title: Synthesis and evaluation of a novel Rhodamine B pyrene [2]rotaxane as an intracellular delivery agent for doxorubicin.
abstract: A novel Rhodamine B-derivatized host [2]rotaxane, containing a dibenzyl-24-crown-8 (DB24C8) ring as the wheel and a pyrene as another fluorophore blocking group, was designed, synthesized and structurally characterized. A comparison of the (1)H NMR spectra of RhBPy [2]rotaxane with those of and DB24C8, nuclear Overhauser effect spectroscopy (NOESY), mass spectrometry and fluorescence spectroscopy confirmed the interlocked nature of RhBPy [2]rotaxane. The temperature dependence of the rotaxane studied by (1)H NMR spectroscopy further demonstrated that RhBPy [2]rotaxane can be applied as a molecular switch. RhBPy [2]rotaxane has also been demonstrated to be an efficient transport agent for delivering the cancer drug doxorubicin (DOX) into tumor cells. Indeed, DOX delivered by RhBPy [2]rotaxane could effectively inhibit tumor cell growth.
authors.affiliation: Department of Biochemical Engineering, Nanjing University of Science and Technology, Chemical Engineering Building B308, 200 Xiaolingwei, Nanjing, 210094, P.R. China. baoxiaofeng@mail.njust.edu.cn.
authors.forename: Jiaxin
authors.initials: J
authors.lastname: Shi
authors.forename: Yuan
authors.initials: Y
authors.lastname: Xu
authors.forename: Xinlong
authors.initials: X
authors.lastname: Wang
authors.forename: Luyong
authors.initials: L
authors.lastname: Zhang
authors.forename: Jing
authors.initials: J
authors.lastname: Zhu
authors.forename: Tao
authors.initials: T
authors.lastname: Pang
authors.forename: Xiaofeng
authors.initials: X
authors.lastname: Bao
mesh_terms: D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004317:Doxorubicin / Q000494:pharmacology*; D016503:Drug Delivery Systems; D004705:Endocytosis / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D042541:Intracellular Space / Q000378:metabolism*; D007700:Kinetics; D008027:Light; D013058:Mass Spectrometry; D066244:Proton Magnetic Resonance Spectroscopy; D011721:Pyrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012235:Rhodamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D043862:Rotaxanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013050:Spectrometry, Fluorescence; D013696:Temperature
chemical_list: D011721:Pyrenes; D012235:Rhodamines; D043862:Rotaxanes; D004317:Doxorubicin; C030984:pyrene; C029773:rhodamine B