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Full-Text Articles in Medicinal-Pharmaceutical Chemistry

E‑Cigarette Airflow Rate Modulates Toxicant Profiles And Can Lead To Concerning Levels Of Solvent Consumption, Tetiana Korzun, Maryana Lazurko, Tetiana Korzun, Ian Munhenzva, Kelley Barsanti, Yilin Huang, R. Paul Jensen, Jorge O. Escobedo, Wentai Luo, David H. Peyton, Robert M. Strongin Jan 2018

E‑Cigarette Airflow Rate Modulates Toxicant Profiles And Can Lead To Concerning Levels Of Solvent Consumption, Tetiana Korzun, Maryana Lazurko, Tetiana Korzun, Ian Munhenzva, Kelley Barsanti, Yilin Huang, R. Paul Jensen, Jorge O. Escobedo, Wentai Luo, David H. Peyton, Robert M. Strongin

Chemistry Faculty Publications and Presentations

Electronic cigarettes enabling enhanced airflow have grown in popularity in recent years. The objective of this study is to show that flow rates modulate the levels of specific aerosol toxicants produced in electronic cigarettes. Flow rates used in various laboratory investigations involving e-cigarettes have varied widely to date, and can thus promote interlaboratory variability in aerosol product profiles. The thermal decomposition of hydroxyacetone and glycolaldehyde is less favorable at lower temperatures, supporting the observations of these products at higher flow rates/lower heating coil temperatures. Higher temperatures promote the formation of acetaldehyde from hydroxyacetone and formaldehyde from both hydroxyacetone and ...


Toxicant Formation In Dabbing: The Terpene Story, Jiries Meehan-Attrash, Wentai Luo, Robert M. Strongin Sep 2017

Toxicant Formation In Dabbing: The Terpene Story, Jiries Meehan-Attrash, Wentai Luo, Robert M. Strongin

Chemistry Faculty Publications and Presentations

Inhalable, noncombustible cannabis products are playing a central role in the expansion of the medical and recreational use of cannabis. In particular, the practice of “dabbing” with butane hash oil has emerged with great popularity in states that have legalized cannabis. Despite their growing popularity, the degradation product profiles of these new products have not been extensively investigated. The study herein focuses on the chemistry of myrcene and other common terpenes found in cannabis extracts. Methacrolein, benzene, and several other products of concern to human health were formed under the conditions that simulated realworld dabbing. The terpene degradation products observed ...


Synthesis And Structure−Activity Relationships Of Tambjamines And B‑Ring Functionalized Prodiginines As Potent Antimalarials, Papireddy Kancharla, Jane Xu Kelly, Kevin A. Reynolds Aug 2015

Synthesis And Structure−Activity Relationships Of Tambjamines And B‑Ring Functionalized Prodiginines As Potent Antimalarials, Papireddy Kancharla, Jane Xu Kelly, Kevin A. Reynolds

Chemistry Faculty Publications and Presentations

Synthesis and antimalarial activity of 94 novel bipyrrole tambjamines (TAs) and a library of B-ring functionalized tripyrrole prodiginines (PGs) against a panel of Plasmodium falciparum strains are described. The activity and structure–activity relationships demonstrate that the ring-C of PGs can be replaced by an alkylamine, providing for TAs with retained/enhanced potency. Furthermore, ring-B of PGs/TAs can be substituted with short alkyl substitutions at either 4-position (replacement of OMe) or 3- and 4-positions without impacting potency. Eight representative TAs and two PGs have been evaluated for antimalarial activity against multidrug-resistant P. yoelii in mice in the dose range ...


Dimethyl Sulfoxide (Dmso) Exacerbates Cisplatin-Induced Sensory Hair Cell Death In Zebrafish (Danio Rerio), Phillip M. Uribe, Melissa A. Mueller, Julia S. Gleichman, Matthew D. Kramer, Qi Wang, Martha Sibrian-Vazquez, Robert M. Strongin, Peter S. Steyger, Douglas A. Cotanche, Jonathan I. Matsui Feb 2013

Dimethyl Sulfoxide (Dmso) Exacerbates Cisplatin-Induced Sensory Hair Cell Death In Zebrafish (Danio Rerio), Phillip M. Uribe, Melissa A. Mueller, Julia S. Gleichman, Matthew D. Kramer, Qi Wang, Martha Sibrian-Vazquez, Robert M. Strongin, Peter S. Steyger, Douglas A. Cotanche, Jonathan I. Matsui

Chemistry Faculty Publications and Presentations

Inner ear sensory hair cells die following exposure to aminoglycoside antibiotics or chemotherapeutics like cisplatin, leading to permanent auditory and/or balance deficits in humans. Zebrafish (Danio rerio) are used to study drug-induced sensory hair cell death since their hair cells are similar in structure and function to those found in humans. We developed a cisplatin dose-response curve using a transgenic line of zebrafish that expresses membrane-targeted green fluorescent protein under the control of the Brn3c promoter/enhancer. Recently, several small molecule screens have been conducted using zebrafish to identify potential pharmacological agents that could be used to protect sensory ...


Reversed Chloroquine Molecules As A Strategy To Overcome Resistance In Malaria, David H. Peyton Mar 2012

Reversed Chloroquine Molecules As A Strategy To Overcome Resistance In Malaria, David H. Peyton

Chemistry Faculty Publications and Presentations

This short review tells the story of how Reversed Chloroquine drugs (RCQs) were developed. These are hybrid molecules, made by combining the quinoline nucleus from chloroquine (CQ) with moieties which are designed to inhibit efflux via known transporters in the membrane of the digestive vacuole of the malaria parasite. The resulting RCQ drugs can have potencies exceeding that of CQ, while at the same time having physical chemical characteristics that may make them favorable as partner drugs in combination therapies. The need for such novel antimalarial drugs will continue for the foreseeable future.


Organometallic Iron(Iii)-Salophene Exerts Cytotoxic Properties In Neuroblastoma Cells Via Mapk Activation And Ros Generation, Kyu Kwang Kim, Rakesh K. Singh, Robert M. Strongin, Richard G. Moore, Laurent Brard, Thilo S. Lange Apr 2011

Organometallic Iron(Iii)-Salophene Exerts Cytotoxic Properties In Neuroblastoma Cells Via Mapk Activation And Ros Generation, Kyu Kwang Kim, Rakesh K. Singh, Robert M. Strongin, Richard G. Moore, Laurent Brard, Thilo S. Lange

Chemistry Faculty Publications and Presentations

The objective of the present study was to investigate the specific effects of Iron(III)-salophene (Fe-SP) on viability, morphology, proliferation, cell cycle progression, ROS generation and pro-apoptotic MAPK activation in neuroblastoma (NB) cells. A NCI-DTP cancer screen revealed that Fe-SP displayed high toxicity against cell lines of different tumor origin but not tumor type-specificity. In a viability screen Fe-SP exhibited high cytotoxicity against all three NB cell lines tested. The compound caused cell cycle arrest in G1 phase, suppression of cells progressing through S phase, morphological changes, disruption of the mitochondrial membrane depolarization potential, induction of apoptotic markers as ...


Antisense-Induced Suppression Of Taxoid 14Β-Hydroxylase Gene Expression In Transgenic Taxus × Media Cells, Feng-Lan Li, Xiao-Jun Ma, Angela Hoffman, Jun-Gui Dai, De-You Qui Jan 2011

Antisense-Induced Suppression Of Taxoid 14Β-Hydroxylase Gene Expression In Transgenic Taxus × Media Cells, Feng-Lan Li, Xiao-Jun Ma, Angela Hoffman, Jun-Gui Dai, De-You Qui

Chemistry Faculty Publications and Presentations

The enzyme taxoid 14β-hydroxylase (14OH) directs a side-route of taxol pathway to 14β-hydroxy taxoids. Suppression of this side-route could increase the production of taxol. To suppress taxoid 14β- hydroxylase gene (14OH) expression in theTaxus × media TM3 cell line, antisense RNA inhibition approach was used in this study. Following the construction of an antisense RNA expression vector of 14OH from Taxus chinensis, the antisense 14OH cDNA (as14OH) was introduced into TM3 cells by Agrobacterium tumefaciens-mediated transformation. Southern blot analysis of hygromycin phosphotransferase gene (HYG) revealed that this selection gene was integrated successfully into the genome of Taxus × media ...


Apoptotic And Chemotherapeutic Properties Of Iron (Iii)-Salophene In An Ovarian Cancer Animal Model, Thilo S. Lange, Carolyn Mccourt, Rakesh K. Singh, Kyu Kwang Kim, Ajay P. Singh, Brian S. Luisi, Onur Alptürk, Robert M. Strongin, Laurent Brard Sep 2009

Apoptotic And Chemotherapeutic Properties Of Iron (Iii)-Salophene In An Ovarian Cancer Animal Model, Thilo S. Lange, Carolyn Mccourt, Rakesh K. Singh, Kyu Kwang Kim, Ajay P. Singh, Brian S. Luisi, Onur Alptürk, Robert M. Strongin, Laurent Brard

Chemistry Faculty Publications and Presentations

The cytotoxicity of organometallic compounds iron(III)-, cobalt(III)-, manganese(II)-, and copper(II)-salophene (-SP) on platinum-resistant ovarian cancer cell lines was compared. Fe-SP displayed selective cytotoxicity (IC(50) at ~1 muM) against SKOV-3 and OVCAR-3 cell lines while Co-SP caused cytotoxic effects only at higher concentrations (IC(50) at 60 muM) and Cu-SP effects were negligible. High cytotoxicity of Mn-SP (30-60 muM) appeared to be nonspecific because the Mn-chloride salt reduced cell viability similarly. The effect of Fe-SP at 1 muM proved to be ovarian cancer cell selective when compared to a panel of cell lines derived from ...


Generation Of Novel Pikromycin Antibiotic Products Through Mutasynthesis, Shuchi Gupta, Venkatraman Lakshmanan, Beom Seok Kim, Robert Fecik, Kevin A. Reynolds Jan 2009

Generation Of Novel Pikromycin Antibiotic Products Through Mutasynthesis, Shuchi Gupta, Venkatraman Lakshmanan, Beom Seok Kim, Robert Fecik, Kevin A. Reynolds

Chemistry Faculty Publications and Presentations

Mutasynthesis in pikromycin PKS: The amenability of pikromycin polyketide synthase to mutational biosynthesis has been demonstrated. A natural triketide and its analogues, activated as N-acetyl-cysteamine thioesters, were synthesized and fed to a pikAI-deleted strain; this led to the production of new antibiotics. A vinyl analogue was found to have better antibacterial activity than pikromycin.


Iron(Iii)-Salophene: An Organometallic Compound With Selective Cytotoxic And Anti-Proliferative Properties In Platinum-Resistant Ovarian Cancer Cells, Thilo S. Lange, Kyu Kwang Kim, Rakesh K. Singh, Robert M. Strongin, Carolyn Mccourt, Laurent Brard May 2008

Iron(Iii)-Salophene: An Organometallic Compound With Selective Cytotoxic And Anti-Proliferative Properties In Platinum-Resistant Ovarian Cancer Cells, Thilo S. Lange, Kyu Kwang Kim, Rakesh K. Singh, Robert M. Strongin, Carolyn Mccourt, Laurent Brard

Chemistry Faculty Publications and Presentations

Background: In this pioneer study to the biological activity of organometallic compound Iron(III)-salophene (Fe-SP) the specific effects of Fe-SP on viability, morphology, proliferation, and cell-cycle progression on platinum-resistant ovariancancer cell lines were investigated.

Methodology/Principal Findings: Fe-SP displayed selective cytotoxicity against SKOV-3 and OVCAR-3 (ovarian epithelial adenocarcinoma) cell lines at concentrations between 100 nM and 1 μM, while the viability of HeLa cells (epithelial cervix adenocarcinoma) or primary lung or skin fibroblasts was not affected. SKOV-3 cells in contrast to fibroblasts after treatment with Fe-SP revealed apparent hallmarks of apoptosis including densely stained nuclear granular bodies within fragmented ...


Unsymmetric Aryl–Alkyl Disulfide Growth Inhibitors Of Methicillin-Resistant Staphylococcus Aureus And Bacillus Anthracis, Edward Turos, Kevin D. Revell, Praveen Ramaraju, Danielle A. Gergeres, Kerriann Greenhalgh, Ashley Young, Nalini Sathyanarayan, Sonja Dickey, Daniel Lim, Mamoun M. Alhamadsheh, Kevin A. Reynolds Jan 2008

Unsymmetric Aryl–Alkyl Disulfide Growth Inhibitors Of Methicillin-Resistant Staphylococcus Aureus And Bacillus Anthracis, Edward Turos, Kevin D. Revell, Praveen Ramaraju, Danielle A. Gergeres, Kerriann Greenhalgh, Ashley Young, Nalini Sathyanarayan, Sonja Dickey, Daniel Lim, Mamoun M. Alhamadsheh, Kevin A. Reynolds

Chemistry Faculty Publications and Presentations

This study describes the antibacterial properties of synthetically-produced mixed aryl alkyl disulfide compounds as a means to control the growth of Staphylococcus aureus and Bacillus anthracis. Some of these compounds exerted strong in vitro bioactivity. Our results indicate that among the twelve different aryl substituents examined, nitrophenyl derivatives provide the strongest antibiotic activities. This may be the result of electronic activation of the arylthio moiety as a leaving group for nucleophilic attack on the disulfide bond. Small alkyl residues on the other sulfur provide the best activity as well, which for different bacteria appears to be somewhat dependent on the ...


Structures Of Four Trans-2-Hydroxy- And Methoxy-2-Methyl-3,4-Dihydro-4-Alkyl-2H,5H-Pyrano[3,2-C][1]Benzopyran-5-Ones, Edward J. Valente, Drake S. Eggleston, Verner Schomaker Mar 1987

Structures Of Four Trans-2-Hydroxy- And Methoxy-2-Methyl-3,4-Dihydro-4-Alkyl-2H,5H-Pyrano[3,2-C][1]Benzopyran-5-Ones, Edward J. Valente, Drake S. Eggleston, Verner Schomaker

Chemistry Faculty Publications and Presentations

Derivatives of 2-methyl-3,4-dihydro-2H,5H-pyrano[ 3,2-c][1]benzopyran-5-one. ( l) Racemic trans- 2-methoxy-4-(2-propyl), Mr= 288·3, monoclinic, P2i/c, a = 13·737 (3), b = 13·228 (6), c = 17·229(4) Å, β = l02·93(2)° , V = 3051·4 Å3, Z = 8 (two molecules/asymmetric unit), Dx = 1·255 g cm- 3, λ(Mo Kα) = O·71073 Å, μ = 0·908 cm-1 , F(OOO) = 1232, T = 298 K, final R = 0·050 for 3988 unique intensities. Dihydropyran rings in C17H2004 are halfchairs, one ...


Structure Of (±)-6-Methyl-6,12-Methano-6H,12H,13H-[1]Benzopyran[4,3-D][1,3]Benzodioxocin-13-One, Gerard Ruggiero, Edward J. Valente, Drake S. Eggleston Jan 1981

Structure Of (±)-6-Methyl-6,12-Methano-6H,12H,13H-[1]Benzopyran[4,3-D][1,3]Benzodioxocin-13-One, Gerard Ruggiero, Edward J. Valente, Drake S. Eggleston

Chemistry Faculty Publications and Presentations

A derivative of warfarin, racemic C19H14O4, Mr = 306·32, monoclinic, Cc, a = 9·594 (2), b = 20·437 (4), c = 7·793 (2) Å, β = 109·94 (3)°, V = l436·4 (11) Å3, Z = 4, Dx = 1·416 g cm-3, λ(Cu) = 1·5418 Å, μ = 7·742 cm-1, F(000) = 640, T = 293 K, final R = 0·053 for 1224 observations. The title molecule, formed by spontaneous dehydration of 2'-hydroxywarfarin, is a cyclic ketal in which the side-chain phenyl is disposed pseudoaxially and is linked through ...


(—)-3-(1-Phenylpropyl)-4-Hydroxycoumarin, Edward J. Valente, W. F. Trager, E. C. Lingafelter Jan 1976

(—)-3-(1-Phenylpropyl)-4-Hydroxycoumarin, Edward J. Valente, W. F. Trager, E. C. Lingafelter

Chemistry Faculty Publications and Presentations

The title compound [generic name: (—)-phenprocoumon], C18H16O3, monoclinic, P21. Z = 4 with two molecules/asymmetric unit, a= 7·171 (1), b = 17·751 (5), c = 11·752 (2) Å, β = 92·58 (2)°, V = 1494 Å3, Dc = 1·28, d0 = 1·30 (2) g cm-3 is pseudoisostructural with the crystalline racemate as suggested by a similarity in cell constants and symmetry. Structural differences involve small translations and where the racemate crystal contains layers of (—) and layers of (+) enantiomers, the (—) crystal contains one layer nearly identical with the (—) layer in ...


The Crystal And Molecular Structure And Absolute Configuration Of (—)-(S)-Warfarin, Edward J. Valente, W. F. Trager, L. H. Jensen Jan 1975

The Crystal And Molecular Structure And Absolute Configuration Of (—)-(S)-Warfarin, Edward J. Valente, W. F. Trager, L. H. Jensen

Chemistry Faculty Publications and Presentations

The crystal and molecular structure and the absolute configuration of (—)-(S)-warfarin, C19H1604, have been determined by X-ray crystallographic techniques. Crystals of (—)-(S)-warfarin are orthorhombic, space group P212121, with a=10·883 (3), b=9·562 (3), and c=14·902 (5) Å. Solution of the structure was by direct methods, and refinement by least-squares calculations led to a conventional R of 0·053 (Mo Kα data). The molecule crystallizes as the intramolecular hemiketal and thus may be described as (2S,4S)-2,3H-2-methyl-4-phenyl-5-oxobenzopyrano[3 ...