Evaluation of the Effect of Geometrical Configuration and Charge of Opioid Antagonists on Their Binding to Receptors

Oon M.B., Nik Ab Rahman N.H., Mohd Noor N., Yazid M.B. 2024. Patient-controlled analgesia morphine for the management of acute pain in the emergency department: A systematic review and meta-analysis. Int. J. Emerg. Med. 17 (1), 37. https://doi.org/10.1186/s12245-024-00615-3

Article  PubMed  PubMed Central  Google Scholar 

Varga B.R., Streicher J.M., Majumdar S. 2023. Strategies towards safer opioid analgesics – A review of old and upcoming targets. Br. J. Pharmacol. 180 (7), 975–993. https://doi.org/10.1111/bph.15760

Article  PubMed  Google Scholar 

Kuzmina N. E., Kuzmin V. S. 2011. The development of ideas about the interaction of drugs with opiate receptors. Uspekhi khimii (Rus.). 80 (2), 157–181.

Bagley J.R., Thomas S.A., Rudo F.G., Spencer H.K., Doorley B.M., Ossipov M.H., Jerussi T.P., Benvenga M.J., Spaulding T. 1991. New 1-(heterocyclylalkyl)-4-(propionanilido)-4-piperidinyl methyl ester and methylene methyl ether analgesics. J. Med. Chem. 34 (2), 827–841. https://doi.org/10.1021/jm00106a051

Article  PubMed  Google Scholar 

Vardanyan R.S., Hruby V.J. 2014. Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications. Future Med. Chem. 6 (4), 385–412. https://doi.org/10.4155/fmc.13.215

Article  PubMed  Google Scholar 

Kelly E., Sutcliffe K., Cavallo D., Ramos-Gonzalez N., Alhosan N., Henderson G. 2023. The anomalous pharmacology of fentanyl. Br. J. Pharmacol. 180 (7), 797–812. https://doi.org/10.1111/bph.15573

Article  PubMed  Google Scholar 

Volpe D.A., McMahon Tobin G.A., Mellon R.D., Katki A.G., Parker R.J., Colatsky T., Kropp T.J., Verbois S.L. 2011. Uniform assessment and ranking of opioid μ receptor binding constants for selected opioid drugs. Regul. Toxicol. Pharmacol. 59 (3), 385–390.https://doi.org/10.1016/j.yrtph.2010.12.007

Article  PubMed  Google Scholar 

Uiba V.V., Krivorotov Denis Viktorovich, Zabelin M.V., Radilov A.S., Rembovsky V.R., Dulov S.A., Kuznetsov V.A., Yerofeev G.G., Martinovich N.V., Sosnov A.V. 2018. Opioid receptor antagonists. From the present to the future. Meditsina ekstremalnikh situatsiy (Rus.). 20 (3), 356–370.

Sosnov A.V., Semchenko F.M., Tokhmakhchi V.N., Sosnova A.A., Vlasov M.I., Radilov A.S., Krivorotov D.V. 2018. Criteria for the selection of compounds for the development of potent analgesics and other centrally acting drugs. Razrabotka i registratsiya lekarstvnnikh sredstv. (Rus.). 3 (24), 114–128.

Waldhoer M., Bartlett S.E., Whistler J.L. 2004. Opioid receptors. Annu. Rev. Biochem. 73, 953–990. https://doi.org/10.1146/annurev.biochem.73.011303.073940

Article  PubMed  Google Scholar 

Adler T.K. 1963. Comparative potencies of codeine and its demethylated metabolites after intraventricular injection in the mouse. J. Pharmacol. Exp. Ther. 140, 155–161.

PubMed  Google Scholar 

Raynor K., Kong H., Chen Y., Yasuda K., Yu L., Bell G.I., Reisine T. 1994. Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors. Mol. Pharmacol. 45 (2), 330–334.

PubMed  Google Scholar 

Varghese V., Hudlicky T. 2014. A short history of the discovery and development of naltrexone and other morphine derivatives. In: Natural products in medicinal chemistry. Ed. Hanessian S. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA, p. 225–250. https://doi.org/10.1002/9783527676545.ch06

Codd E.E., Shank R.P., Schupsky J.J., Raffa R.B. 1995. Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: Structural determinants and role in antinociception. J. Pharmacol. Exp. Ther. 274 (3), 1263–1270.

PubMed  Google Scholar 

Toll L., Berzetei-Gurske I.P., Polgar W.E., Brandt S.R., Adapa I.D., Rodriguez L., Schwartz R.W., Haggart D., O’Brien A., White A., Kennedy J.M., Craymer K., Farrington L., Auh J.S. 1998. Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. NIDA Res. Monogr. 178, 440–466.

PubMed  Google Scholar 

Clark S.D., Abi-Dargham A. 2019. The role of dynorphin and the kappa opioid receptor in the symptomatology of schizophrenia: A review of the evidence. Biol. Psychiatry. 86 (7), 502–511. https://doi.org/10.1016/j.biopsych.2019.05.012

Article  PubMed  Google Scholar 

Krivorotov D.V., Kochura D.M., Dulov S.A., Radilov A.S. 2022. Experimental comparison of lipophilicity of opioid antagonists. Toksikologicheskiy vestnik (Rus.). 30 (3), 149–157. https://doi.org/10.47470/0869-7922-2022-30-3-149-157

Waterhouse R.N. 2003. Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents. Mol. Imaging Biol. 5 (6), 376–389. https://doi.org/10.1016/j.mibio.2003.09.014

Article  PubMed  Google Scholar 

Noha S.M., Schmidhammer H., Spetea M. 2017. Molecular docking, molecular dynamics, and structure-activity relationship explorations of 14-oxygenated N‑methylmorphinan-6-ones as potent μ-opioid receptor agonists. ACS Chem. Neurosci. 8 (6), 1327–1337. https://doi.org/10.1021/acschemneuro.6b00460

Article  PubMed  Google Scholar 

Wu H., Wacker D., Mileni M., Katritch V., Han G.W., Vardy E., Liu W., Thompson A.A., Huang X.P., Carr-oll F.I., Mascarella S.W., Westkaemper R.B., Mosier P.D., Roth B.L., Cherezov V., Stevens R.C. 2012. Structure of the human κ-opioid receptor in complex with JDTic. Nature. 485 (7398), 327–332. https://doi.org/10.1038/nature10939

Article  PubMed  PubMed Central  Google Scholar 

Granier S., Manglik A., Kruse A.C., Kobilka T.S., Thian F.S., Weis W.I., Kobilka B.K. 2012. Structure of the δ-opioid receptor bound to naltrindole. Nature. 485 (7398), 400–404. https://doi.org/10.1038/nature11111

Article  PubMed  PubMed Central  Google Scholar 

Manglik A., Kruse A.C., Kobilka T.S., Thian F.S., Mathiesen J.M., Sunahara R.K., Pardo L., Weis W.I., Kobilka B.K., Granier S. 2012. Crystal structure of the µ-opioid receptor bound to a morphinan antagonist. Nature. 485 (7398), 321–326. https://doi.org/10.1038/nature10954

Article  PubMed  PubMed Central  Google Scholar 

Froimowitz M. 1993. HyperChem: A software package for computational chemistry and molecular modeling. Biotechniques. 14 (6), 1010–1013.

PubMed  Google Scholar 

Bye E. 1976. The crystal structure of morphine hydrate. Acta Chem. Scand. 30 (6), 549–554. https://doi.org/10.3891/acta.chem.scand.30b-0549

Article  Google Scholar 

Gelbrich T., Braun D.E., Griesser U.J. 2012. Morphine hydro-chloride anhydrate. Acta Crystallogr. Sect. E Struct. Rep. Online 68 (Pt 12), o3358–3359. https://doi.org/10.1107/S1600536812046405

Article  PubMed  PubMed Central  Google Scholar 

Canfield D.V., Barrick J., Giessen B.C. 1987. Structure of codeine. Acta Crystallogr. Sect. C Cryst. Struct. Commun. 43 (5), 977–979. https://doi.org/10.1107/S0108270187093363

Article  Google Scholar 

Braun D.E., Gelbrich T., Kahlenberg V., Griesser U.J. 2014. Insights into hydrate formation and stability of morphinanes from a combination of experimental and computational approaches. Mol. Pharm. 11 (9), 3145–3163. https://doi.org/10.1021/mp500334z

Article  PubMed  PubMed Central  Google Scholar 

Ortiz-de León C., Hartwick C.J., Stuedemann C.A., Brogden N.K., MacGillivray L.R. 2022. Mechanochemistry facilitates a single-crystal X-ray structure determination of free base naloxone anhydrate. Cryst. Growth Des. 22 (11), 6622–6626. https://doi.org/10.1021/acs.cgd.2c00831

Article  PubMed  PubMed Central  Google Scholar 

Klein C.L., Majeste R.J., Stevens E.D. 1987. Experimental electron density distribution of naloxone hydrochloride dihydrate, a potent opiate antagonist. J. Am. Chem. Soc. 109 (22), 6675–6681. https://doi.org/10.1021/ja00256a021

Article  Google Scholar 

Scheins S., Messerschmidt M., Morgenroth W., Paulmann C., Luger P. 2007. Electron density analyses of opioids: A comparative study. J. Phys. Chem. A. 111 (25), 5499–5508.https://doi.org/10.1021/jp0709252

Article  PubMed  Google Scholar 

Steinberg B.D., Harris E.T., Foxman B.M., Oliveira M.A., Hickey M.B. 2018. New look at naltrexone hydrochloride hydrates: Understanding phase behavior and characterization of two dihydrate polymorphs. Cryst. Growth Des. 18 (6), 3502–3509. https://doi.org/10.1021/acs.cgd.8b00262

Article  Google Scholar 

Zhuang Y., Wang Y., He B., He X., Zhou X.E., Guo S., Rao Q., Yang J., Liu J., Zhou Q., Wang X., Liu M., Liu W., Jiang X., Yang D., Jiang H., Shen J., Melcher K., Chen H., Jiang Y., Cheng X., Wang M.W., Xie X., Xu H.E. 2022. Molecular recognition of morphine and fentanyl by the human μ-opioid receptor. Cell. 185 (23), 4361–4375.e19. https://doi.org/10.1016/j.cell.2022.09.041

Article  PubMed  Google Scholar 

Claff T., Yu J., Blais V., Patel N., Martin C., Wu L., Han G.W., Holleran B.J., Van der Poorten O., White K.L., Hanson M.A., Sarret P., Gendron L., Cherezov V., Katritch V., Ballet S., Liu Z.J., Müller C.E., Stevens R.C. 2019. Elucidating the active δ-opioid receptor crystal structure with peptide and small-molecule agonists. Sci. Adv. 5 (11), eaax9115. https://doi.org/10.1126/sciadv.aax9115

Wang Y., Zhuang Y., DiBerto J.F., Zhou X.E., Schmitz G.P., Yuan Q., Jain M.K., Liu W., Melcher K., Jiang Y., Roth B.L., Xu H.E. 2023. Structures of the entire human opioid receptor family. Cell, 186 (2), 413–427.e17. https://doi.org/10.1016/j.cell.2022.12.026

Article  PubMed  Google Scholar 

Humphrey W., Dalke A., Schulten K. 1996. VMD: Visual molecular dynamics. J. Mol. Graph. 14 (1), 33–38. https://doi.org/10.1016/0263-7855(96)00018-5

Article  PubMed  Google Scholar 

Sheldrick G.M. 2015. SHELXT–integrated space-group and crystal-structure determination. Acta Crystallogr. A Found. Adv. 71 (Pt 1), 3–8. https://doi.org/10.1107/S2053273314026370

Article  PubMed 

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