Deferoxamine → Fluorescein Desferrioxamine

HRID 1660667Notes

Reaction equation

HRID 1660667 reaction equation
[CH3:1][C:2]([N:4]([OH:39])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([CH2:13][CH2:14][C:15]([N:17]([OH:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([CH2:26][CH2:27][C:28]([N:30]([OH:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=[O:29])=[O:25])=[O:16])=[O:12])=[O:3].[CH:40]1[C:45](N=C=S)=[CH:44][C:43]2[C:49]([O:51][C:52]3([C:62]4[CH:63]=[CH:64][C:65]([OH:67])=[CH:66][C:61]=4[O:60][C:54]4[CH:55]=[C:56]([OH:59])[CH:57]=[CH:58][C:53]3=4)[C:42]=2[CH:41]=1)=[O:50]>C(=O)([O-])[O-].[Na+].[Na+].[Al]>[CH:40]1[CH:45]=[CH:44][C:43]([C:49]([OH:51])=[O:50])=[C:42]([C:52]2[C:53]3[CH:58]=[CH:57][C:56]([OH:59])=[CH:55][C:54]=3[O:60][C:61]3[C:62]=2[CH:63]=[CH:64][C:65]([CH:66]=3)=[O:67])[CH:41]=1.[CH3:1][C:2]([N:4]([OH:39])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([CH2:13][CH2:14][C:15]([N:17]([OH:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([CH2:26][CH2:27][C:28]([N:30]([OH:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=[O:29])=[O:25])=[O:16])=[O:12])=[O:3]

Participants

5

Reactant 2

HCID 2973Deferoxamine2×HCID 18730Fluorescein 5-isothiocyanate2×

Product 1

HCID 86583864Fluorescein Desferrioxamine

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 5359268AluminumSolvent

Procedure

An aliquot of 120 mg of desferrioxamine and 233.64 mg of fluorescein isothiocyanate (FITC) are mixed in 50 mL of 0.1 M sodium carbonate pH 9.5. A molar ratio of 3:1 of FITC: desferrioxamine is used as described in Hentz et al. (1997) Anal. Chem. 69:4994-5000. The reaction mixture is wrapped in aluminum foil to avoid light exposure and allowed to react for at least 24 hours at room temperature. To separate fluorescently labeled desferrioxamine from free fluorescein and free desferrioxamine, the mixture is separated using a P-2 column (Bio-Rad) equilibrated in saline and samples are eluted in 2 mL fractions. The fluorescein-desferrioxamine is eluted in the void volume of the column. The first peak is collected and used for preparing fluorescein-desferrioxamine, desferrioxamine, and rhodamine liposomes.

Workup

  1. customto react for at least 24 hours at room temperature
  2. customTo separate fluorescently labeled desferrioxamine from free fluorescein and free desferrioxamine
  3. customthe mixture is separated
  4. washare eluted in 2 mL fractions
  5. washThe fluorescein-desferrioxamine is eluted in the void volume of the column
  6. customThe first peak is collected
  7. customused for preparing fluorescein-desferrioxamine, desferrioxamine, and rhodamine liposomes

Sources & evidence

ORD record
ord-34cbc220044e4ddfa08a0e8d4e75a805
Source dataset
uspto-grants-2011_10
Patent number
US08029795B2

Reaction notes

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