Self-assembling behavior of pyrimidine analogues: Unveiling the factors behind morphological diversity

Banerjee, Pavel; Pyne, Arghajit; Pal, Siddhartha; Karan, Chandan Kumar; Sarkar, Nilmoni

doi:10.1016/j.jcis.2018.03.058

Cited by 12 publications

(24 citation statements)

References 54 publications

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“…On the other hand, spontaneous self-assembly of small molecule drugs such as 5-fluorouracil (5-FU) cause a notable decrease in its drug efficiency. , 5-FU is cheap and extensively used as a chemotherapeutic drug and radiosensitizer. , But, in recent times, the use of 5-FU has been very much restricted because of its systematic toxicity and resistance. − The design of this particular study is based on our recent efforts to explore and understand the supramolecular fibrillar assembly of uracil derivatives, especially 5-FU in different buffers. , Though the ability of small molecules to form ordered structures at the nanoscale is one of the most promising directions in nanotechnology, merely inducing aggregation is not sufficient. The control and understanding of the self-assembly process has great potential for a multitude of future applications .…”

Section: Introductionmentioning

confidence: 99%

“…In our previous work, we have shown that 5-FU can form different fibrillar morphologies in different buffer systems . 5-FU self-assembles through strong intermolecular hydrogen bonding between −NH···OC–. , Interestingly, in pure water, 5-FU cannot form fibrillar structures because of the tight solvation of hydrogen-bonding groups by water molecules . We have introduced a DMSO–water binary mixture of different compositions as a solvent system of 5-FU.…”

Section: Introductionmentioning

confidence: 99%

“…10−14 The design of this particular study is based on our recent efforts to explore and understand the supramolecular fibrillar assembly of uracil derivatives, especially 5-FU in different buffers. 8,15 Though the ability of small molecules to form ordered structures at the nanoscale is one of the most promising directions in nanotechnology, merely inducing aggregation is not sufficient. The control and understanding of the self-assembly process has great potential for a multitude of future applications.…”

Section: ■ Introductionmentioning

confidence: 99%

“…8 between −NH•••OC−. 8,15 Interestingly, in pure water, 5-FU cannot form fibrillar structures because of the tight solvation of hydrogen-bonding groups by water molecules. 18 We have introduced a DMSO−water binary mixture of different compositions as a solvent system of 5-FU.…”

Section: ■ Introductionmentioning

confidence: 99%

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Selective Self-Assembly of 5-Fluorouracil through Nonlinear Solvent Response Modulates Membrane Dynamics

et al. 2020

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Controllable self-assembly and understanding of the interaction between single metabolite fibrils and live-cell membranes have paramount importance in providing minimal treatment in several neurodegenerative disorders. Here, utilizing the nonlinear nature and peculiar hydrogen bonding behavior of the dimethyl sulfoxide (DMSO)−water mixture, the selective selfassembly of a single metabolite 5-fluorouracil (5-FU) is achieved. A direct correlation between water availability and selective selfassembly of 5-FU is ratified from the excited-state dynamics. The specific fibrillar structures of 5-FU exhibit a great potential to modulate live cell membrane fluidity and model membrane lipid distribution. After 5-FU fibril addition, a disorder of H-bonded water molecules arises several layers beyond the first hydration shell of the polar headgroups, which essentially modifies interfacial water structure and dynamics. Overall, our results shed light on the role of solvent to govern specific self-assembly and also lay the foundation accounting for the earlier stage of several diseases and multidrug resistance.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Selective Self-Assembly of 5-Fluorouracil through Nonlinear Solvent Response Modulates Membrane Dynamics

et al. 2020

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“… 23 , 24 Banerjee et al investigated the effect that different functional groups of self-assembling pyrimidine analogues can have on the final fibrillary network. 25 Roviello et al used UV, CD, and light scattering to investigate the formation of supramolecular networks of two thymidyl dipeptides and assess their interactions with biomolecules. 26 To the best of our knowledge, no detailed investigation is currently available on the self-assembly organization or mechanism of cytosine-based gelators.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Nucleoside-Based Gel: Molecular Dynamics Simulation and Characterization of Its Nanoarchitecture and Self-Assembly Mechanism

et al. 2018

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Among the diversity of existing supramolecular hydrogels, nucleic acid-based hydrogels are of particular interest for potential drug delivery and tissue engineering applications because of their inherent biocompatibility. Hydrogel performance is directly related to the nanostructure and the self-assembly mechanism of the material, an aspect that is not well-understood for nucleic acid-based hydrogels in general and has not yet been explored for cytosine-based hydrogels in particular. Herein, we use a broad range of experimental characterization techniques along with molecular dynamics (MD) simulation to demonstrate the complementarity and applicability of both approaches for nucleic acid-based gelators in general and propose the self-assembly mechanism for a novel supramolecular gelator, N4-octanoyl-2′-deoxycytidine. The experimental data and the MD simulation are in complete agreement with each other and demonstrate the formation of a hydrophobic core within the fibrillar structures of these mainly water-containing materials. The characterization of the distinct duality of environments in this cytidine-based gel will form the basis for further encapsulation of both small hydrophobic drugs and biopharmaceuticals (proteins and nucleic acids) for drug delivery and tissue engineering applications.

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Advances in Self‐Assembly of Metabolite Nanostructures: Physiology, Pathology and Nanotechnology

2022

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Metabolites are immensely important for the routine function of every cell and take part in numerous physiological processes. Yet, in excess amounts, metabolites can self-assemble, giving rise to cytotoxic amyloid-like structures. Such structures may underlie some of the pathological effects associated with inborn error of metabolism disorders characterized by metabolite accumulation due to genetic mutations. Furthermore, such assemblies may have a role in neurodegenerative disorders due to abnormal accumulation. On the other hand, metabolites were shown to form functional assemblies in various organisms. Interestingly, various proteins and peptides showing amyloidal properties also have physiological roles and have been used for the fabrication of functional nanomaterials. Following this notion, metabolite self-assembly could also be utilized due to several advantages including exceptional biocompatibility, inexpensive production, facile modeling and biodegradability in vivo. Co-assembly of metabolites resulting in high rigidity can be further used in different biomedical and nanotechnological applications. Metal-coordinated metabolite assemblies can be used as electrocatalysts in energy harvesting applications. Consequently, the study of metabolite selfassemblies is not only crucial in order to understand their role in normal physiology and in pathology, but can also uncover a new route in exploring the fabrication of organic, biocompatible structures for material sciences and various technological applications.

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Self-assembling behavior of pyrimidine analogues: Unveiling the factors behind morphological diversity

Cited by 12 publications

References 54 publications

Selective Self-Assembly of 5-Fluorouracil through Nonlinear Solvent Response Modulates Membrane Dynamics

Selective Self-Assembly of 5-Fluorouracil through Nonlinear Solvent Response Modulates Membrane Dynamics

Supramolecular Nucleoside-Based Gel: Molecular Dynamics Simulation and Characterization of Its Nanoarchitecture and Self-Assembly Mechanism

Advances in Self‐Assembly of Metabolite Nanostructures: Physiology, Pathology and Nanotechnology

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