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

Research output: Contribution to journalJournal articleResearchpeer-review

Standard

Insulin analog with additional disulfide bond has increased stability and preserved activity. / Vinther, Tine N.; Norrman, Mathias; Ribel, Ulla; Huus, Kasper; Schlein, Morten; Steensgaard, Dorte B.; Pedersen, Thomas Å.; Pettersson, Ingrid; Ludvigsen, Svend; Kjeldsen, Thomas; Jensen, Knud Jørgen; Hubálek, František.

In: Protein Science, Vol. 22, No. 3, 2013, p. 296-305.

Research output: Contribution to journalJournal articleResearchpeer-review

Harvard

Vinther, TN, Norrman, M, Ribel, U, Huus, K, Schlein, M, Steensgaard, DB, Pedersen, TÅ, Pettersson, I, Ludvigsen, S, Kjeldsen, T, Jensen, KJ & Hubálek, F 2013, 'Insulin analog with additional disulfide bond has increased stability and preserved activity', Protein Science, vol. 22, no. 3, pp. 296-305. https://doi.org/10.1002/pro.2211

APA

Vinther, T. N., Norrman, M., Ribel, U., Huus, K., Schlein, M., Steensgaard, D. B., Pedersen, T. Å., Pettersson, I., Ludvigsen, S., Kjeldsen, T., Jensen, K. J., & Hubálek, F. (2013). Insulin analog with additional disulfide bond has increased stability and preserved activity. Protein Science, 22(3), 296-305. https://doi.org/10.1002/pro.2211

Vancouver

Vinther TN, Norrman M, Ribel U, Huus K, Schlein M, Steensgaard DB et al. Insulin analog with additional disulfide bond has increased stability and preserved activity. Protein Science. 2013;22(3):296-305. https://doi.org/10.1002/pro.2211

Author

Vinther, Tine N. ; Norrman, Mathias ; Ribel, Ulla ; Huus, Kasper ; Schlein, Morten ; Steensgaard, Dorte B. ; Pedersen, Thomas Å. ; Pettersson, Ingrid ; Ludvigsen, Svend ; Kjeldsen, Thomas ; Jensen, Knud Jørgen ; Hubálek, František. / Insulin analog with additional disulfide bond has increased stability and preserved activity. In: Protein Science. 2013 ; Vol. 22, No. 3. pp. 296-305.

Bibtex

@article{f84d96362cc44735ba0b9d59fa17fee9,
title = "Insulin analog with additional disulfide bond has increased stability and preserved activity",
abstract = "Insulin is a key hormone controlling glucose homeostasis. All known vertebrate insulin analogs have a classical structure with three 100% conserved disulfide bonds that are essential for structural stability and thus the function of insulin. It might be hypothesized that an additional disulfide bond may enhance insulin structural stability which would be highly desirable in a pharmaceutical use. To address this hypothesis, we designed insulin with an additional interchain disulfide bond in positions A10/B4 based on Cα-Cα distances, solvent exposure, and side-chain orientation in human insulin (HI) structure. This insulin analog had increased affinity for the insulin receptor and apparently augmented glucodynamic potency in a normal rat model compared with HI. Addition of the disulfide bond also resulted in a 34.6°C increase in melting temperature and prevented insulin fibril formation under high physical stress even though the C-terminus of the B-chain thought to be directly involved in fibril formation was not modified. Importantly, this analog was capable of forming hexamer upon Zn addition as typical for wild-type insulin and its crystal structure showed only minor deviations from the classical insulin structure. Furthermore, the additional disulfide bond prevented this insulin analog from adopting the R-state conformation and thus showing that the R-state conformation is not a prerequisite for binding to insulin receptor as previously suggested. In summary, this is the first example of an insulin analog featuring a fourth disulfide bond with increased structural stability and retained function.",
keywords = "Adipocytes, Amino Acid Substitution, Animals, Antigens, CD, Biological Transport, Blood Glucose, Cells, Cultured, Cystine, Dose-Response Relationship, Drug, Drug Stability, Glucose, Humans, Hypoglycemic Agents, Insulin, Regular, Human, Mutant Proteins, Protein Conformation, Protein Stability, Rats, Rats, Mutant Strains, Rats, Wistar, Receptor, Insulin, Recombinant Proteins, Zinc",
author = "Vinther, {Tine N.} and Mathias Norrman and Ulla Ribel and Kasper Huus and Morten Schlein and Steensgaard, {Dorte B.} and Pedersen, {Thomas {\AA}.} and Ingrid Pettersson and Svend Ludvigsen and Thomas Kjeldsen and Jensen, {Knud J{\o}rgen} and Franti{\v s}ek Hub{\'a}lek",
note = "Copyright {\textcopyright} 2012 The Protein Society.",
year = "2013",
doi = "10.1002/pro.2211",
language = "English",
volume = "22",
pages = "296--305",
journal = "Protein Science",
issn = "0961-8368",
publisher = "Wiley-Blackwell",
number = "3",

}

RIS

TY - JOUR

T1 - Insulin analog with additional disulfide bond has increased stability and preserved activity

AU - Vinther, Tine N.

AU - Norrman, Mathias

AU - Ribel, Ulla

AU - Huus, Kasper

AU - Schlein, Morten

AU - Steensgaard, Dorte B.

AU - Pedersen, Thomas Å.

AU - Pettersson, Ingrid

AU - Ludvigsen, Svend

AU - Kjeldsen, Thomas

AU - Jensen, Knud Jørgen

AU - Hubálek, František

N1 - Copyright © 2012 The Protein Society.

PY - 2013

Y1 - 2013

N2 - Insulin is a key hormone controlling glucose homeostasis. All known vertebrate insulin analogs have a classical structure with three 100% conserved disulfide bonds that are essential for structural stability and thus the function of insulin. It might be hypothesized that an additional disulfide bond may enhance insulin structural stability which would be highly desirable in a pharmaceutical use. To address this hypothesis, we designed insulin with an additional interchain disulfide bond in positions A10/B4 based on Cα-Cα distances, solvent exposure, and side-chain orientation in human insulin (HI) structure. This insulin analog had increased affinity for the insulin receptor and apparently augmented glucodynamic potency in a normal rat model compared with HI. Addition of the disulfide bond also resulted in a 34.6°C increase in melting temperature and prevented insulin fibril formation under high physical stress even though the C-terminus of the B-chain thought to be directly involved in fibril formation was not modified. Importantly, this analog was capable of forming hexamer upon Zn addition as typical for wild-type insulin and its crystal structure showed only minor deviations from the classical insulin structure. Furthermore, the additional disulfide bond prevented this insulin analog from adopting the R-state conformation and thus showing that the R-state conformation is not a prerequisite for binding to insulin receptor as previously suggested. In summary, this is the first example of an insulin analog featuring a fourth disulfide bond with increased structural stability and retained function.

AB - Insulin is a key hormone controlling glucose homeostasis. All known vertebrate insulin analogs have a classical structure with three 100% conserved disulfide bonds that are essential for structural stability and thus the function of insulin. It might be hypothesized that an additional disulfide bond may enhance insulin structural stability which would be highly desirable in a pharmaceutical use. To address this hypothesis, we designed insulin with an additional interchain disulfide bond in positions A10/B4 based on Cα-Cα distances, solvent exposure, and side-chain orientation in human insulin (HI) structure. This insulin analog had increased affinity for the insulin receptor and apparently augmented glucodynamic potency in a normal rat model compared with HI. Addition of the disulfide bond also resulted in a 34.6°C increase in melting temperature and prevented insulin fibril formation under high physical stress even though the C-terminus of the B-chain thought to be directly involved in fibril formation was not modified. Importantly, this analog was capable of forming hexamer upon Zn addition as typical for wild-type insulin and its crystal structure showed only minor deviations from the classical insulin structure. Furthermore, the additional disulfide bond prevented this insulin analog from adopting the R-state conformation and thus showing that the R-state conformation is not a prerequisite for binding to insulin receptor as previously suggested. In summary, this is the first example of an insulin analog featuring a fourth disulfide bond with increased structural stability and retained function.

KW - Adipocytes

KW - Amino Acid Substitution

KW - Animals

KW - Antigens, CD

KW - Biological Transport

KW - Blood Glucose

KW - Cells, Cultured

KW - Cystine

KW - Dose-Response Relationship, Drug

KW - Drug Stability

KW - Glucose

KW - Humans

KW - Hypoglycemic Agents

KW - Insulin, Regular, Human

KW - Mutant Proteins

KW - Protein Conformation

KW - Protein Stability

KW - Rats

KW - Rats, Mutant Strains

KW - Rats, Wistar

KW - Receptor, Insulin

KW - Recombinant Proteins

KW - Zinc

U2 - 10.1002/pro.2211

DO - 10.1002/pro.2211

M3 - Journal article

C2 - 23281053

VL - 22

SP - 296

EP - 305

JO - Protein Science

JF - Protein Science

SN - 0961-8368

IS - 3

ER -

ID: 99346558