Organic CO Prodrugs: Structure–CO‐Release Rate Relationship Studies

• Published in: Chemistry : a European journal Vol. 23; no. 41; pp. 9838 - 9845
• Main Authors: Pan, Zhixiang, Chittavong, Vayou, Li, Wei, Zhang, Jun, Ji, Kaili, Zhu, Mengyuan, Ji, Xingyue, Wang, Binghe
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 21.07.2017; Wiley Subscription Services, Inc
• Subjects: Animals; Aqueous solutions; Bacteria; Carbon monoxide; Carbon Monoxide - chemistry; Carbon Monoxide - metabolism; Cell Survival - drug effects; Chemical compounds; Chemistry; Chemistry, Multidisciplinary; click and release; Drug Design; Drugs; Hydrogen-Ion Concentration; Kinetics; Mammals; metal free; Mice; Microscopy, Fluorescence; Myoglobin - chemistry; Myoglobin - metabolism; Physical Sciences; Prodrugs; Prodrugs - chemical synthesis; Prodrugs - chemistry; Prodrugs - toxicity; RAW 264.7 Cells; release rate; Science & Technology; Water - chemistry; DESIGN; DIELS-ALDER REACTIONS; PHOTOCORMS; COMPLEXES; carbon monoxide; click and release; prodrugs; metal free; MOLECULES; DELIVERY; VISIBLE-LIGHT; CARBON-MONOXIDE; release rate; CLICK; FLUORESCENT-PROBE
• ISSN: 0947-6539; 1521-3765; 1521-3765
• DOI: 10.1002/chem.201700936

Carbon monoxide (CO) is an endogenously produced gasotransmitter in mammals, and may have signaling roles in bacteria as well. It has many recognized therapeutic effects. A significant challenge in this field is the development of pharmaceutically acceptable forms of CO delivery with controllable and tunable release rates. Herein, the structure–release rate studies of the first class of organic CO prodrugs that release CO in aqueous solution at neutral pH is described. Structure–CO‐release rate relationship studies of organic CO prodrugs reveal that CO releasing rate can be tuned by modifying the nature of the linker, substituents on dienone ring or linker, and the length of the linker.