NanjingTech) , 30 South Puzhu Road, Nanjing 211816, China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), and ‡School of Pharmaceutical Sciences, Nanjing Tech University (NanjingTech) , 30 South Puzhu Road, Nanjing 211816, China.
authors.forename: Xiaochen
authors.identifier: 0000-0003-4837-9059
authors.initials: X
authors.lastname: Dong
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D002470:Cell Survival / Q000187:drug effects; D003110:Colonic Neoplasms / Q000000981:diagnostic imaging / Q000473:pathology / Q000628:therapy*; D004305:Dose-Response Relationship, Drug; D045325:HCT116 Cells; D006367:HeLa Cells; D006801:Humans; D007202:Indicators and Reagents / Q000737:chemistry / Q000494:pharmacology*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007834:Lasers; D051379:Mice; D008819:Mice, Nude; D015394:Molecular Structure; D053758:Nanoparticles / Q000737:chemistry*; D009374:Neoplasms, Experimental / Q000000981:diagnostic imaging / Q000473:pathology / Q000628:therapy; D061848:Optical Imaging; D010316:Particle Size; D061088:Photoacoustic Techniques; D010789:Phototherapy; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000378:metabolism; D026082:Singlet Oxygen / Q000032:analysis; D013329:Structure-Activity Relationship; D013499:Surface Properties; D014018:Tissue Distribution
chemical_list: D000814:Aniline Compounds; D007202:Indicators and Reagents; D007659:Ketones; D011758:Pyrroles; D017382:Reactive Oxygen Species; C000604894:diketopyrrolopyrrole dye; D026082:Singlet Oxygen
keywords: multifunctional reagents; organic nanoparticles; photoacoustic imaging; phototherapy; tumor