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Potent Uncompetitive Inhibitors of Nicotinamide N-Methyltransferase (NNMT) as In Vivo Chemical Probes

J .Med. Chem. 2022
Publication Date: October 26, 2022
Robert D. Barrows, Daniel E. Jeffries, Mahesh Vishe, Hanna Tukachinsky, Shao-Liang Zheng, Fanfan Li, Zhenjie Ma, Xiaolei Li, Shujuan Jin, Haobin Song, Ruonan Zhang, Shaofeng Zhang, Jing Ni, Haofei Luan, Lei Wen, Yan Rongshan, Chen Ying, and Matthew D. Shair.

High-Affinity Alkynyl Bisubstrate Inhibitors of Nicotinamide N-Methyltransferase (NNMT)

ACS .Med. Chem. 2019
Publication Date: October 7, 2019
Policarpo RL, Decultot L, May E, Kuzmic P, Carlson S, Huang D, Chu V, Wright BA, Dhakshinamoorthy S, Kannt A, Rani S, Dittakavi S, Panarese JD, Gaudet R, Shair MD.

STAT1 S727 Promotes Growth of Neoplasms With JAK-STAT 

EBioMedicine. 2017
Publication Date: December 13, 2017
Nitulescu II, Meyer SC, Wen QJ, Crispino JD, Lexieux ME, Levine RL, Pelish HE, Shair MD

STAT3 Inhibitory Activity of Structurally Simplified Withaferin A Analogues

Organic Letters. 2017
Publication Date: March 28, 2017
Teruyuki T, Ursula S, Pelish HE,  Shair MD.

Identification of Mediator Kinase Substrates in Human Cells using Cortistatin A and Quantitative Phosphoproteomics.

Cell Reports. 2016
Publication Date: March 31, 2016
Poss ZC, Ebmeier CC, Odell AT, Tangpeerachaikul A, Lee T, Pelish HE, Shair MD, Dowell RD, Old WM, Taatjes DJ.

Mediator kinase inhibition further activates super-enhancer-associated genes in AML

Nature 526, 273-276 (2015). Pelish HE, Liau BB, Nitulescu II, Tangpeerachaikul A, Poss ZC, Da Silva DH, Caruso BT, Arefolov A, Fadeyi O, Christie AL, Du K, Banka D, Schneider EV, Jestel A, Zou G, Si C, Ebmeier CC, Bronson RT, Krivtsov AV, Myers AG, Kohl NE, Kung AL, Armstrong SA, Lemieux ME, Taatjes DJ, Shair MD.

Total Synthesis of (-)-Nemorosone and (+)-Secohyperforin.

Organic Letters 17, 3398-3401 (2015). Sparling BA, Tucker JK, Moebius DC, Shair MD.

Broad-range inhibition of enterovirus replication by OSW-1, a natural compound targeting OSBP.

Antiviral Research 117, 110-114 (2015). Albulescu L, Strating JR, Thibaut HJ, Van der Linden L, Shair MD, Neyts J, Van Kuppeveld FJ.

Itraconazole inhibits enterovirus replication by targeting the oxysterol-binding protein.

Cell Reports 10, 600-615 (2015). Strating JR, van der Linden L, Albulescu L, Bigay J, Arita M, Delang L, Leyssen P, van der Schaar HM, Lanke KH, Thibaut HJ, Ulferts R, Drin G, Schlinck N, Wubbolts RW, Sever N, Head SA, Liu JO, Beachy PA, De Matteis MA, Shair MD, Olkkonen VM, Neyts J, van Kuppeveld FJ.

A unified strategy for the synthesis of 7-membered-ring-containing Lycopodium alkaloids.

Journal of the American Chemical Society 136, 13442-13452 (2014). Lee AS, Liau BB, Shair MD.

Synthesis of the C4-epi-lomaiviticin B core reveals subtle stereoelectronic effects.

Organic Letters 15, 2390-2393 (2013). Lee AS, Shair MD.

The small molecule dispergo tubulates the endoplasmic reticulum and inhibits export.

Molecular Biology of the Cell 24, 1020-1029 (2013). Lu L, Hannoush RN, Goess BC, Varadarajan S, Shair MD, Kirchhausen T.

Enantioselective total synthesis of hyperforin.

Journal of the American Chemical Society 135, 644-647 (2013). Sparling BA, Moebius DC, Shair MD.

Total syntheses of HMP-Y1, hibarimicinone, and HMP-P1.

Journal of the American Chemical Society 134, 16765-16772 (2012). Liau BB, Milgram BC, Shair MD.

Gram-scale synthesis of the A’B’-subunit of angelmicin B.

Organic Letters 13, 6436-6439 (2011). Milgram BC, Liau BB, Shair MD.

Natural products reveal cancer cell dependence on oxysterol-binding proteins.

Nature Chemical Biology 7, 639-647 (2011). Burgett AW, Poulsen TB, Wangkanont K, Anderson DR, Kikuchi C, Shimada K, Okubo S, Fortner KC, Mimaki Y, Kuroda M, Murphy JP, Schwalb DJ, Petrella EC,Cornella-Taracido I, Schirle M, Tallarico JA, Shair MD.

Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

Chemistry – A European Journal 16, 13058-13062 (2010). Lee HG, Ahn JY, Lee AS, Shair MD.

Synthesis of the N-(tert-butyloxycarbonyl)-O-triisopropylsilyl-D-pyrrolosamine Glycal of Lomaiviticin A & B via Epimerization of L-Threonine.

Tetrahedron Letters 51, 4310-4312 (2010). Morris WJ, Shair MD.

Total synthesis of (+)-fastigiatine.

Journal of the American Chemical Society 132, 9594-9595 (2010). Liau BB, Shair MD.

Enantioselective synthesis of (+)-cephalostatin 1.

Journal of the American Chemical Society 132, 275-280 (2010). Fortner KC, Kato D, Tanaka Y, Shair MD.

Stereoselective synthesis of 2-deoxy-beta-glycosides using anomeric O-alkylation/arylation.

Organic Letters 11, 9-12 (2009). Morris WJ, Shair MD.

Enantioselective synthesis of (+)-cortistatin a, a potent and selective inhibitor of endothelial cell proliferation.

Journal of the American Chemical Society 130, 16864-16866 (2008). Lee HM, Nieto-Oberhuber C, Shair MD.

Enantioselective synthesis of the central ring system of lomaiviticin A in the form of an unusually stable cyclic hydrate.

Angewandte Chemie International Edition 47, 1680-1684 (2008). Krygowski ES, Murphy-Benenato K, Shair MD.

Stereoelectronic effects dictate mechanistic dichotomy between Cu(II)-catalyzed and enzyme-catalyzed reactions of malonic acid half thioesters.

Journal of the American Chemical Society 129, 6589-6598 (2007). Fortner KC, Shair MD.

Syntheses of the eastern halves of ritterazines B, F, G, and H, leading to reassignment of the 5,5-spiroketal stereochemistry of ritterazines B and F.

Journal of the American Chemical Society 129, 1032-1033 (2007). Phillips ST, Shair MD.

The Cdc42 inhibitor secramine B prevents cAMP-induced K+ conductance in intestinal epithelial cells.

Biochemical Pharmacology 71, 1720-1726 (2006). Pelish HE, Ciesla W, Tanaka N, Reddy K, Shair MD, Kirchhausen T, Lencer WI.

Synthesis of a 10,000-membered library of molecules resembling carpanone and discovery of vesicular traffic inhibitors.

Journal of the American Chemical Society 128, 5391-5403 (2006). Goess BC, Hannoush RN, Chan LK, Kirchhausen T, Shair MD.

Secramine inhibits Cdc42-dependent functions in cells and Cdc42 activation in vitro.

Nature Chemical Biology 2, 39-46 (2006). Pelish HE, Peterson JR, Salvarezza SB, Rodriguez-Boulan E, Chen JL, Stamnes M, Macia E, Feng Y, Shair MD, Kirchhausen T.

Dynamic kinetic resolution during a cascade reaction on substrates with chiral all-carbon quaternary centers.

Journal of the American Chemical Society 127, 7284-7285 (2005). Xu K, Lalic G, Sheehan SM, Shair MD.

Catalytic enantioselective thioester aldol reactions that are compatible with protic functional groups.

Angewandte Chemie International Edition 44, 2259-2261 (2005). Magdziak D, Lalic G, Lee HM, Fortner KC, Aloise AD, Shair MD.

Synthesis of (-)-longithorone A: using organic synthesis to probe a proposed biosynthesis.

Proceedings of the National Academy of Sciences 101, 12036-12041 (2004). Morales CA, Layton ME, Shair MD.

An exceptionally mild catalytic thioester aldol reaction inspired by polyketide biosynthesis.

Journal of the American Chemical Society 125, 2852-2853 (2003). Lalic G, Aloise AD, Shair MD.

Biomimetic synthesis of (-)-longithorone A.

Journal of the American Chemical Society 124, 773-775 (2002). Layton ME, Morales CA, Shair MD.

An alkylsilyl-tethered, high-capacity solid support amenable to diversity-oriented synthesis for one-bead, one-stock solution chemical genetics.

Journal of Combinatorial Chemistry 3, 312-318 (2001). Tallarico JA, Depew KM, Pelish HE, Westwood NJ, Lindsley CW, Shair MD, Schreiber SL, Foley MA.

Use of biomimetic diversity-oriented synthesis to discover galanthamine-like molecules with biological properties beyond those of the natural product.

Journal of the American Chemical Society 123, 6740-6741 (2001). Pelish HE, Westwood NJ, Feng Y, Kirchhausen T, Shair MD.

Reaction microarrays: a method for rapidly determining the enantiomeric excess of thousands of samples.

Journal of the American Chemical Society 123, 361-362 (2001). Korbel GA, Lalic G, Shair MD.

A Highly Efficient and Convergent Reaction for the Synthesis of Bridgehead Enone-Containing Polycyclic Ring Systems 

Angewandte Chemie International Edition 39, 2714-2715 (2000). Sheehan SM, Lalic G, Chen JS, Shair MD.

Synthesis of Cyclooctenones Using Intramolecular Hydroacylation

Journal of the American Chemical Society 122, 12610-12611 (2000). Aloise AD, Layton ME, and Shair  MD.

Solid-Phase Biomimetic Synthesis of Carpanone-like Molecules

Journal of the American Chemical Society 122, 7424-7425 (2000). Lindsley CW, Chan LK, Goess BC, Joseph R, and Shair MD.

Synthesis of (+)CP263,114

Journal of the American Chemical Society 122, 422-423 (2000). Chen C, Layton ME, Sheehan S, & Shair MD.

Stereospecific Synthesis of the CP-263,114 Core Structure

Journal of the American Chemical Society 120, 10784-10785 (1998). Chen C, Layton ME, and Shair MD.

A closer view of an oncoprotein-tumor suppressor interaction

Cell Chemical Biology 4, 791-794 (1997). Shair MD.