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ScholarlyArticle:
      headline:Methods to Generate an Array of Novel Rexinoids by SAR on a Potent Retinoid X Receptor Agonist: A Case Study with NEt-TMN
      pageEnd:121
      pageStart:109
      image:https://media.springernature.com/w153/springer-static/cover/book/978-1-4939-9585-1.jpg
      genre:
         Springer Protocols
      isPartOf:
         name:Retinoid and Rexinoid Signaling
         isbn:
            978-1-4939-9585-1
            978-1-4939-9584-4
         type:Book
      publisher:
         name:Springer New York
         logo:
            url:https://www.springernature.com/app-sn/public/images/logo-springernature.png
            type:ImageObject
         type:Organization
      author:
            name:Carl E. Wagner
            affiliation:
                  name:New College of Interdisciplinary Arts and Sciences, Arizona State University
                  address:
                     name:School of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences, Arizona State University, Glendale, USA
                     type:PostalAddress
                  type:Organization
            email:[email protected]
            type:Person
            name:Peter W. Jurutka
            affiliation:
                  name:New College of Interdisciplinary Arts and Sciences, Arizona State University
                  address:
                     name:School of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences, Arizona State University, Glendale, USA
                     type:PostalAddress
                  type:Organization
            type:Person
      keywords:Retinoid X receptor, Rexinoid, Nuclear receptor, Cutaneous T-cell lymphoma, Synthetic methods, Luciferase assay, Mammalian two hybrid assay
      description:The methods described in this chapter concern procedures for the design, synthesis, and in vitro biological evaluation of an array of potent retinoid-X-receptor (RXR) agonists employing 6-(ethyl(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino)nicotinic acid (NEt-TMN), and recently reported NEt-TMN analogs, as a case study. These methods have been extensively applied beyond the present case study to generate several analogs of other potent RXR agonists (rexinoids), particularly the RXR agonist known as bexarotene (Bex), a Food and Drug Administration (FDA) approved drug for cutaneous T-cell lymphoma that is also often prescribed, off-label, for breast, lung, and other human cancers. Common side effects with Bex treatment include hypertriglyceridemia and hypothyroidism, because of off-target activation or inhibition of other nuclear receptor pathways impacted by RXR. Because rexinoids are often selective for RXR, versus the retinoic-acid-receptor (RAR), cutaneous toxicity is often avoided as a side effect for rexinoid treatment. Several other potent RXR agonists, and their analogs, have been reported in the literature and rigorously evaluated (often in comparison to Bex) as potential cancer therapeutics with unique activity and side-effect profiles. Some of the more prominent examples include LGD100268, CD3254, and 9-cis-UAB30, to name only a few. Hence, the methods described herein are more widely applicable to a diverse array of RXR agonists. In terms of design, the structure-activity relationship (SAR) study is usually performed by modifying three distinct areas of the rexinoid base structure, either of the nonpolar or polar sides of the rexinoid and/or the linkage that joins them. For the synthesis of the modified base-structure analogs, often identical synthetic strategies used to access the base-structure are applied; however, reasonable alternative synthetic routes may need to be explored if the modified analog intermediates encounter bottlenecks where yields are negligible for a given step in the base-structure route. In fact, this particular problem was encountered and successfully resolved in our case study for generating an array of NEt-TMN analogs.
      datePublished:2019
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Book:
      name:Retinoid and Rexinoid Signaling
      isbn:
         978-1-4939-9585-1
         978-1-4939-9584-4
Organization:
      name:Springer New York
      logo:
         url:https://www.springernature.com/app-sn/public/images/logo-springernature.png
         type:ImageObject
      name:New College of Interdisciplinary Arts and Sciences, Arizona State University
      address:
         name:School of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences, Arizona State University, Glendale, USA
         type:PostalAddress
      name:New College of Interdisciplinary Arts and Sciences, Arizona State University
      address:
         name:School of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences, Arizona State University, Glendale, USA
         type:PostalAddress
ImageObject:
      url:https://www.springernature.com/app-sn/public/images/logo-springernature.png
Person:
      name:Carl E. Wagner
      affiliation:
            name:New College of Interdisciplinary Arts and Sciences, Arizona State University
            address:
               name:School of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences, Arizona State University, Glendale, USA
               type:PostalAddress
            type:Organization
      email:[email protected]
      name:Peter W. Jurutka
      affiliation:
            name:New College of Interdisciplinary Arts and Sciences, Arizona State University
            address:
               name:School of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences, Arizona State University, Glendale, USA
               type:PostalAddress
            type:Organization
PostalAddress:
      name:School of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences, Arizona State University, Glendale, USA
      name:School of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences, Arizona State University, Glendale, USA
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