Synthesis and assessment of a maleimide functionalized BF2 azadipyrromethene near-infrared fluorochrome.

作者: Dan Wu , Shane Cheung , Marc Devocelle , Li-Jun Zhang , Zhi-Long Chen

DOI: 10.1039/C5CC06137G

关键词: StereochemistryChemistryIn vivoThiolGlutathioneMaleimideCell-penetrating peptideFluorescenceAzadipyrrometheneConjugateCombinatorial chemistry

摘要: The first water soluble maleimide bearing NIR BF2-azadipyrromethene (NIR-AZA) fluorochrome has been synthesised which is capable of rapid thiol conjugations in with peptides such as glutathione, the cell penetrating peptide (CPP) C(β-A)SKKKKTKV-NH2 and a substituted cRGD. fluorescence imaging showed cellular delivery CPP conjugate effective vivo tumour localization for cRGD conjugate.

参考文章(28)
Samad Mussa Farkhani, Alireza Valizadeh, Hadi Karami, Samane Mohammadi, Nasrin Sohrabi, Fariba Badrzadeh, Cell penetrating peptides: efficient vectors for delivery of nanoparticles, nanocarriers, therapeutic and diagnostic molecules. Peptides. ,vol. 57, pp. 78- 94 ,(2014) , 10.1016/J.PEPTIDES.2014.04.015
Vishal Saxena, Mostafa Sadoqi, Jun Shao, Enhanced photo-stability, thermal-stability and aqueous-stability of indocyanine green in polymeric nanoparticulate systems. Journal of Photochemistry and Photobiology B-biology. ,vol. 74, pp. 29- 38 ,(2004) , 10.1016/J.JPHOTOBIOL.2004.01.002
Vikram J. Pansare, Shahram Hejazi, William J. Faenza, Robert K. Prud’homme, Review of Long-Wavelength Optical and NIR Imaging Materials: Contrast Agents, Fluorophores, and Multifunctional Nano Carriers Chemistry of Materials. ,vol. 24, pp. 812- 827 ,(2012) , 10.1021/CM2028367
Michael J. Hall, Lorcan T. Allen, Donal F. O'Shea, PET modulated fluorescent sensing from the BF2 chelated azadipyrromethene platform. Organic and Biomolecular Chemistry. ,vol. 4, pp. 776- 780 ,(2006) , 10.1039/B514788C
Mariusz Tasior, Donal F. O’Shea, BF2-chelated tetraarylazadipyrromethenes as NIR fluorochromes. Bioconjugate Chemistry. ,vol. 21, pp. 1130- 1133 ,(2010) , 10.1021/BC100051P
Julie Murtagh, Daniel O. Frimannsson, Donal F. O’Shea, Azide conjugatable and pH responsive near-infrared fluorescent imaging probes. Organic Letters. ,vol. 11, pp. 5386- 5389 ,(2009) , 10.1021/OL902140V
Jinbing Xie, Ying Li, Yi Cao, Chun Xu, Mao Xia, Meng Qin, Jiwu Wei, Wei Wang, Photo synthesis of protein-based drug-delivery nanoparticles for active tumor targeting Biomaterials Science. ,vol. 1, pp. 1216- 1222 ,(2013) , 10.1039/C3BM60174A
Alexander L. Vahrmeijer, Merlijn Hutteman, Joost R. van der Vorst, Cornelis J. H. van de Velde, John V. Frangioni, Image-guided cancer surgery using near-infrared fluorescence. Nature Reviews Clinical Oncology. ,vol. 10, pp. 507- 518 ,(2013) , 10.1038/NRCLINONC.2013.123
Raymond M Schiffelers, Gerben A Koning, Timo LM ten Hagen, Marcel HAM Fens, Astrid J Schraa, Adriënne PCA Janssen, Robbert J Kok, Grietje Molema, Gert Storm, Anti-tumor efficacy of tumor vasculature-targeted liposomal doxorubicin Journal of Controlled Release. ,vol. 91, pp. 115- 122 ,(2003) , 10.1016/S0168-3659(03)00240-2
Angela D Ragin, Rashida A Morgan, Jean Chmielewski, Cellular Import Mediated by Nuclear Localization Signal Peptide Sequences Chemistry & Biology. ,vol. 9, pp. 943- 948 ,(2002) , 10.1016/S1074-5521(02)00189-8