Bioconjugation on cube-octameric silsesquioxanes

Fabritz, Sebastian; Hörner, Sebastian; Avrutina, Olga; Kolmar, Harald

doi:10.1039/c2ob26807h

Cited by 43 publications

(49 citation statements)

References 127 publications

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“…Silsesquioxane-containing materials have found uses in catalysis and as model compounds for silica-based materials; as thermoplastics and thermosets, as flame retardants, and as electrolytes, in electronic and photonic devices; in cosmetics, as ionic liquids; and as materials for biological and medical applications, just to list some of them. Summary of different applications can be found in the reported literature (Fabritz et al 2013;Gómez-Romero and Sanchez 2004;Guglielmi et al 2014;Kaneko et al 2012c;Kickelbick 2014;Sanchez et al 2011). …”

Section: Discussionmentioning

confidence: 95%

Architecture of Silsesquioxanes

Dirè

Borovin

Ribot

2016

Handbook of Sol-Gel Science and Technology

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Section: Discussionmentioning

confidence: 95%

Architecture of Silsesquioxanes

Dirè

Borovin

Ribot

2016

Handbook of Sol-Gel Science and Technology

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“…Mono-functionalized hydroxyalkyl POSS molecules were typically made by a corner-capping reaction of incompletely condensed heptaisobutyl POSS trisilanols with e.g., hydroxyalkyltrichlorosilanes [18] or 2-(trichlorosilyl)ethyl acetate, followed by hydrolysis of the relevant ester and yielding mono-hydroxylalkyl derivatives of POSS [23]. POSS having other reactive functional groups e.g., Si–OR, Si–H and C=C can undergo suitable chemical transformations such as substitution and hydrosilylation, leading to a wide range of POSS functional systems [9,24,25]. …”

Section: Introductionmentioning

confidence: 99%

“…This thiol-ene addition [27] serves as a convenient synthetic tool, particularly in the area of POSS materials [17,24,25,26,27,28,29,30,31]. This regioselective process, proceeds under mild conditions and tolerates many solvents, and functional groups.…”

Section: Introductionmentioning

confidence: 99%

Star-Shaped and Linear POSS-Polylactide Hybrid Copolymers

et al. 2015

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Novel octakis-2[(6-hydroxyhexyl)thio]ethyl-octasilsesquioxane (POSS-S-OH) as well as heptaisobutyl-2[(6-hydroxyhexyl)thio]ethyl-octasilsesquioxane (iBu-POSS-S-OH) were synthesized. POSS structures, bearing both types of groups i.e., 2[(6-hydroxyhexyl)thio]ethyl and the vinyl ones, pendant from the octahedral cage are also described. The synthetic pathway involved thiol-ene click reaction of 6-mercapto-1-hexanol (MCH) to octavinyloctasilsesquioxane (POSS-Vi), and heptaisobutylvinyloctasilsesquioxane (iBu-POSS-Vi), in the presence of 2,2′-azobisisobutyronitrile. The functionalized silsesquioxane cages of regular octahedral structure were used further as initiators for ring opening polymerization of l,l-dilactide, catalyzed by tin (II) 2-ethylhexanoate. The polymerization afforded biodegradable hybrid star shape and linear systems with an octasilsesquioxane cage as a core, bearing polylactide arm(s).

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“…9–11 The conjugation of biologically active molecules to the nontoxic and biocompatible POSS core is highly desirable for applications in drug delivery and bioimaging where multivalency is required. 12 …”

Section: Introductionmentioning

confidence: 99%

Branched Polyhedral Oligomeric Silsesquioxane Nanoparticles Prepared via Strain-Promoted 1,3-Dipolar Cycloadditions

Ledin

Friscourt³

et al. 2015

Langmuir

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Conjugation of small organic molecules and polymers to polyhedral oligosilsesquioxane (POSS) cores results in novel hybrid materials with unique physical characteristics. We report here an approach in which star-shaped organic–inorganic scaffolds bearing eight cyclooctyne moieties can be rapidly functionalized via strain-promoted azide–alkyne cycloaddition (SPAAC) to synthesize a series of nearly monodisperse branched core–shell nanoparticles with hydrophobic POSS cores and hydrophilic arms. We established that SPAAC is a robust method for POSS core octafunctionalization with the reaction rate constant of 1.9 × 10−2 M−1 s−1. Functionalization with poly(ethylene glycol) (PEG) azide, fluorescein azide, and unprotected lactose azide gave conjugates which represent different classes of compounds: polymer conjugates, fluorescent dots, and bioconjugates. These resulting hybrid compounds were preliminarily tested for their ability to self-assemble in solution and at the air–water interface. We observed the formation of robust smooth Langmuir monolayers with diverse morphologies. We found that polar lactose moieties are completely submerged into the subphase whereas the relatively hydrophobic fluorescein arms had extended conformation at the interface, and PEG arms were partially submerged. Finally, we observed the formation of stable micelles with sizes between 70 and 160 nm in aqueous solutions with size and morphology of the structures dependent on the molecular weight and the type of the peripheral hydrophilic moieties.

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Bioconjugation on cube-octameric silsesquioxanes

Cited by 43 publications

References 127 publications

Architecture of Silsesquioxanes

Architecture of Silsesquioxanes

Star-Shaped and Linear POSS-Polylactide Hybrid Copolymers

Branched Polyhedral Oligomeric Silsesquioxane Nanoparticles Prepared via Strain-Promoted 1,3-Dipolar Cycloadditions

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