10.1021/acs.joc.9b00561.s002
Wen-Long Huang
Wen-Long
Huang
Xu-Dong Wang
Xu-Dong
Wang
Sen Li
Sen
Li
Rui Zhang
Rui
Zhang
Yu-Fei Ao
Yu-Fei
Ao
Jun Tang
Jun
Tang
Qi-Qiang Wang
Qi-Qiang
Wang
De-Xian Wang
De-Xian
Wang
Anion Transporters Based
on Noncovalent Balance including
Anion−π, Hydrogen, and Halogen Bonding
American Chemical Society
2019
anion binding
Noncovalent Balance
single-crystal structures
halogen-bonding sites
supramolecular chemistry
chloride transporters
novel noncovalent interactions
anticancer activity
1 H NMR titrations
Anion Transporters
theory calculations
IC 50 values
HCT 116
1 c
association constants
gallic acid ester derivatives
transporters 1 exhibit
Fluorescence assays
EC 50
ion transport
compounds 1
cell survival
1 b
Halogen Bonding Anion transmembrane transport
one-pot strategy
di-halogen-substituted triazines
noncovalent bonds
2019-06-17 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Anion_Transporters_Based_on_Noncovalent_Balance_including_Anion_Hydrogen_and_Halogen_Bonding/8337467
Anion transmembrane transport mediated
by novel noncovalent interactions
is of central interest in supramolecular chemistry. In this work,
a series of oxacalix[2]arene[2]triazine-derived transporters <b>1</b> and <b>2</b> bearing anion−π-, hydrogen-,
and halogen-bonding sites in rational proximity were designed and
synthesized by a one-pot strategy starting from gallic acid ester
derivatives and mono- or di-halogen-substituted triazines. <sup>1</sup>H NMR titrations demonstrated efficient binding of <b>1</b> and <b>2</b> toward Cl<sup>–</sup> and Br<sup>–</sup> in solution, giving association constants in the range of 10<sup>2</sup>–10<sup>4</sup> M<sup>–1</sup>. Cooperation
of anion−π, hydrogen, and halogen bonding was revealed
as a driving force for anion binding by single-crystal structures
of two complexes and density functional theory calculations. Fluorescence
assays indicated that compounds <b>1</b> are efficient chloride
transporters with effective concentrations (EC<sub>50</sub>) falling
in the range of 3.1–7.4 μM and following an order of <b>1a</b> > <b>1b</b> > <b>1c</b> > <b>1d</b>.
The contribution of halogen bonding and cooperative noncovalent bonds
to ion transport was then discussed. Significantly, transporters <b>1</b> exhibit high anticancer activity. In the presence of <b>1</b> and KCl (60 mM), the cell survival of HCT116 reduces to
11.9–24.9% with IC<sub>50</sub> values in the range of 52.3–66.4
μM.