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Hydrolysis-Sensitive Dithiolethione Prodrug Micelles.

Hydrolysis-Sensitive Dithiolethione Prodrug Micelles.

Macromolecular bioscience (2015-06-24)

Urara Hasegawa, Naoya Tateishi, Hiroshi Uyama, André J van der Vlies

ABSTRACT

Prodrug micelles carrying 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OH), a compound possessing chemopreventive properties, are prepared from amphiphilic block copolymers linking ADT-OH via an ester bond using glycine (PAM-PGlyADT) and isoleucine linkers (PAM-PIleADT). The release of ADT-OH from the PAM-PIleADT micelles is much slower than the PAM-PGlyADT micelles. The PAM-PGlyADT micelles show comparable toxicity with ADT-OH in different cancer cell lines, whereas the PAM-PIleADT micelles are not toxic up to 400 µM. This ADT-ester prodrug micelle approach enables to modulate the release rate of ADT-OH and thus might find application in cancer therapy and prevention.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer

Sigma-Aldrich

Aluminum oxide, 99.997% trace metals basis

Sigma-Aldrich

Ethyl acetate, anhydrous, 99.8%

Sigma-Aldrich

Calcium hydride, powder, 0-2 mm, reagent grade, ≥90% (gas-volumetric)

Sigma-Aldrich

Dimethyl sulfoxide, anhydrous, ≥99.9%

Sigma-Aldrich

4-(Dimethylamino)pyridine, ReagentPlus^®, ≥99%

Sigma-Aldrich

1-Ethylpiperidine hypophosphite, 95%

Sigma-Aldrich

Aluminum oxide, nanowires, diam. × L 2-6 nm × 200-400 nm

Sigma-Aldrich

Isobutyric acid, ≥99%, FCC, FG

Sigma-Aldrich

Isobutyric acid, natural, ≥99%, FCC, FG

Sigma-Aldrich

Ethyl acetate, ReagentPlus^®, ≥99.8%

Sigma-Aldrich

Methanol-¹²C, 99.95 atom % ¹²C

Supelco

Isobutyric acid, analytical standard

Sigma-Aldrich

DCC, 99%

Sigma-Aldrich

Aluminum oxide, nanopowder, <50 nm particle size (TEM)

Sigma-Aldrich

Ethyl acetate, natural, ≥99%, FCC, FG

Sigma-Aldrich

4-Acryloylmorpholine, 97%, contains 1,000 ppm monomethyl ether hydroquinone as inhibitor

Sigma-Aldrich

Ethyl acetate, ≥99%, FCC, FG

Sigma-Aldrich

Aluminum oxide, single crystal substrate, <0001>

Sigma-Aldrich

Methanol solution, (Methanol:Dimethyl sulfoxide 1:1 (v/v))

Sigma-Aldrich

Ethyl acetate

Sigma-Aldrich

Ethyl acetate

Sigma-Aldrich

Aluminum oxide, Corundum, α-phase, -100 mesh

Sigma-Aldrich

Ethyl acetate, ACS reagent, ≥99.5%

Sigma-Aldrich

Aluminum oxide, fused, powder, primarily α-phase, -325 mesh

Sigma-Aldrich

Methanol solution, NMR reference standard, 4% in methanol-d₄ (99.8 atom % D), NMR tube size 3 mm × 8 in.

Sigma-Aldrich

Aluminum oxide, nanopowder, 13 nm primary particle size (TEM), 99.8% trace metals basis

Sigma-Aldrich

Aluminum oxide, nanoparticles, 30-60 nm particle size (TEM), 20 wt. % in H₂O

Sigma-Aldrich

Aluminum oxide, activated, acidic, Brockmann I, free-flowing, Redi-Dri^™

Sigma-Aldrich

Ethyl acetate, ACS reagent, ≥99.5%