Online citations, reference lists, and bibliographies.
← Back to Search

Solid-state Chemical Stability Of Proteins And Peptides.

M. Lai, E. Topp
Published 1999 · Medicine, Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
Peptide and protein drugs are often formulated in the solid-state to provide stabilization during storage. However, reactions can occur in the solid-state, leading to degradation and inactivation of these agents. This review summarizes the major chemical reactions affecting proteins and peptides in the solid-state: deamidation, peptide bond cleavage, oxidation, the Maillard reaction, beta-elimination, and dimerization/aggregation. Physical and chemical factors influencing these reactions are also discussed. These include temperature, moisture content, excipients, and the physical state of the formulation (amorphous vs crystalline). The review is intended to serve as an aid for those involved in formulation, and to stimulate further research on the determinants of peptide and protein reactivity in the solid-state.
This paper references
10.1016/0006-3002(50)90058-8
Studies of the reaction between proteins and reducing sugars in the ‘dry’ state II. Further observations on the formation of the casein-glucose complex
C. Lea (1950)
10.1111/j.2042-7158.1994.tb03774.x
The Aggregation of Bovine Serum Albumin in Solution and in the Solid State
G. Jordan (1994)
10.1023/A:1018981208076
Moisture-Induced Aggregation of Lyophilized Insulin
H. Costantino (2004)
10.1021/JF00014A036
Preformulation studies oriented toward sustained delivery of recombinant somatotropins
M. Hageman (1992)
10.1016/0168-3659(91)90131-V
Stability of atriopeptin III in poly(d,l-lactide-co-glycolide) microspheres
R. Johnson (1991)
Introduction to physical polymer science
L. Sperling (1986)
10.1016/B978-0-12-591350-8.50028-0
FORMATION AND DECOMPOSITION OF BROWNING INTERMEDIATES AND VISIBLE SUGAR-AMINE BROWNING REACTIONS
K. Eichner (1981)
10.1021/JS960228D
Solid state stability studies of model dipeptides: aspartame and aspartylphenylalanine.
S. S. Leung (1997)
10.1016/B978-0-12-591350-8.50026-7
AUTOXIDATION-INITIATED REACTIONS IN FOODS
M. Karel (1981)
10.1111/J.1399-3011.1993.TB00328.X
Spontaneous chemical degradation of substance P in the solid phase and in solution.
U. Kertscher (1993)
10.1021/JS9802289
Chemical stability of peptides in polymers. 2. Discriminating between solvent and plasticizing effects of water on peptide deamidation in poly(vinylpyrrolidone).
M. Lai (1999)
10.1021/JF00047A007
Differentiating between the Effects of Water Activity and Glass Transition Dependent Mobility on a Solid State Chemical Reaction: Aspartame Degradation
L. Bell (1994)
10.1023/A:1016043715791
Solid-State Stability of Human Insulin I. Mechanism and the Effect of Water on the Kinetics of Degradation in Lyophiles from pH 2–5 Solutions
R. Strickley (2004)
10.1016/0006-3002(49)90100-6
Studies of the reaction between proteins and reducing sugars in the “dry” state: I. The effect of activity of water, of pH and of temperature on the primary reaction between casein and glucose
C. Lea (1952)
Deamidation, isomerization, and racemization at asparaginyl and aspartyl residues in peptides. Succinimide-linked reactions that contribute to protein degradation.
T. Geiger (1987)
10.1073/PNAS.92.24.11234
Stabilization of tetanus and diphtheria toxoids against moisture-induced aggregation.
S. Schwendeman (1995)
10.1021/JS9703378
Effect of high molecular mobility of poly(vinyl alcohol) on protein stability of lyophilized gamma-globulin formulations.
S. Yoshioka (1998)
10.1073/PNAS.90.9.4176
Controlled release of polypeptides from polyanhydrides.
E. Ron (1993)
10.1016/0168-3659(94)00084-8
Importance of in vitro experimental conditions on protein release kinetics, stability and polymer degradation in protein encapsulated poly (d,l-lactic acid-co-glycolic acid) microspheres
T. Park (1995)
Formulation and stability of freeze-dried proteins: effects of moisture and oxygen on the stability of freeze-dried formulations of human growth hormone.
M. J. Pikal (1992)
10.1021/JS980423N
Use of infrared spectroscopy to assess secondary structure of human growth hormone within biodegradable microspheres.
T. H. Yang (1999)
10.3109/03639048809151998
Effect of Moisture on the Stability of Solid Dosage Forms
J. T. Carstensen (1988)
10.1023/A:1012142204132
The Stabilization and Encapsulation of Human Growth Hormone into Biodegradable Microspheres
O. Johnson (2004)
10.1002/JPS.2600820622
Chemical stability of indomethacin in the solid amorphous and molten states.
J. Carstensen (1993)
10.1023/A:1018919508463
Lyophilized Formulations of Recombinant Tumor Necrosis Factor
M. Hora (2004)
10.1007/978-1-4899-1236-7_2
Characterization and formulation considerations for recombinantly derived bovine somatotropin.
S. R. Davio (1993)
10.1002/BIT.260370210
Moisture‐induced aggregation of lyophilized proteins in the solid state
W. Liu (1991)
10.1038/NBT0595-493
Aggregation of a Lyophilized Pharmaceutical Protein, Recombinant Human Albumin: Effect of Moisture and Stabilization by Excipients
H. Costantino (1995)
10.1002/JPS.2600791209
Stability of ribonuclease A in solution and the freeze-dried state.
M. W. Townsend (1990)
10.1023/A:1018998312503
Chemical Pathways of Peptide Degradation. VII. Solid State Chemical Instability of an Aspartyl Residue in a Model Hexapeptide
C. Oliyai (2004)
10.1023/A:1012031012367
The Stability of Recombinant Human Growth Hormone in Poly(lactic-co-glycolic acid) (PLGA) Microspheres
J. Cleland (2004)
10.1021/JS960257O
How does residual water affect the solid-state degradation of drugs in the amorphous state?
E. Shalaev (1996)
10.1021/JS950456S
Effects of reducing sugars on the chemical stability of human relaxin in the lyophilized state.
S. Li (1996)
10.1042/BJ0500713
The reaction between proteins and reducing sugars in the `dry' state. Relative reactivity of the α- and ∈-amino groups of insulin
H. Schwartz (1952)
10.1021/JS9700311
Solid-state stability of human insulin. II. Effect of water on reactive intermediate partitioning in lyophiles from pH 2-5 solutions: stabilization against covalent dimer formation.
R. Strickley (1997)
10.1038/NBT0298-153
Improving protein therapeutics with sustained-release formulations
S. D. Putney (1998)
10.1023/A:1015999012852
Chemical Pathways of Peptide Degradation. III. Effect of Primary Sequence on the Pathways of Deamidation of Asparaginyl Residues in Hexapeptides
Kamlesh Patel (2004)
10.1042/BJ0470626
The reaction between proteins and reducing sugars in the 'dry' state; dried human blood plasma.
C. Lea (1950)
The effects of formulation and moisture on the stability of a freeze-dried monoclonal antibody-vinca conjugate: a test of the WLF glass transition theory.
Roy Ml (1992)
10.1016/0378-5173(90)90221-O
The molecular basis of moisture effects on the physical and chemical stability of drugs in the solid state
C. Ahlneck (1990)
10.1023/A:1016032808039
Oxidation of Human Insulin-like Growth Factor I in Formulation Studies: Kinetics of Methionine Oxidation in Aqueous Solution and in Solid State
J. Fransson (2004)
10.1016/0003-2697(84)90583-9
Proteins: Structures and Molecular Properties
Thomas E. Creighton (1986)
Use of lyoprotectants in the freeze-drying of a model protein, ribonuclease A.
M. W. Townsend (1988)
10.1016/B978-0-12-591350-8.50029-2
THE NONENZYMATIC BROWNING REACTION AS AFFECTED BY WATER IN FOODS
T. Labuza (1981)
10.1002/JPS.2600800116
Nature of aggregates formed during storage of freeze-dried ribonuclease A.
M. W. Townsend (1991)
10.1111/J.1470-8744.1988.TB00023.X
Isolation and Characterization of a Sulfoxide and a Desamido Derivative of Biosynthetic Human Growth Hormone
G. Becker (1988)
10.1021/JS9802493
Secondary structure and protein deamidation.
M. Xie (1999)
Pharmaceutics of protein drugs.
R. Pearlman (1992)
10.1021/JS980227G
Chemical stability of peptides in polymers. 1. Effect of water on peptide deamidation in poly(vinyl alcohol) and poly(vinyl pyrrolidone) matrixes.
M. Lai (1999)
10.1002/JPS.2600831205
Solid-phase aggregation of proteins under pharmaceutically relevant conditions.
H. Costantino (1994)
10.1007/978-1-4899-0664-9_19
Aspartame degradation as a function of "water activity".
L. Bell (1991)
10.1006/ABBI.1996.0305
Physical factors affecting the storage stability of freeze-dried interleukin-1 receptor antagonist: glass transition and protein conformation.
B. Chang (1996)
10.1023/A:1015959604616
The Effects of Formulation Additives on the Degradation of Freeze-Dried Ribonuclease A
M. W. Townsend (2004)
10.1023/A:1015862026539
Chemical Pathways of Peptide Degradation. I. Deamidation of Adrenocorticotropic Hormone
N. P. Bhatt (2004)
10.3109/03639048809152002
THE ROLE OF MOISTURE IN PROTEIN STABILITY
M. J. Hageman (1988)



This paper is referenced by
10.1002/JPS.10216
Peroxide formation in polysorbate 80 and protein stability.
Emily Ha (2002)
10.1007/978-1-59745-569-5_41
Post-translational Processing of Human Interferon- γ Produced in Escherichia coli and Approaches for its Prevention
M. Boyanova (2008)
Characterisation and processing of amorphous binary mixtures with low glass transition temperature
Pekka Hoppu (2008)
10.1016/j.jpba.2015.03.023
Toward greener analytical techniques for the absolute quantification of peptides in pharmaceutical and biological samples.
A. Van Eeckhaut (2015)
10.3233/SPE-2010-0468
Different solid sample preparation methods affecting the spectral similarity of salmon calcitonin
S. Lin (2010)
10.1002/1520-6017(200102)90:2<141::AID-JPS5>3.0.CO;2-Y
Effect of 'pH' on the rate of asparagine deamidation in polymeric formulations: 'pH'-rate profile.
Y. Song (2001)
10.1016/J.BBRC.2004.08.020
Thermal inactivation of protective antigen of Bacillus anthracis and its prevention by polyol osmolytes.
S. Singh (2004)
10.1002/JPS.20620
Impact of freeze-drying on ionization of sulfonephthalein probe molecules in trehalose-citrate systems.
R. Govindarajan (2006)
10.1016/S0022-3549(15)00176-8
Development of pH-Independent Drug Release Formulation Using Lipocalin-Type Prostaglandin D Synthase.
Masashi Mizoguchi (2016)
10.1002/jps.23568
Improving the physical stability of freeze-dried amorphous sugar matrices by compression at several hundreds MPa.
Ryo Kagotani (2013)
10.1016/S0021-9673(01)00875-5
Ni(II)-based immobilized metal ion affinity chromatography of recombinant human prolactin from periplasmic Escherichia coli extracts.
E. Ueda (2001)
10.1016/J.BIOLOGICALS.2004.12.002
A comparison of vials with ampoules for the storage of biological reference materials.
P. Matejtschuk (2005)
10.1016/J.VACCINE.2007.07.009
Quality control of routine, experimental and real-time aged diphtheria toxoids by in vitro analytical techniques.
B. Metz (2007)
10.1002/jps.21825
Mechanisms of protein stabilization in the solid state.
Liuquan (Lucy) Chang (2009)
10.1016/B978-0-08-088504-9.00468-2
Pharmaceutical Proteins – Structure, Stability, and Formulation
H. Schiffter (2011)
10.1016/j.carbpol.2017.08.084
Addition of Pullulan to Trehalose Glasses Improves the Stability of β-Galactosidase at High Moisture Conditions.
N. Teekamp (2017)
10.1023/A:1013054431517
Effect of Moisture on the Stability of a Lyophilized Humanized Monoclonal Antibody Formulation
E. Breen (2004)
10.1007/S00216-003-2381-4
Solid-state NMR studies of pharmaceutical solids in polymer matrices
J. Lubach (2004)
Chemical and Physical Characterization of Therapeutic Proteins in Solution and Amorphous Solids
Sandipan Sinha (2008)
10.1007/s11095-011-0591-6
Kinetics and Mechanisms of Deamidation and Covalent Amide-Linked Adduct Formation in Amorphous Lyophiles of a Model Asparagine-Containing Peptide
Michael P. DeHart (2011)
Purityprofiling of Peptide Drugs
Sylvia Van Dorpe (2011)
10.1128/AEM.01871-14
Absolute Humidity Influences the Seasonal Persistence and Infectivity of Human Norovirus
A. Colas de la Noue (2014)
10.1016/j.jconrel.2014.09.031
Targeting of gastrointestinal tract for amended delivery of protein/peptide therapeutics: strategies and industrial perspectives.
V. Pawar (2014)
10.2144/DEC02STEINHAUER
Single framework recombinant antibody fragments designed for protein chip applications.
C. Steinhauer (2002)
10.1016/J.EJPB.2004.03.020
Investigation of the stabilisation of freeze-dried lysozyme and the physical properties of the formulations.
Y. Liao (2004)
10.5411/WJI.V6.I1.19
Maillard reaction and immunogenicity of protein therapeutics
Rositsa Tsekovska (2016)
10.1007/s00216-010-4308-1
Development of an analytical protocol for a fast, sensitive and specific protein recognition in paintings by enzyme-linked immunosorbent assay (ELISA)
M. Palmieri (2011)
10.1016/j.ejpb.2011.11.012
Development of a pilot-scale manufacturing process for protein-coated microcrystals (PCMC): mixing and precipitation - part I.
C. König (2012)
10.5772/63503
Thermostability of Freeze‐Dried Plant‐Made VLP‐Based Vaccines
Marcin Czyż (2016)
10.1023/B:PHAM.0000036916.96307.d8
Solvent Exchange Method: A Novel Microencapsulation Technique Using Dual Microdispensers
Y. Yeo (2004)
10.7282/T3TT4P86
A systematic study of phosphorescent probes in cryosolvents, amorphous solids, and proteins
Andrew R. Draganski (2014)
Developing a Rational Peptide Ligand Design Method Using CD13 as a Prototype Target Receptor
Zahir Uddin (2019)
See more
Semantic Scholar Logo Some data provided by SemanticScholar