1562-85-2 → HCID 131715861, compound

HRID 1382185Notes

Reaction equation

HRID 1382185 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:14]([OH:15])[CH2:13][C@H:12]([O:16][C@H:17]3[C@@H:22]([OH:23])[CH2:21][C@H:20]([O:24][C@@H:25]4[CH2:30][C@H:29]5[CH2:31][CH2:32][C@H:33]6[C@@:38]7([OH:48])[CH2:39][CH2:40][C@H:41]([C:42]8[CH2:47][O:46][C:44](=[O:45])[CH:43]=8)[C@@:37]7([CH3:49])[C@H:36]([OH:50])[CH2:35][C@@H:34]6[C@@:28]5([CH3:51])[CH2:27][CH2:26]4)[O:19][C@@H:18]3[CH3:52])[O:11][C@@H:10]2[CH3:53])[CH2:5][C@H:4]([OH:54])[C@@H:3]1[OH:55].[CH3:56][N:57]([C:59]1[CH:64]=[CH:63][C:62]2[NH+:65]=[C:66]3[C:72]([O:73][C:61]=2[CH:60]=1)=[C:71]([OH:74])[C:69](=[O:70])[CH:68]=[C:67]3[C:75]([OH:77])=[O:76])[CH3:58].[Cl-:78].Cl.NO>OP([O-])(O)=O.OP([O-])([O-])=O.[Na+].[Na+].[Na+].[Cl-].[Cl-].[K+].[K+].CN(C=O)C>[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:14]([OH:15])[CH2:13][C@H:12]([O:16][C@H:17]3[C@@H:22]([OH:23])[CH2:21][C@H:20]([O:24][C@@H:25]4[CH2:30][C@H:29]5[CH2:31][CH2:32][C@H:33]6[C@@:38]7([OH:48])[CH2:39][CH2:40][C@H:41]([C:42]8[CH2:47][O:46][C:44](=[O:45])[CH:43]=8)[C@@:37]7([CH3:49])[C@H:36]([OH:50])[CH2:35][C@@H:34]6[C@@:28]5([CH3:51])[CH2:27][CH2:26]4)[O:19][C@@H:18]3[CH3:52])[O:11][C@@H:10]2[CH3:53])[CH2:5][C@H:4]([OH:54])[C@@H:3]1[OH:55].[CH3:58][N:57]([C:59]1[CH:64]=[CH:63][C:62]2[NH+:65]=[C:66]3[C:72]([O:73][C:61]=2[CH:60]=1)=[C:71]([OH:74])[C:69](=[O:70])[CH:68]=[C:67]3[C:75]([OH:77])=[O:76])[CH3:56].[Cl-:78]

Participants

6

Reactant 3

HCID 738011562-85-22×HCID 443297Hydroxyamine hydrochlorideHCID 2724385Digoxin2×

Product 1

HCID 131715861HCID 131715861, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24978514Phosphate Buffered SalineSolvent

Procedure

To a stirred solution of 16 mg of sheep anti-digoxin in 10 ml of pH 8.0 phosphate buffered saline at 0° was added dropwise 0.1 ml of a 0.1M solution of gallocyanine NHS ester (prepared by a procedure similar to that of Example 4 for the preparation of the NHS ester of DECAS) in dry DMF over a five minute period. After stirring at 0°-4° for 18 hours, 0.1 ml of 4M hydroxylamine hydrochloride was added all at once and stirring was continued for thirty minutes at 0°-4°. The blue solution was then purified by gel filtration, dialysis, and centrifugation to give 7.6 ml of 1.44 mg/ml blue antibody solution. The solution contained an average of 2.6 moles gallocyanine per mole of anti-digoxin. The absorption maxima of the conjugate were at 278 nm and 625 nm, and the relative quantum yield of the conjugate was determined to be 0.02.

Workup

  1. customprepared by a procedure similar to that of Example 4
  2. stirringstirring
  3. waitwas continued for thirty minutes at 0°-4°
  4. filtrationThe blue solution was then purified by gel filtration, dialysis, and centrifugation
  5. customto give 7.6 ml of 1.44 mg/ml blue antibody solution

Sources & evidence

ORD record
ord-61f8543b7f7945ae8b31e3ffabb5d0e9
Source dataset
uspto-grants-1989_02
Patent number
US04806488

Reaction notes

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