Naphthalene Imide Conjugates: Formation of Supramolecular Assemblies, and the Encapsulation and Release of Dyes through DNA‐Mediated Disassembly

Shankar, Balaraman H.; Jayaram, Dhanya T.; Ramaiah, Danaboyina

doi:10.1002/chem.201502955

Cited by 12 publications

(8 citation statements)

References 59 publications

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“…A few important applications of these functionalized systems have been explored. First, Ramaiah and co-workers reported two new water-soluble amphiphilic conjugates based on naphthalene di- and monoimide chromophores (134, 135) , and investigated their photophysical, self-assembly, and DNA-binding properties . These amphiphilic conjugates exhibited strong interactions with DNA and polynucleotides , for example poly(dG·dC)–poly(dG·dC) and poly(dA·dT)–poly(dA·dT), on the order of 5–8 × 10 –4 M –1 , which was evaluated by photo- and biophysical techniques.…”

Section: Supramolecular Self-assemblymentioning

confidence: 99%

“…First, Ramaiah and co-workers reported two new water-soluble amphiphilic conjugates based on naphthalene di-and monoimide chromophores (134,135), and investigated their photophysical, self-assembly, and DNAbinding properties. 168 These amphiphilic conjugates exhibited strong interactions with DNA and polynucleotides, for example poly(dG•dC)−poly(dG•dC) and poly(dA•dT)−poly(dA•dT), on the order of 5−8 × 10 −4 M −1 , which was evaluated by photo-and biophysical techniques. Interestingly, the amphiphilic conjugate (135) assembled into vesicular aggregates with an approximate diameter of 220 nm in aqueous medium, and these vesicular structures showed a strong affinity for hydrophobic molecules, such as Nile red.…”

Section: Chemical Reviewsmentioning

confidence: 99%

See 1 more Smart Citation

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

et al. 2016

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This comprehensive review surveys developments over the past decade in the field of naphthalene diimides (NDIs). It explores their application toward: supramolecular chemistry; sensors; host-guest complexes for molecular switching devices, such as catenanes and rotaxanes; ion-channels by ligand gating; gelators for sensing aromatic systems; catalysis through anion-π interactions; and NDI intercalations with DNA for medicinal applications. We have also explored new designs, synthesis, and progress in the field of core-substituted naphthalene diimides (cNDIs), and their implications in areas such as artificial photosynthesis and solar cell technology. Also presented are some interesting synthetic routes and procedures that can be used toward further development of NDI-bearing compounds for future applications. Finally, we conclude with our views on NDI chemistry for future research endeavors, and we outline what we believe are the key obstacles that need to be overcome for NDIs to see real world applications.

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Section: Supramolecular Self-assemblymentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

et al. 2016

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“…In addition, the polycyclic spacer assists the peptidic bolas to self-organize in an ordered configuration via aromatic stacking. Polycyclic compounds with naphthalene units such as perylene diimide, , naphthalene diimide, and pyrene have been employed to prepare peptidic bolas with photoluminescence.…”

Section: Applications Of the Self-assembled Peptidic And Amino Acid B...mentioning

confidence: 99%

Self-Assembling Peptidic Bolaamphiphiles for Biomimetic Applications

Lee

Kim

Lee

2021

ACS Biomater. Sci. Eng.

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Bolaamphiphile, which is a class of amphiphilic molecules, has a unique structure of two hydrophilic head groups at the ends of the hydrophobic center. Peptidic bolaamphiphiles that employ peptides or amino acids as their hydrophilic groups exhibit unique biochemical activities when they self-organize into supramolecular structures, which are not observed in a single molecule. The self-assembled peptidic bolaamphiphiles hold considerable promise for imitating proteins with biochemical activities, such as specific affinity toward heterogeneous substances, a catalytic activity similar to a metalloenzyme, physicochemical activity from harmonized amino acid segments, and the capability to encapsulate genes like a viral vector. These diverse activities give rise to large research interest in biomaterials engineering, along with the synthesis and characterization of the assembled structures. This review aims to address the recent progress in the applications of peptidic bolaamphiphile assemblies whose densely packed peptide motifs on their surface and their stacked hydrophobic centers exhibit unique protein-like activity and designer functionality, respectively.

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“…Amphiphiles consisting of π-conjugated chromophores − produce diverse nanostructures by directional molecular interaction. They exhibit low critical aggregation concentration (CAC), high thermal stability, and rich photophysical properties and therefore appear to be better candidates than classical surfactants as supramolecular biomaterials. − In this context, the surface functional group display of the self-assembled structures is an important issue that strongly impacts the multivalent interaction with a desired biological target and therefore influences the biological functions. , We have recently reported − a new class of unsymmetric π-amphiphiles consisting of a hydrophobic naphthalene diimide (NDI) central chromophore, appended with different hydrophilic wedge/functional group in its two opposite arms.…”

Section: Introductionmentioning

confidence: 99%

Directional Supramolecular Assembly of π-Amphiphiles with Tunable Surface Functionality and Impact on the Antimicrobial Activity

et al. 2019

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This article elucidates H-bonding-regulated directional supramolecular assembly of naphthalene diimide (NDI)-derived unsymmetric cationic bola-shaped π-amphiphiles and systematic investigations on the thermodynamics of their interaction with bacteria mimic lipid vesicles and antimicrobial activity with mechanistic insights. Four NDIamphiphiles (NDI-1, NDI-2, NDI-3, and NDI-2a) have been studied, all of which contain a central NDI chromophore, a nonionic wedge, an amine containing a head group, and a hydrazide group. In NDI-2 and NDI-2a, the hydrophilic wedge and the head group (pyridine) are the same but the location of the hydrazide group is different. On the basis of this difference, the pyridyl groups are displayed at the outer and inner walls of the vesicle, respectively. Isothermal titration calorimetry (ITC) studies revealed the spontaneous interaction of NDI-2 assembly with bacteria membrane mimic DPPE liposome (ΔG = −6.35 kcal/mol), whereas the NDI-2a assembly did not interact at all, confirming a strong influence of the H-bonding-regulated functional group display. On the other hand, the location of the hydrazide group remains the same in NDI-1, NDI-2, and NDI-3, but they differ in the head group structure. ITC binding studies confirmed spontaneous interaction of all three assemblies with DPPE liposome with negative ΔG values following the order NDI-1 > NDI-2 > NDI-3, indicating significant influence of the structure of the head group on the interaction with the model membrane. In fact, in all cases, the interaction was favorable both by enthalpy and entropy contribution, indicating dual involvement of the electrostatic interaction and hydrophobic effect. Notably, ΔS value for NDI-1 containing a tertiary amine head group was found to be significantly higher than that for NDI-3 containing a primary amine, which is attributed to the enhanced hydrophobic effect in the former case. Furthermore, ITC experiments revealed no interaction by any of these assemblies with the mammalian cell membrane mimic liposome, indicating their high selectivity toward bacterial membranes. Antimicrobial activity studies showed NDI-2 to be lethal selectively against Gram-positive bacteria, whereas NDI-2a did not show any activity. NDI-3 with a primary amine showed moderate activity but no selectivity over the erythrocytes. NDI-1 with the tertiary amine group was found to be the most outstanding candidate, exhibiting broad-spectrum antimicrobial activity with very low minimum inhibitory concentration values of 15.8 and 62 μg/mL for Staphylococcus aureus and Escherichia coli, respectively, and high selectivity over erythrocytes. These results fully corroborate with the physical insights obtained from the ITC studies on their interaction with the model liposome. Control molecules, lacking either the NDI chromophore or the hydrazide nonionic containing wedge, did not exhibit any notable antibacterial activity. Live-dead assay with fluorescence microscopy studies indicated that the antimicrobial activity of NDI-1 operates through the ...

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Naphthalene Imide Conjugates: Formation of Supramolecular Assemblies, and the Encapsulation and Release of Dyes through DNA‐Mediated Disassembly

Cited by 12 publications

References 59 publications

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

Self-Assembling Peptidic Bolaamphiphiles for Biomimetic Applications

Directional Supramolecular Assembly of π-Amphiphiles with Tunable Surface Functionality and Impact on the Antimicrobial Activity

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