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Functionalized Nucleosides as Supramolecular Synthons and Probes Seergazhi G. Srivatsan* Indian Institute of Science Education and Research (IISER), Pune Dr. Homi Bhabha Road, Pashan, Pune 411008, India *E-mail: [email protected] Remarkable recognition and precise folding properties have rendered nucleic acids as useful supramolecular synthons for constructing programed architectures for applications in nanotechnology. However, scalability and fabrication of nucleic acid nanostructures still remain a major challenge. In this context, the basic components of nucleic acids, nucleosides and nucleotides, when appropriately modified can serve as useful supramolecular synthons and probes. In this presentation, a simple design strategy to construct a new family of supramolecular nucleolipid synthons will be presented. The nucleolipids are made of a heterobicycle-conjugated nucleobase, which serves as the head group and environment- sensitive fluorophore, and classical fatty acid acyl chains attached to the sugar residue as the amphiphilic tail. Depending on the type of modification on the base and sugar residues the nucleolipids self-organize into supramolecular gels, which show aggregation-induced enhanced fluorescence, self-sorting behaviour and surface-switchable properties. 1,2 In the second part of the talk, development of multifunctional nucleoside probes that enable the probing of non-canonical nucleic acid structural motifs in real time, in 3-dimension and in cellular environment will be presented. 3,4

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Page 1: Functionalized Nucleosides as Supramolecular …...Functionalized Nucleosides as Supramolecular Synthons and Probes Seergazhi G. Srivatsan* Indian Institute of Science Education and

Functionalized Nucleosides as Supramolecular Synthons and Probes

SeergazhiG.Srivatsan*IndianInstituteofScienceEducationandResearch(IISER),Pune

Dr.HomiBhabhaRoad,Pashan,Pune411008,India

*E-mail:[email protected]

Remarkable recognition and precise folding properties have rendered nucleic acids as useful supramolecular synthons for constructing programed architectures for applications in nanotechnology. However, scalability and fabrication of nucleic acid nanostructures still remain a major challenge. In this context, the basic components of nucleic acids, nucleosides and nucleotides, when appropriately modified can serve as useful supramolecular synthons and probes. In this presentation, a simple design strategy to construct a new family of supramolecular nucleolipid synthons will be presented. The nucleolipids are made of a heterobicycle-conjugated nucleobase, which serves as the head group and environment-sensitive fluorophore, and classical fatty acid acyl chains attached to the sugar residue as the amphiphilic tail. Depending on the type of modification on the base and sugar residues the nucleolipids self-organize into supramolecular gels, which show aggregation-induced enhanced fluorescence, self-sorting behaviour and surface-switchable properties.1,2 In the second part of the talk, development of multifunctional nucleoside probes that enable the probing of non-canonical nucleic acid structural motifs in real time, in 3-dimension and in cellular environment will be presented.3,4

Page 2: Functionalized Nucleosides as Supramolecular …...Functionalized Nucleosides as Supramolecular Synthons and Probes Seergazhi G. Srivatsan* Indian Institute of Science Education and

References

[1] Nuthanakanti,A.;Srivatsan,S.G.ACSAppl.Mater.Interfaces,2017,9,22864–22874.[2] Nuthanakanti,A.;Srivatsan,S.G.Nanoscale2016,8,3607–3619.[3] Nuthanakanti, A.; Boerneke, M. A.; Hermann, T.; Srivatsan S. G.Angew. Chem. Int. Ed.

2017,56,2640–2644.[4] Manna,S.;Sarkar,D.;Srivatsan,S.G.J.Am.Chem.Soc.2018,140,12622–12633.

www.premc.org/suprabio [email protected]