Doxorubicin Hydrochloride → Doxorubicin

HRID 1168107Notes

Reaction equation

HRID 1168107 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>CN(C)C=O>[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

3

Reactant 1

HCID 443939Doxorubicin Hydrochloride

Product 1

HCID 31703Doxorubicin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving 0.25 g of hydrazone linker-bound mPEG-PLGA obtained in Example 3 and 10 mg of doxorubicin-HCl in 7.5 ml of dimethylformamide, conjugation reaction was performed for 24 hours at room temperature under nitrogen gas to obtain doxorubicin-conjugated micelle monomers. The micelle monomers were dispersed in 300 ml of triple distilled water to form doxorubicin-conjugated sustained release micelles, and free doxorubicin was removed by dialyzing the mixture 5 times against 3 L of triple distilled water each time. Doxorubicin-conjugated sustained release micelles were pelletized by ultracentrifugation, and freeze-dried after removing supernatant, and then, stored in the form of doxorubicin-conjugated micelle monomers. The efficiency of conjugation of doxorubicin was determined analogously as in Example 2(see: Table 3 below).

Workup

  1. dissolutionAfter dissolving

Sources & evidence

ORD record
ord-0556b18caacc48569f6c73034aafdb9d
Source dataset
uspto-grants-2003_09
Patent number
US06623729B2

Reaction notes

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