Fluorinated diphenylalanine analogue based supergelators: a stencil that accentuates the sustained release of antineoplastic drugs

Tiwari, Preeti; Gupta, Arindam; Mehra, Radha Rani; Khan, Nasreen; Harjit, Jeena; Ashby, Charles R.; Basu, Anindya; Tiwari, Amit K.; Singh, Manju; Konar, Anita Dutt

doi:10.1080/10610278.2020.1808892

Cited by 11 publications

(7 citation statements)

References 42 publications

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“…The hydrophobic surface modification method that has been widely used so far is the use of fluorine compounds such as poly(tetrafluoroethylene) (PTFE, Teflon) and perfluoroalkyl groups. − Because fluorine has a small atomic diameter (42 pm) and a large electronegativity (3.98), it is advantageous for lowering the surface free energy. − Stable fluorinated groups decrease the van der Waals potential with the result that electrostatic interactions limit contact between the solid and liquid phases, resulting in wider contact angles . However, several recent reports have shown that the risk of the use of fluorine-based compounds involves risks of environmental contamination and human health issues such as incurable diseases (e.g., thyroid disease, cancer, and Alzheimer’s syndrome), immune disorders, and hormonal disorders. − In addition, a rough-textured surface and low surface energy are required to form a hydrophobic surface.…”

Section: Introductionmentioning

confidence: 99%

Hydrophobic Mesoporous Silica Particles Modified With Nonfluorinated Alkyl Silanes

Pyo

Chang

2021

ACS Omega

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This work reports the preparation of hydrophobic mesoporous silica particles (MSPs) modified with nonfluorinated alkyl silanes. Alkyl silanes were grafted onto the surface of the MSPs as a function of the length of nonfluorinated alkyl chains such as propyltriethoxysilane (C3), octyltriethoxysilane (C8), dodecyltriethoxysilane (C12), and octadecyltriethoxysilane (C18). Moreover, the grafting of the different alkyl silanes onto the surface of MSPs to make them hydrophobic was demonstrated using different conditions such as by changing the pH (0, 4, 6, 8, and 13), solvent type (protic and aprotic), concentration of silanes (0, 0.12, 0.24, 0.36, 0.48, and 0.60 M), reaction time (1, 2, 3, and 4 days), and reaction temperature (25 and 40 °C). The contact angles of the alkyl silane-modified MSPs were increased as a function of the alkyl chain lengths in the order of C18 > C12 > C8 > C3, and the contact angle of C18-modified MSPs was 4 times wider than that of unmodified MSPs. The unmodified MSPs had a contact angle of 25.3°, but C18-modified MSPs had a contact angle of 102.1°. Furthermore, the hydrophobicity of the nonfluorinated alkyl silane-modified MSPs was also demonstrated by the adsorption of a hydrophobic lecithin compound, which showed the increase of lecithin adsorption as a function of the alkyl chain lengths. The cross-linking ratios of the modified silanes on the MSPs were confirmed by solid-state 29Si-MAS nuclear magnetic resonance (NMR) measurement. Consequently, the hydrophobic modification on MSPs using nonfluorinated alkyl silanes was best preferred in a protic solvent, with a reaction time of ∼24 h at 25 °C and at a high concentration of silanes.

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Section: Introductionmentioning

confidence: 99%

Hydrophobic Mesoporous Silica Particles Modified With Nonfluorinated Alkyl Silanes

Pyo

Chang

2021

ACS Omega

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“…To validate the biological evaluation results of the Compounds we performed DFT studies where we calculated three parameters: a) Log P values (that gives a measure of the extent of hydrophobicity); b) HOMO/LUMO difference and c) the zero‐point vibrational energy of the Compounds I–IX ( Figure 6, Table 2). [37–40] The energy minimized structures of the Compounds are presented in Figure 6.…”

Section: Resultsmentioning

confidence: 99%

Substituent Orchestration in Dimethylquinoxaline Derivatives: A Tool for Fishing Out Appropriate CDK5 Inhibitors as Potential Therapeutics for Alzheimer's

Jain

Gupta

Karthikeyan

et al. 2022

Chemistry & Biodiversity

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A set of new heterocyclic analogs (Compounds I-IX), comprising of 6,7 dimethyl Quinoxalines were found to be active against the receptor GSK3β (Compounds IV-V) (Chem. Biodiversity 2021, 18, e2100364). In an effort to modulate effective CDK5 inhibitors herein our hypothesis underpinned to fish out an appropriate derivative from the same quinoxaline series, as these two targets GSK3β and CDK5 shared structural resemblance with each other. Aligned to the goal we have synthesized Compounds I-IX, characterized them using a combination of spectroscopic techniques and evaluated their activities against CDK5. Our analysis reflected that the adjacently located alkoxy/hydroxy functionality derivatives namely Compounds III and VI, to be the most potent (micromolar) amongst others in the series, backed by Density Functional Theory (DFT) calculations and molecular modelling studies. Also, the efficacy of the Compounds I-IX, were monitored in few other members of the CMGC family namely DYRK1A, CLK1and CK1δ that have been known to be directly involved in hyperphosphorylation of Tau. But unfortunately in none of the targets, our quinoxaline series were active. In a nut shell further optimisation of these intelligent nucleus, would not only lead to the discovery of novel pharmacophores, but also marked selectivity against a pool of kinases, thereby implementing a distinct roadmap towards the design of potential therapeutics against Alzheimer's.

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“…Analogues of di-L-phenylalanine are currently being widely investigated in drug delivery, due to the mechanical and morphological advantages. One example is the work reported by Konar et al, in which fluorinated di-L-phenylalanine analogues were used to sustained release of antineoplastic drugs [ 77 ]. They reported the synthesis of two hydrogelators, ( I ) Fmoc–(4-F)–Phe–Phe–OH and ( II ) Fmoc–(3-F)–Phe–Phe–OH, and performed rheological tests to evaluate their mechanical integrity.…”

Section: Hydrogel Mechanical Properties and Stability For Drug Deliverymentioning

confidence: 99%

“…They reported the synthesis of two hydrogelators, ( I ) Fmoc–(4-F)–Phe–Phe–OH and ( II ) Fmoc–(3-F)–Phe–Phe–OH, and performed rheological tests to evaluate their mechanical integrity. The data showed that hydrogelator I (G’(storage modulus) = 1700 Pa) was a stronger gel than hydrogelator II (G’ = 500 Pa) for gels of the same concentration, highlighting the importance of the fluorine position in regulating the mechanical properties [ 77 ]. Further analysis employing FTIR and powder X-ray diffraction (PXRD) indicated a β-sheet structure, which is believed to assemble due to the effective π-π interactions between the aromatic rings of the phenylalanine and Fmoc moieties [ 77 ].…”

Section: Hydrogel Mechanical Properties and Stability For Drug Deliverymentioning

confidence: 99%

“…Schneider and Pochan have reported peptides that can respond to distinct external stimuli and fold into ‘facially amphiphilic’ β-hairpins, and consequently self-assemble into rigid hydrogels [ 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 83 , 84 , 85 , 86 , 87 , 88 , 89 ]. This class of peptides is sometimes named the MAX1 family, as MAX1 is the parent sequence.…”

Section: Hydrogel Mechanical Properties and Stability For Drug Deliverymentioning

confidence: 99%

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Peptide-Based Supramolecular Hydrogels as Drug Delivery Agents: Recent Advances

Oliveira

Gomes

Ferreira

et al. 2022

Gels

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Supramolecular peptide hydrogels have many important applications in biomedicine, including drug delivery applications for the sustained release of therapeutic molecules. Targeted and selective drug administration is often preferential to systemic drug delivery, as it can allow reduced doses and can avoid the toxicity and side-effects caused by off-target binding. New discoveries are continually being reported in this rapidly developing field. In this review, we report the latest developments in supramolecular peptide-based hydrogels for drug delivery, focusing primarily on discoveries that have been reported in the last four years (2018–present). We address clinical points, such as peptide self-assembly and drug release, mechanical properties in drug delivery, peptide functionalization, bioadhesive properties and drug delivery enhancement strategies, drug release profiles, and different hydrogel matrices for anticancer drug loading and release.

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Fluorinated diphenylalanine analogue based supergelators: a stencil that accentuates the sustained release of antineoplastic drugs

Cited by 11 publications

References 42 publications

Hydrophobic Mesoporous Silica Particles Modified With Nonfluorinated Alkyl Silanes

Hydrophobic Mesoporous Silica Particles Modified With Nonfluorinated Alkyl Silanes

Substituent Orchestration in Dimethylquinoxaline Derivatives: A Tool for Fishing Out Appropriate CDK5 Inhibitors as Potential Therapeutics for Alzheimer's

Peptide-Based Supramolecular Hydrogels as Drug Delivery Agents: Recent Advances

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