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Iranian Journal of Pharmaceutical Research
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Balalaie, S., Malakoutikhah, M., Teixido, M., Fathi Vavsari, V., Giralt, E., Haghighatnia, Y., Hamdan, F., Arabanian, A. (2019). Efficient synthesis of norbuprenorphines coupled with enkephalins and investigation of their permeability. Iranian Journal of Pharmaceutical Research, 18(3), 1277-1287. doi: 10.22037/ijpr.2019.14712.12602
Saeed Balalaie; Morteza Malakoutikhah; Meritxell Teixido; Vaezeh Fathi Vavsari; Ernest Giralt; Yaghoub Haghighatnia; Fatima Hamdan; Armin Arabanian. "Efficient synthesis of norbuprenorphines coupled with enkephalins and investigation of their permeability". Iranian Journal of Pharmaceutical Research, 18, 3, 2019, 1277-1287. doi: 10.22037/ijpr.2019.14712.12602
Balalaie, S., Malakoutikhah, M., Teixido, M., Fathi Vavsari, V., Giralt, E., Haghighatnia, Y., Hamdan, F., Arabanian, A. (2019). 'Efficient synthesis of norbuprenorphines coupled with enkephalins and investigation of their permeability', Iranian Journal of Pharmaceutical Research, 18(3), pp. 1277-1287. doi: 10.22037/ijpr.2019.14712.12602
Balalaie, S., Malakoutikhah, M., Teixido, M., Fathi Vavsari, V., Giralt, E., Haghighatnia, Y., Hamdan, F., Arabanian, A. Efficient synthesis of norbuprenorphines coupled with enkephalins and investigation of their permeability. Iranian Journal of Pharmaceutical Research, 2019; 18(3): 1277-1287. doi: 10.22037/ijpr.2019.14712.12602

Efficient synthesis of norbuprenorphines coupled with enkephalins and investigation of their permeability

Article 12, Volume 18, Issue 3, Summer 2019, Page 1277-1287  XML PDF (1.31 MB)
Document Type: Research article
DOI: 10.22037/ijpr.2019.14712.12602
Authors
Saeed Balalaie email 1, 2; Morteza Malakoutikhah3; Meritxell Teixido4; Vaezeh Fathi Vavsari1; Ernest Giralt3; Yaghoub Haghighatnia1; Fatima Hamdan1; Armin Arabanian1
1Peptide Chemistry Research Center, K. N. Toosi University of Technology, 15875-4416, Tehran, Iran.
2Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran.
3Institute for Research in Biomedicine (IRB Barcelona), Barcelona Institute of Science and Technology (BIST), Baldiri Reixac 10, 08028 Barcelona, Spain
4Institute for Research in Biomedicine (IRB Barcelona), Barcelona Institute of Science and Technology (BIST), Baldiri Reixac 10, 08028 Barcelona, Spain.
Abstract
An efficient approach for the synthesis of norbuprenorphin derivatives through coupling of enkephalins and norbuprenorphine intermediate is described. Norbuprenorphine derivative was synthesized from thebaine and then, its reaction with succinic acid and phthalic acid was also studied. Meanwhile, the synthesis of enkephalins was done using solid phase peptide synthesis approach. Furthermore, after cleavage of the peptide from the surface of the resin, the coupling of enkephalins with norbuprenorphine derivative was done using TBTU as a coupling reagent then the derivatives were purified using preparative high-pressure liquid chromatography and their structures were confirmed using high-resolution mass spectrometry data. Later, their permeability across membranes was investigated. After PAMPA studies, it was found that the permeability of all norbuprenorphin-enkephalin derivatives was increased, however, succinic and phthalic acid derivatives showed higher permeability than norbuprenorphine-Leu-enkephalin.
Keywords
Enkephalin; permeability; norbuprenorphine; membrane; coupling; solid phase peptide synthesis
Main Subjects
Medicinal chemistry
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