Literature DB >> 31804076

Synthesis and Characterization of an A6-A11 Methylene Thioacetal Human Insulin Analogue with Enhanced Stability.

Nan Zheng1, Prasoona Karra2, Michael A VandenBerg3, Jin Hwan Kim1, Matthew J Webber3, William L Holland2, Danny Hung-Chieh Chou1.   

Abstract

Insulin has been a life-saving drug for millions of people with diabetes. However, several challenges exist which limit therapeutic benefits and reduce patient convenience. One key challenge is the fibrillation propensity, which necessitates refrigeration for storage. To address this limitation, we chemically synthesized and evaluated a methylene thioacetal human insulin analogue (SCS-Ins). The synthesized SCS-Ins showed enhanced serum stability and aggregation resistance while retaining bioactivity compared with native insulin.

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Year:  2019        PMID： 31804076      PMCID： PMC7217704          DOI： 10.1021/acs.jmedchem.9b01589

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  39 in total

1.  Chemical stability of insulin. 2. Formation of higher molecular weight transformation products during storage of pharmaceutical preparations.

Authors:  J Brange; S Havelund; P Hougaard
Journal:  Pharm Res       Date:  1992-06       Impact factor: 4.200

2.  Design of an active ultrastable single-chain insulin analog: synthesis, structure, and therapeutic implications.

Authors:  Qing-xin Hua; Satoe H Nakagawa; Wenhua Jia; Kun Huang; Nelson B Phillips; Shi-quan Hu; Michael A Weiss
Journal:  J Biol Chem       Date:  2008-03-10       Impact factor: 5.157

3.  Concise synthetic routes to human insulin.

Authors:  Fa Liu; Ethan Y Luo; David B Flora; John P Mayer
Journal:  Org Lett       Date:  2013-02-07       Impact factor: 6.005

Review 4.  Pursuit of a perfect insulin.

Authors:  Alexander N Zaykov; John P Mayer; Richard D DiMarchi
Journal:  Nat Rev Drug Discov       Date:  2016-03-18       Impact factor: 84.694

5.  Substitution of an Internal Disulfide Bridge with a Diselenide Enhances both Foldability and Stability of Human Insulin.

Authors:  Orit Weil-Ktorza; Nischay Rege; Shifra Lansky; Deborah E Shalev; Gil Shoham; Michael A Weiss; Norman Metanis
Journal:  Chemistry       Date:  2019-05-16       Impact factor: 5.236

6.  Supramolecular PEGylation of biopharmaceuticals.

Authors:  Matthew J Webber; Eric A Appel; Brittany Vinciguerra; Abel B Cortinas; Lavanya S Thapa; Siddharth Jhunjhunwala; Lyle Isaacs; Robert Langer; Daniel G Anderson
Journal:  Proc Natl Acad Sci U S A       Date:  2016-11-28       Impact factor: 11.205

7.  Insulin analog with additional disulfide bond has increased stability and preserved activity.

Authors:  Tine N Vinther; Mathias Norrman; Ulla Ribel; Kasper Huus; Morten Schlein; Dorte B Steensgaard; Thomas Å Pedersen; Ingrid Pettersson; Svend Ludvigsen; Thomas Kjeldsen; Knud J Jensen; František Hubálek
Journal:  Protein Sci       Date:  2013-01-17       Impact factor: 6.725

8.  Chemical synthesis of Shiga toxin subunit B using a next-generation traceless "helping hand" solubilizing tag.

Authors:  James M Fulcher; Mark E Petersen; Riley J Giesler; Zachary S Cruz; Debra M Eckert; J Nicholas Francis; Eric M Kawamoto; Michael T Jacobsen; Michael S Kay
Journal:  Org Biomol Chem       Date:  2019-12-03       Impact factor: 3.876

9.  "O-acyl isopeptide method" for peptide synthesis: synthesis of forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH.

Authors:  Taku Yoshiya; Atsuhiko Taniguchi; Youhei Sohma; Fukue Fukao; Setsuko Nakamura; Naoko Abe; Nui Ito; Mariusz Skwarczynski; Tooru Kimura; Yoshio Hayashi; Yoshiaki Kiso
Journal:  Org Biomol Chem       Date:  2007-04-25       Impact factor: 3.876

10.  Mechanism of insulin fibrillation: the structure of insulin under amyloidogenic conditions resembles a protein-folding intermediate.

Authors:  Qing-xin Hua; Michael A Weiss
Journal:  J Biol Chem       Date:  2004-02-26       Impact factor: 5.157
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  4 in total

1.  Improved Handling of Peptide Segments Using Side Chain-Based "Helping Hand" Solubilizing Tools.

Authors:  Michael T Jacobsen; Paul Spaltenstein; Riley J Giesler; Danny Hung-Chieh Chou; Michael S Kay
Journal:  Methods Mol Biol       Date:  2022

2.  A glutamic acid-based traceless linker to address challenging chemical protein syntheses.

Authors:  Riley J Giesler; Paul Spaltenstein; Michael T Jacobsen; Weiliang Xu; Mercedes Maqueda; Michael S Kay
Journal:  Org Biomol Chem       Date:  2021-10-20       Impact factor: 3.890

3.  Discovery of Methylene Thioacetal-Incorporated α-RgIA Analogues as Potent and Stable Antagonists of the Human α9α10 Nicotinic Acetylcholine Receptor for the Treatment of Neuropathic Pain.

Authors:  Nan Zheng; Sean B Christensen; Cheryl Dowell; Landa Purushottam; Jack J Skalicky; J Michael McIntosh; Danny Hung-Chieh Chou
Journal:  J Med Chem       Date:  2021-06-23       Impact factor: 7.446

4.  Facile synthesis of insulin fusion derivatives through sortase A ligation.

Authors:  Maria M Disotuar; Jake A Smith; Jinze Li; Steve Alam; Nai-Pin Lin; Danny Hung-Chieh Chou
Journal:  Acta Pharm Sin B       Date:  2020-11-21       Impact factor: 11.413
  4 in total

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