Expanding the Toolbox of Target Directed Bio-Orthogonal Synthesis: In Situ Direct Macrocyclization by DNA Templates
Ritapa Chaudhuri
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A and 2B Raja S.C. Mullick Road, Jadavpur, Kolkata, 700099 India
Search for more papers by this authorThumpati Prasanth
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A and 2B Raja S.C. Mullick Road, Jadavpur, Kolkata, 700099 India
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research Kolkata, Chunilal Bhawan,168, Maniktala Main Road, P.O. Bengal Chemicals, P.S. Phoolbagan, Kolkata, 700054 India
Search for more papers by this authorCorresponding Author
Dr. Jyotirmayee Dash
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A and 2B Raja S.C. Mullick Road, Jadavpur, Kolkata, 700099 India
Search for more papers by this authorRitapa Chaudhuri
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A and 2B Raja S.C. Mullick Road, Jadavpur, Kolkata, 700099 India
Search for more papers by this authorThumpati Prasanth
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A and 2B Raja S.C. Mullick Road, Jadavpur, Kolkata, 700099 India
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research Kolkata, Chunilal Bhawan,168, Maniktala Main Road, P.O. Bengal Chemicals, P.S. Phoolbagan, Kolkata, 700054 India
Search for more papers by this authorCorresponding Author
Dr. Jyotirmayee Dash
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A and 2B Raja S.C. Mullick Road, Jadavpur, Kolkata, 700099 India
Search for more papers by this authorAbstract
Herein, we demonstrate for the first time that noncanonical DNA can direct macrocyclization-like challenging reactions to synthesize gene modulators. The planar G-quartets present in DNA G-quadruplexes (G4s) provide a size complementary reaction platform for the bio-orthogonal macrocyclization of bifunctional azide and alkyne fragments over oligo- and polymerization. G4s immobilized on gold-coated magnetic nanoparticles have been used as target templates to enable easy identification of a selective peptidomimetic macrocycle. Structurally similar macrocycles have been synthesized to understand their functional role in the modulation of gene function. The innate fluorescence of the in situ formed macrocycle has been utilized to monitor its cellular localization using a G4 antibody and its in cell formation from the corresponding azide and alkyne fragments. The successful execution of in situ macrocyclization in vitro and in cells would open up a new dimension for target-directed therapeutic applications.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
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