公开(公告)号：US20230094737A1

公开(公告)日：2023-03-30

申请号：US17943682

申请日：2022-09-13

申请人： San Diego State University Research Foundation

发明人： Byron W. PURSE ,  Dillon BURNS ,  Kristine TEPPANG ,  Raymond LEE ,  Melissa LOKENSGARD

IPC分类号： C07H19/24 ,  C09K11/06 ,  C12Q1/682 ,  C12Q1/686 ,  G01N21/77

摘要： Herein reported are new tricyclic cytidine compounds, such as 8-diethylamino-tC (8-DEA-tC), that respond to DNA and/or RNA duplex formation with up to a 20-fold increase in fluorescent quantum yield as compared with the free nucleoside, depending on neighboring bases. This turn-on response to duplex formation is by far the greatest of any reported nucleoside analogue that can participate in Watson-Crick base pairing. Measurements of the quantum yield of 8-DEA-tC mispaired with adenosine and, separately, opposite an abasic site show that there is almost no fluorescence increase without the formation of correct Watson-Crick hydrogen bonds. Kinetic isotope effects from the use of deuterated buffer show that the duplex protects 8-DEA-tC against quenching by excited state proton transfer. DFT calculations provide a rationale for the observed photophysical properties that is dependent on duplex integrity and the electronic structure of the analogue.

公开(公告)号：US20200262862A1

公开(公告)日：2020-08-20

申请号：US16346708

申请日：2017-11-09

申请人： San Diego State University Research Foundation

发明人： Byron W. PURSE ,  Dillon BURNS ,  Kristine TEPPANG ,  Raymond LEE ,  Melissa LOKENSGARD

IPC分类号： C07H19/24 ,  C12Q1/686 ,  C12Q1/682 ,  C09K11/06 ,  G01N21/77

摘要： Herein reported are new tricyclic cytidine compounds, such as 8-diethylamino-tC (8-DEA-tC), that respond to DNA and/or RNA duplex formation with up to a 20-fold increase in fluorescent quantum yield as compared with the free nucleoside, depending on neighboring bases. This turn-on response to duplex formation is by far the greatest of any reported nucleoside analogue that can participate in Watson-Crick base pairing. Measurements of the quantum yield of 8-DEA-tC mispaired with adenosine and, separately, opposite an abasic site show that there is almost no fluorescence increase without the formation of correct Watson-Crick hydrogen bonds. Kinetic isotope effects from the use of deuterated buffer show that the duplex protects 8-DEA-tC against quenching by excited state proton transfer. DFT calculations provide a rationale for the observed photophysical properties that is dependent on duplex integrity and the electronic structure of the analogue.