Diketopyrrolopyrrole Derivatives Grafting Hyaluronic Acid for Targeted Photodynamic Therapy

Abstract

Photodynamic therapy (PDT) can effectively avoid the damages on the normal tissues and organs compared to the traditional cancer treatment methods because of its non‐invasive property for the body and high selectivity to tumor site upon light irradiation. Rational design of photosensitizers (PSs) with specific targeting towards tumors and on‐site activation is strongly desirable for precise cancer photodynamic therapy. Herein, a novel hydrophilic tumor‐targeting photosensitizer (DTDPP‐HA) is synthesized by covalently coupling 2,5‐bis‐(6‐bromo‐hexyl)‐3,6‐di‐thiophen‐2‐yl‐2,5‐dihydro‐pyrrolo[3,4‐c]pyrrole‐1,4‐dione (DTDPP) with hyaluronic acid (HA), which presents high singlet oxygen generation and specific targeting to the CD44 receptor overexpressed cancer cells, as well as low dark toxicity and high phototoxicity. More important, both vitro and vivo experiments reveal that DTDPP‐HA can effectively suppress tumor growth. Therefore, the DTDPP‐HA would be a potential and promising theranostic agent for PDT.

Self-quenched ferrocenyl diketopyrrolopyrrole organic nanoparticles with amplifying photothermal effect for cancer therapy

“…The diketopyrrolopyrrole (DPP) unit is an excellent electron acceptor due to its lactam structure, which has already been widely used in organic optical materials due to its excellent light absorption property. 33 – 36 Recently, triphenylamine based thienyl-diketopyrrolopyrrole (DPP-TPA) with a donor–acceptor–donor (D–A–D) structure has shown great promise as a therapeutic agent for PTT with a PTC efficiency of 34.5% as reported by our group. 35 To further improve the PTC efficiency, furyl-diketopyrrolopyrrole derivatives have come into our view.…”

Carrier-free nano-integrated strategy for synergetic cancer anti-angiogenic therapy and phototherapy

“…2a , the SC NP solution presented an apparent fluorescence signal, which was enhanced with the increase in concentration, and the fluorescence imaging intensity presented the brightest signal at 40 μg mL –1 . Ce6 has been proven to be an excellent photosensitizer with efficient ROS generation; thereby, the ROS generation ability of SC NPs was further measured by using 9,10-anthracenediyl-bis(methylene)dimalonic acid (ABDA, absorption peak at 378 nm) 50 as a probe. As shown in Fig.…”

Organic Dye Based Nanoparticles for Cancer Phototheranostics

“…Zhang and co‐workers synthesized an organic molecule 2,5‐bis(6‐bromohexyl)‐3,6‐bis(4‐bromophenyl)pyrrolo[3,4‐ c ]pyrrole‐1,4(2H,5H)‐dione with a plane and large π‐conjugated structure that can conveniently self‐assemble into nanorods through hydrophobic interactions and strong π–π stacking, which proves to be an excellent fluorescence agent for living‐cell imaging . Very recently, our group has developed two DPP derivatives (thiophene or bromothiophene substituted DPP), and used them as water‐soluble PSs for PDT with tumor‐targeting property after grafting hyaluronic acid . In addition, we are devoted to the development of DPP‐based NIR dyes, with introduction of electron donors such as triphenylamine and 4‐dimethylaminobenzophenone onto the electron‐deficient DPP core to construct D–A–D structured dyes, which have much more potential for biological imaging and tumor therapy .…”