Near‐Infrared Hypocrellin Derivatives for Synergistic Photodynamic and Photothermal Therapy

Abstract

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 1 O 2-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.

Near-infrared upper phenyl-fused BODIPY as a photosensitizer for photothermal–photodynamic therapy

“…Dye nanoparticles were prepared by the self-assembly of dye molecules and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] (DSPE-PEG 2000 ) by the nano-deposition method as follows: [45][46][47] in brief, the accurately weighed 1 mg dye molecule was fully dissolved in tetrahydrofuran (THF) solution under ultrasound. This THF solution was gradually added to 10 ml aqueous solution containing 5 mg DSPE-PEG2000 and stirred thoroughly for 24 h to completely remove the THF solvent.…”

FeIII, CuII and ZnII Complexes of the Rigid 9-Oxido-phenalenone Ligand—Spectroscopy, Electrochemistry, and Cytotoxic Properties

“…This is not surprising since derivatives of Hopo [32,33] and especially the naturally occurring derivatives Hypocrellin A and B (Scheme 1) have been studied for quite some time for their cytotoxic properties [34][35][36]. Furthermore, Hypocrellin derivatives [37,38] and complexes of Zn II [39], Cu II [40], Co III [41], Au III , and Pt IV [42] were investigated for their photonuclease activity. Moreover, a Hypocrellin A Zn II complex was reported for the optical recognition of pyrophosphate [43].…”

Recent Advances of Photoactive Near-Infrared Carbon Dots in Cancer Photodynamic Therapy

“…However, visible light displays poor penetration ability in human tissues, which limits its cancer treatment effects [ 9 ]. Thence, a number of NIR organic PSs have been developed and used for cancer PDT due to their high 1 O 2 generation quantum yield (QY) and tissue penetration, such as porphyrin [ 10 ], hypocrellin [ 11 ], and phthalocyanine [ 12 ]. However, such NIR organic PSs have the disadvantages of low water solubility, easy aggregation, and poor tumor-targeting capability, resulting in a series of side effects [ 13 ].…”