Naphthalene Imide Conjugates: Formation of Supramolecular Assemblies, and the Encapsulation and Release of Dyes through DNA-Mediated Disassembly.
We report the synthesis of two new amphiphilic conjugates 1 and 2 based on naphthalene di- and monoimide chromophores and the investigation of their photophysical, self-assembly and DNA-binding properties. These conjugates showed aqueous good solubility and exhibited strong interactions with DNA and polynucleotides such as poly(dG⋅dC)-poly(dG⋅dC) and poly(dA⋅dT)-poly(dA⋅dT). The interaction of these conjugates with DNA was evaluated by photo- and biophysical techniques. These studies revealed that the conjugates interact with DNA through intercalation with association constants in the order of 5-8×10(4)  M(-1) . Of these two conjugates, bolaamphiphile 1 exhibited a supramolecular assembly that formed vesicles with an approximate diameter of 220 nm in the aqueous medium at a critical aggregation concentration of 0.4 mM, which was confirmed by SEM and TEM. These vesicular structures showed a strong affinity for hydrophobic molecules such as Nile red through encapsulation. Uniquely, when exposed to DNA the vesicles disassembled, and therefore this transformation could be utilised for the encapsulation and release of hydrophobic molecules by employing DNA as a stimulus.
Photosciences and Photonics Section, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Trivandrum 695 019 (India).
Balaraman H
BH
Shankar
Photosciences and Photonics Section, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Trivandrum 695 019 (India).
Dhanya T
DT
Jayaram
Photosciences and Photonics Section, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Trivandrum 695 019 (India). rama@niist.res.in, d.ramaiah@gmail.com, rama@rrljorhat.res.in.|CSIR-North East Institute of Science and Technology (CSIR-NEIST), Jorhat 785 006, Assam (India). rama@niist.res.in, d.ramaiah@gmail.com, rama@rrljorhat.res.in.
Danaboyina
D
Ramaiah
D004396:Coloring Agents / Q000737:chemistry*; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D011119:Polynucleotides / Q000737:chemistry* / Q000378:metabolism
D004396:Coloring Agents; D009281:Naphthalenes; D011119:Polynucleotides; C031721:naphthalene; D004247:DNA
DNA binding; amphiphiles; naphthalene imides; self-assembly; vesicles