Synthesis, Characterization and In Vivo Activity of Salmon Calcitonin Coconjugated With Lipid and Polyethylene Glycol

Cheng, Weiqiang; Lim, Lee Yong

doi:10.1002/jps.21524

Cited by 11 publications

(9 citation statements)

References 36 publications

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“…This strategy can insert more hydrophobic amino acids within the peptide backbone [95]. Additionally, improved protection against liver enzyme degradation was demonstrated for a lipidated peptide without loss in biological activity [96] or by reversible/non-reversible conjugation with lipophilic structures that can enhance the transcellular uptake [97,98].…”

Section: Pegylation Strategiesmentioning

confidence: 99%

Current status of selected oral peptide technologies in advanced preclinical development and in clinical trials

Aguirre

Teijeiro‐Osorio

Rosa

et al. 2016

Advanced Drug Delivery Reviews

260

151

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Publication informationAdvanced Drug Delivery Reviews, 106 (Part B):Publisher Elsevier Item record/more information http://hdl.handle.net/10197/7801 Publisher's statementThis is the author's version of a work that was accepted for publication in Advanced Drug Delivery Reviews. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Advanced Drug Delivery Reviews (106, Part B, (2016)

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Section: Pegylation Strategiesmentioning

confidence: 99%

Current status of selected oral peptide technologies in advanced preclinical development and in clinical trials

Aguirre

Teijeiro‐Osorio

Rosa

et al. 2016

Advanced Drug Delivery Reviews

260

151

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“…2PEG‐Mal‐sCT (Figure 2b) was synthesized as previously reported [23] . Mal‐sCT and mPEG‐Suc (MW 5000) at molar ratios of 1 : 3.6 were dissolved in 200 μl of DMF, and 0.6 of TEA was added with stirring for 20 min.…”

Section: Methodsmentioning

confidence: 99%

“…The reaction mix was added to 1 ml of saturated ammonium acetate buffer. 2PEG‐Mal‐sCT was freeze‐dried after purification using a semi‐preparative HPLC C‐18 column and identified to have MW of 15 kDa [23] . Purified 2PEG‐Mal‐sCT was similar to Mal‐PL‐sCT in being a transparent gel‐like semi‐solid.…”

Section: Methodsmentioning

confidence: 99%

“…Mal‐sCT, consisting of sCT conjugated with palmitic acid via non‐reversible thioether bonds at cysteine 1 and cysteine 7, was shown to produce comparable hypocalcaemic activity to sCT in vivo [20] . Further studies led to the development of 2PEG‐Mal‐sCT, which comprises Mal‐sCT co‐conjugated with PEG 5000 at Lys11 and Lys18 [23] . 2PEG‐Mal‐sCT showed significant stability against intestinal enzymes, but the multiple conjugation sites in the peptide also resulted in a complete loss of hypocalcaemic activity, in line with the high risk of compromised peptide bioactivity associated with multiple conjugation sites observed in other studies [24–26] .…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis, characterization and in-vivo activity of a novel salmon calcitonin conjugate containing a novel PEG-lipid moiety

Cheng

Lim

2010

Journal of Pharmacy and Pharmacology

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“…Among all the manufactured analogs, the change in the thermodynamic properties, as well as secondary structure, proves to enhance biological potency when compared to the calcitonin human hormone. Additionally, further research has been performed to produce analogs of salmon calcitonin alone (Cheng and Lim, 2009). One example, Mal-sCT, demonstrates comparable hypocalcemic activity to native sCT in vivo .…”

Section: Calcitonin Family Ligandsmentioning

confidence: 99%

Chemical modification of Class II G protein-coupled receptor ligands: Frontiers in the development of peptide analogs as neuroendocrine pharmacological therapies

Chapter

White

DeRidder

et al. 2010

Pharmacology & Therapeutics

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Recent research and clinical data have begun to demonstrate the huge potential therapeutic importance of ligands that modulate the activity of the secretin-like, Class II, G-protein coupled receptors (GPCRs). Ligands that can modulate the activity of these Class II GPCRs may have important clinical roles in the treatment of a wide variety of conditions such as osteoporosis, diabetes, amyotrophic lateral sclerosis and autism spectrum disorders. While these receptors present important new therapeutic targets, the large glycoprotein nature of their cognate ligands poses many problems with respect to therapeutic peptidergic drug design. These native peptides often exhibit poor bioavailability, metabolic instability, poor receptor selectivity and resultant low potencies in vivo. Recently, increased attention has been paid to the structural modification of these peptides to enhance their therapeutic efficacy. Successful modification strategies have included D-amino acid substitutions, selective truncation, and fatty acid acylation of the peptide. Through these and other processes, these novel peptide ligand analogs can demonstrate enhanced receptor subtype selectivity, directed signal transduction pathway activation, resistance to proteolytic degradation, and improved systemic bioavailability. In the future, it is likely, through additional modification strategies such as addition of circulation-stabilizing transferrin moieties, that the therapeutic pharmacopeia of drugs targeted towards Class II secretin-like receptors may rival that of the Class I rhodopsin-like receptors that currently provide the majority of clinically used GPCR-based therapeutics. Currently, Class IIbased drugs include synthesized analogues of vasoactive intestinal peptide for type 2 diabetes or parathyroid hormone for osteoporosis.

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Synthesis, Characterization and In Vivo Activity of Salmon Calcitonin Coconjugated With Lipid and Polyethylene Glycol

Cited by 11 publications

References 36 publications

Current status of selected oral peptide technologies in advanced preclinical development and in clinical trials

Current status of selected oral peptide technologies in advanced preclinical development and in clinical trials

Design, synthesis, characterization and in-vivo activity of a novel salmon calcitonin conjugate containing a novel PEG-lipid moiety

Chemical modification of Class II G protein-coupled receptor ligands: Frontiers in the development of peptide analogs as neuroendocrine pharmacological therapies

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