A disulfide bond replacement strategy enables the efficient design of artificial therapeutic peptides
We demonstrate that disulfide bond replacement is an efficient strategy for engineering therapeutic peptides. In previous work, short peptide fragments, known as WP9QY, with sequence homology with the predicted ligand contact surface of the receptor activator of NF-κB (RANK) were crosslinked through...
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| Published in | Tetrahedron Vol. 70; no. 42; pp. 7774 - 7779 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
21.10.2014
Elsevier |
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| Abstract | We demonstrate that disulfide bond replacement is an efficient strategy for engineering therapeutic peptides. In previous work, short peptide fragments, known as WP9QY, with sequence homology with the predicted ligand contact surface of the receptor activator of NF-κB (RANK) were crosslinked through intramolecular disulfide bonds to inhibit RANK ligand (RANKL)-induced signaling, osteoclastogenesis, bone resorption in vitro, and bone loss in vivo. We report that replacement of the disulfide bond of WP9QY with an amine cross-linkage results in a significant improvement in enzymatic stability, with only a slight loss of bone resorption-blocking activity in vitro. Furthermore, the WP9QY derivative inhibits bone loss significantly in vivo, whereas the native form of WP9QY was not effective under the same conditions.
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| AbstractList | We demonstrate that disulfide bond replacement is an efficient strategy for engineering therapeutic peptides. In previous work, short peptide fragments, known as WP9QY, with sequence homology with the predicted ligand contact surface of the receptor activator of NF-kappa B (RANK) were crosslinked through intramolecular disulfide bonds to inhibit RANK ligand (RANKL)-induced signaling, osteoclastogenesis, bone resorption in vitro, and bone loss in vivo. We report that replacement of the disulfide bond of WP9QY with an amine cross-linkage results in a significant improvement in enzymatic stability, with only a slight loss of bone resorption-blocking activity in vitro. Furthermore, the WP9QY derivative inhibits bone loss significantly in vivo, whereas the native form of WP9QY was not effective under the same conditions. (C) 2014 Elsevier Ltd. All rights reserved. We demonstrate that disulfide bond replacement is an efficient strategy for engineering therapeutic peptides. In previous work, short peptide fragments, known as WP9QY, with sequence homology with the predicted ligand contact surface of the receptor activator of NF-κB (RANK) were crosslinked through intramolecular disulfide bonds to inhibit RANK ligand (RANKL)-induced signaling, osteoclastogenesis, bone resorption in vitro, and bone loss in vivo. We report that replacement of the disulfide bond of WP9QY with an amine cross-linkage results in a significant improvement in enzymatic stability, with only a slight loss of bone resorption-blocking activity in vitro. Furthermore, the WP9QY derivative inhibits bone loss significantly in vivo, whereas the native form of WP9QY was not effective under the same conditions. [Display omitted] |
| Author | Maeda, Miki Okada, Yohei Ohya, Keiichi Chiba, Kazuhiro Nakae, Takashi Aoki, Kazuhiro |
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| CitedBy_id | crossref_primary_10_1016_j_bmc_2015_03_040 crossref_primary_10_5059_yukigoseikyokaishi_74_588 crossref_primary_10_1002_bip_22625 crossref_primary_10_1002_ange_202004656 crossref_primary_10_1002_anie_202004656 crossref_primary_10_1016_j_tetlet_2015_12_070 crossref_primary_10_1080_00304948_2017_1380492 |
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| Keywords | Bone resorption-blocking activities Disulfide bonds Therapeutic peptides Hydrophobic tags Amine cross-linkages PHASE SYNTHESIS IMI ANALOGS BIOLOGICAL-ACTIVITIES CYSTINE POTENT ALPHA-CONOTOXIN OXYTOCIN CYCLIZATION |
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| Snippet | We demonstrate that disulfide bond replacement is an efficient strategy for engineering therapeutic peptides. In previous work, short peptide fragments, known... |
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| SubjectTerms | Amine cross-linkages Bone resorption-blocking activities Chemistry Chemistry, Organic Disulfide bonds Hydrophobic tags Physical Sciences Science & Technology Therapeutic peptides |
| Title | A disulfide bond replacement strategy enables the efficient design of artificial therapeutic peptides |
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