Complexation of Sulfonamides With β-Cyclodextrin Studied by Experimental and Theoretical Methods

Zoppi, Ariana; Quevedo, Mario Alfredo; Delrivo, Alicia; Longhi, Marcela R.

doi:10.1002/jps.22062

Cited by 34 publications

(27 citation statements)

References 24 publications

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“…However, there are marked differences in the stabilizing effects among different CD, a feature that depends on the shape and volume of the cavity available for inclusion, and in some cases the complexation has a catalyzing rather than a stabilizing effect on the photodegradation process (12). For this reason, state of the art computer based molecular modeling techniques combined with experimental techniques, potentiates the ability to elucidate and further predict the IC three-dimensional structures (9,(13)(14)(15).…”

Section: Doxycycline (Doxmentioning

confidence: 99%

Increasing Doxycycline Hyclate Photostability by Complexation with β-Cyclodextrin

et al. 2014

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Abstract. Doxycycline hyclate (DOX) is a highly photosensitive drug, a feature that limits the stability of the corresponding dosage forms. The main objectives of this work were the preparation and characterization of an inclusion complex of DOX with β-cyclodextrin (βCD) and to investigate if this approach could improve the photostability of the drug. Guest-host interactions were investigated using nuclear magnetic resonance, which were afterwards combined with molecular modeling methods to study the complex formation and its three-dimensional structure was proposed. A freeze-drying method was applied to obtain the complex in the solid state, which was further confirmed by thermal and spectroscopic techniques. To evaluate the complexation effect on DOX integrity, the photostability of the inclusion complex was studied, with a significant decrease in the photodegradation of DOX being found in aqueous solution upon complexation. Finally, the photoprotection produced by the complexation was evaluated by means of an antimicrobial assay. Overall, the presented results suggest that the formulation of DOX complexed with βCD constitutes an interesting approach for the preparation of pharmaceutical dosage forms of DOX with enhanced stability properties.

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Section: Doxycycline (Doxmentioning

confidence: 99%

Increasing Doxycycline Hyclate Photostability by Complexation with β-Cyclodextrin

et al. 2014

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“…An inclusion compound is a complex in which one chemical compound, host, form an enclosed space in which molecules of a second ''guest'' compound are located [4,5]. There are various experimental [6][7][8] and theoretical [9][10][11][12] studies dedicated to examine different aspects of this phenomenon. The cyclic peptides are used as excellent host in host-guest chemistry because they could form inclusion complexes with guest molecules [13][14][15][16][17][18][19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Shahangi

Chermahini

Farrokhpour

et al. 2016

J Incl Phenom Macrocycl Chem

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In this work, the inclusion complexes of leucine as the guest and a series of cyclic peptides with four to nine alanine as building block (host molecules) were investigated by M062X/6-31 ? G (d) level of theory. The calculations predicted the stability of the enantiomers in the cavity of cyclic peptides and the possibility of distinction between the enantiomers for the used level of theory. The results indicated that the most stable aggregate is formed between CyclAla9 and R and S-leucine enantiomers and CyclALA4 have the least interaction with R and S-leucine enantiomers. Geometrical changes of leucine due to complexation and hydrogen bonding were considered. The NBO calculations for analyzing the nature of the intermolecular hydrogen bonds were performed. In another part of this work, the UV absorption spectra of complexes of R, and S-leucine with CyclAla9 calculated using ONIOM method in the gas phase and it was showed that the UV absorption spectroscopy could be used as a chirality discriminator tool in recognition of enantiomers in the gas phase.

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“…Furthermore, sulfonamides can appear as contaminants in various foods, which may cause adverse health effects [15][16][17]. The host-guest type complex formation of these antibiotics with CDs is an extensively studied field [18][19][20][21][22][23][24]. Zoppi et al focus on the increased water solubility of sulfonamide drugs in the presence of native and methylated β-CD [23,24].…”

mentioning

confidence: 99%

“…The host-guest type complex formation of these antibiotics with CDs is an extensively studied field [18][19][20][21][22][23][24]. Zoppi et al focus on the increased water solubility of sulfonamide drugs in the presence of native and methylated β-CD [23,24]. In the case of sulfamethazine (SMT), their nuclear magnetic resonance (NMR) and molecular modeling results demonstrate that SMT included the substituted pyrimidine ring into the β-CD cavity.…”

mentioning

confidence: 99%

“…The pH-responsive host-guest encapsulation is also a highly studied field in material sciences [27] and in pharmacology [28,29]. Therefore, besides the complex stability and stoichiometry of SMT -β-CD complex and along the contradictory description of the related structures [18,23,24], the investigation of the pH dependence interaction of SMT with CDs is also reasonable.In our recent study [30], we demonstrated the importance of pH-dependent dipole moment of SMT molecule, which phenomenon can affect the complex geometry formed with β-CD (BCD) and randomly methylated β-CD (RAMEB) (Figure 1). Now we focus on the thermodynamic properties of the formation of inclusion complexes at different pH values.…”

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Thermodynamic Characterization of the Interaction between the Antimicrobial Drug Sulfamethazine and Two Selected Cyclodextrins

et al. 2019

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Sulfamethazine is a representative member of the sulfonamide antibiotic drugs; it is still used in human and veterinary therapy. The protonation state of this drug affects its aqueous solubility, which can be controlled by its inclusion complexes with native or chemically-modified cyclodextrins. In this work, the temperature-dependent (298-313 K) interaction of sulfamethazine with native and randomly methylated β-cyclodextrins have been investigated at acidic and neutral pH. Surprisingly, the interaction between the neutral and anionic forms of the guest molecule and cyclodextrins with electron rich cavity are thermodynamically more favorable compared to the cationic guest. This property probably due to the enhanced formation of zwitterionic form of sulfamethazine in the hydrophobic cavities of cyclodextrins. Spectroscopic measurements and molecular modeling studies indicated the possible driving forces (hydrophobic interaction, hydrogen bonding, and electrostatic interaction) of the complex formation, and highlighted the importance of the reorganization of the solvent molecules during the entering of the guest molecule into the host's cavity.Molecules 2019, 24, 4565 2 of 12 tissues [13,14]. Furthermore, sulfonamides can appear as contaminants in various foods, which may cause adverse health effects [15][16][17]. The host-guest type complex formation of these antibiotics with CDs is an extensively studied field [18][19][20][21][22][23][24]. Zoppi et al. focus on the increased water solubility of sulfonamide drugs in the presence of native and methylated β-CD [23,24]. In the case of sulfamethazine (SMT), their nuclear magnetic resonance (NMR) and molecular modeling results demonstrate that SMT included the substituted pyrimidine ring into the β-CD cavity. Contradictory, NMR and quantum chemical results of Bani-Yaseen and Mo'ala revealed that complex formation is favorable with inclusion of the aniline moiety through the β-CD cavity [18].Several studies have been performed to get an insight into the factors which affect the thermodynamic and kinetic stability or selectivity of host-guest complexes [25,26], because the deeper understanding of these interactions has high importance. The pH-responsive host-guest encapsulation is also a highly studied field in material sciences [27] and in pharmacology [28,29]. Therefore, besides the complex stability and stoichiometry of SMT -β-CD complex and along the contradictory description of the related structures [18,23,24], the investigation of the pH dependence interaction of SMT with CDs is also reasonable.In our recent study [30], we demonstrated the importance of pH-dependent dipole moment of SMT molecule, which phenomenon can affect the complex geometry formed with β-CD (BCD) and randomly methylated β-CD (RAMEB) (Figure 1). Now we focus on the thermodynamic properties of the formation of inclusion complexes at different pH values. Our aim is to analyze the weak interactions between the pH dependent ionic and neutral forms of SMT and native or methylated CDs at molecular l...

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Complexation of Sulfonamides With β-Cyclodextrin Studied by Experimental and Theoretical Methods

Cited by 34 publications

References 24 publications

Increasing Doxycycline Hyclate Photostability by Complexation with β-Cyclodextrin

Increasing Doxycycline Hyclate Photostability by Complexation with β-Cyclodextrin

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Thermodynamic Characterization of the Interaction between the Antimicrobial Drug Sulfamethazine and Two Selected Cyclodextrins

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