BU72
BU72 is an extremely potent opioid, with one of the highest known affinities for the μ-opioid receptor. In animal studies, it was found to be a potent analgesic, with a slow onset and long duration of action, but was not considered suitable to develop for medical use.[1] It was used to produce the first crystal structure of the active μ-opioid receptor,[2] and is now widely used to model the activation process.[3][4][5] The stereochemistry has recently been revised, with the phenyl group in the (R) configuration,[6] which has been accepted by the authors of the crystal structure.[7]
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Formula | C28H32N2O2 |
Molar mass | 428.576 g·mol−1 |
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References
- Neilan CL, Husbands SM, Breeden S, Ko MC, Aceto MD, Lewis JW, et al. (September 2004). "Characterization of the complex morphinan derivative BU72 as a high efficacy, long-lasting mu-opioid receptor agonist". European Journal of Pharmacology. 499 (1–2): 107–16. doi:10.1016/j.ejphar.2004.07.097. PMID 15363957.
- Huang W, Manglik A, Venkatakrishnan AJ, Laeremans T, Feinberg EN, Sanborn AL, et al. (August 2015). "Structural insights into µ-opioid receptor activation". Nature. 524 (7565): 315–21. Bibcode:2015Natur.524..315H. doi:10.1038/nature14886. PMC 4639397. PMID 26245379.
- Sounier R, Mas C, Steyaert J, Laeremans T, Manglik A, Huang W, et al. (August 2015). "Propagation of conformational changes during μ-opioid receptor activation". Nature. 524 (7565): 375–8. Bibcode:2015Natur.524..375S. doi:10.1038/nature14680. PMC 4820006. PMID 26245377.
- Cheng JX, Cheng T, Li WH, Liu GX, Zhu WL, Tang Y (January 2018). "Computational insights into the G-protein-biased activation and inactivation mechanisms of the μ opioid receptor". Acta Pharmacologica Sinica. 39 (1): 154–164. doi:10.1038/aps.2017.158. PMC 5758664. PMID 29188799.
- Sena DM, Cong X, Giorgetti A (December 2020). "Ligand based conformational space studies of the μ-opioid receptor". Biochimica et Biophysica Acta (BBA) - General Subjects. 1865 (3): 129838. doi:10.1016/j.bbagen.2020.129838. PMID 33373630.
- Munro TA (April 2020). "Revised (β-phenyl) stereochemistry of ultrapotent μ opioid BU72". bioRxiv. doi:10.1101/2020.04.01.020883. S2CID 215551137.
- Huang W, Manglik A, Venkatakrishnan AJ, Laeremans T, Feinberg EN, Sanborn AL, et al. (August 2020). "Author Correction: Structural insights into μ-opioid receptor activation". Nature. 584 (7820): E16. doi:10.1038/s41586-020-2542-z. PMID 32724208.
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