Efficient Synthesis of Norbuprenorphines Coupled with Enkephalins and Investigation of Their Permeability

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BALALAIE SAEED; Malakoutikhah Morteza; Teixido Meritxell; Fathi Vavsari Vaezeh; Giralt Ernest; Haghighatnia Yaghoub; Hamdan Fatima; Arabanian Armin

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Journal Paper

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Journal: Iranian Journal of Pharmaceutical Research Year:2019 | Volume:18 | Issue:3 Page(s): 1277-1287

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Title

Efficient Synthesis of Norbuprenorphines Coupled with Enkephalins and Investigation of Their Permeability

Author(s)

Keywords

Enkephalin

Permeability

Norbuprenorphine

Membrane

Coupling

Solid phase peptide synthesis

Abstract

An efficient approach for the synthesis of norbuprenorphin derivatives through Coupling of Enkephalins and Norbuprenorphine intermediates 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.

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APA: Copy

BALALAIE, SAEED, Malakoutikhah, Morteza, Teixido, Meritxell, Fathi Vavsari, Vaezeh, Giralt, Ernest, Haghighatnia, Yaghoub, Hamdan, Fatima, & Arabanian, Armin. (2019). Efficient Synthesis of Norbuprenorphines Coupled with Enkephalins and Investigation of Their Permeability. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), 18(3), 1277-1287. SID. https://sid.ir/paper/289155/en

Vancouver: Copy

BALALAIE SAEED, Malakoutikhah Morteza, Teixido Meritxell, Fathi Vavsari Vaezeh, Giralt Ernest, Haghighatnia Yaghoub, Hamdan Fatima, Arabanian Armin. Efficient Synthesis of Norbuprenorphines Coupled with Enkephalins and Investigation of Their Permeability. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR)[Internet]. 2019;18(3):1277-1287. Available from: https://sid.ir/paper/289155/en

IEEE: Copy

SAEED BALALAIE, Morteza Malakoutikhah, Meritxell Teixido, Vaezeh Fathi Vavsari, Ernest Giralt, Yaghoub Haghighatnia, Fatima Hamdan, and Armin Arabanian, “Efficient Synthesis of Norbuprenorphines Coupled with Enkephalins and Investigation of Their Permeability,” IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), vol. 18, no. 3, pp. 1277–1287, 2019, [Online]. Available: https://sid.ir/paper/289155/en

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