Über die Anlagerung von Epoxiden an cyclische Iminoester

Feinauer, Roland; Seeliger, Wolfgang

doi:10.1002/jlac.19666980120

Cited by 30 publications

(5 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Benzonitrile (PhCN) was dried over phosphorus pentoxide. The monomers 2-nbutyl-2-oxazoline (BuOx) and 2-benzyl-2-oxazoline (BzOx) were synthesized following the procedure by Seeliger et al 50 The Pt-NHC-complex (Pt-NHC) 51 and the fluorinated curcuminoid derivative (CUR-F 6 ) 52 were synthesized according to the literature (Figure S7). Fruits of Schisandra chinensis were obtained from Naturwaren-Blum (Revensdorf, Germany) and were dried and powdered prior to the extraction procedure.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Investigating the Influence of Aromatic Moieties on the Formulation of Hydrophobic Natural Products and Drugs in Poly(2-oxazoline)-Based Amphiphiles

et al. 2018

View full text Add to dashboard Cite

Many natural compounds with interesting biomedical properties share one physicochemical property, namely, low water solubility. Polymer micelles are, among others, a popular means to solubilize hydrophobic compounds. The specific molecular interactions between the polymers and the hydrophobic drugs are diverse, and recently it has been discussed that macromolecular engineering can be used to optimize drug-loaded micelles. Specifically, π-π stacking between small molecules and polymers has been discussed as an important interaction that can be employed to increase drug loading and formulation stability. Here, we test this hypothesis using four different polymer amphiphiles with varying aromatic content and various natural products that also contain different relative amounts of aromatic moieties. In the case of paclitaxel, having the lowest relative content of aromatic moieties, the drug loading decreases with increasing relative aromatic amount in the polymer, whereas the drug loading of curcumin, having a much higher relative aromatic content, is increased. Interestingly, the loading using schizandrin A, a dibenzo[ a, c]cyclooctadiene lignan with intermediate relative aromatic content is not influenced significantly by the aromatic content of the polymers employed. The very high drug loading, long-term stability, ability to form stable highly loaded binary coformulations in different drug combinations, small-sized formulations, and amorphous structures in all cases corroborate earlier reports that poly(2-oxazoline)-based micelles exhibit an extraordinarily high drug loading and are promising candidates for further biomedical applications. The presented results underline that the interaction between the polymers and the incorporated small molecules may be more complex and are significantly influenced by both sides, the used carrier and drug, and must be investigated in each specific case.

show abstract

Section: ■ Materials and Methodsmentioning

confidence: 99%

Investigating the Influence of Aromatic Moieties on the Formulation of Hydrophobic Natural Products and Drugs in Poly(2-oxazoline)-Based Amphiphiles

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Bases (57) The preparation conditions and general properties are similar to those of the compounds (57). Some examples are given in Table 9.…”

mentioning

confidence: 98%

Recent Syntheses and Reactions of Cyclic Imidic Esters

Seeliger

Aufderhaar

Diepers

et al. 1966

Angew. Chem. Int. Ed. Engl.

266

131

View full text Add to dashboard Cite

“…Benzonitrile (PhCN) was dried over phosphorus pentoxide. The monomers 2-n-butyl-2-oxazoline (BuOx) and 2-benzyl-2-oxazoline (BzOx) were synthesized following the well-known procedure by Seeliger et al [60] The Pt-NHC-complex and melting points (mp) were determined by differential scanning calorimetry (DSC)…”

Section: Methodsmentioning

confidence: 99%

“…Benzonitrile (PhCN) was dried over phosphorus pentoxide. The monomers 2-n-butyl-2-oxazoline (BuOx) and 2-benzyl-2-oxazoline (BzOx) were synthesized following the well-known procedure by Seeliger et al [60] The Pt-NHC-complex (Pt-NHC) [61] and the fluorinated curcuminoid derivative (CUR-F 6 ) [62] were synthesized according to literature (Figure S6). Fruits of Schisandra chinensis were obtained from Naturwaren-Blum (Revensdorf, Germany) and were dried and powdered prior to the extraction procedure.…”

Section: Methodsmentioning

confidence: 99%

Investigating the influence of aromatic moieties on the formulation of hydrophobic natural products and drugs in poly(2-oxazoline) based amphiphiles

Luxenhofer¹,

Lübtow²,

Hahn³

et al. 2018

Preprint

View full text Add to dashboard Cite

Abstract:Many natural compounds with interesting biomedical properties share one physicochemical property, namely a low water solubility. Polymer micelles are, among others, a popular means to solubilize hydrophobic compounds. The specific molecular interactions between the polymers and the hydrophobic drugs are diverse and recently it has been discussed that macromolecular engineering can be used to optimize drug loaded micelles. Specifically, π-π stacking between small molecules and polymers has been discussed as an important interaction that can be employed to increase drug loading and formulation stability. Here, we test this hypothesis using four different polymer amphiphiles with varying aromatic content and various natural products that also contain different relative amounts of aromatic moieties. While in the case of paclitaxel, having the lowest relative content of aromatic moieties, the drug loading decreases with increasing relative aromatic amount in the polymer, the drug loading of curcumin, having a much higher relative aromatic content, is increased.Interestingly, the loading using schizandrin A, a dibenzo[a,c]cyclooctadiene lignan with intermediate relative aromatic content is not influenced significantly by the aromatic content of the polymers employed. The very high drug loading, long term stability, the ability to form stable highly loaded binary coformulations in different drug combinations, small sized formulations and amorphous structures in all cases, corroborate earlier reports that poly(2-oxazoline) based micelles exhibit an extraordinarily high drug loading and are promising candidates for further biomedical applications. The presented results underline that the interaction between the polymers and the incorporated small molecules are complex and must be investigated in every specific case.Introduction:

show abstract

Über die Anlagerung von Epoxiden an cyclische Iminoester

Cited by 30 publications

References 17 publications

Investigating the Influence of Aromatic Moieties on the Formulation of Hydrophobic Natural Products and Drugs in Poly(2-oxazoline)-Based Amphiphiles

Investigating the Influence of Aromatic Moieties on the Formulation of Hydrophobic Natural Products and Drugs in Poly(2-oxazoline)-Based Amphiphiles

Recent Syntheses and Reactions of Cyclic Imidic Esters

Investigating the influence of aromatic moieties on the formulation of hydrophobic natural products and drugs in poly(2-oxazoline) based amphiphiles

Contact Info

Product

Resources

About