Efficient fluorescent recognition of ATP/GTP by a water-soluble bisquinolinium pyridine-2,6-dicarboxamide compound. Crystal structures, spectroscopic studies and interaction mode with DNA

被引：4

作者：

Viviano-Posadas, Alejandro O. ^{[1
]}

Romero-Mendoza, Ulises ^{[1
]}

Bazany-Rodriguez, Ivan J. ^{[1
]}

Velazquez-Castillo, Rocio V. ^{[1
]}

Martinez-Otero, Diego ^{[2
]}

Bautista-Renedo, Joanatan M. ^{[2
]}

Gonzalez-Rivas, Nelly ^{[2
]}

Galindo-Murillo, Rodrigo ^{[3
]}

Salomon-Flores, Maria K. ^{[1
]}

Dorazco-Gonzalez, Alejandro ^{[1
]}

机构：

[1] Univ Nacl Autonoma Mexico, Inst Chem, Ciudad Univ, Mexico City 04510, DF, Mexico

[2] Ctr Conjunto Invest Quim Sustentable UAEM UNAM, Km 14-5 Carrera Toluca Atlacomulco, Toluca De Lerdo 50200, Estado De Mexic, Mexico

[3] Univ Utah, Coll Pharm, Dept Med Chem, 2000 East 30 South Skaggs 306, Salt Lake City, UT 84112 USA

来源：

RSC ADVANCES | 2022年 / 12卷 / 43期

基金：

芬兰科学院;

关键词：

G-QUADRUPLEX; NUCLEOTIDE RECOGNITION; MACROCYCLIC RECEPTORS; ALKALINE-PHOSPHATASE; ANION-BINDING; ATP; PROBE; CHEMOSENSOR; AMBER; GUANOSINE-5'-TRIPHOSPHATE;

D O I：

10.1039/d2ra05040d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The new dicationic pyridine-2,6-dicarboxamide-based compound 1 bearing two N-alkylquinolinium units was synthesized, structurally determined by single-crystal X-ray diffraction, and studied in-depth as a fluorescent receptor for nucleotides and inorganic phosphorylated anions in pure water. The addition of nucleotides to 1 at pH = 7.0 quenches its blue emission with a selective affinity towards adenosine 5'-triphosphate (ATP) and guanosine 5'-tripohosphate (GTP) over other nucleotides such CTP, UTP, ADP, AMP, dicarboxylates and inorganic anions. On the basis of the spectroscopic tools (H-1, P-31 NMR, UV-vis, fluorescence), MS measurements and DFT calculations, receptor 1 binds ATP with high affinity (log K = 5.04) through the simultaneous formation of strong hydrogen bonds and pi-pi interactions between the adenosine fragment and quinolinium ring with binding energy calculated in 8.7 kcal mol(-1). High affinity for ATP/GTP is attributed to the high acidity of amides and preorganized rigid structure of 1. Receptor 1 is an order of magnitude more selective for ATP than GTP. An efficient photoinduced electron transfer quenching mechanism with simultaneous receptor-ATP complexation in both the excited and ground states is proposed. Additionally, multiple spectroscopic studies and molecular dynamics simulations showed that 1 can intercalate into DNA base pairs.

引用

页码：27826 / 27838

页数：13