Solubilisation of camptothecin by nonionic surfactants and alkyldimethylamine oxides

AbstractThe solubilisation of poorly soluble antineoplastic drug camptothecin by nonionic surfactants (polysorbates and octylphenol ethoxylates) and alkyldimethylamine oxide surfactants with the alkyl chain length 8 to 16 carbon atoms was investigated. The hydrophobicity of the solubilising agent turned out to be the primary structural parameter controlling the solubility efficiency of camptothecin in an aqueous solution. The quantitative parameter of solubilisation (drug loading coefficient) provided values in the range of 0.1–1.2% and 0.1–1.0% for alkyldimethylamine oxides and nonionic surfactants, respectively. The decreasing number of oxyethylene units and the extension of the hydrophobic part of nonionic surfactant molecule resulted in the increase of camptothecin solubility. From the dynamic light scattering measurements, the hydrodynamic diameter values of camptothecin-loaded alkyldimethylamine oxide and nonionic micelles were found in the range of 4–42 nm and 5–120 nm, respectively. The experimental values confirmed the increase in micellar size with the increasing alkyl chain length. The values of the packing parameter of camptothecin-loaded dodecyldimethylamine oxide micelles indicate their spherical shape at all the investigated surfactant concentrations. A simple computer model of camptothecin-loaded dodecyldimethylamine oxide micelle provided the diameter of the structure cross section which is consistent with the experimental values.

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Influence of temperature and alkyl chain length on phase behavior in Langmuir monolayers of some oxyethylenated nonionic surfactants

Journal of Colloid and Interface Science ◽

10.1016/j.jcis.2005.07.023 ◽

2006 ◽

Vol 294 (2) ◽

pp. 288-294 ◽

Cited By ~ 16

Author(s):

Md. Nazrul Islam ◽

Teiji Kato

Keyword(s):

Phase Behavior ◽

Chain Length ◽

Nonionic Surfactants ◽

Alkyl Chain ◽

Langmuir Monolayers ◽

Alkyl Chain Length ◽

Influence Of Temperature

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Quantum chemical clarification of the alkyl chain length threshold of nonionic surfactants for monolayer formation at the air/water interface

Physical Chemistry Chemical Physics ◽

10.1039/c6cp00166a ◽

2016 ◽

Vol 18 (11) ◽

pp. 7932-7937

Author(s):

Yu. B. Vysotsky ◽

E. S. Kartashynska ◽

E. A. Belyaeva ◽

D. Vollhardt ◽

V. B. Fainerman ◽

...

Keyword(s):

Chain Length ◽

Quantum Chemical ◽

Theoretical Basis ◽

Nonionic Surfactants ◽

Alkyl Chain ◽

Alkyl Chain Length ◽

Experimental Fact ◽

Water Interface ◽

Monolayer Formation ◽

Air Water Interface

A theoretical basis is introduced for the experimental fact that for various surfactant classes the alkyl chain length threshold varies for the formation of condensed monolayers.

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Effects of alkyl chain length on the solid state phase behaviors of alkyldimethylamine oxide hydrochlorides and hemihydrochlorides

Colloids and Surfaces A Physicochemical and Engineering Aspects ◽

10.1016/s0927-7757(01)00557-x ◽

2001 ◽

Vol 183-185 ◽

pp. 475-485 ◽

Cited By ~ 6

Author(s):

Masahiko Miyahara ◽

Hideya Kawasaki ◽

Tsuyoshi Fukuda ◽

Yukihiro Ozaki ◽

Hiroshi Maeda

Keyword(s):

Solid State ◽

Chain Length ◽

Alkyl Chain ◽

Alkyl Chain Length ◽

Alkyldimethylamine Oxide ◽

Phase Behaviors

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Influence of alkyl chain length on the action of acetylated monoglycerides as plasticizers for poly (vinyl chloride) food packaging film

Food Packaging and Shelf Life ◽

10.1016/j.fpsl.2020.100619 ◽

2021 ◽

Vol 27 ◽

pp. 100619

Author(s):

Chang Woo Kwon ◽

Pahn-Shick Chang

Keyword(s):

Chain Length ◽

Vinyl Chloride ◽

Food Packaging ◽

Alkyl Chain ◽

Alkyl Chain Length ◽

Packaging Film ◽

Poly Vinyl Chloride

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Silver Nanoparticles Stabilized with Phosphorus-Containing Heterocyclic Surfactants: Synthesis, Physico-Chemical Properties, and Biological Activity Determination

Nanomaterials ◽

10.3390/nano11081883 ◽

2021 ◽

Vol 11 (8) ◽

pp. 1883

Author(s):

Martin Pisárčik ◽

Miloš Lukáč ◽

Josef Jampílek ◽

František Bilka ◽

Andrea Bilková ◽

...

Keyword(s):

Silver Nanoparticles ◽

Biological Activity ◽

Zeta Potential ◽

Chain Length ◽

Alkyl Chain ◽

Chemical Properties ◽

Alkyl Chain Length ◽

Microbial Pathogens ◽

Physico Chemical ◽

Phosphorus Containing

Phosphorus-containing heterocyclic cationic surfactants alkyldimethylphenylphospholium bromides with the alkyl chain length 14 to 18 carbon atoms were used for the stabilization of silver nanodispersions. Zeta potential of silver nanodispersions ranges from +35 to +70 mV, which indicates the formation of stable silver nanoparticles (AgNPs). Long-chain heptadecyl and octadecyl homologs of the surfactants series provided the most intensive stabilizing effect to AgNPs, resulting in high positive zeta potential values and smaller diameter of AgNPs in the range 50–60 nm. A comparison with non-heterocyclic alkyltrimethylphosphonium surfactants of the same alkyl chain length showed better stability and more positive zeta potential values for silver nanodispersions stabilized with heterocyclic phospholium surfactants. Investigations of biological activity of phospholium-capped AgNPs are represented by the studies of antimicrobial activity and cytotoxicity. While cytotoxicity results revealed an increased level of HepG2 cell growth inhibition as compared with the cytotoxicity level of silver-free surfactant solutions, no enhanced antimicrobial action of phospholium-capped AgNPs against microbial pathogens was observed. The comparison of cytotoxicity of AgNPs stabilized with various non-heterocyclic ammonium and phosphonium surfactants shows that AgNPs capped with heterocyclic alkyldimethylphenylphospholium and non-heterocyclic triphenyl-substituted phosphonium surfactants have the highest cytotoxicity among silver nanodispersions stabilized by the series of ammonium and phosphonium surfactants.

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