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Dive into the research topics where William A. Maio is active.

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Featured researches published by William A. Maio.


Journal of Medicinal Chemistry | 2008

Malaria-Infected Mice Are Cured by Oral Administration of New Artemisinin Derivatives

Gary H. Posner; Wonsuk Chang; Lindsey C. Hess; Lauren E. Woodard; Sandra Sinishtaj; Aimee R. Usera; William A. Maio; Andrew S. Rosenthal; Alvin S. Kalinda; John G. D'Angelo; Kimberly S. Petersen; Remo Stohler; Jacques Chollet; Josefina Santo-Tomas; Christopher Snyder; Matthias Rottmann; Sergio Wittlin; Reto Brun; Theresa A. Shapiro

In four or five chemical steps from the 1,2,4-trioxane artemisinin, a new series of 23 trioxane dimers has been prepared. Eleven of these new trioxane dimers cure malaria-infected mice via oral dosing at 3 x 30 mg/kg. The clinically used trioxane drug sodium artesunate prolonged mouse average survival to 7.2 days with this oral dose regimen. In comparison, animals receiving no drug die typically on day 6-7 postinfection. At only 3 x 10 mg/kg oral dosing, seven dimers prolong the lifetime of malaria-infected mice to days 14-17, more than double the chemotherapeutic effect of sodium artesunate. Ten new trioxane dimers at only a single oral dose of 30 mg/kg prolong mouse average survival to days 8.7-13.7, and this effect is comparable to that of the fully synthetic trioxolane drug development candidate OZ277, which is in phase II clinical trials.


Angewandte Chemie | 2011

Anion Relay Chemistry: Access to the Type II ARC Reaction Manifold through a Fundamentally Different Reaction Pathway Exploiting 1-Oxa-2-silacyclopentanes and Related Congeners†

Amos B. Smith; Rongbiao Tong; Won-Suk Kim; William A. Maio

Type I and II anion relay chemistry (ARC)[1] exploiting [1,n]-Brook rearrangements[2] (Scheme 1A and B, respectively), comprise an effective set of synthetic tactics that unite multiple components, in a single reaction flask, that permits rapid access to architecturally diverse polyketide and alkaloid molecular arrays.[2]


Journal of Organic Chemistry | 2012

Evolution of a protecting-group-free total synthesis: studies en route to the neuroactive marine macrolide (-)-palmyrolide A.

Rodolfo Tello-Aburto; Tara D. Newar; William A. Maio

A full account of our synthetic work toward the first total synthesis of the neuroactive marine macrolide (-)-palmyrolide A is described. Our first-generation approach aimed to unlock the unknown C(5)-C(7) stereochemical relationship via the synthesis of four diastereomers of palmyrolide A aldehyde, a known degradation product. When these efforts provided inconclusive results, recourse to synthesizing all possible stereocombinations of the 15-membered macrolide was undertaken. These studies were critical in confirming the absolute stereochemistry, yielding the first total synthesis of (+)-ent-palmyrolide A. Subsequent to this work, the first protecting-group-free total synthesis of natural (-)-palmyrolide A is also reported.


PLOS ONE | 2014

The Odorant Receptor Co-Receptor from the Bed Bug, Cimex lectularius L

Immo A. Hansen; Stacy D. Rodriguez; Lisa L. Drake; David P. Price; Brittny N. Blakely; John I. Hammond; Hitoshi Tsujimoto; Erika Y. Monroy; William A. Maio; Alvaro Romero

Recently, the bed bug, Cimex lectularius L. has re-emerged as a serious and growing problem in many parts of the world. Presence of resistant bed bugs and the difficulty to eliminate them has renewed interest in alternative control tactics. Similar to other haematophagous arthropods, bed bugs rely on their olfactory system to detect semiochemicals in the environment. Previous studies have morphologically characterized olfactory organs of bed bugs’ antenna and have physiologically evaluated the responses of olfactory receptor neurons (ORNs) to host-derived chemicals. To date, odorant binding proteins (OBPs) and odorant receptors (ORs) associated with these olfaction processes have not been studied in bed bugs. Chemoreception in insects requires formation of heteromeric complexes of ORs and a universal OR coreceptor (Orco). Orco is the constant chain of every odorant receptor in insects and is critical for insect olfaction but does not directly bind to odorants. Orco agonists and antagonists have been suggested as high-value targets for the development of novel insect repellents. In this study, we have performed RNAseq of bed bug sensory organs and identified several odorant receptors as well as Orco. We characterized Orco expression and investigated the effect of chemicals targeting Orco on bed bug behavior and reproduction. We have identified partial cDNAs of six C. lectularius OBPs and 16 ORs. Full length bed bug Orco was cloned and sequenced. Orco is widely expressed in different parts of the bed bug including OR neurons and spermatozoa. Treatment of bed bugs with the agonist VUAA1 changed bed bug pheromone-induced aggregation behavior and inactivated spermatozoa. We have described and characterized for the first time OBPs, ORs and Orco in bed bugs. Given the importance of these molecules in chemoreception of this insect they are interesting targets for the development of novel insect behavior modifiers.


Journal of Natural Products | 2014

Detailed analysis of (-)-palmyrolide a and some synthetic derivatives as voltage-gated sodium channel antagonists.

Suneet Mehrotra; Brendan M. Duggan; Rodolfo Tello-Aburto; Tara D. Newar; William H. Gerwick; Thomas F. Murray; William A. Maio

A small library of synthetic (−)-palmyrolide A diastereomers, analogues, and acyclic precursors have been examined with respect to their interaction with voltage-gated sodium channels (VGSCs). Toward this goal, the ability of (−)-palmyrolide A and analogues to antagonize veratridine-stimulated Na+ influx in primary cultures of mouse cerebrocortical neurons was assessed. We found that synthetic (−)-palmyrolide A and its enantiomer functioned as VGSC antagonists to block veratridine-induced sodium influx. A detailed NMR and computational analysis of four diastereomers revealed that none had the same combination of shape and electrostatic potential as exhibited by natural (−)-palmyrolide A. These data indicate that the relative configuration about the tert-butyl and methyl substituents appears to be a prerequisite for biological function. Additional testing revealed that the enamide double bond was not necessary for blocking veratridine-induced sodium influx, whereas the acyclic analogues and other macrolide diastereomers tested were inactive as inhibitors of VGSCs, suggesting that the intact macrolide was required.


Bioorganic & Medicinal Chemistry | 2008

Electronically stabilized versions of the antimalarial acetal trioxanes artemether and artesunate

Gary H. Posner; William A. Maio; Alvin S. Kalinda

From 9-substituted DHA, several new artemisinin-derived C-10 acetal ethers and esters were prepared with either a 9-fluoro or a 9-sulfonyl substituent. The very strong inductive electron-withdrawing C-9 substituent is shown to retard considerably C-10 ionization (acid-promoted etherification) of 9-fluoro-DHA and 9-sulfonyl-DHA.


Organic Letters | 2014

The taumycin A macrocycle: asymmetric total synthesis and revision of relative stereochemistry.

Justine N. deGruyter; William A. Maio

The first asymmetric total synthesis and revision of the relative configuration of the 12-membered taumycin A macrocycle is described. Key to the success of this work was a novel α-keto ketene macrocyclization that provided an efficient means by which to access two diastereomers of the desired macrolide without the need to employ additional coupling agents or unnecessary oxidation state adjustments.


Organic Letters | 2018

Lewis-Acid-Mediated Union of Epoxy-Carvone Diastereomers with Anisole Derivatives: Mechanistic Insight and Application to the Synthesis of Non-natural CBD Analogues

Sophia J. Bailey; Rishi R. Sapkota; Alexandra E. Golliher; Barry Dungan; Marat Talipov; F. Omar Holguin; William A. Maio

The use of trimethylsilyl trifluoromethanesulfonate as a mild means to unite epoxy-carvone silyl ethers with anisole derivatives to yield products that are structurally similar to the CBD scaffold is reported. Importantly, unlike related methods, this process can utilize both epoxy-carvone diastereomers and does not require the use of air/moisture-sensitive organometallic reagents. Several examples of aryl nucleophiles as well as mechanistic insight based on in silico computational analysis are presented.


Organic Letters | 2005

New silicon-mediated, sequential ring expansions of n-sized 2-cycloalkenones into hydroxyolefinic n + m + p medium-sized lactones: short synthesis of (-)-phoracantholide-J.

Gary H. Posner; Mark A. Hatcher; William A. Maio


Organic Letters | 2007

Cyclopentanone Ring Expansion Leading to Functionalized δ-Lactams: Short Synthesis of Simple Sedum Alkaloids†

William A. Maio; Sandra Sinishtaj; Gary H. Posner

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Douglas T. Genna

Youngstown State University

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Erika Y. Monroy

New Mexico State University

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Rodolfo Tello-Aburto

New Mexico Institute of Mining and Technology

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Sophia J. Bailey

New Mexico State University

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Tara D. Newar

New Mexico State University

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Aimee R. Usera

Johns Hopkins University

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