Synthesis of 7-azaserotonin: its photophysical properties associated with excited state proton transfer reaction.
We report the synthesis of 3-(2-aminoethyl)-5-ol-1H-pyrrolo[2,3-b]pyridine (7-azaserotonin), which may potentially serve as an agonist or antagonist of serotonin receptors. In alcohols, the solvent (e.g., ethanol) catalyzed proton-transfer reaction takes place for 7-azaserotonin in the excited state, resulting in dual emission. Conversely, excited-state deprotonation takes place in neutral aqueous solution. The unique excitation behavior makes 7-azaserotonin versatile as a potential bioprobe.
Wu
Pei-Wen
PW
Department of Chemistry, National Taiwan University, Taipei 106, Taiwan, and Industrial Technology Research Institute, Chemical Engineering Division, Room 313, Building 17, 321, Kuang Fu Road, Section 2, Hsin Chu 300, Taiwan.
Hsieh
Wan-Ting
WT
Cheng
Yi-Ming
YM
Wei
Ching-Yen
CY
Chou
Pi-Tai
PT
D010777:Photochemistry; D011522:Protons; D012701:Serotonin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C523473:7-azaserotonin; D011522:Protons; D012701:Serotonin