Solvent effects on guanidinium-anion interactions and the problem of guanidinium Y-aromaticity

Rozas, Isabel; Sánchez‐Sanz, Goar; Alkorta, Ibón; Elguero, José

doi:10.1002/poc.3099

Cited by 21 publications

(16 citation statements)

References 43 publications

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“…As the molecules were encapsulated into multilamellar liposomes, the guanidine subunit remained on the outer side of the bilayer pointing outward and thus was enabling the formed vesicle to engage in surface recognition. Supramolecular binding mediated with these guanidine sites is feasible since it is known from the literature that guanidine forms parallel hydrogen bonds with oxoanions [ 48 ] and the same is true for the studied adamantyl aminoguanidines [ 49 ].…”

Section: Adamantane Derivatives In Liposomesmentioning

confidence: 99%

Adamantane in Drug Delivery Systems and Surface Recognition

et al. 2017

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The adamantane moiety is widely applied in design and synthesis of new drug delivery systems and in surface recognition studies. This review focuses on liposomes, cyclodextrins, and dendrimers based on or incorporating adamantane derivatives. Our recent concept of adamantane as an anchor in the lipid bilayer of liposomes has promising applications in the field of targeted drug delivery and surface recognition. The results reported here encourage the development of novel adamantane-based structures and self-assembled supramolecular systems for basic chemical investigations as well as for biomedical application.

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Section: Adamantane Derivatives In Liposomesmentioning

confidence: 99%

Adamantane in Drug Delivery Systems and Surface Recognition

et al. 2017

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“…13 Considering that in the past years we have prepared several series of guanidinium containing derivatives that strongly interact with the minor groove of wild type DNA as well as with AT oligonucleotides, 14−19 in the present article, we aim to analyze the possible cation−π complexes formed between guanidinium and the aromatic systems present in the DNA and RNA bases (adenosine, guanidine, thymidine, cytosine, and uracil) with the final objective of understanding the DNA interactions previously observed by us and to complete our theoretical studies on guanidinium interactions. 20 …”

Section: ■ Introductionmentioning

confidence: 97%

Non-Covalent Interactions: Complexes of Guanidinium with DNA and RNA Nucleobases

et al. 2013

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Considering that guanidine-based derivatives are good DNA minor groove binders, we have theoretically studied, using the Polarizable Continuum model mimicking water solvation, the complexes formed by the biologically relevant guanidinium cation and the DNA and RNA nucleobases (adenine, guanine, cytosine, thymine, and uracil). The interactions established within these complexes both by hydrogen bonds and by cation-π interactions have been analyzed by means of the Atoms in Molecules and Natural Bond Orbital approaches. Moreover, maps of electron density difference have been produced to understand the cation-π complexes. Finally, the NICS and three-dimensional NICS maps of the cation-π complexes have been studied to understand the effect of the guanidinium cation on the aromaticity of the nucleobases.

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“…Regardless of its basicity, the guanidinium cation has important features very useful for target binding such as forming strong HBs and ionic interactions. [23][24][25] Interestingly, the related isouronium cation retains these two binding features and, additionally, is less basic (pK aH = 9.8 (ref. 18)); hence, this cation is very promising as a functional substitute in guanidinium derivatives with therapeutic potential.…”

Section: Introductionmentioning

confidence: 99%

Effect of isouronium/guanidinium substitution on the efficacy of a series of novel anti-cancer agents

et al. 2018

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Considering our hypothesis that the guanidinium moiety in the protein kinase type III inhibitor interacts with a phosphate of ATP within the hinge region, the nature of the interactions established between a model isouronium and the phosphate groups of ATP was computationally analysed indicating that an isouronium derivative of will interact in a similar manner with ATP. Thus, a number of compounds were prepared to assess the effect of the guanidinium/isouronium substitution on cancer cell growth; additionally, the molecular shortening and conformational change induced by replacing the di-substituted guanidine-linker of by an amide was explored. The effect of these compounds on cell viability was tested in human leukaemia, breast cancer and cervical cancer cell lines and the resulting IC values were compared with those of the lead compound . Replacement of the di-substituted guanidine-linker by an amide results in the loss of cytotoxicity; however, substitution of the mono-substituted guanidinium by an isouronium cation seems to be beneficial for cell growth inhibition. Additionally, the effect of these compounds on the MAPK/ERK pathway was studied by means of Western blotting and the results indicate that the isouronium derivative decreases the levels of phosphorylated, and thus activated, ERK (pERK) both in leukaemia and breast cancer cells, whereas lead compound only shows an effect on pERK levels in breast cancer cells. This confirms that both compounds could interfere with the MAPK/ERK pathway although other targets cannot be ruled out.

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Solvent effects on guanidinium-anion interactions and the problem of guanidinium Y-aromaticity

Cited by 21 publications

References 43 publications

Adamantane in Drug Delivery Systems and Surface Recognition

Adamantane in Drug Delivery Systems and Surface Recognition

Non-Covalent Interactions: Complexes of Guanidinium with DNA and RNA Nucleobases

Effect of isouronium/guanidinium substitution on the efficacy of a series of novel anti-cancer agents

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