Dionicio Siegel

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Organization: The University of Texas at Austin
Department: Department of Chemistry and Biochemistry
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Co-reporter:Anders M. Eliasen, Randal P. Thedford, Karin R. Claussen, Changxia Yuan, and Dionicio Siegel
Organic Letters 2014 Volume 16(Issue 14) pp:3628-3631
Publication Date(Web):July 2, 2014
DOI:10.1021/ol501497y
A flow protocol for the generation of phthaloyl peroxide has been developed. This process directly yields phthaloyl peroxide in high purity (>95%) and can be used to bypass the need to isolate and recrystallize phthaloyl peroxide, improving upon earlier batch procedures. The flow protocol for the formation of phthaloyl peroxide can be combined with arene hydroxylation reactions and provides a method for the consumption of peroxide as it is generated to minimize the accumulation of large quantities of peroxide.
Co-reporter:Trevor Johnson, Dionicio Siegel
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 15) pp:3512-3515
Publication Date(Web):1 August 2014
DOI:10.1016/j.bmcl.2014.05.060
The first biological target for the natural product complanadine A has been determined. The pseudosymmetric alkaloid functions as a selective agonist for the Mas-related G protein-coupled receptor X2 (MrgprX2), a G protein-coupled receptor that is highly expressed in neurons. Given the potential of MrgprX2 to function as a modulator of pain, complanadine A represents a new chemical probe to selectively interrogate the physiological function of MrgprX2 as well as a potential lead for the development of antihyperalgesics for the treatment of persistent pain. While complanadine A possess agonistic activity the related natural product lycodine, representing half of complanadine A, lacks activity providing a cursory description of the structural requirements for agonistic activity.
Co-reporter:Abram Axelrod;Anders M. Eliasen;Matthew R. Chin;Katherine Zlotkowski ;Dr. Dionicio Siegel
Angewandte Chemie 2013 Volume 125( Issue 12) pp:3505-3508
Publication Date(Web):
DOI:10.1002/ange.201205837
Co-reporter:Changxia Yuan, Chih-Tsung Chang, and Dionicio Siegel
The Journal of Organic Chemistry 2013 Volume 78(Issue 11) pp:5647-5668
Publication Date(Web):May 1, 2013
DOI:10.1021/jo400695c
The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycodine core.
Co-reporter:Katherine Zlotkowski; Jon Pierce-Shimomura; Dionicio Siegel
ChemBioChem 2013 Volume 14( Issue 3) pp:307-310
Publication Date(Web):
DOI:10.1002/cbic.201200712
Co-reporter:Katherine Zlotkowski;Anders M. Eliasen;Aurpon Mitra ; Dionicio Siegel
ChemBioChem 2013 Volume 14( Issue 17) pp:2338-2344
Publication Date(Web):
DOI:10.1002/cbic.201300399

Abstract

A general protocol for exogenous small-molecule pull-down experiments with Caenorhabditis elegans is described; it provides a link between small-molecule screens in worms and existing mutant and RNAi technologies, thereby enabling organismal mechanism of action studies for the natural product clovanemagnolol. Forward chemical genetic screens followed by mechanism of action studies with C. elegans, when coupled with genetic validation of identified targets to reproduce the small molecule's phenotypic effects, provide a unique platform for discovering the biological targets of compounds that affect multicellular processes. First, the use of an immobilized FK506 derivative and soluble competition experiments with optimally prepared soluble C. elegans proteome successfully identified interactions with FK506 binding proteins 1 to 6. This approach was used to determine an unknown mechanism of action for clovanemagnolol, a small molecule that promotes axonal branching in both primary neuronal cultures and in vivo in C. elegans. Following the synthesis of an appropriately functionalized solid-phase reagent bearing a clovanemagnolol analogue pull-down experiments employing soluble competition identified kinesin light chain-1 (KLC-1), a protein involved in axonal cargo transport, as a putative target. This was corroborated through the use of mutant worms lacking klc-1 and possessing GFP neuronal labeling, reproducing the axonal branching phenotype induced by the small molecule clovanemagnolol.

Co-reporter:Abram Axelrod;Anders M. Eliasen;Matthew R. Chin;Katherine Zlotkowski ;Dr. Dionicio Siegel
Angewandte Chemie International Edition 2013 Volume 52( Issue 12) pp:3421-3424
Publication Date(Web):
DOI:10.1002/anie.201205837
Co-reporter:Zin Khaing, Danby Kang, Andrew M. Camelio, Christine E. Schmidt, Dionicio Siegel
Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 16) pp:4808-4812
Publication Date(Web):15 August 2011
DOI:10.1016/j.bmcl.2011.06.054
The use of small molecule surrogates of growth factors that directly or indirectly promote growth represents an attractive approach to regenerative medicine. With synthetic access to clovanemagnolol, a small molecule initially isolated from the bark of the Bigleaf Magnolia tree, we have examined the small molecule’s ability to promote growth of embryonic hippocampal and cortical neurons in serum-free medium. Comparisons with magnolol, a known promoter of growth, reveals that clovanmagnolol is a potent neurotrophic agent, promoting neuronal growth at concentrations of 10 nM. In addition, both clovanemagnolol and magnolol promote growth through a biphasic dose response.
Co-reporter:Changxia Yuan ; Chih-Tsung Chang ; Abram Axelrod
Journal of the American Chemical Society 2010 Volume 132(Issue 17) pp:5924-5925
Publication Date(Web):April 13, 2010
DOI:10.1021/ja101956x
A total synthesis of the Lycopodium alkaloid (+)-complanadine A is described. Complanadine A has been shown to induce the secretion of neurotrophic factors from 1321N1 cells, promoting the differentiation of PC-12 cells. The use of a simplifying metal mediated [2+2+2] + [2+2+2] sequence using a silyl-substituted diyne and 2 equiv of the corresponding alkyne-nitrile has provided rapid access to the natural product.
Co-reporter:Xu Cheng, Nicole L. Harzdorf, Travis Shaw and Dionicio Siegel
Organic Letters 2010 Volume 12(Issue 6) pp:1304-1307
Publication Date(Web):February 16, 2010
DOI:10.1021/ol100214x
Separate short and modular syntheses of the isomeric natural products caryolanemagnolol and clovanemagnolol have been achieved starting from commercially available (−)-caryophyllene. The postulated biosynthetic pathways guided the syntheses of the neuroregenerative small molecules allowing their assembly in as few as two steps.
2-Propen-1-one, 3-(dimethylamino)-1-(2-hydroxy-4,5-dimethoxyphenyl)-, (2E)-
3-IODO-6,7-DIMETHOXY-4H-CHROMEN-4-ONE
2-[4-(4-Methoxyphenyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
5-HYDROXY-6-METHOXY-3,4-DIHYDRO-2H-NAPHTHALEN-1-ONE
Cyclooxygenase 2
1,2-Benzenedicarbonyl dichloride, 4,5-dichloro-