A Synthetic Supramolecular Receptor for the Hydrosulfide Anion

被引：40

作者：

Hartle, Matthew D. ^{[1
,2
]}

Hansen, Ryan J. ^{[1
,2
]}

Tresca, Blakely W. ^{[1
,2
]}

Prakel, Samuel S. ^{[1
,2
]}

Zakharov, Lev N. ^{[1
,2
,3
]}

Haley, Michael M. ^{[1
,2
]}

Pluth, Michael D. ^{[1
,2
]}

Johnson, Darren W. ^{[1
,2
]}

机构：

[1] Univ Oregon, Inst Mat Sci, Dept Chem & Biochem, Eugene, OR 97403 USA

[2] Univ Oregon, Inst Mol Biol, Eugene, OR 97403 USA

[3] Univ Oregon, CAMCOR Ctr Adv Mat Characterizat Oregon, Eugene, OR 97403 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 38期

基金：

美国国家科学基金会;

关键词：

anion binding; gasotransmitters; molecular recognition; sulfide; supramolecular chemistry; HYDROGEN-SULFIDE; FREE-ENERGY; SENSOR; RECOGNITION; MOLECULES; BINDING; PROBES; ION; H2S;

D O I：

10.1002/anie.201605757

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hydrogen sulfide (H2S) has emerged as a crucial biomolecule in physiology and cellular signaling. Key challenges associated with developing new chemical tools for understanding the biological roles of H2S include developing platforms that enable reversible binding of this important biomolecule. The first synthetic small molecule receptor for the hydrosulfide anion, HS-, using only reversible, hydrogen-bonding interactions in a series of bis(ethynylaniline) derivatives, is reported. Binding constants of up to 90300 +/- 8700m(-1) were obtained in MeCN. The fundamental science of reversible sulfide binding, in this case featuring a key CHS hydrogen bond, will expand the possibility for discovery of sulfide protein targets and molecular recognition agents.

引用

页码：11480 / 11484

页数：5

共 39 条

[1] [Anonymous], 2013, ANGEW CHEM, V125, P10465
[2] [Anonymous], 2013, ANGEW CHEM, V125, P10460
[3] [Anonymous], 2014, ANGEW CHEM, V126, P11682
[4] Leveraging Material Properties in Fluorescence Anion Sensor Arrays: A General Approach
Anzenbacher, Pavel, Jr.
Liu, Yuanli
Palacios, Manuel A.
Minami, Tsuyoshi
Wang, Zhuo
Nishiyabu, Ryuhei
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (26) : 8497 - 8506
[5] Experimental evidence for interactions between anions and electron-deficient aromatic rings
Berryman, Orion B.
Johnson, Darren W.
[J]. CHEMICAL COMMUNICATIONS, 2009, (22) : 3143 - 3153
[6] Neutral CH and cationic CH donor groups as anion receptors
Cai, Jiajia
Sessler, Jonathan L.
[J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (17) : 6198 - 6213
[7] Anion Complexation and The Hofmeister Effect
Carnegie, Ryan S.
Gibb, Corinne L. D.
Gibb, Bruce C.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (43) : 11498 - 11500
[8] Arylethynyl receptors for neutral molecules and anions: emerging applications in cellular imaging
Carroll, Calden N.
Naleway, John J.
Haley, Michael M.
Johnson, Darren W.
[J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) : 3875 - 3888
[9] Identification and characterization of a bacterial hydrosulphide ion channel
Czyzewski, Bryan K.
Wang, Da-Neng
[J]. NATURE, 2012, 483 (7390) : 494 - U155
[10] Desiraju G.R., 1999, The Weak Hydrogen Bond

← 1 2 3 4 →