1312103-95-9Relevant academic research and scientific papers
Guanosine-based hydrogen-bonded 2D scaffolds: Metal-free formation of G-quartet and G-ribbon architectures at the solid/liquid interface
Garah, Mohamed El,Perone, Rosaria C.,Bonilla, Alejandro Santana,Haar, Sébastien,Campitiello, Marilena,Gutierrez, Rafael,Cuniberti, Gianaurelio,Masiero, Stefano,Ciesielski, Artur,Samorì, Paolo
, p. 11677 - 11680 (2015)
We report on the synthesis and self-assembly of three novel lipophilic guanosine derivatives exposing a ferrocene moiety in the C(5′) position of the sugar unit. Their self-association in solution, and at the solid/liquid interface, can be tuned by varying the size and nature of the C(8)-substituent, leading to the generation of either G-ribbons, lamellar G-dimer based arrays or the G4 cation-free architectures.
Influence of chlorine substitution on the hydrolytic stability of biaryl ether nucleoside adducts produced by phenolic toxins
Kuska, Michael S.,Majdi Yazdi, Mohadeseh,Witham, Aaron A.,Dahlmann, Heidi A.,Sturla, Shana J.,Wetmore, Stacey D.,Manderville, Richard A.
, p. 7176 - 7185 (2013/08/23)
A kinetic study is reported for the acid-catalyzed hydrolysis of oxygen (O)-linked biaryl ether 8-2′-deoxyguanosine (dG) adducts produced by phenolic toxins following metabolism into phenoxyl radical intermediates. Strikingly, the reaction rate of hydrolysis at pH 1 decreases as electron-withdrawing chlorine (Cl) substituents are added to the phenoxyl ring. The Hammett plot for hydrolysis at pH 1 shows a linear negative slope with ρX = -0.65, implying that increased Cl-substitution diminishes the rate of hydrolysis by lowering N7 basicity. Spectrophotometric titration provided an N7H+ pKa value of 1.1 for the unsubstituted adduct 8-phenoxy-dG (Ph-O-dG). Model pyridine compounds suggest N7H+ pKa values of 0.92 and 0.37 for 4-Cl-Ph-O-dG and 2,6-dichloro-Ph-O-dG (DCP-O-dG), respectively. Density functional theory (DFT) calculations also highlight the ability of the 8-phenoxy substituent to lower N7 basicity and predict a preference for N 3-protonation for highly chlorinated O-linked 8-dG adducts in water. The calculations also provide a rationale for the hydrolytic reactivity of O-linked 8-dG adducts in the gas-phase, as determined using electrospray mass spectrometry (ESI-MS). The inclusion of our data now establishes that the order of hydrolytic reactivity at neutral pH for bulky 8-dG adducts is N-linked > C-linked > O-linked, which correlates with their relative ease of N 7-protonation.
Synthesis of 8-phenoxy-2′-deoxyguanosine nucleoside analogues
Dahlmann, Heidi A.,Sturla, Shana J.
experimental part, p. 2987 - 2992 (2011/06/28)
Nucleobase adducts, which form in vivo by nucleophilic attack of nucleobases on electrophilic chemical species, can impact on the conformation and biological influences of the adducted nucleoside. Contemporary studies aim to address the occurrence and relevance of 8-phenoxypurine adducts. However, preparative techniques for synthesizing these nucleosides have not previously been described. Reported herein is a relatively facile synthesis of 8-dG phenol adducts using a wide variety of electron-donating, electron-withdrawing, and sterically demanding phenols. 8-Phenoxy-2′-deoxyguanosines have been synthesized by nucleophilic substitution withvarious electron-donating, electron-withdrawing, and sterically bulky phenols.
