KMap

Eugene Mash

Professor, Chemistry and Biochemistry-Sci,

Member of the Graduate Faculty,

Chemistry & Biochemistry - Sci
emash@arizona.edu

520/621-6321

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

	2022	$130.0K	Active
(LTW) Novel Therapeutic Delivery System for Pediatric IBD
	2017	$28.9K
The Development of a Solvent Free Process to Prepare DNAN
	2015	$330.0K
UNS: Oligomers Derived from Emerging Nitroaromatic Pollutants in Anaerobic Environments: Mechanisms, Fate and Toxicity
	2015	$110.0K
Development of New Liquid Crystalline Polyamides with Bicyclo[8.8.8] Hexacosane Flexible Segments
	2009	$871.4K
Targeting Pancreatic Cancer
	2009	$234.9K
Novel Inhibitors of AKT Signaling in Pancreatic Cancer
	2009	$15.0K
Arizona Partners in Science Program
	2008	$1.3M
Multimeric Ligands for Targeting Melanoma
	2006	$7.8M
Southwest Environmental Health Sciences Center
	2006	$1.0M
Redox-Sensitive & Blood-pool Contrast Agents for Magnetic Resonance Imaging

Technologies / Patents

	2021	Method and Compositions for Orally Administered Contrast Agents for MR Imaging
	2020	Nitration of Aromatic Compounds
	2016	Method and Compositions for Targeted Drug Delivery to the Lower GI Tract
	2016	Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same
	2016	Method Of Screening For Colon Cancer Using Biomarkers
	2015	Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same
	2013	Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same
	1899	Nitration of Aromatic Compounds
	1899	Small Molecule Inhibitors of the Pleckstrin Homology Domain and Methods for Using Same
	1899	Method and Compositions for Orally Administered Contrast Agents for MR Imaging
	1899	Conjugates For Detection Of Axillary Lymph Node Metastases

News

2015	'Molecular Truck' Could Deliver New Treatment
2014	UA Discovery Shows Curcumin Blocks the Metastasis of Colon Cancer by a Novel Mechanism
2008	Couple's Gift Brings Nobel Laureate to UA

Publications (123)

Recent

2019	Coupling reactions between reduced intermediates of insensitive munitions compound analog 4-nitroanisole
2017	Magnetic resonance imaging of RRx-001 pharmacodynamics in preclinical tumors
2017	Solvent-free nitration of electron-rich arenes
2016	Magnetic Resonance Imaging Identifies Differential Response to Pro-Oxidant Chemotherapy in a Xenograft Model
2015	Trigonal scaffolds for multivalent targeting of melanocortin receptors
2015	Synthesis and bioactivity of MSH4 oligomers prepared by an A(2) + B-2 strategy
2015	Development of a time-resolved fluorescence probe for evaluation of competitive binding to the cholecystokinin 2 receptor
2015	Linear scaffolds for multivalent targeting of melanocortin receptors
2014	IMPROVED SYNTHESIS OF 10-(2-ALKYLAMINO-2-OXOETHYL)-1,4,7,10-TETRAAZACYCLODODECANE-1,4,7-TRIACETIC ACID DERIVATIVES BEARING ACID-SENSITIVE LINKERS
2014	Spectrophotometric determination and removal of unchelated europium ions from solutions containing Eu-diethylenetriaminepentaacetic acid chelate-peptide conjugates
2014	pTyr421 cortactin is overexpressed in colon cancer and is dephosphorylated by curcumin: involvement of non-receptor type 1 protein tyrosine phosphatase (PTPN1)
2014	Synthesis of 13C and 15N labeled 2,4-dinitroanisole
2014	Crystal Engineering with 1,4-Piperazine-2,5-diones
2013	Substrate-dependent ligand inhibition of the human organic cation transporter OCT2
2013	Synthesis and characterization of time-resolved fluorescence probes for evaluation of competitive binding to melanocortin receptors
2013	Demonstration of a sucrose-derived contrast agent for magnetic resonance imaging of the GI tract
2012	Design, synthesis, and testing of a molecular truck for colonic delivery of 5-aminosalicylic acid
2012	Redox-active magnetic resonance imaging contrast agents: studies with thiol-bearing 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid derivatives
2012	Heterobivalent ligands target cell-surface receptor combinations in vivo
2012	Tumor xenograft response to redox-active therapies assessed by magnetic resonance imaging using a thiol-bearing DOTA complex of gadolinium
2012	Organic 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
2011	Cell-specific targeting by heterobivalent ligands
2011	On the synthesis of 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10- tetraazacyclododecane
2011	Development of sulfonamide AKT PH domain inhibitors
2011	A sucrose-derived scaffold for multimerization of bioactive peptides
2011	α-Tocopheryloxyacetic acid: a novel chemotherapeutic that stimulates the antitumor immune response
2011	Recent development of anticancer therapeutics targeting AKT
2010	Synthesis and characterization of a Eu-DTPA-PEGO-MSH(4) derivative for evaluation of binding of multivalent molecules to melanocortin receptors
2010	A solanesol-derived scaffold for multimerization of bioactive peptides
2010	Molecular pharmacology and antitumor activity of PHT-427, a novel akt/phosphatidylinositide-dependent protein kinase 1 pleckstrin homology domain inhibitor
2010	Synthesis of the conformationally constrained tyrosine analogues, (R)- and (S)-5-hydroxy-2-aminoindan-2-carboxylic acids
2010	A synchrotron study of (2R,5′S)-5′-benzyl-5-bromo-6-methoxy- spiro-[indane-2,2′-piperazine]-3′,6′-dione dimethyl-formamide solvate
2010	Design, synthesis, and evaluation of 1,4,7,10-tetraazacyclododecane-1,4,7- triacetic acid derived, redox-sensitive contrast agents for magnetic resonance imaging
2009	Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain
2009	In vitro and in vivo activity of novel small-molecule inhibitors targeting the pleckstrin homology domain of protein kinase B/AKT
2009	Conformational analysis of bridgehead-substituted bicyclo[m.m.m]alkanes and bicyclo[8.8.n]alkanes
2009	Synthesis 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
2008	Discovery of a novel class of AKT pleckstrin homology domain inhibitors
2008	NOTE: Synthesis and characterization of a poly(acrylamide) with pendant 1,4-piperazine-2,5-dione moieties via post-polymerization cyclization
2008	Organic 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
2007	Squalene-derived flexible linkers for bioactive peptides
2007	Design, synthesis, and validation of a branched flexible linker for bioactive peptides
2006	Arsenite and monomethylarsonous acid generate oxidative stress response in human bladder cell culture
2006	Preface
2006	Monomethylarsonous acid induces transformation of human bladder cells
2006	Deoxycholic acid induces intracellular signaling through membrane perturbations
2006	Synthesis 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
2006	Redox-sensitive contrast agents for MRI based on reversible binding of thiols to serum albumin
2005	Organic 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)]
2005	Synthesis of 1,10-dimethylbicyclo[8.8.8]hexacosane and 1,10- dihydroxybicyclo[8.8.8]hexacosane
2005	Synthesis of [ sup 14 /sup C]-imexon
2004	Tris[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
2003	An efficient synthesis of sodium dimethylarsinate- sup 14 /sup C
2003	Organic crystal engineering with piperazine-2,5-diones. 4. Crystal packing of piperazinediones derived from 2-amino-7-cyano-4-methoxyindan-2-carboxylic acid
2003	Crystal engineering of a liquid crystalline piperazinedione
2002	Synthesis and structure of the glutathione conjugate of chloroacetaldehyde
2002	Use of 9-methylfluorene as an indicator in the titration of common group IA and group IIA organometallic reagents
2001	Monomethylarsonous acid (MMA sup III /sup ) and arsenite: LD sub 50 /sub in hamsters and in vitro inhibition of pyruvate dehydrogenase
2001	Stereochemical aspects of vinylcyclohexene bioactivation in rodent hepatic microsomes and purified human cytochrome P450 enzyme systems
2000	Synthesis of (S)-(-)-β-cuparenone and (S)-(-)-cuparene
2000	Intermolecular and intramolecular reactions of resolved 2-alkoxytetrahydrofuran-3-yl and 2-alkoxytetrahydropyran-3-yl radicals
2000	NBD-TMA: A novel fluorescent substrate of the peritubular organic cation transporter of renal proximal tubules
2000	Synthesis of 7-alkoxyquinolines, coumarins, and resorufins
2000	The crystal packing of a strongly dipolar piperazinedione
1999	Organic 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
1999	Organic crystal engineering with piperazine-2,5-diones. 1. Crystal packing of piperazinediones derived from substituted 2-aminoindan-2- carboxylic acids
1999	Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 6. Stereocontrolled synthesis of tricyclo[m.n.0.0]alkenones
1999	2,2',3,3',6,6'-Hexachlorobiphenyl hydroxylation by active site mutants of cytochrome P450 2B1 and 2B11
1998	Near diffraction-limited laser emission from a polymer in a high finesse planar cavity
1998	Whispering-gallery-mode oscillation in a polymer microring laser
1998	Synthesis and characterization of highly efficient photorefractive polymer composites with long phase stability
1998	Vertical-cavity surface-emitting polymer laser
1998	Whispering-gallery-mode microring laser using a conjugated polymer
1998	Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 5. α'-Alkylations of bicycle[m.1.0]alkan-2-ones
1998	Synthesis of the mono-cysteine disulfide of meso-2,3-dimercaptosuccinic acid
1998	A cytochrome P450 terpenoid hydroxylase linked to the suppression of insect juvenile hormone synthesis
1997	Improved syntheses of 2,2',3,3',6,6'-hexachlorobiphenyl
1997	Diastereoselective Manipulations of Bicyclo[m.1.0]alkane Derivatives. 4. Reactions of Nucleophiles with Bicyclo[m.1.0]alk-3-en-2-ones
1997	Recent advances in photorefractive polymers and liquid crystals
1997	Monobenzylation of 1,n-diols via dibutylstannylene intermediates
1997	Diastereoselective 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
1997	Development 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
1997	Synthesis of ethyl N-(diphenyl)methyl-1,2,3,4- tetrahydroisoquinoline-3-carboxylates
1997	On the reported intermediacy of vinyl radicals in spontaneous polymerization: An ESR-spin trapping study and its significance for the bond forming initiation theory
1996	Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 2. Nucleophilic additions to the carbonyl carbons of bicyclot[m.1.0]alkan-2-ones
1996	Development of molecular mechanics torsion parameters for α,β-cyclopropyl ketones and conformational analysis of bicyclo[m.1.0]alkan-2-ones
1996	Syntheses and spectroscopic characterizations of oxidative metabolites of 4-vinylcyclohexene II diol-epoxides
1996	Engineering molecular solids
1995	Synthesis of the enantiomers of 4-vinylcyclohexene
1994	Syntheses and spectroscopic characterizations of oxidative metabolites of 4-vinylcyclohexene
1993	An efficient stereoconvergent synthesis of the 4-ethylamino-2,4-dideoxy-l-threo-pentopyranose component of the calicheamicins and esperamicins
1992	Systematic search of transition state conformations
1992	Acid-catalyzed dehydration for the design of chemical amplification resists
1991	Structure of an enantiomerically pure tetrahydropyranyl ether
1991	Enantiomerically pure acetals in organic synthesis. 3. A synthesis of (R)-mevalonic acid lactone
1991	Enantiomerically pure acetals in organic synthesis. 1. Chromatographic separability of furanoside and pyranoside acetals derived from α-hydroxy esters
1991	Enantiomerically pure acetals in organic synthesis. 2. Diastereoselective alkylation of enantiomeric lithio alkyl lactyl tetrahydropyranosides and related enolates
1991	Acid-catalyzed pinacol rearrangement. Chemically amplified reverse polarity change
1991	Negative chemical amplification resist systems based on polyhydroxystyrenes and N-substituted imides or aldehydes
1990	Diastereoselective 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
1990	Mechanistic studies of diastereoselective cyclopropanation via homochiral ketals. 2. Studies with conformationally restricted 2-cyclohexen-1-one ketals
1990	A new synthetic approach to the C-D ring portion of streptonigrin analogues
1990	Mechanistic studies of diastereoselective cyclopropanation via homochiral ketals. 1. Dioxolane structural effects
1989	Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation of α,β-unsaturated ketals derived from (S,S)-(-)-hydrobenzoin
1989	Selective inactivation of rat liver cytochromes P-450 by 21-chlorinated steroids
1989	Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation of medium and large ring α,α-unsaturated ketals derived from 1,4-di-O-benzyl-L-threitol
1989	Homochiral ketals in organic synthesis. Enantioselective synthesis and absolute configuration of (-)-modhephene
1989	Homochiral acetals in organic synthesis. A general enantioselective entry to carbohydrate derivatives from non-carbohydrate precursors
1988	Homochiral ketals in organic sythesis. Simple chromatographic resolution of diastereomeric α-hydroxycycloalkanone ketals
1988	Homochiral ketals in organic synthesis. Enantioselective preparation of (+)-modhephene
1988	Selective inactivation by 21-chlorinated steroids of rabbit liver and adrenal microsomal cytochromes P-450 involved in progesterone hydroxylation
1987	Homochiral ketals in organic synthesis. Enantioselective synthesis of (+)-β-eudesmol
1987	Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation of α,β-unsaturated ketals derived from 1,4-D1-O-benzyl-l-threitol
1987	Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects
1987	Homochiral ketals in organic synthesis. Enantioselective synthesis and absolute configuration of (-)-chokol A
1986	Homochiral ketals in organic synthesis. Enantioselective synthesis of [m.n.1] Propellanones
1986	Homochiral ketals in organic synthesis. Enantioselective synthesis of (R)-muscone
1985	Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation
1981	Farnesylpyrophosphate synthetase. Evidence for a rigid geranyl cation-pyrophosphate anion pair
1979	Farnesyl pyrophosphate synthetase. Mechanistic studies of the 1′-4 coupling reaction in the terpene biosynthetic pathway [13]
1978	Farnesyl pyrophosphate synthetase. Mechanistic studies of the 1'-4 coupling reaction with 2-fluorogeranyl pyrophosphate.
1977	Prenyltransferase. New evidence for an ionization-condensation-elimination mechanism with 2-fluorogeranyl pyrophosphate [15]

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