Réaction #1702030

ord-f0917811e57c4986afcf74b3f33aedeb

Équation de réaction

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
[Na]
sodium
N[C@@H](CS(=O)(=O)O)C(=O)O
cysteic acid
[Na]
sodium
N[C@@H](CS(=O)(=O)O)C(=O)O
cysteic acid
→
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

Réactifs

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
[Na]
sodium
N[C@@H](CS(=O)(=O)O)C(=O)O
cysteic acid
[Na]
sodium
N[C@@H](CS(=O)(=O)O)C(=O)O
cysteic acid
—
methyl ester
—
methyl ester

Réactifs

Aucun

Solvants

—
solution

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ConcentrationThe doxorubicin concentration in the obtained formulation
  2. 2
    AutreThe solution obtained
  3. 3
    Filtrationwas filtered through 0.2 mm
  4. 4
    Filtrationfilter
  5. 5
    Autrefreeze dried
  6. 6
    FiltrationThe filtration

Mode opératoire

50 ml doxorubicin hydrochloride solution (8.6 mg/ml) was added drop-wise under stirring to 200 ml of a solution containing sodium salt of methyl ester of N-all-trans-retinoyl cysteic acid (3 mg/mL) and sodium salt of methyl ester of 13-cis-retinoyl cysteic acid (3 mg/ml) in 500 ml round-bottom flask. Stirring was continued for an additional 20 min. The doxorubicin concentration in the obtained formulation was 1.6 mg/ml. The solution obtained was filtered through 0.2 mm filter and freeze dried. The filtration did not result in reduction of doxorubicin concentration.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08765173B2uspto-grants-2014_07