Better Peptides via Chemical Glycosylation: Somatostatin Analogues Having a Human Complex-Type N-Glycan with Improved Drug Properties.
chemical glycosylation
human complex-type oligosaccharide
octreotide
somatostatin (SRIF)
somatostatin receptor subtype (sst)
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
02 Jun 2023
02 Jun 2023
Historique:
received:
13
01
2023
medline:
5
6
2023
pubmed:
23
3
2023
entrez:
22
3
2023
Statut:
ppublish
Résumé
Somatostatin (somatotropin release-inhibiting factor, SRIF) is a growth hormone inhibitory factor in the form of a 14- or 28-amino acid peptide. SRIF affects several physiological functions through its action on five distinct SRIF receptor subtypes (sst1-5). Native SRIF has only limited clinical applications due to its rapid degradation in plasma. To overcome this obstacle, we have developed glycosylated SRIF analogues that possess not only metabolic stability but also high affinity to all five receptor subtypes by attaching human complex-type oligosaccharides. Such glycosylated SRIF analogues with improved pharmacokinetic profiles could be potent and novel therapeutic drugs for SRIF-related diseases in which several SRIF receptor subtypes are closely involved, and also shed light on new indications. Our results show that chemical glycosylation can be a powerful tool for the development of peptide and protein analogues superior to the original molecules with enhanced drug properties.
Identifiants
pubmed: 36945747
doi: 10.1002/chem.202300111
doi:
Substances chimiques
Receptors, Somatostatin
0
Somatostatin
51110-01-1
Polysaccharides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300111Subventions
Organisme : GlyTech, Inc.
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
J. L. Lau, M. K. Dunn, Bioorg. Med. Chem. 2018, 26, 2700-2707.
K. Fosgerau, T. Hoffman, Drug Discov. 2015, 20, 122-128.
L. H. Brinckerhoff, V. V. Kalashnikov, L. W. Thompson, G. V. Yamshchikov, R. A. Pierce, H. S. Galavotti, V. H. Engelhard, C. L. Slingluff Jr., Int. J. Cancer 1999, 83, 326-334;
A. Rozek, J.-P. S. Powers, C. L. Friedrich, R. E. W. Hancock, Biochemistry 2003, 42, 14130-14138;
B. S. Osborn, L. Sekut, M. Corcoran, C. Poortman, B. Sturm, G. Chen, D. Mather, H. L. Lin, T. J. Parry, Eur. J. Pharm. 2002, 456, 149-158;
E. M. Bech, S. L. Pedersen, K. J. Jensen, ACS Med. Chem. Lett. 2018, 9, 577-580;
J. M. Harris, R. B. Chess, Nat. Rev. Drug Discovery 2003, 2, 214-221.
R. Apweiler, H. Hermjakob, N. Sharon, Biochim. Biophys. Acta 1999, 1473, 4-8.
A. Varki, Glycobiology 2017, 27, 3-49.
I. Sakamoto, K. Tezuka, K. Fukae, K. Ishii, K. Taduru, M. Maeda, M. Ouchi, K. Yoshida, Y. Nambu, J. Igarashi, N. Hayashi, T. Tsuji, Y. Kajihara, J. Am. Chem. Soc. 2012, 134, 5428-5431;
H. Ochiai, K. Yoshida, H. Shibutani, A. Kanatani, Y. Nishiuchi, Chem. Pharm. Bull. 2019, 67, 236-243.
M. Theodoropoulou, G. K. Stalla, Front. Neuroendocrinol. 2013, 34, 228-252.
D. Cuevas-Ramos, M. Fleseriu, J. Mol. Endocrinol. 2014, 52, R223-R240.
D. Cuevas-Ramos, M. Fleseriu, Drug Des. Dev. Ther. 2016, 10, 227-239.
A. Helenius, M. Aebi, Annu. Rev. Biochem. 2004, 73, 1019-1049.
S. Thobhani, C.-T. Yuen, M. J. A. Bailey, C. Jones, Glycobiology 2009, 19, 201-211;
S. S. Park, J. Park, J. Ko, L. Chen, D. Meriage, J. Crouse-Zeineddini, W. Wong, B. A. Kerwin, J. Pharm. Sci. 2009, 98, 1688-1699.
M. R. Pratt, C. R. Bertozzi, Chem. Soc. Rev. 2005, 34, 58-68;
L. Liu, C. S. Bennett, C.-H. Wong, Chem. Commun. 2006, 21-33;
H. Hojo, Y. Nakahara, Pept. Sci. 2007, 88, 23-48;
C. Unverzagt, Y. Kajihara, Chem. Soc. Rev. 2013, 42, 4408-4420;
J. D. Lin, X.-W. Liu, Chem. Asian J. 2020, 15, 2548-2557.
Y. Kajihara, Y. Suzuki, N. Yamamoto, K. Sasaki, T. Sakakibara, L. R. Juneja, Chem. Eur. J. 2004, 10, 971-985.
N. Yamamoto, Y. Ohmori, T. Sakakibara, K. Sasaki, L. R. Juneja, Y. Kajihara, Angew. Chem. Int. Ed. 2003, 42, 2537-2540;
Angew. Chem. 2003, 115, 2641-2644.
N. Yamamoto, T. Sakakibara, Y. Kajihara, Tetrahedron Lett. 2004, 45, 3287-3290.
H. Tanaka, T. Tsunoda, I. Nukaya, A. Sette, K. Matsuda, Y. Umano, H. Yamaue, K. Takesako, H. Tanimura, Br. J. Cancer 2001, 84, 94-99.
G. G. Glenner, C. W. Wong, Biochem. Biopys. Res. Commun. 1984, 120, 885-890.
B. A. Yankner, L. K. Duffy, D. A. Kirschner, Science 1990, 250, 279-282.
H. Naiki, K. Higuchi, M. Hosokawa, T. Takeda, Anal. Biochem. 1989, 177, 244-249.
M. A. Hossain, R. Okamoto, J. A. Karas, P. Praveen, M. Liu, B. E. Forbes, J. D. Wade, Y. Kajihara, J. Am. Chem. Soc. 2020, 142, 1164-1169;
M. Liu, P. Zhao, M. H. Uddin, W. Li, F. Lin, C. Chandrashekar, Y. Nishiuchi, Y. Kajihara, B. E. Forbes, D. Wootten, J. D. Wade, M. A. Hossain, Bioconjugate Chem. 2021, 32, 2148-2153.
C. Chandrashekar, M. A. Hossain, J. D. Wade, Front. Chem. 2021, 9, 650025.
A. M. Sinclair, S. Elliottg, J. Pharm. Sci. 2005, 94, 1626-1635.
J. Eng, W. A. Kleinman, L. Singh, G. Singh, J. P. Raufman, J. Biol. Chem. 1992, 267, 7402-7405;
J. M. Egan, A. R. Clocquet, D. Elahi, J. Clin. Endocrinol. Metab. 2002, 87, 1282-1290.
Y. Kajihara, T. Tsuji, Y. Nambu, K. Ishii, K. Yoshida, K. Tezuka, WO2011052523 A1, 2011.
H. Hibino, Y. Miki, Y. Nishiuchi, J. Pept. Sci. 2012, 18, 763-769.
B. Kamber, A. Hartmann, K. Eisler, B. Riniker, H. Rink, P. Sieber, W. Rittel, Helv. Chim. Acta 1980, 63, 899-915;
E. V. Kudryavtseva, M. V. Sidorova, M. V. Ovchinnikov, Zh. D. Bespalova, V. N. Bushuev, J. Pept. Res. 1997, 49, 52-58.
Y. Fujiwara, K. Akaji, Y. Kiso, Chem. Pharm. Bull. 1994, 42, 724-726;
H. Hibino, Y. Nishiuchi, Org. Lett. 2012, 14, 1926-1929.
Y.-C. Cheng, W. H. Prusoff, Biochem. Pharmacol. 1973, 22, 3099-3108.
K. Öberg, L. Kvols, M. Caplin, G. D. Fave, W. der Herder, G. Rindi, P. Ruszniewski, E. A. Woltering, B. Wiedenmann, Ann. Oncol. 2004, 15, 966-973.
M. A. Sheridan, J. D. Kittilson, B. J. Slagter, Amer. Zool. 2000, 40, 269-286.
H. A. Schmid, P. Schoeffter, Neuroendocrinology 2004, 80 Suppl 1, 47-50.
R. Urso, P. Blardi, G. Giorgi, Eur. Rev. Med. Pharmacol. Sci. 2002, 6, 33-44.
A. L. T. Sørensen, H. Clausen, H. H. Wandall, Biochim. Biophys. Acta 2012, 1820, 1797-1808.
A. Ogura, T. Tahara, S. Nozaki, K. Morimoto, Y. Kizuka, S. Kitazume, M. Hara, S. Kojima, H. Onoe, A. Kurbangalieva, N. Taniguchi, Y. Watanabe, K. Tanaka, Sci. Rep. 2016, 6, 21797;
I. Smirnov, R. Sibgatullina, S. Urano, T. Tahara, P. Ahmadi, Y. Watanabe, A. R. Pradipta, A. Kurbangalieva, K. Tanaka, Small 2020, 16, 2004831.
L. Yuan, J. Wang, W. Shen, Pharm. Res. 2005, 22, 220-227.