Advances in the stability challenges of bioactive peptides and improvement strategies

Ahmed, 2022, Role of structural properties of bioactive peptides in their stability during simulated gastrointestinal digestion: a systematic review, Trends Food Sci. Technol., 120, 265, 10.1016/j.tifs.2022.01.008 Aiedeh, 1997, Chitosan microcapsules as controlled release systems for insulin, J. Microencapsul., 14, 567, 10.3109/02652049709006810 Arbour, 2020, Recent advances in the synthesis of C-terminally modified peptides, Org. Biomol. Chem., 18, 7253, 10.1039/D0OB01417F Asaduzzaman, 2015, Recovery of functional materials with thermally stable antioxidative properties in squid muscle hydrolyzates by subcritical water, J. Food Sci. Technol.Mysore, 52, 793, 10.1007/s13197-013-1107-7 Banting, 1962, Pancreatic extracts in the treatment of diabetes mellitus: preliminary report, Can. Med. Assoc. J., 87, 1062 Baptista, 2020, Use of static and dynamic in vitro models to simulate Prato cheese gastrointestinal digestion: effect of Lactobacillus helveticus LH-B02 addition on peptides bioaccessibility, LWT--Food Sci. Technol., 134, 11, 10.1016/j.lwt.2020.110229 Bianchi, 2013, A PEGylated analog of the gut hormone oxyntomodulin with long-lasting antihyperglycemic, insulinotropic and anorexigenic activity, Bioorg. Med. Chem., 21, 7064, 10.1016/j.bmc.2013.09.016 Bork, 2007, Treatment of acute edema attacks in hereditary angioedema with a bradykinin receptor-2 antagonist (Icatibant), J. Allergy Clin. Immunol., 119, 1497, 10.1016/j.jaci.2007.02.012 Bottger, 2017, Differential stability of therapeutic peptides with different proteolytic cleavage sites in blood, plasma and serum, PLoS One, 12, 15, 10.1371/journal.pone.0178943 Brodkorb, 2019, INFOGEST static in vitro simulation of gastrointestinal food digestion, Nat. Protoc., 14, 991, 10.1038/s41596-018-0119-1 Cardle, 2021, Optimized serum stability and specificity of an αvβ6 integrin-binding peptide for tumor targeting, J. Biol. Chem., 296, 10.1016/j.jbc.2021.100657 Cavaco, 2021, The challenge of peptide proteolytic stability studies: scarce data, difficult readability, and the need for harmonization, Angew. Chem., Int. Ed., 60, 1686, 10.1002/anie.202006372 Chen, 2012, The effect of molecular weights on the survivability of casein-derived antioxidant peptides after the simulated gastrointestinal digestion, Innovat. Food Sci. Emerg. Technol., 16, 341, 10.1016/j.ifset.2012.07.009 Chia, 2021, A review on the metabolism of 25 peptide drugs, Int. J. Pept. Res. Therapeut., 27, 1397, 10.1007/s10989-021-10177-0 Cian, 2019, Bioactive Phaseolus lunatus peptides release from maltodextrin/gum Arabic microcapsules obtained by spray drying after simulated gastrointestinal digestion, Int. J. Food Sci. Technol., 54, 2002, 10.1111/ijfs.14031 Cui, 2015, Liposomes containing cholesterol analogues of botanical origin as drug delivery systems to enhance the oral absorption of insulin, Int. J. Pharm., 489, 277, 10.1016/j.ijpharm.2015.05.006 D'Addio, 2016, New and evolving techniques for the characterization of peptide therapeutics, J. Pharmaceut. Sci., 105, 2989, 10.1016/j.xphs.2016.06.011 De Rosa, 2021, Probing the helical stability in a VEGF-mimetic peptide, Bioorg. Chem., 116, 8, 10.1016/j.bioorg.2021.105379 Di, 2015, Strategic approaches to optimizing peptide ADME properties, AAPS J., 17, 134, 10.1208/s12248-014-9687-3 Diana, 2010, Structural analysis of a helical peptide unfolding pathway, Chem.--Eur. J., 16, 5400, 10.1002/chem.200903428 Ding, 2014, Transport of egg white ACE-inhibitory peptide, Gln-ile-Gly-Leu-phe, in human intestinal caco-2 cell monolayers with cytoprotective effect, J. Agric. Food Chem., 62, 3177, 10.1021/jf405639w Elkinton, 1949, Effects of pituitary adrenocorticotropic hormone therapy, J. Am. Med. Assoc., 141, 1273, 10.1001/jama.1949.02910180001001 Enciso, 2015, Influence of pH and sequence in peptide aggregation via molecular simulation, J. Chem. Phys., 143, 2934, 10.1063/1.4935707 Fan, 2019, Identification and availability of peptides from lactoferrin in the gastrointestinal tract of mice, Food Funct., 10, 879, 10.1039/C8FO01998C Frokjaer, 2005, Protein drug stability: a formulation challenge, Nat. Rev. Drug Discov., 4, 298, 10.1038/nrd1695 Gallego, 2016, Transepithelial transport of dry-cured ham peptides with ACE inhibitory activity through a Caco-2 cell monolayer, J. Funct.Foods, 21, 388, 10.1016/j.jff.2015.11.046 Gao, 2018, The modification and design of antimicrobial peptide, Curr. Pharmaceut. Des., 24, 904, 10.2174/1381612824666180213130318 Gasteiger, 2005 Guruprasad, 1990, Correlation between stability of a protein and its dipeptide composition: a novel approach for predicting in vivo stability of a protein from its primary sequence, Protein Eng., 4, 155, 10.1093/protein/4.2.155 Hall, 2014, Biotransformation and in vivo stability of protein biotherapeutics: impact on candidate selection and pharmacokinetic profiling, Drug Metabol. Dispos.: The Biological Fate of Chemicals, 42, 1873, 10.1124/dmd.114.058347 Hao, 2020, Angiotensin I-converting enzyme (ACE) inhibitory and antioxidant activity of umami peptides after in vitro gastrointestinal digestion, J. Agric. Food Chem., 68, 8232, 10.1021/acs.jafc.0c02797 Hartmann, 2007, Food-derived peptides with biological activity: from research to food applications, Curr. Opin. Biotechnol., 18, 163, 10.1016/j.copbio.2007.01.013 Hung, 2017, Structure-activity relationship study of the tumour-targeting peptide A20FMDV2 via modification of Lys16, Leu13, and N- and/or C-terminal functionality, Eur. J. Med. Chem., 136, 154, 10.1016/j.ejmech.2017.05.008 Iwaniak, 2019, Elucidation of the role of in silico methodologies in approaches to studying bioactive peptides derived from foods, J. Funct.Foods, 61, 14, 10.1016/j.jff.2019.103486 Jia, 2017, D-amino acid substitution enhances the stability of antimicrobial peptide polybia-CP, Acta Biochim. Biophys. Sin., 49, 916, 10.1093/abbs/gmx091 Jin, 2016, Peptide profiling and the bioactivity character of yogurt in the simulated gastrointestinal digestion, J. Proteonomics, 141, 24, 10.1016/j.jprot.2016.04.010 Katsila, 2012, Peptide and protein drugs: the study of their metabolism and catabolism by mass spectrometry, Mass Spectrom. Rev., 31, 110, 10.1002/mas.20340 Klein, 2018, Proteolytic cleavage-mechanisms, function, and "omic" approaches for a near-ubiquitous posttranslational modification, Chem. Rev., 118, 261, 10.1021/acs.chemrev.7b00120 Lai, 2021, Recent advances in proteolytic stability for peptide, protein, and antibody drug discovery, Expet Opin. Drug Discov., 16, 1467, 10.1080/17460441.2021.1942837 Lau, 2018, Therapeutic peptides: historical perspectives, current development trends, and future directions, Bioorg. Med. Chem., 26, 2700, 10.1016/j.bmc.2017.06.052 Leach, 2015, Pharmacokinetics of single and repeat doses of icatibant, Clin. Pharmacol.Drug Dev., 4, 105, 10.1002/cpdd.138 Lee, 2019, A comprehensive review on current advances in peptide drug development and design, Int. J. Mol. Sci., 20, 10.3390/ijms20102383 Li, 2018, A novel natural influenza A H1N1 virus neuraminidase inhibitory peptide derived from cod skin hydrolysates and its antiviral mechanism, Mar. Drugs, 16, 10.3390/md16100377 Li, 2021, N-terminal acetylation of antimicrobial peptide L163 improves its stability against protease degradation, J. Pept. Sci., 27, 10.1002/psc.3337 Liu, 2020, N-Terminal myristoylation enhanced the antimicrobial activity of antimicrobial peptide PMAP-36PW, Front. Cell. Infect. Microbiol., 10, 10.3389/fcimb.2020.00450 Lopez-Morales, 2019, Determination of peptide profile consistency and safety of collagen hydrolysates as quality attributes, J. Food Sci., 84, 430, 10.1111/1750-3841.14466 Lopez-Sanchez, 2016, Effects of heat and pH treatments and in vitro digestion on the biological activity of protein hydrolysates of Amaranthus hypochondriacus L. grain, J. Food Sci. Technol.Mysore, 53, 4298, 10.1007/s13197-016-2428-0 Low, 2020, A proopiomelanocortin-derived peptide sequence enhances plasma stability of peptide drugs, FEBS (Fed. Eur. Biochem. Soc.) Lett., 594, 2840, 10.1002/1873-3468.13855 Lu, 2020, D- and unnatural amino acid substituted antimicrobial peptides with improved proteolytic resistance and their proteolytic degradation characteristics, Front. Microbiol., 11, 10.3389/fmicb.2020.563030 Maack, 1979, Renal filtration, transport, and metabolism of low-molecular-weight proteins: a review, Kidney Int., 16, 251, 10.1038/ki.1979.128 Mage, 2021, Fourier-transform infrared (FTIR) fingerprinting for quality assessment of protein hydrolysates, LWT--Food Sci. Technol., 152, 10.1016/j.lwt.2021.112339 Malmsten, 2006, Soft drug delivery systems, Soft Matter, 2, 760, 10.1039/b608348j Mao, 2021, The metabolic stability of antimicrobial peptides Ik8 in plasma and liver S9, Applied Sciences-Basel, 11 Marseglia, 2019, Simulated gastrointestinal digestion of cocoa: detection of resistant peptides and in silico/in vitro prediction of their ace inhibitory activity, Nutrients, 11, 17, 10.3390/nu11050985 Matsuda, 2019, SurE is a trans-acting thioesterase cyclizing two distinct non-ribosomal peptides, Org. Biomol. Chem., 17, 1058, 10.1039/C8OB02867B Meibohm, 2012, Characterizing the impact of renal impairment on the clinical pharmacology of biologics, J. Clin. Pharmacol., 52, 54S, 10.1177/0091270011413894 Merrifield, 1965, Solid-phase peptide synthese, Endeavour, 24, 3, 10.1016/0160-9327(65)90090-6 Miguel, 2008, Transepithelial transport across Caco-2 cell monolayers of antihypertensive egg-derived peptides. PepT1-mediated flux of Tyr-Pro-lle, Mol. Nutr. Food Res., 52, 1507, 10.1002/mnfr.200700503 Minekus, 2014, A standardised static in vitro digestion method suitable for food - an international consensus, Food Funct., 5, 1113, 10.1039/C3FO60702J Minkiewicz, 2008, BIOPEP database and other programs for processing bioactive peptide sequences, J. AOAC Int., 91, 965, 10.1093/jaoac/91.4.965 Minkiewicz, 2019, BIOPEP-UWM database of bioactive peptides: current opportunities, Int. J. Mol. Sci., 20, 23, 10.3390/ijms20235978 Mirzaei, 2020, The stability of antioxidant and ACE-inhibitory peptides as influenced by peptide sequences, LWT--Food Sci. Technol., 130, 9, 10.1016/j.lwt.2020.109710 Mirzaei, 2020, The stability of antioxidant and ACE-inhibitory peptides as influenced by peptide sequences, LWT--Food Sci. Technol., 130, 10.1016/j.lwt.2020.109710 Mirzaei, 2021, Bioactive peptides from yeast: a comparative review on production methods, bioactivity, structure-function relationship, and stability, Trends Food Sci. Technol., 118, 297, 10.1016/j.tifs.2021.10.008 Mitragotri, 2014, Overcoming the challenges in administering biopharmaceuticals: formulation and delivery strategies, Nat. Rev. Drug Discov., 13, 655, 10.1038/nrd4363 Morikawa, 2005, alpha-helical polypeptide microcapsules formed by emulsion-templated self-assembly, Chem.--Eur. J., 11, 1574, 10.1002/chem.200400751 Muttenthaler, 2021, Trends in peptide drug discovery, Nat. Rev. Drug Discov., 20, 309, 10.1038/s41573-020-00135-8 Niu, 2014, Enhanced oral absorption of insulin-loaded liposomes containing bile salts: a mechanistic, Int. J. Pharm., 460, 119, 10.1016/j.ijpharm.2013.11.028 Nuijens, 2019, Natural occurring and engineered enzymes for peptide ligation and cyclization, Front. Chem., 7, 10.3389/fchem.2019.00829 Ohsawa, 2008, Producibility and digestibility of antihypertensive beta-casein tripeptides, Val-Pro-Pro and Ile-Pro-Pro, in the gastrointestinal tract: analyses using an in vitro model of mammalian gastrointestinal digestion, J. Agric. Food Chem., 56, 854, 10.1021/jf072671n Panchin, 2020, Drug discovery today: no molecules required, Bmj Evidence-Based Medicine, 25 Parmentier, 2011, Stability of liposomes containing bio-enhancers and tetraether lipids in simulated gastro-intestinal fluids, Int. J. Pharm., 405, 210, 10.1016/j.ijpharm.2010.12.005 Pernot, 2011, Stability of peptides and therapeutic success in cancer, Expet Opin. Drug Metabol. Toxicol., 7, 793, 10.1517/17425255.2011.574126 Picariello, 2010, Peptides surviving the simulated gastrointestinal digestion of milk proteins: biological and toxicological implications, J. Chromatogr., B: Anal. Technol. Biomed. Life Sci., 878, 295, 10.1016/j.jchromb.2009.11.033 Piekielna, 2013, Cyclization in opioid peptides, Curr. Drug Targets, 14, 798, 10.2174/1389450111314070008 Pollaro, 2010, Strategies to prolong the plasma residence time of peptide drugs, Medchemcomm, 1, 319, 10.1039/C0MD00111B Ramezanzade, 2021, Cross-linked chitosan-coated liposomes for encapsulation of fish-derived peptide, LWT--Food Sci. Technol., 150, 8, 10.1016/j.lwt.2021.112057 Salim, 2020, Dual-function peptides derived from egg white ovalbumin: bioinformatics identification with validation using in vitro assay, J. Funct.Foods, 64, 12 Savoie, 2005, In vitro determination of the release kinetics of peptides and free amino acids during the digestion of food proteins, J. AOAC Int., 88, 935, 10.1093/jaoac/88.3.935 Shen, 2001, Remineralization of enamel subsurface lesions by sugar-free chewing gum containing casein phosphopepticle-amorphous calcium phosphate, J. Dent. Res., 80, 2066, 10.1177/00220345010800120801 Singh, 2021, Bioactive peptides in the management of lifestyle-related diseases: current trends and future perspectives, Crit. Rev. Food Sci. Nutr., 10, 14 So, 2021, On-resin ugi reaction for C-terminally modified and head-to-tail cyclized antibacterial peptides, Org. Lett., 23, 8277, 10.1021/acs.orglett.1c03014 Sonesson, 2013, In vitro and in vivo human metabolism of degarelix, a gonadotropin-releasing hormone receptor blocker, Drug Metabol. Dispos., 41, 1339, 10.1124/dmd.113.051706 Tan, 2017, Myristic acid-modified thymopentin for enhanced plasma stability and immune-modulating activity, Int. Immunopharm., 47, 88, 10.1016/j.intimp.2017.03.025 Tao, 2017, Techniques for biological fingerprinting of traditional Chinese medicine, Trac. Trends Anal. Chem., 97, 272, 10.1016/j.trac.2017.09.008 Teng, 2012, Intestinal absorption and first-pass metabolism of polyphenol compounds in rat and their transport dynamics in caco-2 cells, PLoS One, 7, 9, 10.1371/journal.pone.0029647 Toplak, 2016, Peptiligase, an enzyme for efficient chemoenzymatic peptide synthesis and cyclization in water, Adv. Synth. Catal., 358, 2140, 10.1002/adsc.201600017 Tu, 2019, Identification and characterization of a novel casein anticoagulant peptide derived from in vivo digestion, Food Funct., 10, 2552, 10.1039/C8FO02546K Udenigwe, 2014, Bioinformatics approaches, prospects and challenges of food bioactive peptide research, Trends Food Sci. Technol., 36, 137, 10.1016/j.tifs.2014.02.004 Udenigwe, 2017, Food matrix interaction and bioavailability of bioactive peptides: two faces of the same coin?, J. Funct.Foods, 35, 9, 10.1016/j.jff.2017.05.029 Vazquez-Leyva, 2019, Identity profiling of complex mixtures of peptide products by structural and mass mobility orthogonal analysis, Anal. Chem., 91, 14392, 10.1021/acs.analchem.9b02873 Vermeirssen, 2004, A quantitative in silico analysis calculates the angiotensin I converting enzyme (ACE) inhibitory activity in pea and whey protein digests, Biochimie, 86, 231, 10.1016/j.biochi.2004.01.003 Vernen, 2019, Characterization of tachyplesin peptides and their cyclized analogues to improve antimicrobial and anticancer properties, Int. J. Mol. Sci., 20, 10.3390/ijms20174184 Vigneaud, 1953, The synthesis of an octapeptide with hormonal activity of oxytocin, J. Am. Chem. Soc., 75, 328, 10.1021/ja01115a553 Wang, 2017, Optimization of the extraction and stability of antioxidative peptides from mackerel (pneumatophorus japonicus) protein, BioMed Res. Int. Wang, 2019, Influence of peptide characteristics on their stability, intestinal transport, and in vitro bioavailability: a review, J. Food Biochem., 43, 6, 10.1111/jfbc.12571 Wang, 2021, The effect of structural modification of antimicrobial peptides on their antimicrobial activity, hemolytic activity, and plasma stability, J. Pept. Sci., 27, 13, 10.1002/psc.3306 Werner, 2016, Peptide backbone composition and protease susceptibility: impact of modification type, position, and tandem substitution, Chembiochem, 17 Wilkins, 1999, Protein identification and analysis tools in the ExPASy server, Methods Mol. Biol., 112, 531 Wu, 2019, Bioactive protein/peptides of flaxseed: a review, Trends Food Sci. Technol., 92, 184, 10.1016/j.tifs.2019.08.017 Xiao, 2020, Chicken breast-derived alcohol dehydrogenase-activating peptides in response to physicochemical changes and digestion simulation: the vital role of hydrophobicity, Food Res. Int., 136, 9, 10.1016/j.foodres.2020.109592 Xie, 2015, Hydrophobicity exerts different effects on bioavailability and stability of antioxidant peptide fractions from casein during simulated gastrointestinal digestion and Caco-2 cell absorption, Food Res. Int., 76, 518, 10.1016/j.foodres.2015.06.025 Yamagami, 2021, Peptide head-to-tail cyclization: a "molecular claw" approach, Eur. J. Org Chem., 2021, 3133, 10.1002/ejoc.202100185 Yang, 2017, Stability assessment of a new antithrombotic small peptide, Arg-Gly-Asp-Trp-Arg (RGDWR), and its derivative, Biotechnol. Lett., 39, 1183, 10.1007/s10529-017-2346-x Yao, 2018, Metabolism of peptide drugs and strategies to improve their metabolic stability, Curr. Drug Metabol., 19, 892, 10.2174/1389200219666180628171531 Yap, 2020, In vivo challenges of anti-diabetic peptide therapeutics: gastrointestinal stability, toxicity and allergenicity, Trends Food Sci. Technol., 105, 161, 10.1016/j.tifs.2020.09.005 Yuan, 2018, Preparation and identification of novel inhibitory angiotensin-I-converting enzyme peptides from tilapia skin gelatin hydrolysates: inhibition kinetics and molecular docking, Food Funct., 9, 5251, 10.1039/C8FO00569A Yun, 2019, N-terminal modification of the tetrapeptide arg-Leu-Tyr-Glu, a vascular endothelial growth factor receptor-2 (VEGFR-2) antagonist, improves antitumor activity by increasing its stability against serum peptidases, Mol. Pharmacol., 96, 692, 10.1124/mol.119.117234 Zhang, 2009, Preparation and characterization of coacervate microcapsules for the delivery of antimicrobial oyster peptides, Drug Dev. Ind. Pharm., 35, 369, 10.1080/03639040802369255 Zhang, 2019, Chemoselective peptide cyclization and bicyclization directly on unprotected peptides, J. Am. Chem. Soc., 141, 12274, 10.1021/jacs.9b03623 Zheng, 2019, In vitro metabolic stability of a casein-derived dipeptidyl peptidase-IV (DPP-IV) inhibitory peptide VPYPQ and its controlled release from casein by enzymatic hydrolysis, J. Agric. Food Chem., 67, 10604, 10.1021/acs.jafc.9b03164 Zhou, 2009, Studies of poly(ethylene glycol) modification of HM-3 polypeptides, Bioconjugate Chem., 20, 932, 10.1021/bc900070r Zhu, 2014, Stability of an antioxidant peptide extracted from Jinhua ham, Meat Sci., 96, 783, 10.1016/j.meatsci.2013.09.004