Reaction #637507

ord-b591766626c745f0a9a57ca2344fd3c7

Reaction equation

COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
Doxorubicin hydrochloride
CCCCC=C(C#N)C(=O)[O-]
n-butylcyanoacrylate
→
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
Doxorubicin

Reactants

COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
Doxorubicin hydrochloride
—
dextran
CCCCC=C(C#N)C(=O)[O-]
n-butylcyanoacrylate

Reagents

None

Solvents

O
water
Cl
HCl

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added to the reaction flask
  2. 2
    Filtrationfiltered through 0.8 μm membrane
  3. 3
    Filtrationfilter (Nuclepore Track-Etch membrane, Whatman, USA)
  4. 4
    Otherwas kept in a refrigerator at 4° C.

Procedure

100 μl of n-butylcyanoacrylate monomer was added to 1% dextran solution in 8 mL of 0.01 M HCl under constant stirring at 600 rpm. Doxorubicin hydrochloride powder 50 mg was dissolved in 2 mL of distilled water and after 40 minutes the solution was added to the reaction flask. After 4 hours the pH of the nanoparticle suspension was adjusted at 7 and filtered through 0.8 μm membrane filter (Nuclepore Track-Etch membrane, Whatman, USA). The doxorubicin-loaded nanoparticle suspension was kept in a refrigerator at 4° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07947308B2uspto-grants-2011_05