1. Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates
Mariya I Meschaninova, Darya S Novopashina, Olga A Semikolenova, Vladimir N Silnikov, Alya G Venyaminova Molecules. 2019 Nov 22;24(23):4266. doi: 10.3390/molecules24234266.
A novel and convenient approach for the solid-phase 5'-functionalization of oligonucleotides is proposed in this article. The approach is based on the activation of free 5'-hydroxyl of polymer support-bound protected oligonucleotides by N,N'-disuccinimidyl carbonate followed by interaction with amino-containing ligands. Novel amino-containing derivatives of closo-dodecaborate, estrone, cholesterol, and α-tocopherol were specially prepared. A wide range of oligonucleotide conjugates bearing closo-dodecaborate, short peptide, pyrene, lipophilic residues (cholesterol, α-tocopherol, folate, estrone), aliphatic diamines, and propargylamine were synthesized and characterized to demonstrate the versatility of the approach. The developed method is suitable for the conjugate synthesis of oligonucleotides of different types (ribo-, deoxyribo-, 2'-O-methylribo-, and others).
2. Solubility of N, N'-Disuccinimidyl Carbonate and its relevance to polysaccharide functionalization
Tingyu Li, David Vanderah Anal Biochem. 2021 Aug 1;626:114250. doi: 10.1016/j.ab.2021.114250. Epub 2021 May 12.
N, N'-Disuccinimidyl Carbonate (DSC) is a common reagent for the functionalization of polysaccharides for affinity chromatography. Difficulty in the removal of excess DSC after the functionalization reaction promoted the studies of its solubilities in organic solvents. Surprisingly, DSC has low solubility in several common organic solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, and isopropanol. It is slightly soluble in acetone and acetonitrile, soluble in dimethylformamide, and very soluble in dimethyl sulfoxide. Solvent effect on DSC's use in the functionalization of the Sepharose-6-fastflow resin from GE Healthcare was also studied. While dimethyl sulfoxide did not improve the functionalization reaction, it proved to be an effective solvent removing excess DSC after the functionalization reaction.
3. The Covalent Tethering of Poly(ethylene glycol) to Nylon 6 Surface via N, N'-Disuccinimidyl Carbonate Conjugation: A New Approach in the Fight against Pathogenic Bacteria
Sumita Swar, Veronika Máková, Ivan Stibor Polymers (Basel). 2020 Sep 24;12(10):2181. doi: 10.3390/polym12102181.
Different forms of unmodified and modified Poly(ethylene glycols) (PEGs) are widely used as antifouling and antibacterial agents for biomedical industries and Nylon 6 is one of the polymers used for biomedical textiles. Our recent study focused on an efficient approach to PEG immobilization on a reduced Nylon 6 surface via N,N'-disuccinimidyl carbonate (DSC) conjugation. The conversion of amide functional groups to secondary amines on the Nylon 6 polymer surface was achieved by the reducing agent borane-tetrahydrofuran (BH3-THF) complex, before binding the PEG. Various techniques, including water contact angle and free surface energy measurements, atomic force microscopy, scanning electron microscopy, X-ray photoelectron spectroscopy, and Fourier-transform infrared spectroscopy, were used to confirm the desired surface immobilization. Our findings indicated that PEG may be efficiently tethered to the Nylon 6 surface via DSC, having an enormous future potential for antifouling biomedical materials. The bacterial adhesion performances against S. aureus and P. aeruginosa were examined. In vitro cytocompatibility was successfully tested on pure, reduced, and PEG immobilized samples.
