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H. Stöckmann, A. Neves, Shaun Stairs, Heather Ireland-Zecchini, K. Brindle, F. Leeper (2011)
Development and evaluation of new cyclooctynes for cell surface glycan imaging in cancer cells.Chemical science, 2 5
D. Nauman, C. Bertozzi (2001)
Kinetic parameters for small-molecule drug delivery by covalent cell surface targeting.Biochimica et biophysica acta, 1568 2
A. Dirks, J. Cornelissen, Floris van Delft, Jan van Hest, R. Nolte, A. Rowan, F. Rutjes (2007)
From (bio)Molecules to Biohybrid Materials with the Click Chemistry ApproachQsar & Combinatorial Science, 26
Udayanath Aich, Christopher Campbell, Noha Elmouelhi, Christopher Weier, S. Sampathkumar, Sean Choi, K. Yarema (2008)
Regioisomeric SCFA attachment to hexosamines separates metabolic flux from cytotoxicity and MUC1 suppression.ACS chemical biology, 3 4
M. Betenbaugh, N. Arden, T. Nivitchanyong (2004)
Cell Engineering Blocks Cell Stress and Improves Biotherapeutic ProductionBioProcessing Journal, 3
Udayanath Aich, M. Meledeo, S. Sampathkumar, Jie Fu, Mark Jones, Christopher Weier, S. Chung, Benjamin Tang, Ming Yang, J. Hanes, K. Yarema (2010)
Development of delivery methods for carbohydrate-based drugs: controlled release of biologically-active short chain fatty acid-hexosamine analogsGlycoconjugate Journal, 27
S. Sampathkumar, Mark Jones, M. Meledeo, Christopher Campbell, Sean Choi, Kaoru Hida, Prasra Gomutputra, Anthony Sheh, Tim Gilmartin, S. Head, K. Yarema (2006)
Targeting glycosylation pathways and the cell cycle: sugar-dependent activity of butyrate-carbohydrate cancer prodrugs.Chemistry & biology, 13 12
G. Lemieux, K. Yarema, Christina Jacobs, C. Bertozzi (1999)
Exploiting differences in sialoside expression for selective targeting of MRI contrast reagentsJournal of the American Chemical Society, 121
Zhiyun Wang, Jian Du, P. Che, M. Meledeo, K. Yarema (2009)
Hexosamine analogs: from metabolic glycoengineering to drug discovery.Current opinion in chemical biology, 13 5-6
Lifang Yang, J. Nyalwidhe, Siqi Guo, R. Drake, O. Semmes, S. Petratos, Ian Smith, Hisashi Yamanaka, Michael Gross, Q-G Hu, J. Voorberg, A. Meijer (2011)
Targeted Identification of Metastasis-associated Cell-surface Sialoglycoproteins in Prostate CancerMolecular & Cellular Proteomics : MCP, 10
Non-radioactive targeting of multiple classes of protein post-translational modifications (PTMs) with click chemistry
Codelli (2008)
Second-generation difluorinated cyclooctynes for copper-free click chemistryJ Am Chem Soc, 130
G. Jourdian, L. Dean, S. Roseman (1971)
The sialic acids. XI. A periodate-resorcinol method for the quantitative estimation of free sialic acids and their glycosides.The Journal of biological chemistry, 246 2
Yarema Yarema, Mahal Mahal, Bruehl Bruehl, Rodriguez Rodriguez, Bertozzi Bertozzi (1998)
Metabolic delivery of ketone groups to sialic acid residues. Application to cell surface glycoform engineeringJ Biol Chem, 273
Christopher Benjamin, Ronald Hiebsch, D. Jones (1998)
Caspase activation in MCF7 cells responding to etoposide treatment.Molecular pharmacology, 53 3
H. Kayser, R. Zeitler, C. Kannicht, D. Grunow, R. Nuck, W. Reutter (1992)
Biosynthesis of a nonphysiological sialic acid in different rat organs, using N-propanoyl-D-hexosamines as precursors.The Journal of biological chemistry, 267 24
Mark Jones, Howard Teng, Jun Rhee, Nicholas Lahar, Gautam Baskaran, K. Yarema (2004)
Characterization of the cellular uptake and metabolic conversion of acetylated N‐acetylmannosamine (ManNAc) analogues to sialic acidsBiotechnology and Bioengineering, 85
T. Hsu, S. Hanson, Kuniyuki Kishikawa, Sheng-Kai Wang, M. Sawa, Chi‐Huey Wong (2007)
Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cellsProceedings of the National Academy of Sciences, 104
Pamela Chang, Xing Chen, C. Smyrniotis, Alexander Xenakis, Tianshun Hu, C. Bertozzi, Peng Wu (2009)
Metabolic labeling of sialic acids in living animals with alkynyl sugars.Angewandte Chemie, 48 22
Christopher Campbell, S. Sampathkumar, K. Yarema (2007)
Metabolic oligosaccharide engineering: perspectives, applications, and future directions.Molecular bioSystems, 3 3
P. Chefalo, Yanbin Pan, N. Nagy, Zhongwu Guo, C. Harding (2006)
Efficient metabolic engineering of GM3 on tumor cells by N-phenylacetyl-D-mannosamine.Biochemistry, 45 11
Chung-Yi Wu, Chi‐Huey Wong (2011)
Chemistry and glycobiology.Chemical communications, 47 22
L. Mahal, K. Yarema, C. Bertozzi (1997)
Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis.Science, 276 5315
S. Sampathkumar, Adrienne Li, Mark Jones, Zhonghui Sun, K. Yarema (2006)
Metabolic installation of thiols into sialic acid modulates adhesion and stem cell biologyNature Chemical Biology, 2
P. Chefalo, Yanbin Pan, N. Nagy, C. Harding, Zhongwu Guo (2003)
Preparation and immunological studies of protein conjugates of N-acylneuraminic acidsGlycoconjugate Journal, 20
I. Kii, Akira Shiraishi, Toshiyuki Hiramatsu, T. Matsushita, H. Uekusa, S. Yoshida, Makoto Yamamoto, A. Kudo, M. Hagiwara, T. Hosoya (2010)
Strain-promoted double-click reaction for chemical modification of azido-biomolecules.Organic & biomolecular chemistry, 8 18
Christopher Campbell, Udayanath Aich, Christopher Weier, Jean Wang, Sean Choi, Mary Wen, K. Maisel, S. Sampathkumar, K. Yarema (2008)
Targeting pro-invasive oncogenes with short chain fatty acid-hexosamine analogues inhibits the mobility of metastatic MDA-MB-231 breast cancer cells.Journal of medicinal chemistry, 51 24
S. Sampathkumar, Christopher Campbell, Christopher Weier, K. Yarema (2006)
Short-chain fatty acid-hexosamine cancer prodrugs : the sugar matters!Drugs of The Future, 31
Kolb (2001)
Click chemistry: Diverse chemical function from a few good reactionsAngew Chem Int Ed, 40
Shoufa Han, B. Collins, P. Bengtson, J. Paulson (2005)
Homomultimeric complexes of CD22 in B cells revealed by protein-glycan cross-linkingNature Chemical Biology, 1
J. Au, M. Wientjes, Rajee Kumar, Dong Li (1999)
Kinetics of hallmark biochemical changes in paclitaxel-induced apoptosisAAPS PharmSci, 1
John-hwa Lee, T. Baker, L. Mahal, J. Zabner, C. Bertozzi, D. Wiemer, M. Welsh (1999)
Engineering Novel Cell Surface Receptors for Virus-mediated Gene Transfer*The Journal of Biological Chemistry, 274
Eliana Saxon, C. Bertozzi (2000)
Cell surface engineering by a modified Staudinger reaction.Science, 287 5460
Zhengmao Hua, A. Lvov, Trevor Morin, William Kobertz (2011)
Chemical control of metabolically-engineered voltage-gated K+ channels.Bioorganic & medicinal chemistry letters, 21 17
E. Kim, S. Sampathkumar, Mark Jones, Jun Rhee, Gautam Baskaran, S. Goon, K. Yarema (2004)
Characterization of the Metabolic Flux and Apoptotic Effects of O-Hydroxyl- and N-Acyl-modified N-Acetylmannosamine Analogs in Jurkat Cells*Journal of Biological Chemistry, 279
Noha Elmouelhi, Udayanath Aich, Venkata Paruchuri, M. Meledeo, Christopher Campbell, Jean Wang, Raja Srinivas, Hargun Khanna, K. Yarema (2009)
Hexosamine template. A platform for modulating gene expression and for sugar-based drug discovery.Journal of medicinal chemistry, 52 8
Jian Du, M. Meledeo, Zhiyun Wang, S. Hargun, Khanna, Venkata Paruchuri, K. Yarema (2009)
Metabolic glycoengineering: sialic acid and beyond.Glycobiology, 19 12
Zhiyun Wang, Zhonghui Sun, Adrienne Li, K. Yarema (2006)
Roles for UDP-GlcNAc 2-Epimerase/ManNAc 6-Kinase outside of Sialic Acid BiosynthesisJournal of Biological Chemistry, 281
J. Holub, K. Kirshenbaum (2010)
Tricks with clicks: modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition.Chemical Society reviews, 39 4
Zhiyun Wang, Zhonghui Sun, Adrienne Li, K. Yarema (2006)
ROLES FOR GNE OUTSIDE OF SIALIC ACID BIOSYNTHESIS : MODULATION OF SIALYLTRANSFERASE AND BiP EXPRESSION , GM 3 AND GD 3 BIOSYNTHESIS , PROLIFERATION AND APOPTOSIS , AND ERK 1 / 2 PHOSPHORYLATION
Heinz Möller, Verena Böhrsch, L. Lucka, C. Hackenberger, S. Hinderlich (2011)
Efficient metabolic oligosaccharide engineering of glycoproteins by UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase (GNE) knock-down.Molecular bioSystems, 7 7
Disaccharide uptake and priming in animal cells: Inhibition of sialyl Lewis X by acetylated GalIl1-4GlcNAcI3-O-naphthalenemethanol
Jian Du, P. Che, Zhiyun Wang, Udayanath Aich, K. Yarema (2011)
Designing a binding interface for control of cancer cell adhesion via 3D topography and metabolic oligosaccharide engineering.Biomaterials, 32 23
Vu Hong, N. Steinmetz, M. Manchester, M. Finn (2010)
Labeling live cells by copper-catalyzed alkyne--azide click chemistry.Bioconjugate chemistry, 21 10
Matteo Zanda (2008)
SYNFORM ISSUE 2008/11Synfacts, 2008
Christina Jacobs, S. Goon, K. Yarema, S. Hinderlich, H. Hang, D. Chai, C. Bertozzi, C. Bertozzi (2001)
Substrate specificity of the sialic acid biosynthetic pathway.Biochemistry, 40 43
P. Tangvoranuntakul, P. Gagneux, Sandra Díaz, M. Bardor, N. Varki, A. Varki, E. Muchmore (2003)
Human uptake and incorporation of an immunogenic nonhuman dietary sialic acidProceedings of the National Academy of Sciences of the United States of America, 100
A. Sarkar, T. Fritz, W. Taylor, J. Esko (1995)
Disaccharide uptake and priming in animal cells: inhibition of sialyl Lewis X by acetylated Gal beta 1-->4GlcNAc beta-O-naphthalenemethanol.Proceedings of the National Academy of Sciences of the United States of America, 92
Yoshihito Tanaka, Jennifer Kohler (2008)
Photoactivatable crosslinking sugars for capturing glycoprotein interactions.Journal of the American Chemical Society, 130 11
K. Yarema, S. Goon, C. Bertozzi (2001)
Metabolic selection of glycosylation defects in human cellsNature Biotechnology, 19
Sarah Luchansky, S. Argade, B. Hayes, C. Bertozzi (2004)
Metabolic functionalization of recombinant glycoproteins.Biochemistry, 43 38
M. Bond, Haochi Zhang, Peter Vu, Jennifer Kohler (2009)
Photocrosslinking of glycoconjugates using metabolically incorporated diazirine-containing sugarsNature Protocols, 4
Scott Laughlin, Jeremy Baskin, S. Amacher, C. Bertozzi (2008)
In Vivo Imaging of Membrane-Associated Glycans in Developing ZebrafishScience, 320
H. Kolb, M. Finn, K. Sharpless (2001)
Click Chemistry: Diverse Chemical Function from a Few Good Reactions.Angewandte Chemie, 40 11
A. Neves, H. Stöckmann, Rebecca Harmston, Helen Pryor, Israt Alam, Heather Ireland-Zecchini, D. Lewis, S. Lyons, F. Leeper, K. Brindle (2011)
Imaging sialylated tumor cell glycans in vivoThe FASEB Journal, 25
David Amo, W. Wang, Hao Jiang, C. Besanceney, Amy Yan, M. Levy, Yi Liu, F. Marlow, Peng Wu (2010)
Biocompatible copper(I) catalysts for in vivo imaging of glycans.Journal of the American Chemical Society, 132 47
K. Yarema, L. Mahal, Richard Bruehl, Elena Rodriguez, C. Bertozzi (1998)
Metabolic Delivery of Ketone Groups to Sialic Acid ResiduesThe Journal of Biological Chemistry, 273
Lars Mantey, O. Keppler, M. Pawlita, W. Reutter, S. Hinderlich (2001)
Efficient biochemical engineering of cellular sialic acids using an unphysiological sialic acid precursor in cells lacking UDP‐N‐acetylglucosamine 2‐epimeraseFEBS Letters, 503
K. Yarema (2002)
A Metabolic Substrate-Based Approach to Engineering New Chemical Reactivity into Cellular Sialoglycoconjugates
Metabolic oligosaccharide engineering (MOE) is a maturing technology capable of modifying cell surface sugars in living cells and animals through the biosynthetic installation of non‐natural monosaccharides into the glycocalyx. A particularly robust area of investigation involves the incorporation of azide functional groups onto the cell surface, which can then be further derivatized using “click chemistry.” While considerable effort has gone into optimizing the reagents used for the azide ligation reactions, less optimization of the monosaccharide analogs used in the preceding metabolic incorporation steps has been done. This study fills this void by reporting novel butanoylated ManNAc analogs that are used by cells with greater efficiency and less cytotoxicity than the current “gold standard,” which are peracetylated compounds such as Ac4ManNAz. In particular, tributanoylated, N‐acetyl, N‐azido, and N‐levulinoyl ManNAc analogs with the high flux 1,3,4‐O‐hydroxyl pattern of butanoylation were compared with their counterparts having the pro‐apoptotic 3,4,6‐O‐butanoylation pattern. The results reveal that the ketone‐bearing N‐levulinoyl analog 3,4,6‐O‐Bu3ManNLev is highly apoptotic, and thus is a promising anti‐cancer drug candidate. By contrast, the azide‐bearing analog 1,3,4‐O‐Bu3ManNAz effectively labeled cellular sialoglycans at concentrations ∼3‐ to 5‐fold lower (e.g., at 12.5–25 µM) than Ac4ManNAz (50–150 µM) and exhibited no indications of apoptosis even at concentrations up to 400 µM. In summary, this work extends emerging structure activity relationships that predict the effects of short chain fatty acid modified monosaccharides on mammalian cells and also provides a tangible advance in efforts to make MOE a practical technology for the medical and biotechnology communities. Biotechnol. Bioeng. 2012; 109:992–1006. © 2011 Wiley Periodicals, Inc.
Biotechnology and Bioengineering – Wiley
Published: Apr 1, 2012
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