Synthesis of radiolabeled chiral probes for binding and receptor studies: Radiolabeled juvenoids and inositol phosphates

Thesis/Dissertation · Fri Jan 01 04:00:00 EST 1988

OSTI ID:6940433

Boehm, M F

This study is composed of two parts. Part I describes the synthesis of seven high specific activity radioligands for the characterization of macromolecular receptors for juvenile hormone analog-type labeled insect growth regulators. These radioligands include (1) ({sup 125}I)-radioiodinated iodovinyl methoprenol and iodovinyl methoprene (2000 Ci/mmol), (2) ({sup 3}H)-labeled (7S)-methoprene and (7S)-hydroprene (>60 Ci/mmol), potent dodecadienoate insect growth regulators, (3) ({sup 3}H)-labeled fenoxycarb (Maag) and S-31183 Sumitomo, phenoxyphenyl ether IGRs, and (4) ({sup 3}H)-methoprene diazoketone, a photoaffinity label for characterizing receptor sites. The attempted synthesis of high specific activity tritium labeled JH III is also described. Biological studies utilizing these radioligands show separate nuclear receptor proteins for JH homologs and juvenoids. Part II describes the preparation of enantiomerically enriched radiolabeled myo-inositol-1,3,4-trisphosphate (myo-Ins(1,3,4)P{sub 3}) and fluorinated analogs of myo-Ins(1,3,4)P{sub 3} for examining receptors for myo-Ins(1,3,4)P{sub 3}. Three compounds have been synthesized. These include 2-fluoro- and 2,2-difluoro-2-deoxy analogs of DL-myo-Ins(1,3,4)P{sub 3}, D- and L-myo-Ins(1,3,4)P{sub 3} at >95% enantiomeric excess and, D-and L-({sup 3}H)-myo-Ins(1,3,4)P{sub 3} enantiomers with specific activities of 15 Ci/mmol.

• Research Organization: State Univ. of New York, Stony Brook, NY (USA)
• OSTI ID: 6940433
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ANIMALS
ARTHROPODS
CHEMICAL COMPOSITION
CHEMICAL PREPARATION
ESTERS
HORMONES
HYDROGEN COMPOUNDS
INSECTS
INVERTEBRATES
ISOTOPE APPLICATIONS
LIGANDS
LIPIDS
MEMBRANE PROTEINS
ORGANIC COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHOLIPIDS
PROTEINS
RECEPTORS
SYNTHESIS
TRACER TECHNIQUES
TRITIUM COMPOUNDS