Experimental and theoretical investigation of conformational states and noncovalent interactions in crystalline sulfonamides with a methoxyphenyl moiety

Kowalik, Mateusz; Brzeski, Jakub; Gawrońska, Małgorzata; Kazimierczuk, Katarzyna; Makowski, Mariusz

doi:10.1039/d1ce00869b

Cited by 14 publications

(12 citation statements)

References 114 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The preliminary studies were performed with a well-known DNA intercalator: ethidium bromide (EB, a model molecule). The EB is described by a high value of the binding constant to the DNA, and its thermodynamic characteristic of binding to the said biomolecule has been well described in other types of experiments. − The sulfonamides have been selected as the main research object due to their proven antibiotic and anticancer properties. − Therefore, the second small compound that has been selected for the research was sulfathiazole (STZ), a chemotherapeutic agent with a strong bacteriostatic effect. Its interaction with DNA in solutions was proven by our group using spectrophotometric titration .…”

Section: Introductionmentioning

confidence: 84%

“… 17 − 21 The sulfonamides have been selected as the main research object due to their proven antibiotic and anticancer properties. 22 − 27 Therefore, the second small compound that has been selected for the research was sulfathiazole (STZ), a chemotherapeutic agent with a strong bacteriostatic effect. Its interaction with DNA in solutions was proven by our group using spectrophotometric titration.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Application of the SwitchSense Technique for the Study of Small Molecules’ (Ethidium Bromide and Selected Sulfonamide Derivatives) Affinity to DNA in Real Time

et al. 2022

Self Cite

View full text Add to dashboard Cite

The discovery and introduction of the switchSense technique in the chemical laboratory have drawn well-deserved interest owing to its wide range of applications. Namely, it can be used to determine the diameter of proteins, alterations in their tertiary structures (folding), and many other conformational changes that are important from a biological point of view. The essence of this technique is based on its ability to study of the interactions between an analyte and a ligand in real time (in a buffer flow). Its simplicity, on the other hand, is based on the use of a signaling system that provides information about the ongoing interactions based on the changes in the fluorescence intensity. This technique can be extremely advantageous in the study of new pharmaceuticals. The design of compounds with biological activity, as well as the determination of their molecular targets and modes of interactions, is crucial in the search for new drugs and the fight against drug resistance. This article presents another possible application of the switchSense technique for the study of the binding kinetics of small model molecules such as ethidium bromide (EB) and selected sulfonamide derivatives with DNA in the static and dynamic modes at three different temperatures (15, 25, and 37 °C) each. The experimental results remain in very good agreement with the molecular dynamics docking ones. These physicochemical insights and applications obtained from the switchSense technique allow for the design of an effective strategy for molecular interaction assessments of small but pharmaceutically important molecules with DNA.

show abstract

Section: Introductionmentioning

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Application of the SwitchSense Technique for the Study of Small Molecules’ (Ethidium Bromide and Selected Sulfonamide Derivatives) Affinity to DNA in Real Time

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…The ∇ 2 ρ values of 5 out of 88 contacts are less than zero, which demonstrates that the density is locally concentrated, resulting in covalent bond or covalent character of interaction. 24 Based on ∇ 2 ρ and H BCP (total electron energy density at bond critical point), Rozas and co-workers classified hydrogen bonds as follows: (i) ∇ 2 ρ > 0 and H BCP > 0 for weak hydrogen bonds, (ii) ∇ 2 ρ > 0 and H BCP < 0 for medium and strong hydrogen bonds, and (iii) ∇ 2 ρ < 0 and H BCP < 0 for very strong hydrogen bonds. 66 Therefore, the 5 contacts are very strong hydrogen bonds.…”

Section: As Shown In Table 5 H•••h Hydrogen-bonding Interactions (N••...mentioning

confidence: 99%

“…21 MEPSs were computed at the same level of theory using the Multiwfn 3.8 program and plotted using VMD. 24,44,45 QTAIM analysis was carried out on geometry optimized cocrystal structures using a periodic plane wave DFT using the QE package. 46 Ultrasoft pseudopotential with kinetic energy cutoff 45 and 425 Ry charge density cutoff was employed for the calculations.…”

Section: ■ Introductionmentioning

confidence: 99%

Experimental and Theoretical Investigation of Hydrogen-Bonding Interactions in Cocrystals of Sulfaguanidine

Huang

Cheemarla

Tiana

et al. 2023

Crystal Growth & Design

View full text Add to dashboard Cite

Pharmaceutical cocrystals, a type of multicomponent crystalline material incorporating two or more molecular and/or ionic compounds connected by noncovalent interactions (such as hydrogen bonds, π–π interactions, and halogen bonds), are attracting increasing attention in crystal engineering. Sulfaguanidine (SGD), one of the most frequently used sulfonamide compounds, was chosen as a model compound in this work to further investigate the hydrogen bond interactions in cocrystals, since it possesses various hydrogen bond donor and acceptor sites. Five cocrystals of SGD, synthesized successfully by slurry and slow evaporation methods, were fully characterized by thermal analysis, X-ray techniques, and Fourier transform infrared spectroscopy. To gain insight into the nature of hydrogen-bonding interactions, theoretical calculations including the analysis of Hirshfeld surface, MEPS (molecular electrostatic potential surface), and QTAIM (quantum theory of atoms in molecules) were conducted. The results are a part of a systematic study of cocrystals of sulfonamides that aims to establish synthon hierarchies in cocrystals containing molecules with multiple hydrogen-bonding functional groups.

show abstract

“…Non-covalent interactions [ 1 , 2 , 3 , 4 , 5 , 6 ] (NCIs) play a key role in the modulation of supramolecular organizations [ 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ], which is useful for targeted crystal design [ 7 , 8 , 9 , 11 , 12 , 15 , 16 , 17 , 18 , 19 ] and the fabrication of functional materials [ 20 ], as well as for enhancing catalytic activity [ 21 , 22 ] and reactivity [ 23 , 24 , 25 , 26 , 27 , 28 ]. All of these factors contributed to the motivation behind supramolecular chemistry studies utilizing a diversity of NCIs.…”

Section: Introductionmentioning

confidence: 99%

Structure-Directing Interplay between Tetrel and Halogen Bonding in Co-Crystal of Lead(II) Diethyldithiocarbamate with Tetraiodoethylene

Зеленков

Ivanov

Tyumentsev

et al. 2022

IJMS

View full text Add to dashboard Cite

The co-crystallization of the lead(II) complex [Pb(S2CNEt2)2] with tetraiodoethylene (C2I4) gave the co-crystal, [Pb(S2CNEt2)2]∙½C2I4, whose X-ray structure exhibits only a small change of the crystal parameters than those in the parent [Pb(S2CNEt2)2]. The supramolecular organization of the co-crystal is largely determined by an interplay between Pb⋯S tetrel bonding (TeB) and I⋯S halogen bonding (HaB) with comparable contributions from these non-covalent contacts; the TeBs observed in the parent complex, [Pb(S2CNEt2)2], remain unchanged in the co-crystal. An analysis of the theoretical calculation data, performed for the crystal and cluster models of [Pb(S2CNEt2)2]∙½C2I4, revealed the non-covalent nature of the Pb⋯S TeB (−5.41 and −7.78 kcal/mol) and I⋯S HaB (−7.26 and −11.37 kcal/mol) interactions and indicate that in the co-crystal these non-covalent forces are similar in energy.

show abstract

Experimental and theoretical investigation of conformational states and noncovalent interactions in crystalline sulfonamides with a methoxyphenyl moiety

Cited by 14 publications

References 114 publications

Application of the SwitchSense Technique for the Study of Small Molecules’ (Ethidium Bromide and Selected Sulfonamide Derivatives) Affinity to DNA in Real Time

Application of the SwitchSense Technique for the Study of Small Molecules’ (Ethidium Bromide and Selected Sulfonamide Derivatives) Affinity to DNA in Real Time

Experimental and Theoretical Investigation of Hydrogen-Bonding Interactions in Cocrystals of Sulfaguanidine

Structure-Directing Interplay between Tetrel and Halogen Bonding in Co-Crystal of Lead(II) Diethyldithiocarbamate with Tetraiodoethylene

Contact Info

Product

Resources

About