Near‐Infrared Hypocrellin Derivatives for Synergistic Photodynamic and Photothermal Therapy

• Published in: Chemistry, an Asian journal Vol. 15; no. 21; pp. 3462 - 3468
• Main Authors: Ding, Ying, Liu, Weimin, Wu, Jiasheng, Zheng, Xiuli, Ge, Jiechao, Ren, Haohui, Zhang, Wenjun, Lee, Chun‐Sing, Wang, Pengfei
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 02.11.2020
• Subjects: Absorption spectra; Animals; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Cell Line, Tumor; Cell Survival - drug effects; Chemistry; Derivatives; Female; Hypocrellin derivatives; Infrared Rays; Mammary Neoplasms, Experimental - diagnostic imaging; Mammary Neoplasms, Experimental - drug therapy; Mice; Optical Imaging; Perylene - analogs & derivatives; Perylene - chemical synthesis; Perylene - chemistry; Perylene - pharmacology; Phenol - chemical synthesis; Phenol - chemistry; Phenol - pharmacology; Photodynamic therapy; Photosensitivity; Photosensitizing Agents - chemical synthesis; Photosensitizing Agents - chemistry; Photosensitizing Agents - pharmacology; Photothermal conversion; Photothermal Therapy; Polyethylene glycol; Quinones - chemical synthesis; Quinones - chemistry; Quinones - pharmacology; Singlet oxygen; Synergistic effect; Theranostic Nanomedicine; Photothermal therapy; Photodynamic therapy; Synergistic effect; Hypocrellin derivatives
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.202000911

Hypocrellin B (HB) derived from naturally produced hypocrellins has attracted considerable attention in photodynamic therapy (PDT) because of its excellent photosensitive properties. However, the weak absorption within a “phototherapy window” (600–900 nm) and poor water solubility of HB have limited its clinical application. In this study, two HB derivatives (i. e., HE and HF) were designed and synthesized for the first time by introducing two different substituent groups into the HB structure. The obtained derivatives showed a broad absorption band covering the near‐infrared (NIR) region, NIR emission (peaked at 805 nm), and singlet oxygen quantum yields of 0.27/0.31. HE‐PEG‐NPs were also prepared using 2‐distearoyl‐sn‐glycero‐3‐phosphoethanolamine‐N‐[methoxy(polyethyleneglycol)‐2000] (DSPE‐mPEG2000) to achieve excellent dispersion in water and further explored their practical applications. HE‐PEG‐NPs not only retained their 1O2‐generating ability, but also exhibited a photothermal conversion efficiency of 25.9%. In vitro and in vivo therapeutic results revealed that the synergetic effect of HE‐PEG‐NPs on PDT and photothermal therapy (PTT) could achieve a good performance. Therefore, HE‐PEG‐NPs could be regarded as a promising phototheranostic agent. HE‐PEG‐NPs based on novel HB derivatives with NIR absorption and emission have been prepared and could serve as a promising therapeutic agent for fluorescence imaging‐guided photodynamic and photothermal therapy.