138385-37-2Relevant academic research and scientific papers
Chemical Proteomics Approach for Profiling the NAD Interactome
?ileikyt?, Justina,Sundalam, Sunil,David, Larry L.,Cohen, Michael S.
, p. 6787 - 6791 (2021)
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.
The synthesis and biological evaluation of benzamide riboside and its phosphordiamidates prodrugs
Zhou, Jianning,Tan, Chunyan,Zhang, Nan,Fan, Jian,Guo, Chun,Jiang, Yuyang
scheme or table, p. 787 - 790 (2009/04/06)
In order to overcome the drug resistance and enhance the membrane penetration ability of benzamide riboside [BR, (1-β-D-ribofuranosyl) benzene-3-carboxamide], which is a novel C-glycoside analogue of nicotinamide riboside and has excellent cytotoxic activity, we designed and synthesized two phosphordiamidates (1a and 1b) as prodrugs to deliver phosphorylated BR into cells. However, the bioactivity evaluation shows that 1a and 1b have lower biological activity (IC50 > 200 μM and 173 μM, respectively) compared to BR. This might be due to the fact that 1a and 1b could only serve as the BR depot form and thus could not be metabolized to the phosporylatd benzamide riboside. Copyright Taylor & Francis Group, LLC.
Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogues
Krohn,Heins,Wielckens
, p. 511 - 517 (2007/10/02)
The C-glycosidic nicotinamide riboside analogue (2) was prepared by reaction of ribonolactone 24 with the lithiated oxazoline 19 followed by triethylsilane reduction to 26 and deprotection. Selective phosphorylation to the pseudonucleotide 34 was effected
