Guanidinium cation

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The guanidinium cation is a positively charged ion derived from guanidine, characterized by the formula C(NH2)3+. It plays a significant role in biochemistry and molecular biology, particularly in protein folding and stabilization, due to its ability to form strong hydrogen bonds and interact with various biomolecules.

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Key research themes

1. How does guanidinium cation interact with proteins and influence molecular recognition and stability?

This research area investigates the nature of guanidinium cation interactions particularly with aromatic amino acids in proteins via cation-π and hydrogen bonding mechanisms, and how these interactions modulate protein structure, stability, and binding affinities. Understanding these interactions is critical for drug design, protein engineering, and molecular recognition processes involving guanidinium derivatives.

Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions

by Isabel Rozas

2023, Molecules

Key finding: Using DFT and PCM-water solvation, this study demonstrated that guanidinium forms stable complexes with aromatic amino acids (phenylalanine, histidine, tryptophan, tyrosine) through both cation-π and hydrogen bonding. The... Read more

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2. What are the transport and physicochemical properties of guanidinium-based ionic liquids and their influence on material behavior?

This theme covers the synthesis and characterization of guanidinium ionic liquids (ILs), focusing on how structural variations (protic vs. aprotic, side chain length) and molecular interactions affect transport properties such as viscosity and conductivity. Investigating these properties underpins the development of advanced functional fluids for applications ranging from electrochemistry to gas absorption.

Transport properties of protic and aprotic guanidinium ionic liquids

by Rolf Hempelmann

2021, RSC Advances

Key finding: The study synthesized a series of novel protic and aprotic guanidinium ILs based on tetramethylguanidinium cations paired with various anions and showed that protic ILs form extensive hydrogen bonding networks influencing... Read more

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3. How does guanidinium cation modulate nucleic acid structures, particularly guanine quadruplexes, and influence their stability and cation selectivity?

Research in this area explores the interaction of guanidinium-related cations with guanine quadruplex (GQ) DNA structures, focusing on how cations stabilize the GQ through size, desolvation, and electrostatic effects, which impact biological functions and therapeutic targeting. Clarifying the role of alkali metal cations and guanidinium-like species advances understanding of quadruplex folding and potential pharmacological modulation.

The role of alkali metal cations in the stabilization of guanine quadruplexes: why K<sup>+</sup> is the best

by Célia Fonseca Guerra

2024, Physical Chemistry Chemical Physics

Key finding: By using dispersion-corrected DFT calculations and energy decomposition analysis, the study clarified that both desolvation energy and ionic radius equally govern alkali metal cation binding affinity to guanine quadruplexes,... Read more

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4. What are the neuromodulatory and neuroprotective roles of guanine-based purines like guanosine in the central nervous system (CNS)?

This theme investigates the extracellular functions of guanosine and guanine nucleotides in the CNS, including their modulation of glutamatergic neurotransmission, neuroprotection in degenerative diseases, and intracellular mechanisms mitigating oxidative stress and mitochondrial dysfunction. Elucidating these pathways informs therapeutic strategies for brain disorders.

Guanosine: a Neuromodulator with Therapeutic Potential in Brain Disorders

by Tharine Dal-Cim

2025, Aging and disease

Key finding: The review synthesized in vivo and in vitro evidence that guanosine acts extracellularly to modulate glutamate receptors and transporters, prevents excitotoxicity, mitigates oxidative damage and inflammation, and promotes... Read more

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5. How can guanidinium and related compounds be developed as broad-spectrum antibacterial and antimicrobial agents?

This research cluster focuses on the synthesis, structural modification, and biological evaluation of guanidinium derivatives as antibacterial agents against pathogens, emphasizing mechanisms involving electrostatic interactions disrupting bacterial membranes, biofilm inhibition, and antimicrobial activity profiles.

Alkyl-guanidine Compounds as Potent Broad-Spectrum Antibacterial Agents: Chemical Library Extension and Biological Characterization

by Carolina Pasero

2025, Journal of Medicinal Chemistry

Key finding: The study developed a synthetic library of dimeric alkyl-guanidine derivatives demonstrating potent antibacterial activity against Gram-positive and Gram-negative bacteria with MIC values as low as 1–8 µg/mL. Structural... Read more

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Antimicrobial Activity of a Cationic Guanidine Compound against Two Pathogenic Oral Bacteria

by marcela holmberg

2024, International Journal of Microbiology

Key finding: The polyguanidine compound CatDex showed significant inhibitory activity against Streptococcus mutans and Porphyromonas gingivalis, two important oral pathogens, with MIC of 50 μM. The antimicrobial effect increased over time... Read more

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A combination therapy strategy for treating antibiotic resistant biofilm infection using a guanidinium derivative and nanoparticulate Ag(0) derived hybrid gel conjugate

by Ananta Dey

2023, Chemical Science

Key finding: This study developed a guanidinium-based hybrid gel conjugated with Ag(0) nanoparticles that effectively inhibited biofilm formation and dispersed established biofilms of drug-resistant bacteria. The conjugate eradicated... Read more

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6. How is guanidine biosynthesized biologically and what is its significance as a nitrogen-rich compound in sustainability and biotechnology?

Emerging research addresses biosynthetic pathways of guanidine in microorganisms, its role as a nitrogen-rich metabolite with high nitrogen content, and the potential for sustainable photosynthetic production using engineered cyanobacteria. These insights reveal guanidine’s promise as a renewable nitrogen-based energy carrier and biotechnological product.

Photosynthetic production of the nitrogen-rich compound guanidine

by Ruanbao Zhou

2024, Green Chemistry

Key finding: This study engineered cyanobacteria to overexpress the ethylene-forming enzyme (EFE), resulting in in vivo accumulation of guanidine via a proposed guanidine biosynthesis cycle driven by photosynthetically generated ATP and... Read more

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7. What is the role of guanidinium cations as collectors in mineral flotation and their adsorption behavior on mineral surfaces?

This area explores guanidinium and substituted guanidinium cations as cationic collectors in reverse flotation processes, studying their adsorption on aluminosilicate minerals such as kaolinite and iron oxides like goethite. The goal is to understand molecular-level adsorption mechanisms and substituent effects for optimized mineral beneficiation.

Adsorption of guanidinium collectors on aluminosilicate minerals – a density functional study

by Baskar Prathab

2022, Physical Chemistry Chemical Physics

Key finding: Using DFT, the study characterized guanidinium and substituted guanidinium cations' adsorption on kaolinite and goethite basal surfaces, revealing that electrostatic interactions, hydrogen bonding, and substituent electronic... Read more

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All papers in Guanidinium cation

Zn(ii)–nucleobase metal–organic nanofibers and nanoflowers: synthesis and photocatalytic application

by Tridib Kumar Sarma

2025, New Journal of Chemistry

The interaction of Zn2+ ions with pure nucleobases guanine and cytosine under alkaline conditions leads to the formation of nanoscale metal–organic nanofibers and nanoflowers with excellent photocatalytic activity for the degradation of... more

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

by José Elguero

2024, The Journal of Physical Chemistry B

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... more

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Peptide/β-Peptoid Hybrids with Activity against Vancomycin-Resistant Enterococci: Influence of Hydrophobicity and Structural Features on Antibacterial and Hemolytic Properties

by Bolette Skive

2023, International Journal of Molecular Sciences

This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY

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Isolation of high-quality DNA in 16 aromatic and medicinal Colombian species using silica-based extraction columns

by Nelson Enrique Vega Vela

2023, Agronomia Colombiana

Las especies vegetales aromáticas y medicinales son un recurso valioso para la investigación y el desarrollo de agentes farmacéuticos, cosméticos, agrícolas y de alimentos, debido a la alta cantidad de fitoquímicos bioactivos que... more

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Equilibrium CO 2 solubility and thermophysical properties of aqueous blends of 1-(2-aminoethyl) piperazine and N-methyldiethanolamine

by Sukanta Dash

2023, Fluid Phase Equilibria

The present work reports new experimental CO 2 solubility data of CO 2 absorption in aqueous mixture of 1-(2-aminoethyl)piperazine (AEP) and N-methyldiethanolamine (MDEA) over the MDEA AEP y y : have been considered as 0.

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Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions

by Isabel Rozas

2023, Molecules

Continuing with our interest in the guanidinium group and the different interactions than can establish, we have carried out a theoretical study of the complexes formed by this cation and the aromatic amino acids (phenylalanine,... more

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Scheduling the blended solution as industrial CO2 absorber in separation process by back-propagation artificial neural networks

by Yadollah Abdollahi

2022, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy

h i g h l i g h t s Experimental performance: to obtain the enough viscosity data as actual responses. Modeling process: learning and validation test to obtain the final model. The model was used to navigate the fabrication of the blended... more

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Peptide/β-Peptoid Hybrids with Ultrashort PEG-Like Moieties: Effects on Hydrophobicity, Antibacterial Activity and Hemolytic Properties

by Henrik Franzyk

2022

PEGylation of antimicrobial peptides as a shielding tool that increases stability toward proteolytic degradation typically leads to concomitant loss of activity, whereas incorporation of ultrashort PEG-like amino acids (sPEGs) remains... more

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Microstructures, interactions and dynamics properties studies of aqueous guanidinium triflate ionic liquid from molecular dynamics simulations

by Asrina Sairi

2022, Journal of Molecular Liquids

In order to understand the phase equilibrium behavior of aqueous ionic liquids (ILs) guanidinium triflate [gua][OTf] solution (binary solvent) at 7 different molar fractions of water ranged from 0.1 to 0.7 at 440.15 K classical molecular... more

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Computing the Structural Dynamics of RVFV L Protein Domain in Aqueous Glycerol Solutions

by Swabir Silayi

2021, Biomolecules

Many biological and biotechnological processes are controlled by protein–protein and protein–solvent interactions. In order to understand, predict, and optimize such processes, it is important to understand how solvents affect protein... more

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Peptide/β-Peptoid Hybrids with Activity against Vancomycin-Resistant Enterococci: Influence of Hydrophobicity and Structural Features on Antibacterial and Hemolytic Properties

by Ilona Domraceva

2021, International Journal of Molecular Sciences

Infections with enterococci are challenging to treat due to intrinsic resistance to several antibiotics. Especially vancomycin-resistant Enterococcus faecium and Enterococcus faecalis are of considerable concern with a limited number of... more

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Improved proteolytic stability and potent activity against Leishmania infantum trypanothione reductase of α/β-peptide foldamers conjugated to cell-penetrating peptides

by Antonio Jiménez-Ruiz

2021, European Journal of Medicinal Chemistry

The objective of the current study was to enhance the proteolytic stability of peptide-based inhibitors that target critical protein-protein interactions at the dimerization interface of Leishmania infantum trypanothione reductase... more

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Facially Amphiphilic Cholic AcidLysine Conjugates as Promising Antimicrobials

by Poonam singla

2021

The emergence of multidrug-resistant microbes is a significant health concern posing a constant need for new antimicrobials. Membrane-targeting antibiotics are promising candidates with reduced ability of microbes to develop resistance.... more

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Binaphthyl scaffolded peptoids via ring-closing metathesis reactions and their anti-bacterial activities

by Adel Garas

2021, Bioorganic & Medicinal Chemistry Letters

An efficient synthesis of four new acyclic and four new cyclic binaphthyl-based cationic peptoids is described. These compounds had anti-bacterial activities with MIC values of 4-62 lg/mL against Staphylococcus aureus.

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Parallel β-Sheet Assemblies at Interfaces

by Markus Weygand

2021, Chemphyschem

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Relative Solvent Exposure of the Alpha-Helix and Beta-Sheet in Water Determines the Initial Stages of Urea and Guanidinium Chloride-Induced Denaturation of Alpha/Beta Proteins

by Sridip Parui

2021, J. Phys. Chem. B

Among several denaturants, urea and guanidinium chloride (GdmCl) are the two strong and extensively used denaturants in unfolding experiments. However, the sequences of events in terms of secondary structure melting of several proteins in... more

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Guanidino groups greatly enhance the action of antimicrobial peptidomimetics against bacterial cytoplasmic membranes

by David Gidalevitz

2017, Biochimica et Biophysica Acta (BBA) - Biomembranes

a b s t r a c t 1 1

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Low pressure solubilities of CO2 in guanidinium trifluoromethanesulfonate-MDEA systems

by Mohamed Aroua

2015, Fluid Phase Equilibria

It is an urgent act to limit greenhouse gas emissions to avoid the harmful effects of climate changes. In this work, the binary and ternary systems of guanidinium trifluoromethanesulfonate ([gua][OTf]) in N-methyldiethanolamine (MDEA)... more

Fig. 1. (a) Structure of guanidinium trifluoromethanesulfonate, ([gua][OTf]) with molecular weight 209.15gmol-. (b) Structure of N-methyldiethanolamine, (MDEA) with molecular weight 119.16 gmol~!.

Fig. 2. Schematic diagram of the experimental set-up.

Fig. 4. Viscosity eet te 1M MDEA as function of temperatures. (1) this work; (x) Derks et al. [38]; (-) Teng et al. [39]; (A) Arachchige et al. [40]. Fig. 3. Density of aqueous 1M MDEA as function of temperatures. (()) this work; (}) Muhammad et al. [37]; (@) Derks et al. [38].

Fig. 5. CO solubility of aqueous 4M MDEA as function of CO; partial pressures. (C1) this work; (A) Benamor and Aroua [36].

Fig. 6. Density of the binary systems at different molar fraction as function of temperatures. (1) 4M MDEA; (}) 1M MDEA; (@) 4M [gua][OTf]; (a) 1M [gua] [OTf].

Fig. 8. Comparison in density between [gua][OTf]-H20 i.e., 4 M [gua][OTf] and 1M [gua][OTf] with [hmim][Br]-H20 [41] and [BuPy][BF4]-H20 [42]. (1) 4M [gua] [OTF]; (©) 1M [gua][OTf]; (@) [hmim][Br]-H20; (ml) [bmim] BF4]-H20.

Standard uncertainties: u are u(T) =0.01 K; u(x)=0.0001 and u(P)=1kPa. Relative standard uncertainty: u,(7)=0.03. M: concentration, mol/dm?. The activation energy, Eq correlated parameters for viscosities at various concentrations. Table 9

Fig. 9. Density comparison between calculated and measured density of 4M MDEA+2M [gua][OTf], 4M MDEA+1M [gua][OTf], 3M MDEA +1M [gua][OTf], 4 MDEA and 1M [gua][OTf]. Table 6 shows that the changes in the coefficients of thermal expansion values and the variation of volume expansion of the studied systems are dependent on temperature. Since the densities decreased linearly with temperature, it is obvious that a, values are all positive but slightly increases with temperature. Similar trends of densities are observed for the thermal expansion

Fig. 10. Viscosity of various concentrations of [gua][OTf]—H20. (1) 4M [gua][OTf]; (a4) 1M [gua][OTf]; (CO) 0.9M [gua][OTf]; (ml) 0.7M [gua][OTf]; (A) 0.5 M [gua] [OTf]; (@) 0.3 M [gua][OTf]; (<) 0.1 M [gua][OTf].

Fig. 11. Viscosity of various concentrations of the ternary systems at different temperature. (<)4M MDEA +2M [gua][OTf]; (@)4M MDEA+1M [gua][OTf]; (A) 4M MDEA +0.9M [gua][OTf]; (ml) 4M MDEA+0.7M [gua][OTf]; (©) 4M MDEA +0.5 M [gua][OTf]; (A) 4M MDEA+0.3M [gua][OTf]; (4) 4M MDEA +0.1M [gua] [OT#].

Fig. 12. Comparison of viscosity between [bmim][BF4]-H20 (0.001 M [bmim][BF4], 0.01 M [bmim][BF,], 0.02 M [bmim][BF,] and 0.04 M [bmim][BF,]) and [gua][OTf]- H,0 (0.1M [gua][OTf], 0.3 M [gua][OTf], 0.5 M [gua][OTf], 0.7 M [gua][OTf], 0.9M [gua][OTf] and 1M [gua][OTf]) at 298.2 K [45]. (1) [bmim][BF4]-H20; (a) [gua] [OTf]-H20.

Fig. 13. Comparison between calculated and measured viscosities for the binary systems and ternary systems.

Fig. 14. CO2 loading for the binary systems at 303.2 K at different CO2 partial pressure. (gl) 4M MDEA; (<) 1M MDEA; (A) 4M [gua][OTf]; (O) 1M [gu

Fig. 15. CO2 loading for the ternary systems at 303.2K at different CO. partial pressure. (ll) 4M MDEA +1M [gua][OTf]; (<) 3M MDEA+ 1M [gua][OTf]; (a) 2M MDEA +2M [gua][OTf]; (©) 1M MDEA+3M [gua][OTf].

5HCO3~ — H*+CO377 Fig. 16. Comparison of CO loading in 4M MDEA+1M [gua][OTf] and 4M1B (4M MDEA +1M [bmim][BF4]) systems. (A) 4M MDEA+1M [gua][OTf]; (ml) 4M1B.

Fig. 17. Correlation results of CO2 absorption in 4M MDEA, 4M MDEA +1M [gua][OTf], 3 M MDEA+ 1 M [gua][OTf] and 2M MDEA +2M [gua][OTf] systems at 303.2 K. (@) 4M MDEA; (mi) 4M MDEA +1M [gua][OTf]; (#) 3M MDEA+1M [gua][OTf]; (&) 2M MDEA +2M [gua][OTf]. was carried out to determine the root mean squared error (RMSE) as an error function by the testing data set and quick propagation (QP) algorithm. The training was repeated 10 times for each node in order to avoid random correlation due to the random initialization of the weight [50]. Among the repeated results, the architectures with minimum RMSE were selected as the best topologies for each node in hidden layer. As a result, the topology with 13 nodes in hidden layer presented the lowest RMSE which was selected as efficient model of [gua][OTf] systems. As Fig. 18 shows, the ANN model contains three variables ([gua][OTf], MDEA and CO2) in input, 13 nodes in hidden and one response (COz solubility) in output layers (QP-3-13-1). In the productive process, the impor- tance of the fabrication effective variables is determined to control the excess amount and determinate the effectivity of the ANN modeling of [gua][OTf]-MDEA systems for low pressure CO2 solubility was carried out by NeuralPower software version 2.525 [27,30,50] . The concentration of [gua][OTf], MDEA and the concentration of injected CO, in mole were selected as indepen- dent variables (inputs); while mole of COz absorbed was selected as dependent variable (output). Therefore, the ANN was made of 3 neurons as its input layer and a neuron in output layer. The structure of the hidden layer was determined by examining a series of topologies with varied nodes from 1 to 15. The model training

Fig. 18. The QP-3-13-1 model of [gua][OTf]-MDEA systems, the input layer contains of 3 variables ([gua][OTf], MDEA and CO2), the hidden layer has 13 nodes which obtained by learning process and 1 response, solubility of the injected CO, is in output layers.

Fig. 19. The model calculated importance of the input variables of [gua][OTf]- MDEA systems which are [gua][OTf], MDEA and concentration of injected CO into the system. The importance of [gua][OTf], MDEA and injected CO2 was 68%, 16% and 16%, respectively.

The sample provenance table for the compounds system. Table 1

Standard uncertainties: u are u(T) =0.01 K; u(x)=0.0001 and u(P)=1 kPa. Compositions of binary and ternary systems. Table 2

Comparison of density and viscosity for pure MDEA and CO, solubility for aqueous 4M MDEA at different temperature, atmospheric pressure. Standard uncertainties: u are u(T) =0.01 K; u(x)=0.0001 and u(P)=1kPa. Relative standard uncertainty: u, are u,(p)=0.001 and u,(7n)=0.03. Table 3

Standard uncertainties: u are u(T)=0.01 K, u(x)=0.0001 and u(P)=1kPa. M: concentration, mol/dm?. Validation experiments on 4M MDEA system at 303.2 K with the presence of 100% CO2 containing a known amount of NaHCO3 at atmospheric pressure.

Calculated and measured density data for studied systems at atmospheric pressure with @ and # values. Table 5

Standard uncertainties: u are u(T)=0.01 K, u(x)=0.0001 and u(P)=1k Pa. Relative standard uncertainty, u, are u,()=0.001. M: concentration, mol/dm?. coefficients. The values of a» increased from 6.1795 x10~© to 7.9184 x 10-° K~! with increasing of [gua][OTf] composition in the systems. The coefficients of thermal expansion values for the systems studied in this work are calculated based on the measured density data using Eq. (5).

Standard uncertainties: u are u(T) =0.01 K; u(x)=0.0001 and u(P)=1k Pa. Relative standard uncertainty: u,(71)=0.03. M: concentration, mol/dm?. Effect of [gua][OTf] to 4M MDEA on viscosity at atmospheric pressure.

Standard uncertainties: u are u(T) =0.01 K; u(x)=0.0001 and u(P)=1kPa. Relative standard uncertainty: u,(7)=0.03. M: concentration, mol/dm*. Viscosities of binary systems [gua][OTf] at atmospheric pressure.

Standard uncertainties, u are u(T) =0.01K, u(x)=0.0001 and u(P)=1k Pa. Relative standard uncertainty: u, are u,()=0.001. M: concentration, mol/dm?. Coefficients of thermal expansion for binary and ternary systems using Eq. (5).

Effect of MDEA concentration with CO loading and duration time to reach equilibrium at 303.2 K. and u(P)=1kPa. M: concentration, mol/dm?. Standard uncertainties: u are u(T)=0.01 K, u(x)=0.0001, u(n)=0.001 Table 10

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Low pressure solubilities of CO2 in guanidinium trifluoromethanesulfonate–MDEA systems

by Mohamed Aroua

2015, Fluid Phase Equilibria

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Guanidino groups greatly enhance the action of antimicrobial peptidomimetics against bacterial cytoplasmic membranes

by Ivan Kuzmenko and

2015, Biochimica et Biophysica Acta (BBA) - Biomembranes

Antimicrobial peptides or their synthetic mimics are a promising class of potential new antibiotics. Herein we assess the effect of the type of cationic side chain (i.e., guanidino vs. amino groups) on the membrane perturbing mechanism of... more

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Amphiphilic Four-Helix Bundle Peptides Designed for Light-Induced Electron Transfer Across a Soft Interface

by Joseph Strzalka

2015, Nano Letters

A family of four-helix bundle peptides were designed to be amphiphilic, possessing distinct hydrophilic and hydrophobic domains along the length of the bundle's exterior. This facilitates their vectorial insertion across a soft interface... more

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A new natural spiro heterocyclic compound and the cytotoxic activity of the secondary metabolites from Juniperus brevifolia leaves

by Ana Seca

2015, Fitoterapia

A new natural spiro heterocyclic compound and the cytotoxic activity of the secondary metabolites from Juniperus brevifolia leaves A new natural spiro compound 3,4-dehydrotheaspirone 1 and the known arctiol... more

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Guanidino groups greatly enhance the action of antimicrobial peptidomimetics against bacterial cytoplasmic membranes

by Konstantin Andreev

2015, Biochimica et Biophysica Acta (BBA) - Biomembranes

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Equilibrium Solubility of Carbon Dioxide in an Aqueous Mixture of N -Methyldiethanolamine and Diisopropanolamine: An Experimental and Modeling Study

by behrouz nonahal

2015, Journal of Chemical & Engineering Data

In the present work, the equilibrium solubility of carbon dioxide was measured for three different aqueous mixture of N-methyldiethanolamine (MDEA) and diisopropanolamine (DIPA). The sum of the mass fraction of MDEA and DIPA for each... more

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Antimicrobial peptidomimetics: reinterpreting nature to deliver innovative therapeutics

by Andrea C. Rinaldi

2013, Frontiers in immunology

NATURAL ANTIMICROBIAL PEPTIDES: A PALETTE OF EXTRAORDINARY COLORS. Virtually all multicellular organisms must ward off pathogenic microbes in order to survive and thrive on this planet. To accomplish this, most metazoans rely on... more

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