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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.

Publication ,  Journal Article
Foulon, CF; Alston, KL; Zalutsky, MR
Published in: Bioconjug Chem
1997

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.

Duke Scholars

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Published In

Bioconjug Chem

DOI

ISSN

1043-1802

Publication Date

1997

Volume

8

Issue

2

Start / End Page

179 / 186

Location

United States

Related Subject Headings

  • Tissue Distribution
  • Streptavidin
  • Radiopharmaceuticals
  • Organic Chemistry
  • Molecular Structure
  • Mice, Inbred BALB C
  • Mice
  • Iodine Radioisotopes
  • In Vitro Techniques
  • Drug Stability
 

Citation

Published In

Bioconjug Chem

DOI

ISSN

1043-1802

Publication Date

1997

Volume

8

Issue

2

Start / End Page

179 / 186

Location

United States

Related Subject Headings

  • Tissue Distribution
  • Streptavidin
  • Radiopharmaceuticals
  • Organic Chemistry
  • Molecular Structure
  • Mice, Inbred BALB C
  • Mice
  • Iodine Radioisotopes
  • In Vitro Techniques
  • Drug Stability