Design, Synthesis, and Biological Evaluation of Ganglioside Hp-s1 Analogues Varying at Glucosyl Moiety

Jung Tung Hung; Chun Hong Yeh; Shih An Yang; Chiu Ya Lin; Hung Ju Tai; Ganesh B. Shelke; Daggula Mallikarjuna Reddy; Alice L. Yu; Shun Yuan Luo

doi:10.1021/acschemneuro.6b00069

Design, Synthesis, and Biological Evaluation of Ganglioside Hp-s1 Analogues Varying at Glucosyl Moiety

Jung Tung Hung, Chun Hong Yeh, Shih An Yang, Chiu Ya Lin, Hung Ju Tai, Ganesh B. Shelke, Daggula Mallikarjuna Reddy, Alice L. Yu, Shun Yuan Luo^*

^*Corresponding author for this work

Graduate Institute of Biomedical Sciences

Research output: Contribution to journal › Journal Article › peer-review

11 Scopus citations

Abstract

Ganglioside Hp-s1 is isolated from the ovary of sea urchin Diadema setosum. It exhibited better neuritogenic activity than GM1 in pheochromocytoma 12 cells. To explore the roles of glucosyl moiety of Hp-s1 in contributing to the neurogenic activity, we developed feasible procedures for synthesis of Hp-s1 analogues (2a-2f). The glucosyl moiety of Hp-s1 was replaced with α-glucose, α-galactose, β-galactose, α-mannose, and β-mannose, and their biological activities on SH-SY5Y cells and natural killer T (NKT) cells were evaluated. We found that the orientation of C-2 hydroxyl group at glucosyl moiety of Hp-s1 plays an important role to induce neurite outgrowth of SH-SY5Y cells. Surprisingly, compound 2d could activate NKT cells to produce interleukin 2, although it did not show great activity on neurite outgrowth of SH-SY5Y cells. In general, the Hp-s1 might be considered as a lead compound for the development of novel drugs aimed at modulating the activity of neuronal cells.

Original language	English
Pages (from-to)	1107-1111
Number of pages	5
Journal	ACS Chemical Neuroscience
Volume	7
Issue number	8
DOIs	https://doi.org/10.1021/acschemneuro.6b00069
State	Published - 17 08 2016

Bibliographical note

Publisher Copyright:
© 2016 American Chemical Society.

Keywords

Ganglioside Hp-s1
SH-SY5Y cells
glucosyl moiety of Hp-s1
neurogenic activity

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title = "Design, Synthesis, and Biological Evaluation of Ganglioside Hp-s1 Analogues Varying at Glucosyl Moiety",

abstract = "Ganglioside Hp-s1 is isolated from the ovary of sea urchin Diadema setosum. It exhibited better neuritogenic activity than GM1 in pheochromocytoma 12 cells. To explore the roles of glucosyl moiety of Hp-s1 in contributing to the neurogenic activity, we developed feasible procedures for synthesis of Hp-s1 analogues (2a-2f). The glucosyl moiety of Hp-s1 was replaced with α-glucose, α-galactose, β-galactose, α-mannose, and β-mannose, and their biological activities on SH-SY5Y cells and natural killer T (NKT) cells were evaluated. We found that the orientation of C-2 hydroxyl group at glucosyl moiety of Hp-s1 plays an important role to induce neurite outgrowth of SH-SY5Y cells. Surprisingly, compound 2d could activate NKT cells to produce interleukin 2, although it did not show great activity on neurite outgrowth of SH-SY5Y cells. In general, the Hp-s1 might be considered as a lead compound for the development of novel drugs aimed at modulating the activity of neuronal cells.",

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AU - Lin, Chiu Ya

AU - Tai, Hung Ju

AU - Shelke, Ganesh B.

AU - Reddy, Daggula Mallikarjuna

AU - Yu, Alice L.

AU - Luo, Shun Yuan

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Design, Synthesis, and Biological Evaluation of Ganglioside Hp-s1 Analogues Varying at Glucosyl Moiety

Abstract

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Keywords

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