Insulin Prodrugs with Programmed Chemical Release of an Intramolecular Cross-Link

Brandenburg Dietrich (1972) Preparation of NαA1, NεB29-Adipoylinsulin, an Intramolecularly Crosslinked Derivative of Beef Insulin. Hoppe-Seyler’s Zeitschrift für physiologische Chemie 353:869–73

Article  CAS  PubMed  Google Scholar 

Brandenburg, Dietrich, Walter Puls (1975) Insulin derivatives crosslinked by a dicarboxylic acid moiety. US Patent 3907763A

Brunel FM, Mayer JP, Gelfanov VM, Zaykov AN, Finan B, Perez-Tilve D, DiMarchi RD (2019) A disulfide scan of insulin by [3 + 1] methodology exhibits site-specific influence on bioactivity. ACS Chem Biol 14:1829–1835

Article  CAS  PubMed  Google Scholar 

Chamberlain MJ, Stimmler L (1967) The Renal Handling of Insulin. J Clin Investig 46:911–919

Article  CAS  PubMed  PubMed Central  Google Scholar 

De A, DiMarchi RD (2008) Investigation of the feasibily of an amide-based prodrug under physiological conditions. Int J Pept Res Ther 14:255–262

Article  CAS  Google Scholar 

Derewenda U, Derewenda Z, Dodson EJ, Dodson GG, Bing X, Markussen J (1991) X-ray analysis of the single chain B29–A1 peptide-linked insulin molecule: A completely inactive analogue. J Mol Biol 220:425–433

Article  CAS  PubMed  Google Scholar 

Dietrich B, Wollmer A (1973) The effect of a non-peptide interchain crosslink on the reoxidation of reduced insulin. Hoppe-Seylers Zeitschrift für Physiologische Chemie 354:613–27

Article  Google Scholar 

DiMarchi, Richard D, Binbin Kou (2015) Amide based glucagon and superfamily peptide prodrugs. US Patent 8969288B2

DiMarchi, Richard D, Binbin Kou, Shujiang Cheng (2014) Amide based insulin prodrugs. US Patent 8697632B2

Duckworth WC (1988) Insulin degradation: mechanisms, products, and significance. Endocr Rev 9:319–345

Article  CAS  PubMed  Google Scholar 

Fischer PM (2003) Diketopiperazines in peptide and combinatorial chemistry. J Pept Sci 9:9–35

Article  CAS  PubMed  Google Scholar 

Freychet P, Brandenburg D, Wollmer A (1974) Receptor-binding assay of chemically modified insulins. Diabetologia 10:1–5

Article  CAS  PubMed  Google Scholar 

Glidden MD, Yang Y, Smith NA, Phillips NB, Carr K, Wickramasinghe NP, Ismail-Beigi F, Lawrence MC, Smith BJ, Weiss MA (2018) Solution structure of an ultra-stable single-chain insulin analog connects protein dynamics to a novel mechanism of receptor binding. J Biol Chem 293:69–88

Article  CAS  PubMed  Google Scholar 

Gomes P, Vale N, Moreira R (2007) Cyclization-activated prodrugs. Molecules (Basel, Switzerland) 12:2484–2506

Article  CAS  PubMed  Google Scholar 

Hansen, Ryan J, Gordon B Cutler Jr, Andrew Vick, Anja Koester, Shun Li, Angela M Siesky, and John M Beals. 2012. "LY2605541: leveraging hydrodynamic size to develop a novel basal insulin." In Diabetes, A228-A28. AMER DIABETES ASSOC 1701 N BEAUREGARD ST, ALEXANDRIA, VA 22311–1717 USA.

Hirsch IB, Juneja Rattan, John MB, Caryl JA, Wright EE Jr (2020) The evolution of insulin and how it informs therapy and treatment choices. Endocrine Reviews 41:733–55

Article  PubMed  PubMed Central  Google Scholar 

Hoeg-Jensen T (2021) Review: glucose-sensitive insulin. Molecular Metabolism 46:101107

Article  CAS  PubMed  Google Scholar 

Jonassen I, Hoeg-Jensen T, Havelund S, Ribel-Madsen U, Tagmose TM, Madsen P (2005) Novel insulin derivatives. WO Patent 2005012347A3

Jones RH, Dron DI, Ellis MJ, Sönksen PH, Brandenburg D (1976) Biological properties of chemically modified insulins. I. Biological activity of proinsulin and insulin modified at A1-glycine and B29-lysine. Diabetologia 12:601–608

Article  CAS  PubMed  Google Scholar 

Kjeldsen TB, Hubálek F, Hjørringgaard CU, Tagmose TM, Nishimura E, Stidsen CE, Porsgaard T, Fledelius C, Refsgaard HHF, Gram-Nielsen S, Naver H, Pridal L, Hoeg-Jensen T, Jeppesen CB, Manfè V, Ludvigsen S, Lautrup-Larsen I, Madsen P (2021) Molecular engineering of insulin icodec, the first acylated insulin analog for once-weekly administration in humans. J Med Chem 64:8942–8950

Article  CAS  PubMed  Google Scholar 

Kurtzhals P, Østergaard S, Nishimura E, Kjeldsen T (2023) Derivatization with fatty acids in peptide and protein drug discovery. Nat Rev Drug Discovery 22:59–80

Article  CAS  PubMed  Google Scholar 

Lin S-Y, Wang S-L (2012) Advances in simultaneous DSC–FTIR microspectroscopy for rapid solid-state chemical stability studies: Some dipeptide drugs as examples. Adv Drug Deliv Rev 64:461–478

Article  CAS  PubMed  Google Scholar 

Liu L (2018) Pharmacokinetics of monoclonal antibodies and Fc-fusion proteins. Protein Cell 9:15–32

Article  CAS  PubMed  Google Scholar 

Martins JP, Kennedy PJ, Santos HA, Barrias C, Sarmento B (2016) A comprehensive review of the neonatal Fc receptor and its application in drug delivery. Pharmacol Ther 161:22–39

Article  CAS  PubMed  Google Scholar 

Menting JG, Yang Y, Chan SJ, Phillips NB, Smith BJ, Whittaker J, Wickramasinghe NP, Whittaker LJ, Pandyarajan V, Wan Z-l, Yadav SP, Carroll JM, Strokes N, Roberts CT, Ismail-Beigi F, Milewski W, Steiner DF, Chauhan VS, Ward CW, Weiss MA, Lawrence MC (2014) Protective hinge in insulin opens to enable its receptor engagement. Proc Natl Acad Sci 111:E3395–E3404

Article  CAS  PubMed  PubMed Central  Google Scholar 

Moyers JS, Hansen RJ, Day JW, Dickinson CD, Zhang C, Ruan X, Ding L, Brown RM, Baker HE, Beals JM (2022) Preclinical characterization of LY3209590, a novel weekly basal insulin Fc-fusion protein. J Pharmacol Exp Ther 382:346–355

Article  CAS  PubMed  Google Scholar 

Nakagawa SH, Tager HS (1989) Perturbation of insulin-receptor interactions by intramolecular hormone cross-linking. J Biol Chem 264:272–279

Article  CAS  PubMed  Google Scholar 

Oimomi M, Hatanaka H, Yoshimura Y, Yokono K, Baba S, Taketomi Y (2008) Carbamylation of insulin and its biological activity. Nephron 46:63–66

Article  Google Scholar 

Rosenstock J, Del Prato S (2022) Basal weekly insulins: the way of the future! Metabolism 126:154924

Article  CAS  PubMed  Google Scholar 

Rosenstock Julio, Juneja Rattan, Beals John M, Moyers Julie S, Ilag Liza, McCrimmon Rory J (2024) The basis for weekly insulin therapy: evolving evidence with insulin icodec and insulin Efsitora Alfa. Endo Rev. https://doi.org/10.1210/endrev/bnad037

Article  Google Scholar 

Santos C, Mateus ML, Paula A, dos Santos R, de Moreira E, Oliveira PG (2005) Cyclization-activated prodrugs Synthesis, reactivity and toxicity of dipeptide esters of paracetamol. Bioorg Med Chem Lett 15:1595–98

Article  CAS  PubMed  Google Scholar 

Sims EK, Carr ALJ, Oram RA, DiMeglio LA, Evans-Molina C (2021) 100 years of insulin: celebrating the past, present and future of diabetes therapy. Nat Med 27:1154–1164

Article  CAS  PubMed  PubMed Central  Google Scholar 

Sinha VP, Choi SL, Soon DK, Mace KF, Yeo KP, Lim ST, Howey DC (2014) Single-dose pharmacokinetics and glucodynamics of the novel, long-acting basal insulin LY2605541 in healthy subjects. J Clin Pharmacol 54:792–799

Article  CAS  PubMed  Google Scholar 

Smith NA, Menting JG, Weiss MA, Lawrence MC, Smith BJ (2022) Single-chain insulin analogs threaded by the insulin receptor αCT domain. Biophys J 121:4063–4077

Article  CAS  PubMed  PubMed Central  Google Scholar 

Sonne O (1988) Receptor-mediated endocytosis and degradation of insulin. Physiol Rev 68:1129–1196

Article  CAS  PubMed  Google Scholar 

Stark GR (1965) Reactions of cyanate with functional groups of proteins. III. Reactions with amino and carboxyl groups*. Biochemistry 4:1030–1036

Article  CAS 

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