Esterase-Sensitive and pH-Controlled Carbon Monoxide Prodrugs for Treating Systemic Inflammation

被引：57

作者：

Ji, Xingyue ^{[1
,2
,3
]}

Pan, Zhixiang ^{[1
,2
]}

Li, Chunjie ^{[4
]}

Kang, Ting ^{[4
]}

De la Cruz, Ladie Kimberly C. ^{[1
,2
]}

Yang, Lingyun ^{[1
,2
]}

Yuan, Zhengnan ^{[1
,2
]}

Ke, Bowen ^{[4
]}

Wang, Binghe ^{[1
,2
]}

机构：

[1] Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA

[2] Georgia State Univ, Ctr Diagnost & Therapeut, Atlanta, GA 30303 USA

[3] Soochow Univ, Coll Pharmaceut Sci, Dept Med Chem, Suzhou 215021, Jiangsu, Peoples R China

[4] Sichuan Univ, West China Hosp, Translat Neurosci Ctr, Lab Anesthesia & Crit Care Med,Dept Anesthesiol, Chengdu 610041, Sichuan, Peoples R China

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2019年 / 62卷 / 06期

基金：

中国国家自然科学基金;

关键词：

CHEMICAL STRATEGY; CO; RELEASE; MOLECULES; LIGHT; COMPLEXES; DELIVERY; INJURY; CELLS; CLICK;

D O I：

10.1021/acs.jmedchem.9b00073

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A bottleneck for developing CO-based therapeutics is the lack of a safe and controllable delivery form. Herein, we describe efforts toward organic CO prodrugs with dual-responsive endogenous triggers. One representative CO prodrug showed significant anti-inflammatory effects both in vitro and in a LPS-simulated systemic inflammation model. These results firmly establish such CO prodrugs as either research tools or candidate compounds for the treatment of systemic inflammation or inflammation related organ injuries.

引用

页码：3163 / 3168

页数：6

共 39 条

[1] μ2-Alkyne dicobalt(0)hexacarbonyl complexes as carbon monoxide-releasing molecules (CO-RMs): probing the release mechanism [J].

Atkin, Anthony J. ;

Williams, Sophie ;

Sawle, Philip ;

Motterlini, Roberto ;

Lynam, Jason M. ;

Fairlamb, Ian J. S. .

DALTON TRANSACTIONS, 2009, (19) :3653-3656

[2] Making Sense of the Cytokine Storm: A Conceptual Framework for Understanding, Diagnosing, and Treating Hemophagocytic Syndromes [J].

Canna, Scott W. ;

Behrens, Edward M. .

PEDIATRIC CLINICS OF NORTH AMERICA, 2012, 59 (02) :329-+

[3] Cardioprotective actions by a water-soluble carbon monoxide-releasing molecule [J].

Clark, JE ;

Naughton, P ;

Shurey, S ;

Green, CJ ;

Johnson, TR ;

Mann, BE ;

Foresti, R ;

Motterlini, R .

CIRCULATION RESEARCH, 2003, 93 (02) :E2-E8

[4] Click, Release, and Fluoresce: A Chemical Strategy for a Cascade Prodrug System for Codelivery of Carbon Monoxide, a Drug Payload, and a Fluorescent Reporter [J].

De La Cruz, Ladie Kimberly C. ;

Benoit, Stephane L. ;

Pan, Zhixiang ;

Yu, Bingchen ;

Maier, Robert J. ;

Ji, Xingyue ;

Wang, Binghe .

ORGANIC LETTERS, 2018, 20 (04) :897-900

[5] Carbon-Monoxide-Releasing Molecules for the Delivery of Therapeutic CO In Vivo [J].

Garcia-Gallego, Sandra ;

Bernardes, Goncalo J. L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) :9712-9721

[6] Carbon monoxide - physiology, detection and controlled release [J].

Heinemann, Stefan H. ;

Hoshi, Toshinori ;

Westerhausen, Matthias ;

Schiller, Alexander .

CHEMICAL COMMUNICATIONS, 2014, 50 (28) :3644-3660

[7] Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide [J].

Henry, Lucas ;

Schneider, Christoph ;

Muetzel, Benedict ;

Simpson, Peter V. ;

Nagel, Christoph ;

Fucke, Katharina ;

Schatzschneider, Ulrich .

CHEMICAL COMMUNICATIONS, 2014, 50 (99) :15692-15695

[8] Strategies toward Organic Carbon Monoxide Prodrugs [J].

Ji, Xingyue ;

Wang, Binghe .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (06) :1377-1385

[9] pH-Sensitive metal-free carbon monoxide prodrugs with tunable and predictable release rates [J].

Ji, Xingyue ;

De La Cruz, Ladie Kimberly C. ;

Pan, Zhixiang ;

Chittavong, Vayou ;

Wang, Binghe .

CHEMICAL COMMUNICATIONS, 2017, 53 (69) :9628-9631

[10] An esterase-activated click and release approach to metal-free CO-prodrugs [J].

Ji, Xingyue ;

Ji, Kaili ;

Chittavong, Vayou ;

Yu, Bingchen ;

Pan, Zhixiang ;

Wang, Binghe .

CHEMICAL COMMUNICATIONS, 2017, 53 (59) :8296-8299

← 1 2 3 4 →