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Photo of Eugene Mash(emash)

Eugene Mash

Professor, Chemistry and Biochemistry-Sci,
Member of the Graduate Faculty,

Chemistry & Biochemistry - Sci
emash@arizona.edu
520/621-6321
UAVitae logo
Grant: $11.8M
Eugene Mash experts in organic chemistry, biochemistry, molecular biology, inorganic chemistry, biomaterials, drug delivery, pharmacology, mri, tissue engineering, enzymology, medicinal chemistry, spectroscopy, polymer chemistry, plasmonics, chemistry, photonics, organometallic chemistry, dti, cytochrome p450, catalysis, organic synthesis, analytical chemistry, computational chemistry, molecular dynamics, nonlinear optics, urologic oncology, cancer biology, biophysics, theoretical chemistry, chemical physics, liquid crystals, entomology, nanophotonics, nephrology, crystallography, bioinorganic chemistry, bioactive peptides, computational biology, bioinformatics, immunology, cancer immunotherapy, regenerative medicine, pharmaceutics, ophthalmology, radiation oncology, condensed matter physics
Courses
Mechanisms of Organic Reactions 
Advanced Organic Synthesis 
Lectures in Organic Chemistry 
Organic Structural Analysis Laboratory 
Synthetic and Mechanistic Organic Chemistry 
Biochemistry 
Recent Grants
Logo of (LTW) Novel Therapeutic Delivery System for Pediatric IBD funding agency
2022 $130.0KActive
(LTW) Novel Therapeutic Delivery System for Pediatric IBD
Logo of The Development of a Solvent Free Process to Prepare DNAN funding agency
2017 $28.9K
The Development of a Solvent Free Process to Prepare DNAN
Logo of UNS: Oligomers Derived from Emerging Nitroaromatic Pollutants in Anaerobic Environments: Mechanisms, Fate and Toxicity funding agency
2015 $330.0K
UNS: Oligomers Derived from Emerging Nitroaromatic Pollutants in Anaerobic Environments: Mechanisms, Fate and Toxicity
Logo of Development of New Liquid Crystalline Polyamides with Bicyclo[8.8.8] Hexacosane Flexible Segments funding agency
2015 $110.0K
Development of New Liquid Crystalline Polyamides with Bicyclo[8.8.8] Hexacosane Flexible Segments
Logo of Targeting Pancreatic Cancer funding agency
2009 $871.4K
Targeting Pancreatic Cancer
Logo of Novel Inhibitors of AKT Signaling in Pancreatic Cancer funding agency
2009 $234.9K
Novel Inhibitors of AKT Signaling in Pancreatic Cancer
Logo of Arizona Partners in Science Program funding agency
2009 $15.0K
Arizona Partners in Science Program
Logo of Multimeric Ligands for Targeting Melanoma funding agency
2008 $1.3M
Multimeric Ligands for Targeting Melanoma
Logo of Southwest Environmental Health Sciences Center funding agency
2006 $7.8M
Southwest Environmental Health Sciences Center
Logo of Redox-Sensitive & Blood-pool Contrast Agents for Magnetic Resonance Imaging funding agency
2006 $1.0M
Redox-Sensitive & Blood-pool Contrast Agents for Magnetic Resonance Imaging
Technologies / Patents
Logo of Method and Compositions for Orally Administered Contrast Agents for MR Imaging
2021Method and Compositions for Orally Administered Contrast Agents for MR Imaging 
Logo of Nitration of Aromatic Compounds
2020Nitration of Aromatic Compounds 
Logo of Method and Compositions for Targeted Drug Delivery to the Lower GI Tract
2016Method and Compositions for Targeted Drug Delivery to the Lower GI Tract 
Logo of Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same
2016Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same 
Logo of Method Of Screening For Colon Cancer Using Biomarkers
2016Method Of Screening For Colon Cancer Using Biomarkers 
Logo of Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same
2015Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same 
Logo of Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same
2013Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same 
Logo of Nitration of Aromatic Compounds
1899Nitration of Aromatic Compounds 
Logo of Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same
1899Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same 
Logo of Method and Compositions for Orally Administered Contrast Agents for MR Imaging
1899Method and Compositions for Orally Administered Contrast Agents for MR Imaging 
Logo of Conjugates For Detection Of Axillary Lymph Node Metastases
1899Conjugates For Detection Of Axillary Lymph Node Metastases 
News
2015'Molecular Truck' Could Deliver New Treatment  
2014UA Discovery Shows Curcumin Blocks the Metastasis of Colon Cancer by a Novel Mechanism 
2008Couple's Gift Brings Nobel Laureate to UA 
Publications (123)
Recent
2019Coupling reactions between reduced intermediates of insensitive munitions compound analog 4-nitroanisole 
2017Magnetic resonance imaging of RRx-001 pharmacodynamics in preclinical tumors 
2017Solvent-free nitration of electron-rich arenes 
2016Magnetic Resonance Imaging Identifies Differential Response to Pro-Oxidant Chemotherapy in a Xenograft Model 
2015Trigonal scaffolds for multivalent targeting of melanocortin receptors 
2015Synthesis and bioactivity of MSH4 oligomers prepared by an A(2) + B-2 strategy 
2015Development of a time-resolved fluorescence probe for evaluation of competitive binding to the cholecystokinin 2 receptor 
2015Linear scaffolds for multivalent targeting of melanocortin receptors 
2014IMPROVED SYNTHESIS OF 10-(2-ALKYLAMINO-2-OXOETHYL)-1,4,7,10-TETRAAZACYCLODODECANE-1,4,7-TRIACETIC ACID DERIVATIVES BEARING ACID-SENSITIVE LINKERS 
2014Spectrophotometric determination and removal of unchelated europium ions from solutions containing Eu-diethylenetriaminepentaacetic acid chelate-peptide conjugates 
2014pTyr421 cortactin is overexpressed in colon cancer and is dephosphorylated by curcumin: involvement of non-receptor type 1 protein tyrosine phosphatase (PTPN1) 
2014Synthesis of 13C and 15N labeled 2,4-dinitroanisole 
2014Crystal Engineering with 1,4-Piperazine-2,5-diones 
2013Substrate-dependent ligand inhibition of the human organic cation transporter OCT2 
2013Synthesis and characterization of time-resolved fluorescence probes for evaluation of competitive binding to melanocortin receptors 
2013Demonstration of a sucrose-derived contrast agent for magnetic resonance imaging of the GI tract 
2012Design, synthesis, and testing of a molecular truck for colonic delivery of 5-aminosalicylic acid 
2012Redox-active magnetic resonance imaging contrast agents: studies with thiol-bearing 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid derivatives 
2012Heterobivalent ligands target cell-surface receptor combinations in vivo 
2012Tumor xenograft response to redox-active therapies assessed by magnetic resonance imaging using a thiol-bearing DOTA complex of gadolinium 
2012Organic crystal engineering with 1,4-piperazine-2,5-diones. 8. Synthesis, crystal packing, and thermochemistry of piperazinediones derived from 2-amino-4,7-dialkoxyindan-2-carboxylic acids 
2011Cell-specific targeting by heterobivalent ligands 
2011On the synthesis of 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10- tetraazacyclododecane 
2011Development of sulfonamide AKT PH domain inhibitors 
2011A sucrose-derived scaffold for multimerization of bioactive peptides 
2011α-Tocopheryloxyacetic acid: a novel chemotherapeutic that stimulates the antitumor immune response 
2011Recent development of anticancer therapeutics targeting AKT 
2010Synthesis and characterization of a Eu-DTPA-PEGO-MSH(4) derivative for evaluation of binding of multivalent molecules to melanocortin receptors 
2010A solanesol-derived scaffold for multimerization of bioactive peptides 
2010Molecular pharmacology and antitumor activity of PHT-427, a novel akt/phosphatidylinositide-dependent protein kinase 1 pleckstrin homology domain inhibitor 
2010Synthesis of the conformationally constrained tyrosine analogues, (R)- and (S)-5-hydroxy-2-aminoindan-2-carboxylic acids 
2010A synchrotron study of (2R,5′S)-5′-benzyl-5-bromo-6-methoxy- spiro-[indane-2,2′-piperazine]-3′,6′-dione dimethyl-formamide solvate 
2010Design, synthesis, and evaluation of 1,4,7,10-tetraazacyclododecane-1,4,7- triacetic acid derived, redox-sensitive contrast agents for magnetic resonance imaging 
2009Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain 
2009In vitro and in vivo activity of novel small-molecule inhibitors targeting the pleckstrin homology domain of protein kinase B/AKT 
2009Conformational analysis of bridgehead-substituted bicyclo[m.m.m]alkanes and bicyclo[8.8.n]alkanes 
2009Synthesis of conformationally constrained diaminodicarboxylic acid derivatives 
2008(S,S)-4′′-Cyano-7,7′′-dimeth-oxy-3′, 6′-dioxodispiro-[indane-2,2′-piperazine-5′, 2′′-indane]-4-carboxamide methanol solvate: Inter-rupting the amide-to-amide hydrogen-bonded tape 
2008Discovery of a novel class of AKT pleckstrin homology domain inhibitors 
2008NOTE: Synthesis and characterization of a poly(acrylamide) with pendant 1,4-piperazine-2,5-dione moieties via post-polymerization cyclization 
2008Organic crystal engineering with 1,4-piperazine-2,5-diones. 7. Crystal packing of piperazinediones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid 
2007Squalene-derived flexible linkers for bioactive peptides 
2007Design, synthesis, and validation of a branched flexible linker for bioactive peptides 
2006Arsenite and monomethylarsonous acid generate oxidative stress response in human bladder cell culture 
2006Preface 
2006Monomethylarsonous acid induces transformation of human bladder cells 
2006Deoxycholic acid induces intracellular signaling through membrane perturbations 
2006Synthesis and fluorescence of N,N,N-trimethyl-2-[methyl (7-nitrobenzo[c][l,2,5]oxadiazol-4-yl) amino]ethanaminium iodide, a pH-insensitive reporter of organic cation transport 
2006Redox-sensitive contrast agents for MRI based on reversible binding of thiols to serum albumin 
2005Organic crystal engineering with 1,4-piperazine-2,5-diones. 6. Studies of the hydrogen-bond association of cyclo[(2-methylamino-4,7-dimethoxyindan-2- carboxylic acid)(2-amino-4,7-dimethoxyindan-2-carboxylic acid)] 
2005Synthesis of 1,10-dimethylbicyclo[8.8.8]hexacosane and 1,10- dihydroxybicyclo[8.8.8]hexacosane 
2005Synthesis of [ sup 14 /sup C]-imexon 
2004Tris[2-(2-oxidophenyl)-5-phenyl-1,3,4-oxadiazole-κ sup 2 /sup O sup 2 /sup ,N sup 3 /sup ]aluminium 0.167-hydrate 
2003An efficient synthesis of sodium dimethylarsinate- sup 14 /sup C 
2003Organic crystal engineering with piperazine-2,5-diones. 4. Crystal packing of piperazinediones derived from 2-amino-7-cyano-4-methoxyindan-2-carboxylic acid 
2003Crystal engineering of a liquid crystalline piperazinedione 
2002Synthesis and structure of the glutathione conjugate of chloroacetaldehyde 
2002Use of 9-methylfluorene as an indicator in the titration of common group IA and group IIA organometallic reagents 
2001Monomethylarsonous acid (MMA sup III /sup ) and arsenite: LD sub 50 /sub in hamsters and in vitro inhibition of pyruvate dehydrogenase 
2001Stereochemical aspects of vinylcyclohexene bioactivation in rodent hepatic microsomes and purified human cytochrome P450 enzyme systems 
2000Synthesis of (S)-(-)-β-cuparenone and (S)-(-)-cuparene 
2000Intermolecular and intramolecular reactions of resolved 2-alkoxytetrahydrofuran-3-yl and 2-alkoxytetrahydropyran-3-yl radicals 
2000NBD-TMA: A novel fluorescent substrate of the peritubular organic cation transporter of renal proximal tubules 
2000Synthesis of 7-alkoxyquinolines, coumarins, and resorufins 
2000The crystal packing of a strongly dipolar piperazinedione 
1999Organic crystal engineering with piperazine-2,5-diones. 2. Crystal packing of weakly dipolar piperazinediones derived from 2-amino-4-bromo-7- methoxyindan-2-carboxylic acid 
1999Organic crystal engineering with piperazine-2,5-diones. 1. Crystal packing of piperazinediones derived from substituted 2-aminoindan-2- carboxylic acids 
1999Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 6. Stereocontrolled synthesis of tricyclo[m.n.0.0]alkenones 
19992,2',3,3',6,6'-Hexachlorobiphenyl hydroxylation by active site mutants of cytochrome P450 2B1 and 2B11 
1998Near diffraction-limited laser emission from a polymer in a high finesse planar cavity 
1998Whispering-gallery-mode oscillation in a polymer microring laser 
1998Synthesis and characterization of highly efficient photorefractive polymer composites with long phase stability 
1998Vertical-cavity surface-emitting polymer laser 
1998Whispering-gallery-mode microring laser using a conjugated polymer 
1998Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 5. α'-Alkylations of bicycle[m.1.0]alkan-2-ones 
1998Synthesis of the mono-cysteine disulfide of meso-2,3-dimercaptosuccinic acid 
1998A cytochrome P450 terpenoid hydroxylase linked to the suppression of insect juvenile hormone synthesis 
1997Improved syntheses of 2,2',3,3',6,6'-hexachlorobiphenyl 
1997Diastereoselective Manipulations of Bicyclo[m.1.0]alkane Derivatives. 4. Reactions of Nucleophiles with Bicyclo[m.1.0]alk-3-en-2-ones 
1997Recent advances in photorefractive polymers and liquid crystals 
1997Monobenzylation of 1,n-diols via dibutylstannylene intermediates 
1997Diastereoselective manipulations of bicyclo[m.1.0] alkane derivatives. 3. Nucleophilic additions to the carbonyl carbon of (1R,8R)-Bicyclo[6.1.0]nonan-2,6-dione 2-(2S,3S)-1,4-Di-O-methyl-1,2,3,4-butane ketal 
1997Development of Molecular Mechanics Torsion Parameters for α,β-Cyclopropyl α′,β′-Enones and Conformational Analysis of Bicyclo[m.1.0]alk-3-en-2-ones 
1997Synthesis of ethyl N-(diphenyl)methyl-1,2,3,4- tetrahydroisoquinoline-3-carboxylates 
1997On the reported intermediacy of vinyl radicals in spontaneous polymerization: An ESR-spin trapping study and its significance for the bond forming initiation theory 
1996Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 2. Nucleophilic additions to the carbonyl carbons of bicyclot[m.1.0]alkan-2-ones 
1996Development of molecular mechanics torsion parameters for α,β-cyclopropyl ketones and conformational analysis of bicyclo[m.1.0]alkan-2-ones 
1996Syntheses and spectroscopic characterizations of oxidative metabolites of 4-vinylcyclohexene II diol-epoxides 
1996Engineering molecular solids 
1995Synthesis of the enantiomers of 4-vinylcyclohexene 
1994Syntheses and spectroscopic characterizations of oxidative metabolites of 4-vinylcyclohexene 
1993An efficient stereoconvergent synthesis of the 4-ethylamino-2,4-dideoxy-l-threo-pentopyranose component of the calicheamicins and esperamicins 
1992Systematic search of transition state conformations 
1992Acid-catalyzed dehydration for the design of chemical amplification resists 
1991Structure of an enantiomerically pure tetrahydropyranyl ether 
1991Enantiomerically pure acetals in organic synthesis. 3. A synthesis of (R)-mevalonic acid lactone 
1991Enantiomerically pure acetals in organic synthesis. 1. Chromatographic separability of furanoside and pyranoside acetals derived from α-hydroxy esters 
1991Enantiomerically pure acetals in organic synthesis. 2. Diastereoselective alkylation of enantiomeric lithio alkyl lactyl tetrahydropyranosides and related enolates 
1991Acid-catalyzed pinacol rearrangement. Chemically amplified reverse polarity change 
1991Negative chemical amplification resist systems based on polyhydroxystyrenes and N-substituted imides or aldehydes 
1990Diastereoselective manipulations of conformationally restricted enantiomerically pure bicyclo[m.1.0]alkanes. 1. Nucleophilic additions to the carbonyl carbons of bicyclo[m.1.0]alkan-2-ones 
1990Mechanistic studies of diastereoselective cyclopropanation via homochiral ketals. 2. Studies with conformationally restricted 2-cyclohexen-1-one ketals 
1990A new synthetic approach to the C-D ring portion of streptonigrin analogues 
1990Mechanistic studies of diastereoselective cyclopropanation via homochiral ketals. 1. Dioxolane structural effects 
1989Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation of α,β-unsaturated ketals derived from (S,S)-(-)-hydrobenzoin 
1989Selective inactivation of rat liver cytochromes P-450 by 21-chlorinated steroids 
1989Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation of medium and large ring α,α-unsaturated ketals derived from 1,4-di-O-benzyl-L-threitol 
1989Homochiral ketals in organic synthesis. Enantioselective synthesis and absolute configuration of (-)-modhephene 
1989Homochiral acetals in organic synthesis. A general enantioselective entry to carbohydrate derivatives from non-carbohydrate precursors 
1988Homochiral ketals in organic sythesis. Simple chromatographic resolution of diastereomeric α-hydroxycycloalkanone ketals 
1988Homochiral ketals in organic synthesis. Enantioselective preparation of (+)-modhephene 
1988Selective inactivation by 21-chlorinated steroids of rabbit liver and adrenal microsomal cytochromes P-450 involved in progesterone hydroxylation 
1987Homochiral ketals in organic synthesis. Enantioselective synthesis of (+)-β-eudesmol 
1987Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation of α,β-unsaturated ketals derived from 1,4-D1-O-benzyl-l-threitol 
1987Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects 
1987Homochiral ketals in organic synthesis. Enantioselective synthesis and absolute configuration of (-)-chokol A 
1986Homochiral ketals in organic synthesis. Enantioselective synthesis of [m.n.1] Propellanones 
1986Homochiral ketals in organic synthesis. Enantioselective synthesis of (R)-muscone 
1985Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation 
1981Farnesylpyrophosphate synthetase. Evidence for a rigid geranyl cation-pyrophosphate anion pair 
1979Farnesyl pyrophosphate synthetase. Mechanistic studies of the 1′-4 coupling reaction in the terpene biosynthetic pathway [13] 
1978Farnesyl pyrophosphate synthetase. Mechanistic studies of the 1'-4 coupling reaction with 2-fluorogeranyl pyrophosphate. 
1977Prenyltransferase. New evidence for an ionization-condensation-elimination mechanism with 2-fluorogeranyl pyrophosphate [15] 
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