362-75-4Relevant articles and documents
Copper-Catalyzed Intramolecular Alkoxylation of Purine Nucleosides: One-Step Synthesis of 5′-O,8-Cyclopurine Nucleosides
Yu, Mingwu,Wang, Zhiqian,Hu, Junbin,Li, Shunlai,Du, Hongguang
, p. 9446 - 9453 (2015)
A novel copper-catalyzed intramolecular dehydrogenative alkoxylation of purine nucleosides has been developed successfully, providing the 5′-O,8-cyclopurine nucleosides in one-step with a yield up to 90%. The method, which utilized an inexpensive CuCl catalyst and a di-tert-butyl peroxide (DTBP) oxidant was suitable in a broad substrate scope and proceeded well even in gram scale.
Synthesis and cytostatical evaluation of cytidine- and adenosine-5'-hexadecylphosphate and their phosphonate analogs
Brachwitz,Bergmann,Thomas,Berdel,Langen,Wollny
, p. 143 - 149 (1997)
Four phospholipid conjugates containing the non-cytotoxic nucleosides cytidine and adenosine were prepared by condensation reactions, and their cytotoxic activity was tested in vitro against the human immortalized mammary epithelial cell H184 A1N4, the human mammary tumor cells MaTu and MCF7 and the B lymphoblast cell line Daudi. The synthesized compounds showed considerable activity towards H184 A1N4, MaTu and Daudi cells, but they were not effective against MCF7 cells. The phosphorus moiety - either monophosphate or monophosphonate - does not influence the effectiveness of the phospholipid derivatives in the case of the solid tumor cell lines and H184 A1N4. The leukemic Daudi cell line is strongly sensitive towards the different types of ester as well as to the type of the nucleoside component. Adenosine-5'-hexadecylphosphate proved to be the most potent compound among the substances prepared (IC50: 9.0 μmol).
Charge-Tagged DNA Radicals in the Gas Phase Characterized by UV/Vis Photodissociation Action Spectroscopy
Dang, Andy,Liu, Yue,Ture?ek, Franti?ek,Urban, Jan
, p. 7772 - 7777 (2020)
Adenosine radicals tagged with a fixed-charge group were generated in the gas phase and structurally characterized by tandem mass spectrometry, deuterium labeling, and UV/Vis action spectroscopy. Experimental results in combination with Born–Oppenheimer molecular dynamics, ab initio, and excited-state calculations led to unambiguous assignment of adenosine radicals as N-7 hydrogen atom adducts. The charge-tagged radicals were found to be electronically equivalent to natural DNA nucleoside radicals.
Design, Synthesis, and Characterization of Sulfamide and Sulfamate Nucleotidomimetic Inhibitors of hHint1
Shah, Rachit,Strom, Alexander,Zhou, Andrew,Maize, Kimberly M.,Finzel, Barry C.,Wagner, Carston R.
, p. 780 - 784 (2016)
Hint1 has recently emerged to be an important target of interest due to its involvement in the regulation of a broad range of CNS functions including opioid signaling, tolerance, neuropathic pain, and nicotine dependence. A series of inhibitors were rationally designed, synthesized, and tested for their inhibitory activity against hHint1 using isothermal titration calorimetry (ITC). The studies resulted in the development of the first small-molecule inhibitors of hHint1 with submicromolar binding affinities. A combination of thermodynamic and high-resolution X-ray crystallographic studies provides an insight into the biomolecular recognition of ligands by hHint1. These novel inhibitors have potential utility as molecular probes to better understand the role and function of hHint1 in the CNS.
Chemical Proteomics Approach for Profiling the NAD Interactome
?ileikyt?, Justina,Sundalam, Sunil,David, Larry L.,Cohen, Michael S.
supporting information, p. 6787 - 6791 (2021/05/29)
Nicotinamide adenine dinucleotide (NAD+) is a multifunctional molecule. Beyond redox metabolism, NAD+ has an equally important function as a substrate for post-translational modification enzymes, the largest family being the poly-ADP-ribose polymerases (PARPs, 17 family members in humans). The recent surprising discoveries of noncanonical NAD (NAD+/NADH)-binding proteins suggests that the NAD interactome is likely larger than previously thought; yet, broadly useful chemical tools for profiling and discovering NAD-binding proteins do not exist. Here, we describe the design, synthesis, and validation of clickable, photoaffinity labeling (PAL) probes, 2- and 6-ad-BAD, for interrogating the NAD interactome. We found that 2-ad-BAD efficiently labels PARPs in a UV-dependent manner. Chemical proteomics experiments with 2- and 6-ad-BAD identified known and unknown NAD+/NADH-binding proteins. Together, our study shows the utility of 2- and 6-ad-BAD as clickable PAL NAD probes.
Tightly linked morpholino-nucleoside chimeras: new, compact cationic oligonucleotide analogues
Batta, Gyula,Bege, Miklós,Bereczki, Ilona,Borbás, Anikó,Debreczeni, Nóra,Herczeg, Mihály,Herczegh, Pál
supporting information, p. 8711 - 8721 (2021/10/22)
The polyanionic phosphodiester backbone of nucleic acids contributes to high nuclease sensitivity and low cellular uptake and is therefore a major obstacle to the biological application of native oligonucleotides. Backbone modifications, particularly charge alterations is a proven strategy to provide artificial oligonucleotides with improved properties. Here, we describe the synthesis of a new type of oligonucleotide analogues consisting of a morpholino and a ribo- or deoxyribonucleoside in which the 5′-amino group of the nucleoside unit provides the nitrogen of the morpholine ring. The synthetic protocol is compatible with trityl and dimethoxytrityl protecting groups and azido functionality, and was extended to the synthesis of higher oligomers. The chimeras are positively charged in aqueous medium, due to theN-alkylated tertiary amine structure of the morpholino unit.