Physical Characterization of Inclusion Complexes of Triphenyl Phosphate and Cyclodextrins in Solution

Zhang, Nanshan; Zane, Cody Patrick; Chen, Yufei; Yıldırım, Erol; Hinks, D. G.; Tonelli, Alan E.; Vinueza, Nelson R.; Pasquinelli, Melissa A.

doi:10.1021/acs.jpcb.9b09029

Cited by 7 publications

(4 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The study was done by using a variety of experimental characterization tools. We also performed molecular modeling studies of the 1:2 TPP:CD ICs with α-CD, β-CD, and γ-CD, with head-to-head (HH), head-to-tail (HT), and tail-to-tail (TT) packing structures since for CD ICs, a 1:2 stoichiometry of guest:CD is common for a variety of ICs, − although the molecular modeling results are put in the context of the calculations performed previously for the 1:1 stoichiometries …”

Section: Resultsmentioning

confidence: 99%

Improved Eco-Friendliness of a Common Flame Retardant through Inclusion Complexation with Cyclodextrins

Zhang

Yıldırım

Zane

et al. 2019

ACS Appl. Polym. Mater.

Self Cite

View full text Add to dashboard Cite

Triphenyl phosphate (TPP) is used as a plasticizer and a flame retardant worldwide. However, in recent years, TPP has been detected in indoor/outdoor air and biota at high concentrations, and exposure to TPP has been indicated as possibly leading to obesity and osteoporosis in humans. Cyclodextrins (CDs) are known to form inclusion complexes (ICs) with a wide variety of guests due to their ring/cavity structure. The capability of β-CD to form an IC with TPP was recently reported by us, and those studies also revealed that poly(ethylene terephthalate) surfaces treated with TPP−β-CD ICs performed effectively as a flame retardant while also reducing the amount of TPP needed for flame retardancy by at least a factor of 10. Thus, the focus here is whether TPP can form stable ICs with other CDs. Quantum chemistry calculations reveal that IC formation with both α-CD and γ-CD is feasible. However, results from a series of characterization methods indicate that γ-CD forms stable ICs with TPP, but α-CD does not. In terms of the stability of these ICs, for γ-CD, differential scanning calorimetry reveals that the thermal stability of TPP increases via IC formation, and 1 H NMR data indicate that the molar ratio of TPP to γ-CD is 1:2, which coincides with our previous work for IC formation with β-CD. In contrast, another previous study from our laboratories indicates that CD ICs in aqueous solution possess a 1:1 stoichiometry for both β-CD and γ-CD. Quantum chemistry calculations suggest that different ratios were observed due to one of the CDs being more weakly bound and thus able to disassociate under certain conditions. Molecular dynamics simulations indicate that TPP is only released from the ICs with both stoichiometries at temperatures above the degradation temperature of CDs. Thus, these studies suggest that ICs with the common flame retardant TPP and both β-CD and γ-CD are stable under normal conditions and that IC formation enables the unnecessary release of the flame retardant during use to be avoided. Therefore, forming ICs prior to treatment on polymer substrates with flame retardants like TPP that are known to have health and environmental risks is an eco-friendly alternative to current treatment practices.

show abstract

Section: Resultsmentioning

confidence: 99%

Improved Eco-Friendliness of a Common Flame Retardant through Inclusion Complexation with Cyclodextrins

Zhang

Yıldırım

Zane

et al. 2019

ACS Appl. Polym. Mater.

Self Cite

View full text Add to dashboard Cite

show abstract

“…This allows for an effective immobilization and a reduced load of flame retardants, and eliminates unnecessary FR agent loss during the shelf life of flame-retardant products [26]. The excellent performances of CDs in OPFRs have been reported in a number of publications, and they are able to form ICs with, for instance, TPP [27,40], RDP [41], N,N ′ -diamyl-p-phenylphosphonicdiamide (P-MA) [29], Antiblaze RD-1 [31], and N,N ′ -dibutyl-phosphate diamide (DBPDA) [28].…”

Section: Introductionmentioning

confidence: 96%

“…They also examined the flame retardancy of cellulose acetate butyrate fibers using γ-CD as an additive. A combined experimental and computational method helped explore the underling mechanism of [host:guest] complexes between CDs and FRs, and provided a better understanding of CD complexation with guest molecules [27,40]. Our understanding of the CD complexes with DOPO at a molecular level is, however, still quite limited.…”

Section: Introductionmentioning

confidence: 99%

Computational Insights into Cyclodextrin Inclusion Complexes with the Organophosphorus Flame Retardant DOPO

Ma,

Zhang,

Zhang

et al. 2024

Molecules

View full text Add to dashboard Cite

Cyclodextrins (CDs) were used as green char promoters in the formulation of organophosphorus flame retardants (OPFRs) for polymeric materials, and they could reduce the amount of usage of OPFRs and their release into the environment by forming [host:guest] inclusion complexes with them. Here, we report a systematic study on the inclusion complexes of natural CDs (α-, β-, and γ-CD) with a representative OPFR of DOPO using computational methods of molecular docking, molecular dynamics (MD) simulations, and quantum mechanical (QM) calculations. The binding modes and energetics of [host:guest] inclusion complexes were analyzed in details. α-CD was not able to form a complete inclusion complex with DOPO, and the center of mass distance [host:guest] distance amounted to 4–5 Å. β-CD and γ-CD allowed for a deep insertion of DOPO into their hydrophobic cavities, and DOPO was able to frequently change its orientation within the γ-CD cavity. The energy decomposition analysis based on the dispersion-corrected density functional theory (sobEDAw) indicated that electrostatic, orbital, and dispersion contributions favored [host:guest] complexation, while the exchange–repulsion term showed the opposite. This work provides an in-depth understanding of using CD inclusion complexes in OPFRs formulations.

show abstract

“…Generally, most drugs have undesirable side effects as they interact with other body parts. These side effects hinder developing a strategy for optimum medications for several diseases, for example, infectious diseases, neurodegenerative diseases, and cancer. − To overcome this aspect, significant efforts have been focused on preparing inclusion complexes (IC) − by combining the drug and cyclodextrins (CD) as a safe drug delivery pathway. Cyclodextrin-based inclusion complexes can camouflage the unexpected characteristics of the drugs and generally cause a synergistic effect.…”

Section: Introductionmentioning

confidence: 99%

Insights into the Formations of Host–Guest Complexes Based on the Benzimidazolium Based Ionic Liquids−β-Cyclodextrin Systems

et al. 2021

View full text Add to dashboard Cite

Inclusion complexation is one of the best strategies for developing a controlled release of a toxic drug without unexpected side effects from the very beginning of the administration to the target site. In this study, three benzimidazolium based ionic liquids (ILs) having bromide anion and cation bearing long alkyl chains, hexyl-([C 6 CFBim]Br), octyl-([C 8 CFBim]Br), and decyl-([C 10 CFBim]Br) were designed and synthesized as antibacterial drugs. Inclusion complexes (ICs) of studied ILs have been prepared by the combination of β-cyclodextrin (β-CD), considering these conjugations should enhance the benignity of ILs and make them potential candidates for the controlled drug release. Characterizations and structural analysis of studied ICs have been performed by 1 H NMR, 2D-ROESY NMR, FT-IR, HRMS, TGA, DSC, surface tension, ionic conductivity, dynamic light scattering (DLS), and isothermal titration calorimetry (ITC). Further, the morphology of the ICs has been analyzed by SEM and TEM. Furthermore, neat ILs and ICs have been treated against Escherichia coli and Bacillus subtilis to investigate their antibacterial activity, which confirms the prevention of bacterium growth and the shrinkage of the bacterial cell wall. The findings of this work provide the proof of concept that studied benzimidazolium based ILs-β-CD host−guest complexes should act as a potential candidate in controlled drug delivery and other biomedical applications.

show abstract

Physical Characterization of Inclusion Complexes of Triphenyl Phosphate and Cyclodextrins in Solution

Cited by 7 publications

References 49 publications

Improved Eco-Friendliness of a Common Flame Retardant through Inclusion Complexation with Cyclodextrins

Improved Eco-Friendliness of a Common Flame Retardant through Inclusion Complexation with Cyclodextrins

Computational Insights into Cyclodextrin Inclusion Complexes with the Organophosphorus Flame Retardant DOPO

Insights into the Formations of Host–Guest Complexes Based on the Benzimidazolium Based Ionic Liquids−β-Cyclodextrin Systems

Contact Info

Product

Resources

About