Self-assembly of isomannide-based monoesters of C<sub>18</sub>-fatty acids and their cellular uptake studies

Dhasaiyan, Prabhu; Parekh, Nimisha; Reddy, T. Vijai Kumar; Rani, G. Sandhya; Devi, B.L.A. Prabhavathi; Prasad, B. L. V.

doi:10.1039/c6ra05608c

Cited by 4 publications

(2 citation statements)

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“…Focusing on chiral bio-based materials, among compounds belonging to the chiral pool, a great deal of attention was addressed to isohexides, namely isomannide and isosorbide, used mainly in the polymer, cosmetic, and pharmaceutical industries (Figure 1) [16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

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Control of Molecular Packing in Crystal and Electron Communication of Two Ferrocenyl Moieties across Chiral Isomannide or Isosorbide Bridge

et al. 2023

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Intramolecular electronic communication between electrochemically active groups connected by a bridging moiety can be modified through small changes in the spatial disposition of the redox active moieties and/or by the nature of the central core. In this study, chiral bio-based compounds, namely isomannide and isosorbide, were employed as cheap and easy-to-functionalize chiral scaffolds to bridge two ferrocenyl electroactive moieties. The crystal structures of both bis-ferrocenyl diester complexes were studied and they showed that the chirality of the bridge results in an open or tight helical crystal packing. The electron communication between the two electroactive units in the mixed valent monocations was also investigated using electrochemistry (cyclic voltammetry and differential pulsed voltammetry), and spectroelectrochemistry in the UV-Vis NIR. A computational study through time-dependent DFT was also employed to gain greater insight into the results obtained.

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Section: Introductionmentioning

confidence: 99%

“…isosorbide, used mainly in the polymer, cosmetic, and pharmaceutical industries (Figure 1) [16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Control of Molecular Packing in Crystal and Electron Communication of Two Ferrocenyl Moieties across Chiral Isomannide or Isosorbide Bridge

et al. 2023

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Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

Tangadanchu

Gundabathini

Bethala

et al. 2020

Journal of Heterocyclic Chem

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A new series of isomannide monoundecenoate-based 1,2,3-triazole analogs 6a-e were designed by employing click chemistry in good yields. in vitro bioactive assay manifested that the several target compounds exhibited promising antibacterial and antifungal activities. Notably, compounds having phenyl substituted triazole 6a, and hydroxy phenyl substituted triazole 6b possessed highly selective promising inhibition towards Gram-positive bacterial strains namely Bacillus subtilis and Staphylococcus aureus with MIC value of 3.9 μg/ mL. Further, these potential hybrids (6a and 6b) also exhibited highly impressive antifungal activity against the tested panel of Candida strains with MIC value of 3.9 μg/mL. Based on our in vitro preliminary antimicrobial study, these two compounds 6a and 6b have been identified as potential antimicrobial lead compounds. Moreover, all prepared derivatives were also evaluated for their in vitro cytotoxic activities against A549, MCF7, DU145 and HeLa cancer cell lines. The results indicated that only the hydroxy phenyl substituted triazole analog 6b displayed good cytotoxic activity towards all tested human cancer cell lines without any significant effects on normal cell line (HUVEC).

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Exploiting isohexide scaffolds for the preparation of chiral ionic liquids tweezers

Zullo

Górecki

Guazzelli

et al. 2021

Journal of Molecular Liquids

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Self-assembly of isomannide-based monoesters of C₁₈-fatty acids and their cellular uptake studies

Abstract: The self-assembling behavior of oleic, elaidic and stearic acid-isomannide glycolipids is revealed.

Cited by 4 publications

References 46 publications

Control of Molecular Packing in Crystal and Electron Communication of Two Ferrocenyl Moieties across Chiral Isomannide or Isosorbide Bridge

Control of Molecular Packing in Crystal and Electron Communication of Two Ferrocenyl Moieties across Chiral Isomannide or Isosorbide Bridge

Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

Exploiting isohexide scaffolds for the preparation of chiral ionic liquids tweezers

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Self-assembly of isomannide-based monoesters of C18-fatty acids and their cellular uptake studies

Abstract: The self-assembling behavior of oleic, elaidic and stearic acid-isomannide glycolipids is revealed.

Cited by 4 publications

References 46 publications

Control of Molecular Packing in Crystal and Electron Communication of Two Ferrocenyl Moieties across Chiral Isomannide or Isosorbide Bridge

Control of Molecular Packing in Crystal and Electron Communication of Two Ferrocenyl Moieties across Chiral Isomannide or Isosorbide Bridge

Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

Exploiting isohexide scaffolds for the preparation of chiral ionic liquids tweezers

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Self-assembly of isomannide-based monoesters of C₁₈-fatty acids and their cellular uptake studies