2024

In vivo–Active Soluble Epoxide Hydrolase–targeting PROTACs with Improved Potency and Stability

Keita Nakane, Christophe Morisseau, Presley D. Dowker-Key, Gabrielle Benitez, Jennifer T. Aguilan, Emiko Nagai, Simone Sidoli, Bruce D. Hammock, Ahmed Bettaieb, Kosaku Shinoda, Seiya Kitamura*

bioRxiv (preprint) 2024, https://www.biorxiv.org/content/10.1101/2024.07.23.604814v1

tags: PROTACs, soluble epoxide hydrolase, ER stress

Insights into the Interaction Landscape of the EVH1 Domain of Mena

Lanette LaComb, Agnidipta Ghosh, Jeffrey B. Bonanno, Daniel J. Nilson, Alex J. Poppel, Lucas Dada, Sean M. Cahill, Juan Pablo Maianti, Seiya Kitamura, David Cowburn, Steven C. Almo*

Biochemistry 2024, https://pubs.acs.org/doi/full/10.1021/acs.biochem.4c00331

tags: Biochemistry, cancer

Ultrapotent influenza hemagglutinin fusion inhibitors developed through SuFEx-enabled high-throughput medicinal chemistry

Seiya Kitamura, Ting-Hui Lin, Chang-Chun David Lee, Akihiro Takamura, Rameshwar U. Kadam, Ding Zhang, Xueyong Zhu, Lucas Dada, Emiko Nagai, Wenli Yu, Yao Yao, K. Barry Sharpless, Ian A. Wilson, and Dennis W. Wolan*

Proc. Nat. Acad. Sci. USA 2024, https://doi.org/10.1073/pnas.231067712

tags: High-throughput medicinal chemistry, infectious disease, SuFEx, inhibition

SuFEx-based chemical diversification for the systematic discovery of CRBN molecular glues

Trever R. Carter, Natalia Milosevich, Lucas Dada, James B. Shaum, K. Barry Sharpless, Seiya Kitamura, Michael A. Erb

Bioorganic & Medicinal Chemistry 2024, doi.org/10.1016/j.bmc.2024.117699

tags: High-throughput medicinal chemistry, molecular glues, SuFEx, cancer, inhibition

2023

PROTAC-mediated selective degradation of cytosolic soluble epoxide hydrolase enhances ER-stress reduction

Yuxin Wang, Christophe Morisseau, Akihiro Takamura, Debin Wan, Dongyang Li, Simone Sidoli, Jun Yang, Dennis W. Wolan, Bruce D. Hammock, Seiya Kitamura*

ACS Chem. Biol. 2023, 18, 4, 884–896

tags: PROTACs, soluble epoxide hydrolase, ER stress

2022

The Development of the Bengamides as New Antibiotics against Drug-Resistant Bacteria

Cristina Porras-Alcalá,Federico Moya-Utrera,Miguel García-Castro,Antonio Sánchez-Ruiz,Juan Manuel López-Romero,María Soledad Pino-González,Amelia Díaz-Morilla,Seiya Kitamura,Dennis W. Wolan, José Prados,Consolación Melguizo,Iván Cheng-Sánchez, and Francisco Sarabia

https://www.mdpi.com/1660-3397/20/6/373

tags: Antibiotics, bacteria

Diversity oriented clicking delivers β-substituted alkenyl sulfonyl fluorides as covalent human neutrophil elastase inhibitors

Yunfei Cheng, Gencheng Li, Christopher J. Smedley, Marie-Claire Giel, Seiya Kitamura, Jordan L. Woehl, Giulia Bianco, Stefano Forli, Joshua A. Homer, John R. Cappiello, Dennis W. Wolan, John E. Moses, and K. Barry Sharpless

https://www.pnas.org/doi/10.1073/pnas.2208540119

tags: SuFEx, diversity-oriented click chemistry, protease, inhibition

PROTAC-mediated selective degradation of cytosolic soluble epoxide hydrolase enhances ER-stress reduction

Yuxin Wang, Christophe Morisseau, Akihiro Takamura, Debin Wan, Dongyang Li, Dennis W. Wolan, Bruce D. Hammock, Seiya Kitamura

bioRxiv 2022.01.20.477134

tags: PROTACs, soluble epoxide hydrolase, ER stress

2021

Metabolomics activity screening of T cell–induced colitis reveals anti-inflammatory metabolites

Montenegro-Burke, J.R., Kok, B.K., Guijas, C., Domingo-Almenara, X., Moon, C., Galmozzi, A., Kitamura, S., Eckmann, L., Saez, E., Siuzdak, G.E., Wolan, D.W.

Science Signaling 2021 Vol 14, Issue 702

tags: microbiome, metabolomics, proteomics

A photoaffinity probe that targets folate-binding proteins.

Takamura, A., Thuy-Boun, P.S., Kitamura, S., Han, Z., Wolan, D.W.

Bioorg. Med. Chem. Lett. 2021 40, 127903

tags: microbiome, folate, ABPP, photo-activatable probe, proteomics

Chemical Inhibition of ENL/AF9 YEATS Domains in Acute Leukemia

Garnar-Wortzel, L.^#, Bishop, T. ^# , Kitamura, S. ^#(co-first author), Milosevich, N., Asiaban, J., Zhang, X., Zheng, Q., Chen, E., Ramos, A., Ackerman, C., Hampton, E., Chatterjee, A., Young, T., Hull, M., Sharpless K.B., Cravatt, B., Wolan, D. W., Erb, M.^*

ACS Cen. Sci. 2021, 7, 5, 815–830

tags: High-throughput medicinal chemistry, PROTAC, SuFEx, epigenetics, inhibition

2020

Synthetic elaboration of native DNA by RASS (SENDR).

Flood, D.T., Knouse, K.W., Vantourout, J.C., Kitamura, S., Sanchez, B.B., Sturgell, E.J., Chen, J.S., Wolan, D.W., Baran, P.S., Dawson, P.E.

ACS Cen. Sci. 2020 6, 1789-1799

tags: Bioconjugation, hNE inhibition

Discovery of small-molecule enzyme activators by activity-based protein profiling.

Kok, B.P., Ghimire, S., Kim, W., Chatterjee, S., Johns, T., Kitamura, S., Eberhardt, J., Ogaswara, D., Xu, J., Sukiasyan, A., Kim, S.M., Godio, C., Bittencourt, J.M., Cameron, M., Galmozzi, A., Forli, S, Wolan, D.W., Cravatt, B.F., Boger, D.L., Saez, E.

Nat. Chem. Biol. 2020 16, 997-1005

tags: activator, new modality, protease

An irreversible inhibitor to probe the role of Streptococcus pyogenes cysteine protease SpeB in evasion of host complement defenses.

Woehl, J.L.^#, Kitamura, S.^# (co-first author), Dillon, N., Han, Z., Edgar, L.J., Nizet, V., Wolan, D.W.

ACS Chem. Biol. 2020 15, 2060–2069

tags: microbiome, protease, ABPP, proteomics

An influenza A hemagglutinin small-molecule fusion inhibitor identified by a new high-throughput fluorescence polarization screen.

Yao, Y., Kadam, R.U., Lee, C.-C.D., Woehl, J.L., Chen, E., Wu, N.C., Zhu, X., Kitamura, S., Wilson, I.A., Wolan, D.W.

Proc. Nat. Acad. Sci. USA 2020 117, 18431-18438

tags: infectious diseases, inhibitor, screening

Sulfur(VI) fluoride exchange (SuFEx)-enabled high-throughput medicinal chemistry.

Kitamura, S., Zheng, Q., Woehl, J.L., Solania, A., Chen, E., Dillon, N., Hull, M.V., Kotaniguchi, M., Cappiello, J.R., Kitamura, S., Nizet, V., Sharpless, K.B., Wolan, D.W.

J. Am. Chem. Soc. 2020 142, 10899–10904

tags: High-throughput medicinal chemistry, SuFEx, protease

Diversity oriented clicking (DOC): Divergent synthesis of SuFExable pharmacophores from 2-substituted-alkynyl-1-sulfonyl fluoride (SASF) hubs.

Smedley, C.J., Li, G., Barrow, A.S., Gialelis, T.L., Giel, M.-C., Ottonello, A., Cheng, Y., Kitamura, S., Wolan, D.W., Sharpless, K.B., Moses, J.E.

Angew. Chem. Int. Ed. 2020 59, 12460-12469

tags: SuFEx, click chemistry, infectious diseases

Genetic basis for the cooperative bioactivation of plant lignans by Eggerthella lenta and other human gut bacteria.

Bess, E.N., Bisanz, J.E., Yarza, F., Bustion, A., Rich, B.E., Li, X., Kitamura, S., Waligurski, E., Ang, Q.Y., Alba, D.L., Spanogiannopoulos, P., Nayfach, S., Koliwad, S.K., Wolan, D.W., Franke, A.A., Turnbaugh, P.J.

Nat. Microbiol. 2020 5, 56-66

tags: microbiome, metabolites, food

2019

SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase.

Zheng, Q., Woehl, J.L., Kitamura S., Santos-Martins, D., Smedley, C.J., Lia, G., Forli, S., Moses, J.E., Wolan, D.W., Sharpless, K.B.

Proc. Nat. Acad. Sci. USA 2019 116, 18808-18814

tags: SuFEx, screening, hNE inhibition

Nanobody-based binding assay for the discovery of potent inhibitors of CFTR inhibitory factor (Cif)

Vasylieva, N., Kitamura, S., Dong, J., Barnych, B., Hvorecny, K.L., Madden, D.R., Gee, S.J., Wolan, D.W., Morisseau, C., Hammock, B.D.

Analyt. Chim. Acta 2019 1057, 106-113

tags: infectious diseases, screening, inhibitor

2018

Probing substrate recognition of bacterial lipoprotein signal peptidase using FRET reporters

Kitamura, S., Wolan, D.W.

FEBS Lett. 2018 592, 2289-2296

tags: infectious diseases, protease, inhibitor

Lipoprotein signal peptidase inhibitors with antibiotic properties identified through design of a robust in vitro HT platform

Kitamura, S., Owensby, A., Wall, D., Wolan, D.W.

Cell Chem. Biol. 2018 25, 301-308

tags: infectious diseases, protease, screening, inhibitor

2017

Occurrence of urea-based soluble epoxide hydrolase inhibitors from the plants in the order Brassicales

S Kitamura, C Morisseau, TR Harris, B Inceoglu, BD Hammock

PloS one 12 (5), e0176571

tags: food, inhibitor, hydrolase

Active-site flexibility and substrate specificity in a bacterial virulence factor: Crystallographic snapshots of an epoxide hydrolase

Kelli L Hvorecny, Christopher D Bahl, Seiya Kitamura, Kin Sing Stephen Lee, Bruce D Hammock, Christophe Morisseau, Dean R Madden

Structure 25 (5), 697-707. e4

tags: infectious diseases, structure

2016

Rational Design of Potent and Selective Inhibitors of an Epoxide Hydrolase Virulence Factor from Pseudomonas aeruginosa

S Kitamura, KL Hvorecny, J Niu, BD Hammock, DR Madden, C Morisseau

Journal of medicinal chemistry 59 (10), 4790-4799

tags: infectious diseases, structure, inhibitor, hydrolase

2015

Potent Natural Soluble Epoxide Hydrolase Inhibitors from Pentadiplandra brazzeana Baillon: Synthesis, Quantification, and Measurement of Biological Activities In Vitro and In Vivo

Seiya Kitamura, Christophe Morisseau, Bora Inceoglu, Shizuo G Kamita, Gina R De Nicola, Maximilienne Nyegue, Bruce D Hammock

PLoS One 10 (2), e0117438

tags: food, inhibitor, hydrolase

2014

Structural requirement and stereospecificity of tetrahydroquinolines as potent ecdysone agonists

S Kitamura, T Harada, H Hiramatsu, R Shimizu, H Miyagawa, Y Nakagawa

Bioorganic & medicinal chemistry letters 24 (7), 1715-1718

tags: agonist, chirality