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Journal articles on the topic 'Heterobifunctional'

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Author: Grafiati

Published: 4 June 2021

Last updated: 20 February 2023

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1

Kim, Yong Joo, Yukio Nagasaki, Kazunori Kataoka, Masao Kato, Masayuki Yokoyama, Teruo Okano, and Yasuhisa Sakurai. "Heterobifunctional poly(ethylene oxide)." Polymer Bulletin 33, no. 1 (June 1994): 1–6. http://dx.doi.org/10.1007/bf00313466.

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2

Ji, Tae H., and Inhae Ji. "Heterobifunctional photoaffinity labeling reagents." Pharmacology & Therapeutics 43, no. 3 (January 1989): 321–32. http://dx.doi.org/10.1016/0163-7258(89)90013-2.

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3

Shriver-Lake, Lisa C., Brian Donner, Rebecca Edelstein, Kristen Breslin, Suresh K. Bhatia, and Frances S. Ligler. "Antibody immobilization using heterobifunctional crosslinkers." Biosensors and Bioelectronics 12, no. 11 (December 1997): 1101–6. http://dx.doi.org/10.1016/s0956-5663(97)00070-5.

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4

Pairault, Noël, Hui Zhu, Dennis Jansen, Alexander Huber, Constantin G. Daniliuc, Stefan Grimme, and Jochen Niemeyer. "Heterobifunctional Rotaxanes for Asymmetric Catalysis." Angewandte Chemie 132, no. 13 (January 16, 2020): 5140–45. http://dx.doi.org/10.1002/ange.201913781.

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5

Pairault, Noël, Hui Zhu, Dennis Jansen, Alexander Huber, Constantin G. Daniliuc, Stefan Grimme, and Jochen Niemeyer. "Heterobifunctional Rotaxanes for Asymmetric Catalysis." Angewandte Chemie International Edition 59, no. 13 (March 23, 2020): 5102–7. http://dx.doi.org/10.1002/anie.201913781.

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6

Galdeano, Carles. "Expanding the Toolbox of E3 Ligases for Protein Degradation: Targeting the “Undruggable” Fbw7 E3 Ligase." Proceedings 22, no. 1 (November 12, 2019): 101. http://dx.doi.org/10.3390/proceedings2019022101.

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7

Steinebach, Christian, Hannes Kehm, Stefanie Lindner, Lan Phuong Vu, Simon Köpff, Álvaro López Mármol, Corinna Weiler, et al. "PROTAC-mediated crosstalk between E3 ligases." Chemical Communications 55, no. 12 (2019): 1821–24. http://dx.doi.org/10.1039/c8cc09541h.

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8

Bloemen, M., L. Vanpraet, M. Ceulemans, T. N. Parac-Vogt, K. Clays, N. Geukens, A. Gils, and T. Verbiest. "Selective protein purification by PEG–IDA-functionalized iron oxide nanoparticles." RSC Advances 5, no. 82 (2015): 66549–53. http://dx.doi.org/10.1039/c5ra11614g.

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9

Salerno, Gianluca, Simona Scarano, Marianna Mamusa, Marco Consumi, Stefano Giuntini, Antonella Macagnano, Stefano Nativi, et al. "A small heterobifunctional ligand provides stable and water dispersible core–shell CdSe/ZnS quantum dots (QDs)." Nanoscale 10, no. 42 (2018): 19720–32. http://dx.doi.org/10.1039/c8nr05566a.

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10

Dupuis, Gilles. "An asymmetrical disulfide-containing photoreactive heterobifunctional reagent designed to introduce radioactive labeling into biological receptors." Canadian Journal of Chemistry 65, no. 10 (October 1, 1987): 2450–53. http://dx.doi.org/10.1139/v87-409.

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The synthesis of succinimido 1-amino-(4-azidosalicyloyl)-3,4-dithio-5-carboxylate, a heterobifunctional photoaffinity labeling reagent, is described. The cross-linker possesses an asymmetrical disulfide bond, and a general method for generating a spacer arm bearing an asymmetrical or symmetrical disulfide bond is detailed. The heterobifunctional reagent has been obtained in a minimum of steps and intermediates have been characterized. It is further shown that the reagent can be trace-labeled with [125I]-iodine and it has been used to modify phytohemagglutinin, a model protein. Upon irradiation, polymeric phytohemagglutinin derivatives are produced, as evidenced by electrophoretic analysis.

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11

Sibley, Christopher D., and John S. Schneekloth. "Heterobifunctional molecules tackle targeted protein dephosphorylation." Trends in Pharmacological Sciences 43, no. 4 (April 2022): 263–65. http://dx.doi.org/10.1016/j.tips.2022.01.005.

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12

Ji, Inhae, Jaekyoon Shin, and Tae H. Ji. "Radioiodination of a photoactivatable heterobifunctional reagent." Analytical Biochemistry 151, no. 2 (December 1985): 348–49. http://dx.doi.org/10.1016/0003-2697(85)90186-1.

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13

Dai, Jingwen, Zili Li, Taisheng Wang, and Ruke Bai. "A highly stable and versatile heterobifunctional fluoroalkylation reagent for preparation of fluorinated organic compounds." Organic & Biomolecular Chemistry 14, no. 19 (2016): 4382–86. http://dx.doi.org/10.1039/c6ob00637j.

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14

António, João P. M., Hélio Faustino, and Pedro M. P. Gois. "A 2-formylphenylboronic acid (2FPBA)-maleimide crosslinker: a versatile platform for Cys-peptide–hydrazine conjugation and interplay." Organic & Biomolecular Chemistry 19, no. 28 (2021): 6221–26. http://dx.doi.org/10.1039/d1ob00917f.

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15

Ho, Hien The, Alexandre Bénard, Gwenaël Forcher, Maël Le Bohec, Véronique Montembault, Sagrario Pascual, and Laurent Fontaine. "Azlactone-based heterobifunctional linkers with orthogonal clickable groups: efficient tools for bioconjugation with complete atom economy." Organic & Biomolecular Chemistry 16, no. 39 (2018): 7124–28. http://dx.doi.org/10.1039/c8ob01807c.

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16

Yang, Yifei, Zhenwei Wu, Pan Chen, Peiyuan Zheng, Huibin Zhang, and Jinpei Zhou. "Proteolysis-targeting chimeras mediate the degradation of bromodomain and extra-terminal domain proteins." Future Medicinal Chemistry 12, no. 18 (September 2020): 1669–83. http://dx.doi.org/10.4155/fmc-2017-0264.

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Bromodomain and extra-terminal domain (BET) protein family plays an important role in regulating gene transcription preferentially at super-enhancer regions and has been involved with several types of cancers as a candidate. Up to now, there are 16 pan-BET inhibitors in clinical trials, however, most of them have undesirable off-target and side-effects. The proteolysis-targeting chimeras technology through a heterobifunctional molecule to link the target protein and E3 ubiquitin ligase, causes the target’s ubiquitination and subsequent degradation. By using this technology, the heterobifunctional small-molecule BET degraders can induce BET protein degradation. In this review, we discuss the advances in the drug discovery and development of BET-targeting proteolysis-targeting chimeras.

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17

Maurizi, Lionel, Vanessa Bellat, Mathieu Moreau, Emmanuel De Maistre, Julien Boudon, Laure Dumont, Franck Denat, David Vandroux, and Nadine Millot. "Titanate nanoribbon-based nanobiohybrid for potential applications in regenerative medicine." RSC Advances 12, no. 41 (2022): 26875–81. http://dx.doi.org/10.1039/d2ra04753e.

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Titanate nanoribbons functionalized by heterobifunctional polymer and type I collagen for cellular adhesion and proliferation. This new nanobiohybrid affected neither cytotoxicity nor platelet aggregation ability.

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18

Pahattuge, Thilanga N., J. Matt Jackson, Rane Digamber, Harshani Wijerathne, Virginia Brown, Malgorzata A. Witek, Chamani Perera, Richard S. Givens, Blake R. Peterson, and Steven A. Soper. "Visible photorelease of liquid biopsy markers following microfluidic affinity-enrichment." Chemical Communications 56, no. 29 (2020): 4098–101. http://dx.doi.org/10.1039/c9cc09598e.

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19

Goodwin, Andrew P., Stephanie S. Lam, and Jean M. J. Fréchet. "Rapid, Efficient Synthesis of Heterobifunctional Biodegradable Dendrimers." Journal of the American Chemical Society 129, no. 22 (June 2007): 6994–95. http://dx.doi.org/10.1021/ja071530z.

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20

Lala, Anil K., H. F. Batliwala, and R. M. Mogre. "A new radioactive diazofluorene based heterobifunctional reagent." Journal of Biosciences 14, no. 2 (June 1989): 127–32. http://dx.doi.org/10.1007/bf02703164.

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21

Agarwal, Deepali, Kushal Sen, and M. L. Gulrajani. "Application of heterobifunctional reactive dyes on silk." Journal of the Society of Dyers and Colourists 112, no. 1 (October 22, 2008): 10–16. http://dx.doi.org/10.1111/j.1478-4408.1996.tb01748.x.

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22

Tomczyk, T., J. M. Arencibia, M. Milewicz, D. Trębicka, J. Skalska, K. Poniatowska, J. Adamczyk, et al. "Development of selective MCL-1 heterobifunctional degraders." European Journal of Cancer 174 (October 2022): S104. http://dx.doi.org/10.1016/s0959-8049(22)01076-0.

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23

Li, Jane, Curtis F. Crasto, James S. Weinberg, Mansoor Amiji, Dinesh Shenoy, Srinivas Sridhar, Glenn J. Bubley, and Graham B. Jones. "An approach to heterobifunctional poly(ethyleneglycol) bioconjugates." Bioorganic & Medicinal Chemistry Letters 15, no. 24 (December 2005): 5558–61. http://dx.doi.org/10.1016/j.bmcl.2005.08.108.

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24

Antonovič, Leposava, Petr Hodek, Stanislav Smrček, Petr Novák, Mirek Šulc, and Henry W. Strobel. "Heterobifunctional Photoaffinity Probes for Cytochrome P450 2B." Archives of Biochemistry and Biophysics 370, no. 2 (October 1999): 208–15. http://dx.doi.org/10.1006/abbi.1999.1408.

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25

Brownsey, Duncan K., Ben C. Rowley, Evgueni Gorobets, Benjamin S. Gelfand, and Darren J. Derksen. "Rapid synthesis of pomalidomide-conjugates for the development of protein degrader libraries." Chemical Science 12, no. 12 (2021): 4519–25. http://dx.doi.org/10.1039/d0sc05442a.

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Current methods for the preparation of heterobifunctional pomalidomide-conjugates rely on methods that are often low yielding and produce intractable byproducts. Herein we describe our strategy for the succinct preparation of pomalidomide-linkers.

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26

Ma, He-Ming, Yun Liu, Ying-Xuan Liu, Jin-Jun Qiu, and Cheng-Mei Liu. "Vinyl benzoxazine: a novel heterobifunctional monomer that can undergo both free radical polymerization and cationic ring-opening polymerization." RSC Advances 5, no. 124 (2015): 102441–47. http://dx.doi.org/10.1039/c5ra18058a.

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A novel heterobifunctional monomer (6-ethenyl-3-phenyl-3,4-dihydro-2H-1,3-benzoxazine (VBOZO)) containing both a vinyl group and benzoxazine group was successfully prepared and the homo- and copolymerization reactions of this monomer were studied.

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27

Schembri, Mark A., and Per Klemm. "Heterobinary Adhesins Based on theEscherichia coli FimH Fimbrial Protein." Applied and Environmental Microbiology 64, no. 5 (May 1, 1998): 1628–33. http://dx.doi.org/10.1128/aem.64.5.1628-1633.1998.

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ABSTRACT The FimH adhesin of Escherichia coli type 1 fimbriae confers the ability to bind to d-mannosides by virtue of a receptor-binding domain located in its N-terminal region. This protein was engineered into a heterobifunctional adhesin by introducing a secondary binding site in the C-terminal region. The insertion of histidine clusters into this site resulted in coordination of various metal ions by recombinant cells expressing chimeric FimH proteins. In addition, libraries consisting of random peptide sequences inserted into the FimH display system and screened by a “panning” technique were used to identify specific sequences conferring the ability to adhere to Ni2+ and Cu2+. Recombinant cells expressing heterobifunctional FimH adhesins could adhere simultaneously to both metals and saccharides. Finally, combining the metal-binding modifications with alterations in the natural receptor-binding region demonstrated the ability to independently modulate the binding of FimH to two ligands simultaneously.

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28

Heitel, Pascal. "Emerging TACnology: Heterobifunctional Small Molecule Inducers of Targeted Posttranslational Protein Modifications." Molecules 28, no. 2 (January 10, 2023): 690. http://dx.doi.org/10.3390/molecules28020690.

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Posttranslational modifications (PTMs) play an important role in cell signaling and they are often deregulated in disease. This review addresses recent advances in the development of heterobifunctional small molecules that enable targeting or hijacking PTMs. This emerging field is spearheaded by proteolysis-targeting chimeras (PROTACs), that induce ubiquitination of their targets and, thus, tag them for degradation by the proteasome. Within the last decade, several improvements have been made to enhance spatiotemporal control of PROTAC-induced degradation as well as cell permeability. Inspired by the success story of PROTACs, additional concepts based on chimeric small molecules have emerged such as phosphatase-recruiting chimeras (PhoRCs). Herein, an overview of strategies causing (de-)phosphorylation, deubiquitination as well as acetylation is provided, and the opportunities and challenges of heterobifunctional molecules for drug discovery are highlighted. Although significant progress has been achieved, a plethora of PTMs have not yet been covered and PTM-inducing chimeras will be helpful tools for chemical biology and could even find application in pharmacotherapy.

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29

Lu, Changhai, and Wen Zhong. "Synthesis of Propargyl-Terminated Heterobifunctional Poly(ethylene glycol)." Polymers 2, no. 4 (October 13, 2010): 407–17. http://dx.doi.org/10.3390/polym2040407.

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30

Sabnis, Ram W. "Heterobifunctional Compounds as BRAF Degraders for Treating Cancer." ACS Medicinal Chemistry Letters 13, no. 3 (February 7, 2022): 332–33. http://dx.doi.org/10.1021/acsmedchemlett.2c00039.

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31

Wang, Wesley W., Li-Yun Chen, Jacob M. Wozniak, Appaso M. Jadhav, Hayden Anderson, Taylor E. Malone, and Christopher G. Parker. "Targeted Protein Acetylation in Cells Using Heterobifunctional Molecules." Journal of the American Chemical Society 143, no. 40 (September 30, 2021): 16700–16708. http://dx.doi.org/10.1021/jacs.1c07850.

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32

Cavell, Ronald G., Robert W. Reed, Kattesh V. Katti, Maravanji S. Balakrishna, Paul W. Collins, Vivian Mozol, and Ingrid Bartz. "Heterobifunctional Phosphorus-Nitrogen Compounds: Iminophosphoranophosphines and Their Complexes." Phosphorus, Sulfur, and Silicon and the Related Elements 76, no. 1-4 (March 1993): 9–12. http://dx.doi.org/10.1080/10426509308032345.

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33

Vadala, M. L., M. S. Thompson, M. A. Ashworth, Y. Lin, T. P. Vadala, R. Ragheb, and J. S. Riffle. "Heterobifunctional Poly(ethylene oxide) Oligomers Containing Carboxylic Acids." Biomacromolecules 9, no. 3 (March 2008): 1035–43. http://dx.doi.org/10.1021/bm701067d.

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34

Crocker, Peter J., Nobuyuki Imai, Krishnan Rajagopalan, Michael A. Boggess, Stefan Kwiatkowski, Lori D. Dwyer, Thomas C. Vanaman, and David S. Watt. "Heterobifunctional cross-linking agents incorporating perfluorinated aryl azides." Bioconjugate Chemistry 1, no. 6 (November 1990): 419–24. http://dx.doi.org/10.1021/bc00006a008.

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35

Reddy, Rajarathnam E., Yon-Yih Chen, Donald D. Johnson, Gangamani S. Beligere, Sushil D. Rege, You Pan, and John K. Thottathil. "An Efficient Synthesis of a Heterobifunctional Coupling Agent." Bioconjugate Chemistry 16, no. 5 (September 2005): 1323–28. http://dx.doi.org/10.1021/bc040259x.

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36

Bieniarz, Christopher, Mazhar Husain, Grady Barnes, Carol A. King, and Christopher J. Welch. "Extended Length Heterobifunctional Coupling Agents for Protein Conjugations." Bioconjugate Chemistry 7, no. 1 (January 1996): 88–95. http://dx.doi.org/10.1021/bc950080+.

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37

Burkinshaw, S. M., and M. Paraskevas. "The dyeing of silk: Part 4 heterobifunctional dyes." Dyes and Pigments 88, no. 3 (March 2011): 396–402. http://dx.doi.org/10.1016/j.dyepig.2010.08.018.

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38

Fischer, Lutz, and Juri Rappsilber. "False discovery rate estimation and heterobifunctional cross-linkers." PLOS ONE 13, no. 5 (May 10, 2018): e0196672. http://dx.doi.org/10.1371/journal.pone.0196672.

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39

Sharma, Chiranjeev, Myeong A. Choi, Yoojin Song, and Young Ho Seo. "Rational Design and Synthesis of HSF1-PROTACs for Anticancer Drug Development." Molecules 27, no. 5 (March 2, 2022): 1655. http://dx.doi.org/10.3390/molecules27051655.

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PROTACs employ the proteosome-mediated proteolysis via E3 ligase and recruit the natural protein degradation machinery to selectively degrade the cancerous proteins. Herein, we have designed and synthesized heterobifunctional small molecules that consist of different linkers tethering KRIBB11, a HSF1 inhibitor, with pomalidomide, a commonly used E3 ligase ligand for anticancer drug development.

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40

Wigle, Tim J., Yue Ren, Jennifer R. Molina, Danielle J. Blackwell, Laurie B. Schenkel, Kerren K. Swinger, Kristy Kuplast‐Barr, et al. "Targeted Degradation of PARP14 Using a Heterobifunctional Small Molecule." ChemBioChem 22, no. 12 (May 4, 2021): 2107–10. http://dx.doi.org/10.1002/cbic.202100047.

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41

Guillaumet, G屍ald, Thierry Besson, Benoit Joseph, Pascale Moreau, Marie-Claude Viaud, and G屍ard Coudert. "Synthesis and Fluorescent Properties of New Heterobifunctional Fluorescent Probes." HETEROCYCLES 34, no. 2 (1992): 273. http://dx.doi.org/10.3987/com-91-5899.

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42

Singh, Yashveer, Nicolas Spinelli, Eric Defrancq, and Pascal Dumy. "A novel heterobifunctional linker for facile access to bioconjugates." Organic & Biomolecular Chemistry 4, no. 7 (2006): 1413. http://dx.doi.org/10.1039/b518151h.

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43

OHNISHI, MIKIO, HIROYUKI SUGIMOTO, HIDENORI YAMADA, TAIJI IMOTO, KIYOSHI ZAITSU, and YOSUKE OHKURA. "Heterobifunctional reagents for cross-linking of sugar with protein." CHEMICAL & PHARMACEUTICAL BULLETIN 33, no. 2 (1985): 674–78. http://dx.doi.org/10.1248/cpb.33.674.

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44

Imai, Nobuyuki, Tadashi Kometani, Peter J. Crocker, Jean B. Bowdan, Ayhan Demir, Lori D. Dwyer, Dennis M. Mann, Thomas C. Vanaman, and David S. Watt. "Photoaffinity heterobifunctional crosslinking reagents based on N-(azidobenzoyl)tyrosines." Bioconjugate Chemistry 1, no. 2 (March 1990): 138–43. http://dx.doi.org/10.1021/bc00002a008.

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45

Imai, Nobuyuki, Lori D. Dwyer, Tadashi Kometani, Tae Ji, Thomas C. Vanaman, and David S. Watt. "Photoaffinity heterobifunctional crosslinking reagents based on azide-substituted salicylates." Bioconjugate Chemistry 1, no. 2 (March 1990): 144–48. http://dx.doi.org/10.1021/bc00002a009.

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46

Heindel, Ned D., Huiru Zhao, Roger A. Egolf, Chien Hsing Chang, Keith J. Schray, Jacqueline G. Emrich, Joanne P. McLaughlin, and David V. Woo. "A novel heterobifunctional linker for formyl to thiol coupling." Bioconjugate Chemistry 2, no. 6 (November 1991): 427–30. http://dx.doi.org/10.1021/bc00012a008.

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47

Johnson, Gary M., James P. Albarella, and Christoph Petry. "Heterobifunctional Cross-Linkers Containing 4,9-Dioxa-1,12-dodecanediamine Spacers." Bioconjugate Chemistry 8, no. 3 (May 1997): 447–52. http://dx.doi.org/10.1021/bc970026o.

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48

Hypolite, Claire L., Terri L. McLernon, Derek N. Adams, Kenneth E. Chapman, Curtis B. Herbert, C. C. Huang, Mark D. Distefano, and Wei-Shou Hu. "Formation of Microscale Gradients of Protein Using Heterobifunctional Photolinkers." Bioconjugate Chemistry 8, no. 5 (September 1997): 658–63. http://dx.doi.org/10.1021/bc9701252.

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49

Johnson, Gary M., James P. Albarella, and Christoph Petry. "Heterobifunctional Cross-Linkers Containing 4,9-Dioxa-1,12-dodecanediamine Spacers." Bioconjugate Chemistry 9, no. 2 (March 1998): 304. http://dx.doi.org/10.1021/bc9800062.

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50

Bettinger, Thierry, Jean-Serge Remy, Patrick Erbacher, and Jean-Paul Behr. "Convenient Polymer-Supported Synthetic Route to Heterobifunctional Polyethylene Glycols." Bioconjugate Chemistry 9, no. 6 (November 1998): 842–46. http://dx.doi.org/10.1021/bc980039h.

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