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Synthesis and preliminary biological evaluation of (3-iodobenzoyl)norbiotinamide and ((5-iodo-3-pyridinyl)carbonyl)norbiotinamide: two radioiodinated biotin conjugates with improved stability.
- Source :
-
Bioconjugate chemistry [Bioconjug Chem] 1997 Mar-Apr; Vol. 8 (2), pp. 179-86. - Publication Year :
- 1997
-
Abstract
- A new class of radioiodinated biotin conjugated is described in which the amido bond between biotin and the labeled prosthetic group is reversed. One conjugate, (3-[125I]iodobenzoyl)norbiotinamide (4c, [125I]IBB) was labeled with Na125I in one step from (3-(tributylstannyl)benzoyl)norbiotinamide (4b, TBB) via a demetalation reaction. However, the analogous reaction with ((5-(tributylstannyl)-3-pyridinyl)carbonyl)norbiotinamide (6b, TPB) failed to yield ((5-[131I]iodo-3-pyridinyl)carbonyl)norbiotinamide (6c, [131I]IPB, necessitating a two-step approach for synthesizing [131I]IPB. The binding of [125I]IBB and [131I]IPB to streptavidin in vitro was identical to that of biotinyl-3-[125I]iodoanilide, a conjugate with an amido bond with normal configuration. Both [125I]IBB and [131I]IPB were stable in serum while the first-generation compound was rapidly degraded. The biodistribution patterns of [125I]IBB and [131I]IPB in mice are consistent with limited degradation of these conjugates by biotinidase and deiodinases.
- Subjects :
- Animals
Bacterial Proteins metabolism
Biotin chemical synthesis
Biotin chemistry
Drug Stability
In Vitro Techniques
Iodine Radioisotopes pharmacokinetics
Mice
Mice, Inbred BALB C
Molecular Structure
Radiopharmaceuticals chemical synthesis
Radiopharmaceuticals pharmacokinetics
Streptavidin
Tissue Distribution
Biotin analogs & derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 1043-1802
- Volume :
- 8
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Bioconjugate chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 9095358
- Full Text :
- https://doi.org/10.1021/bc970006m