Clofarabine - CAS 123318-82-1
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Not Intended for Therapeutic Use. For research use only.
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Nucleoside Antimetabolite/Analog
Clofarabine inhibits the enzymatic activities of ribonucleotide reductase (IC50 = 65 nM) and DNA polymerase.
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1. Synthesis, cytotoxicity and cellular uptake studies of N3 functionalized Re(CO)3 thymidine complexes
Mark D. Bartholoma, Anthony R. Vortherms, Jon Zubieta*. Dalton Trans., 2011, 40, 6216–6225
For nucleoside analogs to exhibit their cytotoxicity, they need to enter into the intracellular space across the plasma membrane. Because of their hydrophilic character, however, they cannot cross cellular membranes by simple diffusion and transport occurs through carrier proteins in the form of specific nucleoside transporters. Once inside the cell, nucleoside-based anticancer agents are metabolized and either inhibit enzymes involved in DNA synthesis and/or are incorporated into DNA, thus affecting its structural integrity. This latter effect results in chain termination or deformation inducing apoptosis. Prominent examples of clinically relevant anticancer agents are the purine analogs fludarabine (2-CdA, 2-chlorodeoxyadenosine) used in the treatment of lymphoproliferative malignancies and the cytidine derivative cytarabine (ara-C, 1-β-D-arabinosilfuranosilcytosine) for acute leukaemia. The pyrimidine analogs gemcitabine (dFdC, 2’, 2’-difluorodeoxycytidine) and capecitabine are used for the treatment of solid tumors. More recently, clofarabine (Cl–F-araA, 2-chloro-2’-fluoro-deoxy-9-b-arabinosyladenine) has been used for relapsed and refractory pediatric acute lymphoblastic leukemia and troxacitabine (OddC, (-)-2’-deoxy-3’-oxacitabine) has demonstrated efficacy in both solid and hematological malignancies in clinical trials.
2. Diastereoselective self-assembly of clofarabine lipids
Peter Sandin, Francesca Baldelli Bombelli, Debora Berti*. New J. Chem., 2014, 38, 5247—5253
Clofarabine is a cytotoxic deoxyadenosine analogue that received accelerated approval in 2004 from FDA and recently fromEMEA for the treatment of pediatric acute lymphoblastic leukemia, currently under clinical trials for some adult solid tumors. A dose-dependent severe myelosuppression represents its most serious side-effect. Like for many other nucleosidic chemotherapeutics, a pro-nucleotide approach, with a specific lipid carrier linked to the nucleoside via a covalent phosphodiester bond, can reduce these effects, improve pharmacokinetic behavior and over-come or decrease the development of resistance against the drug. Recently we have synthesized a specific conjugate of clofarabine with a synthetic dialkyl lipid phosphate, (1,Fig.1),whichshowed improved pharmacokinetic, pharmacodynamic and toxicologic properties compared to free clofarabine.
3. Bioinspired systems in supramolecular chemistry and nanotechnology – introducing the SupraBio themed issue
Michel Camplo, Jean-Manuel Raimundo, Laurence Navailles, Mark W. Grinstaffc and Philippe Barthelemy*. New J. Chem., 2014, 38, 5120—5121
The active field of DNA molecules is also discussed. In their Letter, A. Arbuzova and coworkers describe the DNA-controlled aggregation of virus-like particles (DOI: 10.1039/C4NJ00724G). In another contribution, E. Stulz and colleagues discuss the EPR spectroscopy of Cu-porphyrin–DNA conjugates (DOI: 10.1039/C4NJ00673A). Hybrid molecules involving lipids and nucleic acids are presented and described in several contributions, including nucleolipids as building blocks for the synthesisof nanoparticles (K. Oumzil et al., DOI: 10.1039/C4NJ00559G), the self-assembly properties of clofarabine lipids (D. Berti et al., DOI: 10.1039/C4NJ00856A), and lipid–oligonucleotide conjugates by A. Gissot et al. (DOI: 10.1039/C4NJ00850B).
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CAS 123318-82-1 Clofarabine

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