Molecular drug-organiser: Synthesis, characterization and biological evaluation of penicillin V and/or nalidixic acid calixarene-based podands

Salem, Adel Ben; Sautrey, Guillaume; Fontanay, Stéphane; Duval, Raphaël E.; Regnouf‐de‐Vains, Jean‐Bernard

doi:10.1016/j.bmc.2011.10.031

Cited by 16 publications

(13 citation statements)

References 39 publications

(16 reference statements)

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“…The β-lactams' carboxylic acids were protected as pivavoyloxymethyl esters and reacted with the calixarene diester to form diamide 1 [14]. Although antimicrobial data were not published, this route led the way to an analogue, 2, in which penicillin V was appended to the calixarene [15] and tested against Gram-positive and Gram-negative bacteria [16]. The group also prepared a nalidixic acid delivering prodrug, 3.…”

Section: Incorporation Of Antibiotic Motifsmentioning

confidence: 99%

“…Reaction of the sodium salt of nalidixic acid with dibromopropane followed by Oalkylation of 4-t-butylcalix [4]arene in the 1,3-positions gave the disubstituted calixarene in 65% yield [17]. A fourth derivative incorporating nalidixic acid and penicillin V substituents on opposite rings, 4, was prepared and tested for antimicrobial activity [16]. Given the poor aqueous solubilities of these 4-t-butylcalix [4]arene derivatives, antimicrobial disc-diffusion tests were done in dimethyl sulfoxide with the pure solvent as a control.…”

Section: Incorporation Of Antibiotic Motifsmentioning

confidence: 99%

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Antimicrobial Activity of Calixarenes and Related Macrocycles

et al. 2020

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Calixarenes and related macrocycles have been shown to have antimicrobial effects since the 1950s. This review highlights the antimicrobial properties of almost 200 calixarenes, resorcinarenes, and pillararenes acting as prodrugs, drug delivery agents, and inhibitors of biofilm formation. A particularly important development in recent years has been the use of macrocycles with substituents terminating in sugars as biofilm inhibitors through their interactions with lectins. Although many examples exist where calixarenes encapsulate, or incorporate, antimicrobial drugs, one of the main factors to emerge is the ability of functionalized macrocycles to engage in multivalent interactions with proteins, and thus inhibit cellular aggregation.

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Section: Incorporation Of Antibiotic Motifsmentioning

confidence: 99%

Section: Incorporation Of Antibiotic Motifsmentioning

confidence: 99%

Antimicrobial Activity of Calixarenes and Related Macrocycles

et al. 2020

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“…The biopharmaceutical and biological applications of calixarenes have been reviewed 263, 287 . Examples include 4-tert-butylcalix[4]arene containing penicillin V and nalidixic acid 293 ; calixarene–cyclodextrin heterodimers for sustained release of docetaxel 294 ; and a hybrid liposomal PEGylated calix[4]arene for delivery of curcumin 295 . Other supramolecular structures (or hybrids formed with other nanostructures) that have been used for biomedical applications based on host-guest interactions include cryptands, crown ethers, and pillararenes 260, 263, 296-298 .…”

Section: - Ncs As Platforms For Ddssmentioning

confidence: 99%

Nanocaged platforms: modification, drug delivery and nanotoxicity. Opening synthetic cages to release the tiger

et al. 2017

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Nanocages (NCs) have emerged as a new class of drug-carriers, with a wide range of possibilities in multi-modality medical treatments and theranostics. Nanocages can overcome such limitations as high toxicity caused by anti-cancer chemotherapy or by the nanocarrier itself, due to their unique characteristics. These properties consist of: (1) a high loading-capacity (spacious interior); (2) porous structure (analogous to openings between the bars of the cage); (3) enabling smart release (a key to unlock the cage); and (4) a low likelihood of unfavorable immune responses (the outside of the cage is safe). In this review, we cover different classes of NC structures such as virus-like particles (VLPs), protein NCs, DNA NCs, supramolecular nanosystems, hybrid metal-organic NCs, gold NCs, carbon-based NCs and silica NCs. Moreover, NC-assisted drug delivery including modification methods, drug immobilization, active targeting, and stimulus-responsive release mechanisms are discussed, highlighting advantages, disadvantages and challenges. Finally, translation of NCs into clinical applications, and an up-to-date assessment of the nanotoxicology considerations of NCs are presented.

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“…Similarly, calixarene functionalized with four platinum(II) centers at its lower rim known as calixplatin has also been found as a potential anticancer agent when tested against different human carcinoma cell lines. [74] Salem et al [75] installed quinolone nalidixic acid and the β-lactam penicillin V (two well-known antibiotic heterocycles) at lower rim of calix [4]arene (Scheme 5). The resulting functionalized macrocycle 10 has been evaluated against two Gram-negative and three Gram-positive bacterial strains, using disk diffusion method.…”

Section: S C H E M E 2 Synthesis Of Calixcephem 5 S C H E M E 3 Synthmentioning

confidence: 99%

Functionalized calix[4]arenes as potential therapeutic agents

2017

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Calixarenes, composed of phenolic units linked by methylene bridges at the 2,6-positions, represent a versatile class of macrocyclic compounds in supramolecular chemistry that can host small molecules or ions in their well-defined hydrophobic cavities. In recent years, it has been recognized that this class of compounds has the potential to serve as platform for the design of biological active compounds. Therefore, the calixarenes functionalized with different pharmacophoric groups have been synthesized as target structure by many researchers and were further evaluated for their biological activities. Owing to their promising biological activities such as antiviral, antibacterial, antifungal, and anticancer, the functionalized calixarenes are recently receiving increased attention from pharmaceutical/medicinal chemistry community. In this review, we summarize and discuss the synthetic approaches and the biological potential of functionalized calixarenes, mainly focusing on the selected recent studies for a comprehensive and target-oriented information, which could help in the design and synthesis of new therapeutic agents leading to the development of clinically viable drugs based on these macrocyles. K E Y W O R D Sbiological activity, calixarenes, cone conformation, functionalization, upper/lower rim/annulus

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Molecular drug-organiser: Synthesis, characterization and biological evaluation of penicillin V and/or nalidixic acid calixarene-based podands

Cited by 16 publications

References 39 publications

Antimicrobial Activity of Calixarenes and Related Macrocycles

Antimicrobial Activity of Calixarenes and Related Macrocycles

Nanocaged platforms: modification, drug delivery and nanotoxicity. Opening synthetic cages to release the tiger

Functionalized calix[4]arenes as potential therapeutic agents

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