Ellipilli, Satheesh published the artcileFluorinated peptide nucleic acids with fluoroacetyl side chain bearing 5-(F/CF3)-uracil: Synthesis and cell uptake studies, COA of Formula: C4H6BrFO2, the publication is Journal of Organic Chemistry (2016), 81(15), 6364-6373, database is CAplus and MEDLINE.
Fluorine incorporation into organic mols. imparts favorable physicochem. properties such as lipophilicity, solubility and metabolic stability necessary for drug action. Toward such applications using peptide nucleic acids (PNA), we herein report the chem. synthesis of fluorinated PNA monomers and biophys. studies of derived PNA oligomers containing fluorine in in the acetyl side chain (-CHF-CO-) bearing nucleobase uracil (5-F/5-CF3-U). The crystal structures of fluorinated racemic PNA monomers reveal interesting base pairing of enantiomers and packing arrangements directed by the chiral F substituent. Reverse phase HPLC show higher hydrophobicity of fluorinated PNA oligomers, dependent on the number and site of the fluorine substitution: fluorine on carbon adjacent to the carbonyl group induces higher lipophilicity than fluorine on nucleobase or in the backbone. The PNA oligomers containing fluorinated bases form hybrids with cDNA/RNA with slightly lower stability compared to that of unmodified aeg PNA, perhaps due to electronic effects. The uptake of fluorinated homooligomeric PNAs by HeLa cells was as facile as that of nonfluorinated PNA. In conjunction with our previous work on PNAs fluorinated in backbone and at N-terminus, it is evident that the fluorinated PNAs have potential to emerge as a new class of PNA analogs for applications in functional inhibition of RNA.
Journal of Organic Chemistry published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, COA of Formula: C4H6BrFO2.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary