Synthesis and alkali metal binding properties of novel N-adamantylaza-crown ethers

Mlinarić‐Majerski, Kata; Ramljak, Tatjana Šumanovac

doi:10.1016/s0040-4020(02)00444-1

Cited by 24 publications

(9 citation statements)

References 26 publications

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“…DAC compounds effectively inhibit growth in both cell lines. This is in line with previously published activities on other tumour cell lines and could be related to crown ether affinity for alkali cations (especially for potassium ion), better extraction capabilities and lipophilicity 19 , 20 . For most compounds, A2780/Adr were slightly more resistant as compared to A2780.…”

Section: Discussionsupporting

confidence: 92%

“…The exceptions to the “rule” are DACs with the shortest side chain (DAC-1 and −1Amide). This correlates to their affinity for alkali cations (especially K + ) and better extraction capabilities (Supplementary Tables S1 and S2 ) 19 , 20 .…”

Section: Resultsmentioning

confidence: 88%

“…The synthesis of monoaza-crown ethers and diaza-crown ethers was based on N -alkylation of monoaza- and diaza-18-crown-6 with the corresponding adamantyl tosylates or the coupling reactions with corresponding acyl chlorides followed by reduction of the obtained crown ethers with LiAlH 4 . Detailed syntheses of MAC-2 to MAC-3Amide and DAC-1 to DAC-3Amide are shown in Supplementary information 20 , 21 . Syntheses of new compounds: MAC-1, MAC-1Amide, MAC-4, and MAC-4Amide, as well as DAC-4 and DAC-4Amide are described in the Supplementary information of this paper (Supplementary Figs S1 and S2 ).…”

Section: Resultsmentioning

confidence: 99%

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Crown ethers reverse P-glycoprotein-mediated multidrug resistance in cancer cells

Guberović

Marjanović

Mioč

et al. 2018

Sci Rep

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Multidrug resistance (MDR) is a widespread phenomenon exhibited by many cancers and represents a fundamental obstacle for successful cancer treatments. Tumour cells commonly achieve MDR phenotype through overexpression and/or increased activity of ABC transporters. P-glycoprotein transporter (P-gp, ABCB1) is a major cause of MDR and therefore represents a valuable target for MDR reversal. Several naturally occurring potassium ionophores (e.g. salinomycin) were shown to inhibit P-gp effectively. We have previously shown antitumour activity of a number of 18-crown-6 ether compounds that transport potassium ions across membranes. Here we present data on P-gp inhibitory activity of 16 adamantane-substituted monoaza- and diaza-18-crown-6 ether compounds, and their effect on MDR reversal in model cell lines. We show that crown ether activity depends on their lipophilicity as well as on the linker to adamantane moiety. The most active crown ethers were shown to be more effective in sensitising MDR cells to paclitaxel and adriamycin than verapamil, a well-known P-gp inhibitor. Altogether our data demonstrate a novel use of crown ethers for inhibition of P-gp and reversal of MDR phenotype.

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Section: Discussionsupporting

confidence: 92%

Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 99%

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Crown ethers reverse P-glycoprotein-mediated multidrug resistance in cancer cells

Guberović

Marjanović

Mioč

et al. 2018

Sci Rep

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“…5 In addition, there are number of papers describing crown ethers which contain a polycyclic moiety. 6 Incorporation of a rigid polycyclic molecule such as cubane, 7 pentacycloundecane, 8 3,5-disubstituted-4-oxaheksacy-clo[5.4.1.0 2,6 .0 3,10 .0 5,9 .0 8,11 ]dodecane, 9 2-oxaadamantane 6b,10 and adamantane 10b,11 into crown ethers should affect their conformational mobility and complexation abilities. The lipophilic polycyclic moiety is expected to increase the solubility of crown ethers in nonpolar media and thereby increase their ability for metal ion complexation and ion transport.…”

Section: Introductionmentioning

confidence: 99%

“…11 In the case of methylene linkage, complexation ability of nitrogen atom is preserved, but the resulting ligand is more flexible. In an attempt to rationalize the experimental results and to investigate relationship between conformational flexibility and extraction properties of crown compounds 16, we performed conformational analysis of investigated compounds using Monte Carlo algorithm.…”

Section: Introductionmentioning

confidence: 99%

Alkali Metal Ion Complexation of Adamantane Functionalized Diaza-bibracchial Lariat Ethers

Ramljak¹,

Mlinarić‐Majerski²,

Bertoša³

2012

Croat. Chem. Acta

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Abstract. A series of adamantane functionalized diaza-lariat ethers 1-6 have been prepared and alkali metal picrate extraction profiles determined. The ability of aza-crown ethers 1-6 to extract the alkali metal picrates was compared with that of diaza-18-crown-6 (7) and N,N '-dibenzodiaza-18-crown-6 (8). Na + and K + transport across bulk liquid membrane was also measured. The results of alkali metal cation extraction experiments showed that lariat ethers 2 and 3, in which the adamantane molecule is linked to the diaza-18-crown-6 by amine bond, have better complexation abilities for all cations compared to the parent crown ethers 7 and 8, as well as a significantly higher selectivity for K + than diaza-18-crown-6. However, diazalariat ether 1 showed reduced, and 4-6 negligible extractability towards any of the alkali cations. Monte Carlo conformational analysis pointed to the importance of conformational flexibility of the investigated compounds for their extraction ability of alkali cations.(doi: 10.5562/cca2100)

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Supramolecular Architectures

2024

The Chemistry of Diamondoids

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The influence of molecular interactions is wide ranging, affecting properties as diverse as luminescence, electrical transport (charge hopping and, thus, interstrand mobility and spin coherence length), as well as chemical and mechanical stability. Accurate control of such interactions is needed to allow optimum exploitation of the properties of molecular materials, not only in today's most common optoelectronic devices such as lightemitting diodes (LEDs), field-effect transistors (FETs), and photovoltaic diodes (PVDs), but also in new or emerging applications, for example in the area of artificial noses and muscles or in general for nanoelectromechanical systems (NEMS). Controlled and directed self-organization is the ultimate instrument for achieving such an aim, as it is only by mastering noncovalent interactions that control at the molecular level can be achieved.

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Synthesis and alkali metal binding properties of novel N-adamantylaza-crown ethers

Cited by 24 publications

References 26 publications

Crown ethers reverse P-glycoprotein-mediated multidrug resistance in cancer cells

Crown ethers reverse P-glycoprotein-mediated multidrug resistance in cancer cells

Alkali Metal Ion Complexation of Adamantane Functionalized Diaza-bibracchial Lariat Ethers

Supramolecular Architectures

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