Adamantane Derivatives Containing Thiazole Moiety: Synthesis, Antiviral and Antibacterial Activity

Stankova, Ivanka; Chuchkov, Kiril; Chayrov, Radoslav; Mukova, Luchia; Galabov, Angel S.; Marinkova, Dessislava; Danalev, Dancho

doi:10.1007/s10989-019-09983-4

Cited by 17 publications

(12 citation statements)

References 25 publications

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“…With the purpose of tuning their photophysical properties, aggregation ability, and targeting, a tailored set of dianionic tridentate N^N^N luminophoric ligands with variable substitution patterns were employed. These moieties included CF 3 (as it favors aggregation , ), tert -butyl ( t bu increases the bulk of the complex and avoids aggregation), and adamantyl ( ada further increases the hydrophobicity and interacts with bacteria − ). To promote the specific interaction with bacterial cells and biofilms, the monodentate pyridine-based coligand was conjugated with a maltohexaose chain, which provides H 2 O solubility yet without electrostatic charge.…”

Section: Introductionmentioning

confidence: 99%

Conjugated Pt(II) Complexes as Luminescence-Switch-On Reporters Addressing the Microenvironment of Bacterial Biofilms

et al. 2021

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In this work, the synthesis, structural and photophysical characterization of six phosphorescent H 2 O-soluble Pt(II) complexes are reported while addressing their emission maxima, photoluminescence quantum yields (Φ L ), lifetimes (τ), aggregation tendency, and microenvironment sensitivity as a function of the substitution pattern on the main tridentate luminophore. Different ancillary ligands, namely, a trisulfonated phosphane and maltohexaose-conjugated pyridines (with or without amide bridges), were introduced and evaluated for the realization of switch-on-photoluminescent labels reporting on the microenvironment sensed in biofilms of Gram + and Gram − models, namely, Staphylococcus aureus and Escherichia coli. With the aid of confocal luminescence micro(spectro)scopy, we observed that selected complexes specifically interact with the biofilms while leaving planktonic cells unlabeled. By using photoluminescence lifetime imaging microscopy, excited-state lifetimes within S. aureus biofilms were measured. The photoluminescence intensities were drastically boosted, and the excited state lifetimes were significantly prolonged upon binding to the viscous biofilm matrix, mainly due to the suppression of radiationless deactivation pathways upon shielding from physical quenching processes, such as interactions with solvent molecules and 3 O 2 . The best performances were attained for non-aggregating complexes with maltohexaose targeting units and without amide bridges. Notably, in the absence of the maltodextrin, a hydrophobic adamantyl moiety suffices to attain a sizeable labeling capacity. Moreover, photoluminescence studies showed that selected complexes can also effectively interact with E. coli biofilms, where the bacterial cells are able to partially uptake the maltodextrin-based agents. In summary, the herein introduced concepts enable the development of specific biofilm reporters providing spatial resolution as well as lifetime-and spectrum-based readouts. Considering that most theragnostic agents reported so far mainly address metabolically active bacteria at the surface of biofilms but without reaching cells deeply immersed in the matrix, a new platform with a clear structure-property correlation is provided for the early detection of such bacterial arrays.

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Section: Introductionmentioning

confidence: 99%

Conjugated Pt(II) Complexes as Luminescence-Switch-On Reporters Addressing the Microenvironment of Bacterial Biofilms

et al. 2021

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“…The authors [ 34 ] synthesized adamantane derivatives (rimantadine and amantadine) modified with glycyl-thiazole ( Figs. 6a, 6b, 6e, and 6f ) and glycyl-thiazole-thiazole molecules ( Figs.…”

Section: Adamantane-type Derivatives With Anti-viral Activitymentioning

confidence: 99%

Physiologically Active Compounds Based on Membranotropic Cage Carriers–Derivatives of Adamantane and Polyhedral Boron Clusters (Review)

Авдеева

Garaev

Малинина

et al. 2022

Russ. J. Inorg. Chem.

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Data on compounds based on cage structures―boron clusters (polyhedral boron hydrides, carboranes, metallacarboranes) and compounds of the adamantane series, which possess physiological activity, have been generalized. The main emphasis is placed on the antiviral activity of the compounds. The mechanism of the possible action of the replication inhibitors of influenza A virus strains is considered, the molecular model of viroporin inhibitors is discussed. The proposed model consists of a cage hydrophobic core that performs the function of a membranotropic carrier (a boron cluster or adamantane fragment), into which physiologically active functional groups are introduced. The relationship between the structure of the cage compound with the introduced substitute and the biologically active properties of this molecular structure has been analyzed.

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“…Its incorporation into EDOT might result in a PEDOT variant with enhanced antiviral properties or decreased cytotoxicity. 27 We hypothesized that incorporating these biologically important side groups into PEDOT would create hybrid materials of particular interest for biointerfacing.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of maleimide functionalized poly(3,4-ethylenedioxythiophene) (PEDOT) polymers

et al. 2022

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Adamantane Derivatives Containing Thiazole Moiety: Synthesis, Antiviral and Antibacterial Activity

Cited by 17 publications

References 25 publications

Conjugated Pt(II) Complexes as Luminescence-Switch-On Reporters Addressing the Microenvironment of Bacterial Biofilms

Conjugated Pt(II) Complexes as Luminescence-Switch-On Reporters Addressing the Microenvironment of Bacterial Biofilms

Physiologically Active Compounds Based on Membranotropic Cage Carriers–Derivatives of Adamantane and Polyhedral Boron Clusters (Review)

Synthesis and characterization of maleimide functionalized poly(3,4-ethylenedioxythiophene) (PEDOT) polymers

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