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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

Aluminum oxide, mesoporous, MSU-X (wormhole), average pore size 3.8 nm

Sigma-Aldrich

Triethylamine, puriss. p.a., ≥99.5% (GC)

Sigma-Aldrich

Triethylamine, for amino acid analysis, ≥99.5% (GC)

Sigma-Aldrich

Triethylamine, BioUltra, ≥99.5% (GC)

Sigma-Aldrich

Hydrogen peroxide solution, 30 % (w/w) in H₂O, contains stabilizer

Sigma-Aldrich

N,N-Dimethylformamide, for molecular biology, ≥99%

Sigma-Aldrich

Hydrogen peroxide solution, 34.5-36.5%

Sigma-Aldrich

Thiazolyl Blue Tetrazolium Bromide, 98%

Sigma-Aldrich

Thiazolyl Blue Tetrazolium Bromide, powder, BioReagent, suitable for cell culture, suitable for insect cell culture, ≥97.5% (HPLC)

Sigma-Aldrich

Triethylamine, ≥99.5%

Sigma-Aldrich

Triethylamine, ≥99%

Sigma-Aldrich

Methanol, NMR reference standard

Sigma-Aldrich

Ninhydrin, ACS reagent

Sigma-Aldrich

Diethyl ether

Sigma-Aldrich

Triethylamine, ≥99.5%

Sigma-Aldrich

Sodium sulfate, ≥99.99% trace metals basis

Sigma-Aldrich

Acryloyl chloride, ≥97%, contains ~400 ppm phenothiazine as stabilizer

Sigma-Aldrich

Acryloyl chloride, 97.0%, contains <210 ppm MEHQ as stabilizer

Sigma-Aldrich

Chloroform, anhydrous, contains amylenes as stabilizer, ≥99%

Sigma-Aldrich

Sodium sulfate, BioUltra, anhydrous, ≥99.0% (T)

Sigma-Aldrich

Potassium bicarbonate, BioUltra, ≥99.5% (T)

Sigma-Aldrich

Dimethyl sulfoxide, for molecular biology

Sigma-Aldrich

Dimethyl sulfoxide, PCR Reagent

Sigma-Aldrich

Dimethyl sulfoxide, ≥99.5% (GC), suitable for plant cell culture

Sigma-Aldrich

Dimethyl sulfoxide, Hybri-Max^™, sterile-filtered, BioReagent, suitable for hybridoma, ≥99.7%

Sigma-Aldrich

Ninhydrin, suitable for amino acid detection