Triethylamine → Doxorubicin

HRID 1053315Notes

Reaction equation

HRID 1053315 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:14]3=[C:15]([OH:32])[C:16]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][C:26]=5[O:30][CH3:31])[C:20](=[O:21])[C:17]=4[C:18]([OH:19])=[C:13]3[CH2:12][C@@:11]([OH:37])([C:33]([CH2:35][OH:36])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:38])[C@@H:3]1[OH:39].Cl.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:14]3=[C:15]([OH:32])[C:16]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][C:26]=5[O:30][CH3:31])[C:20](=[O:21])[C:17]=4[C:18]([OH:19])=[C:13]3[CH2:12][C@@:11]([OH:37])([C:33]([CH2:35][OH:36])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:38])[C@@H:3]1[OH:39]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 443939Doxorubicin Hydrochloride

Product 1

HCID 31703Doxorubicin

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

300 mg of mPEG2000-PLGA2000-TB as prepared in Example 1 and 40 mg of doxorubicin hydrochloride were dissolved in chloroform at 40 □. 0.1 ml of triethylamine was added and stirred at room temperature for 1 h. The organic solvent was removed by rotary evaporation and 50 ml of 10 mM HBS buffer was added to dissolve the drug-contained thin film. The triethylamine hydrochloride was removed by dialysis or ultrafiltration, then 250 mg of gelatin was added. The solution was sterilized through a 0.22 μm membrane filter and lyophilized to obtain the lyophilized powder of doxorubicin micelle. It was shown by LC-MS/MS analysis that the drug encapsulation efficiency was 94.7% and the drug loading efficiency was more than 22.47%. The average particle diameter was 19.4 nm, and the polydispersity index (PDI) was 0.04.

Workup

  1. customThe organic solvent was removed by rotary evaporation and 50 ml of 10 mM HBS
  2. additionbuffer was added
  3. dissolutionto dissolve the drug-contained thin film
  4. customThe triethylamine hydrochloride was removed by dialysis or ultrafiltration
  5. addition250 mg of gelatin was added
  6. filtrationfilter

Sources & evidence

ORD record
ord-20182c118f614fb9a438c1838eedb04e
Source dataset
uspto-grants-2016_07
Patent number
US09393312B2

Reaction notes

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