120500-90-5Relevant articles and documents
Diketopyrrolopyrrole Bis-Phosphonate Conjugate: A New Fluorescent Probe for In Vitro Bone Imaging
Chiminazzo, Andrea,Borsato, Giuseppe,Favero, Alessia,Fabbro, Chiara,McKenna, Charles E.,Dalle Carbonare, Luca Giuseppe,Valenti, Maria Teresa,Fabris, Fabrizio,Scarso, Alessandro
, p. 3617 - 3626 (2019)
The synthesis of a conjugate molecule between an unusual red-fluorescent diketopyrrolopyrrole (DPP) unit and a bis-phosphonate (BP) precursor by a click-chemistry strategy to target bone tissue and monitor the interaction is reported. After thorough investigation, conjugation through a triazole unit between a γ-azido rather than a β-azido BP and an alkyne-functionalized DPP fluorophore group turned out to be the winning strategy. Visualization of the DPP-BP conjugate on osteoclasts and specific antiresorption activity were successfully demonstrated.
A Thienyl-Substituted Diketopyrrolopyrrole Derivative with Efficient Reactive Oxygen Species Generation for Photodynamic Therapy
Shi, Huaxia,Sun, Wucheng,Wang, Qiang,Gu, Guiying,Si, Weili,Huang, Wei,Zhang, Qi,Dong, Xiaochen
, p. 515 - 520 (2016)
Reducing the energy gap of photosensitizer between singlet and triplet states (ΔEST) can improve the efficiency of intersystem crossing, further enhancing the resulting generation of reactive oxygen species for photodynamic therapy. In this study, two photosensitizer chromophores—phenyl-substituted diketopyrrolopyrrole and thienyl-substituted diketopyrrolopyrrole (TDPP)—were synthesized. Theoretical calculations indicate that TDPP can greatly reduce the ΔEST (0.48 eV) relative to that of diketopyrrolopyrrole (0.66 eV). Experiments confirmed that TDPP generates reactive oxygen species more efficiently than diketopyrrolopyrrole. After conjugation of TDPP with methoxy poly(ethylene glycol)carboxyl (mPEG-COOH), the resulting TDPP-mPEG has excellent water solubility, biocompatibility and photostability. When it serves as photosensitizer for photodynamic therapy, in vitro and in vivo measurements indicate that TDPP-mPEG can effectively inhibit tumor growth and shows great potential for the treatment of cancer in the clinic.
Fluorine Directed Two-Dimensional Cruciform π-π Stacking in Diketopyrrolopyrroles
Calvo-Castro, Jesus,Morris, Graeme,Kennedy, Alan R.,McHugh, Callum J.
, p. 5385 - 5393 (2016)
Enhanced bulk dimensionality in organic materials employed in optoelectronic devices is desirable and can overcome fabrication issues related to structural defects and grain boundaries. Herein, we report a novel fluorinated diketopyrrolopyrrole single cry