Unknown

Dataset Information

0

Design, synthesis, and evaluation of biotinylated opioid derivatives as novel probes to study opioid pharmacology.


ABSTRACT: A generally applicable strategy of chemically labeling (-)-morphine (1) is described. The synthesis starts from commercially available starting materials and can be completed in two steps with an overall yield of 23%. In silico simulation and NMR results show that the binding of (-)-morphine to one of its molecular targets, toll-like receptor 4 (TLR4), was not affected by the modification. Secreted embryonic alkaline phosphatase (SEAP) reporter assay results demonstrate that C(3) biotinylated and unmodified (-)-morphine show similar biological activities in live cells. To our knowledge, these studies provide the first practical and concise method to label various opioid derivatives, a group of important therapeutics in pain management, for biochemical/pharmacological studies.

SUBMITTER: Li Y 

PROVIDER: S-EPMC2636689 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

altmetric image

Publications

Design, synthesis, and evaluation of biotinylated opioid derivatives as novel probes to study opioid pharmacology.

Li Ya Y   Chase Anna R AR   Slivka Peter F PF   Baggett Clyde T CT   Zhao Tina X TX   Yin Hang H  

Bioconjugate chemistry 20081201 12


A generally applicable strategy of chemically labeling (-)-morphine (1) is described. The synthesis starts from commercially available starting materials and can be completed in two steps with an overall yield of 23%. In silico simulation and NMR results show that the binding of (-)-morphine to one of its molecular targets, toll-like receptor 4 (TLR4), was not affected by the modification. Secreted embryonic alkaline phosphatase (SEAP) reporter assay results demonstrate that C(3) biotinylated an  ...[more]

Similar Datasets

| S-EPMC6596340 | biostudies-literature
| S-EPMC8725855 | biostudies-literature
| S-EPMC4648120 | biostudies-literature
| S-EPMC3541990 | biostudies-literature
| S-EPMC10440426 | biostudies-literature
| S-EPMC6652023 | biostudies-literature
| S-EPMC6385123 | biostudies-literature
| S-EPMC8624111 | biostudies-literature
| S-EPMC8200971 | biostudies-literature
| S-EPMC6804295 | biostudies-literature