103882-85-5Relevant articles and documents
Unprecedented gas-phase chiroselective logic gates
Botta, Bruno,Fraschetti, Caterina,D'Acquarica, Ilaria,Sacco, Fabiola,Mattay, Jochen,Letzel, Matthias C.,Speranza, Maurizio
, p. 1717 - 1719 (2011)
The gas-phase encounters between 2-aminobutane and proton-bound chiral resorcin[4]arene/nucleoside complexes behave in the gas phase as supramolecular "chiroselective logic gates" by releasing the nucleoside depending on the resorcin[4]arene and the 2-aminobutane configurations.
Mechanochemical activation of disulfide-based multifunctional polymers for theranostic drug release
Shi, Zhiyuan,Song, Qingchuan,G?stl, Robert,Herrmann, Andreas
, p. 1668 - 1674 (2021)
Drug delivery systems responsive to physicochemical stimuli allow spatiotemporal control over drug activity to overcome limitations of systemic drug administration. Alongside, the non-invasive real-time tracking of drug release and uptake remains challenging as pharmacophore and reporter function are rarely unified within one molecule. Here, we present an ultrasound-responsive release system based on the mechanochemically induced 5-exo-trigcyclization upon scission of disulfides bearing cargo molecules attachedviaβ-carbonate linker within the center of a water soluble polymer. In this bifunctional theranostic approach, we release one reporter molecule per drug molecule to quantitatively track drug release and distribution within the cell in real-time. We useN-butyl-4-hydroxy-1,8-naphthalimide and umbelliferone as fluorescent reporter molecules to accompany the release of camptothecin and gemcitabine as clinically employed anticancer agents. The generality of this approach paves the way for the theranostic release of a variety of probes and drugs by ultrasound.
A novel anticancer theranostic pro-prodrug based on hypoxia and photo sequential control
Feng, Weipei,Gao, Chunyue,Liu, Wei,Ren, Huihui,Wang, Chao,Ge, Kun,Li, Shenghui,Zhou, Guoqiang,Li, Hongyan,Wang, Shuxiang,Jia, Guang,Li, Zhenhua,Zhang, Jinchao
, p. 9434 - 9437 (2016)
A novel anticancer pro-prodrug (GMC-CAE-NO2) with diagnosis and therapy functions based on hypoxia and photo sequential control was designed. It provides a platform for constructing theranostic pro-prodrugs to release active drugs controlled by hypoxic status and UV illumination.
Efficient syntheses of clofarabine and gemcitabine from 2-deoxyribonolactone
Cen, Yana,Sauve, Anthony A.
, p. 113 - 122 (2010)
The development of a new methodology to achieve electrophilic fluorination of triisopropylsilyl-protected 2-deoxyribonolactone has been employed to synthesize clofarabine and gemcitabine with improved synthetic efficiency versus prior synthetic methods. These studies highlight the versatility of this new methodology to obtain medically relevant 2′-fluoronucleosides.
Selective Activation of a Prodrug by Thioredoxin Reductase Providing a Strategy to Target Cancer Cells
Li, Xinming,Hou, Yanan,Meng, Xianke,Ge, Chunpo,Ma, Huilong,Li, Jin,Fang, Jianguo
, p. 6141 - 6145 (2018)
Elevated reactive oxygen species and antioxidant defense systems have been recognized as one of the hallmarks of cancer cells. As a major regulator of the cellular redox homeostasis, the selenoprotein thioredoxin reductase (TrxR) is increasingly considered as a promising target for anticancer drug development. The current approach to inhibit TrxR predominantly relies on the modification of the selenocysteine residue in the C-terminal active site of the enzyme, in which it is hard to avoid the off-target effects. By conjugating the anticancer drug gemcitabine with a 1,2-dithiolane scaffold, an unprecedented prodrug strategy is disclosed that achieves a specific release of gemcitabine by TrxR in cells. As overexpression of TrxR is frequently found in different types of tumors, the TrxR-dependent prodrugs are promising for further development as cancer chemotherapeutic agents.
Synthesis and in vitro anticancer activity of new gemcitabine-nucleoside analogue dimers containing methyltriazole or ester-methyltriazole linker
Trznadel, Roksana,Singh, Aleksandra,Kleczewska, Natalia,Liberska, Joanna,Ruszkowski, Piotr,Celewicz, Lech
, p. 2587 - 2594 (2019/08/12)
Two series of novel gemcitabine-nucleoside analogue dimers were synthesized using the ‘click’ chemistry approach. In the first series of dimers (21–30), the nucleoside units were connected with a stable methyltriazole 4N-3′(or 5′)C linker whereas in the second series (31–40) with a cleavable ester-methyltriazole 4N-3′(or 5′)C linker. Dimers 21–40 were evaluated for their cytotoxic activity in five human cancer cell lines such as cervical (HeLa), nasopharyngeal (KB), lung (A549), brain (U87), liver (HepG2) and normal dermal fibroblast cell line (HDF) using the sulforhodamine B (SRB) assay. Compound 29 comprising two gemcitabine (dFdC) units exhibited the highest activity among dimers 21–30. The activity of compound 29 was higher than that of dFdC in all the studied cancer cell lines. A similar order of activity was observed for compounds 25, 28, and 30. The best activity among all the dimers synthesized was displayed by compound 39, comprising two gemcitabine units with a cleavable linker. The activity of compound 39 was 5 to 9 times higher than that of dFdC, depending on the cell line. In addition, marked cytotoxic activity was shown by compounds 31, 36, 38, and 40.
