Tetrahydroselenophene. A Unique Structural Motif for Biochemical Applications

Author(s): Kenta Arai , Michio Iwaoka .

Journal Name: Current Organic Chemistry

Volume 20 , Issue 2 , 2016

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Abstract:

A tetrahydroselenophene (selenolane) skeleton, which is a five-membered heterocycle containing a selenium atom, has attracted increasing interest due to the significant stability and the high redox activity. Several water- soluble tetrahydroselenophene derivatives having one or two hydrophilic functional groups (e.g., OH and NH2) have been synthesized and applied to biological phenomena relevant to the redox homeostasis. In the first part of this mini review, the structure and redox properties of such water-soluble cyclic selenides and their oxidized forms (i.e., selenoxides) are reviewed. Then, three applications of tetrahydroselenophene derivatives to biologically important issues, i.e., our attempts (1) to design selenide-based mimics of well-known selenoenzyme glutathione peroxidase (GPx), which catalyzes reduction of harmful hydroperoxides (ROOH), (2) to elucidate oxidative folding pathways of proteins that couple with thiol-disulfide redox reactions of cysteine residues existing in the polypeptide chain, and (3) to model molecular chaperone- like functions of protein disulfide isomerase (PDI), which helps a nascent protein chain fold into the native structure in endoplasmic reticulum, are summarized. Finally, it is concluded that tetrahydroselenophenes will be useful structural motifs for molecular design of functional selenium compounds with versatile utilities, such as selenoenzyme mimics and selenium antioxidant drugs for prevention or treatment of diseases caused by aberration of redox homeostasis in cells.

Keywords: Selenolane, water-soluble selenide, glutathione peroxidase, selenoxide, antioxidant, protein folding.

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Article Details

VOLUME: 20
ISSUE: 2
Year: 2016
Page: [155 - 165]
Pages: 11
DOI: 10.2174/1385272819666150724233306
Price: $58

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