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

634875

Sigma-Aldrich

Aluminum oxide, single crystal substrate, <0001>

676780

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

M1775

Sigma-Aldrich

Methanol, Absolute - Acetone free

676934

Sigma-Aldrich

1,4-Dioxane, ACS reagent, ≥99.0%

154903

Sigma-Aldrich

Methanol, ACS spectrophotometric grade, ≥99.9%

179957

Sigma-Aldrich

Methanol, Laboratory Reagent, ≥99.6%

199974

Sigma-Aldrich

Aluminum oxide, activated, neutral, Brockmann I

199966

Sigma-Aldrich

Aluminum oxide, activated, acidic, Brockmann I

D201863

Sigma-Aldrich

1,4-Dioxane, ReagentPlus^®, ≥99%, contains ≤25 ppm BHT as stabilizer

D65100

Sigma-Aldrich

Dichloromethane, contains 40-150 ppm amylene as stabilizer, ACS reagent, ≥99.5%

267740

Sigma-Aldrich

Aluminum oxide, pore size 58 Å, ~150 mesh

179337

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

199443

Sigma-Aldrich

Aluminum oxide, activated, basic, Brockmann I

320269

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

33147

Sigma-Aldrich

1,4-Dioxane, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.5% (GC)

676853

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

799319

Sigma-Aldrich

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

494453

Sigma-Aldrich

Dichloromethane, biotech. grade, 99.9%, contains 40-150 ppm amylene as stabilizer

414069

Sigma-Aldrich

Aluminum oxide, pellets, 3 mm

494437

Sigma-Aldrich

Methanol, BioReagent, ≥99.93%

799300

Sigma-Aldrich

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

32213

Sigma-Aldrich

Methanol, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)

229423

Sigma-Aldrich

Aluminum oxide, powder, 99.99% trace metals basis

24233

Sigma-Aldrich

Dichloromethane, puriss., meets analytical specification of Ph. Eur., NF, ≥99% (GC)

342688

Sigma-Aldrich

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

320390

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

24229

Sigma-Aldrich

Methanol, puriss., meets analytical specification of Ph Eur, ≥99.7% (GC)

342653

Sigma-Aldrich

Aluminum oxide, fused, powder, primarily α-phase, 100-200 mesh

360481

Sigma-Aldrich

1,4-Dioxane, ACS reagent, ≥99.0%, contains ≤25 ppm BHT as stabilizer

234745

Sigma-Aldrich

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