Link-N

{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | image = Link-N_structure.png | image_class = skin-invert-image | width = 300  | tradename = | pregnancy_category = | routes_of_administration = | class = | ATC_prefix = | ATC_suffix = | ATC_supplemental =  | legal_status =  | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =  | CAS_number = 197295-74-2 | PubChem = 175678601 | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 129980411 | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand =  | IUPAC_name = <nowiki>(3S)-3-amino-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-carbamimidamido-1-[[(2S)-1-[[(2S,3S)-1-[[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-4-oxobutanoic acid</nowiki> | C = 81 | H = 120 | N = 26 | O = 29 | StdInChI = 1S/C81H120N26O29/c1-9-37(6)63(78(133)104-56(80(135)136)22-43-30-88-34-92-43)106-65(120)38(7)93-67(122)46(11-10-16-89-81(84)85)94-73(128)53(25-60(114)115)101-71(126)51(21-42-29-87-33-91-42)98-74(129)54(26-61(116)117)100-68(123)48(18-36(4)5)103-79(134)64(39(8)109)107-76(131)49(19-40-12-14-44(110)15-13-40)97-72(127)52(24-58(83)111)99-75(130)55(27-62(118)119)102-77(132)57(31-108)105-69(124)47(17-35(2)3)96-70(125)50(20-41-28-86-32-90-41)95-66(121)45(82)23-59(112)113/h12-15,28-30,32-39,45-57,63-64,108-110H,9-11,16-27,31,82H2,1-8H3,(H2,83,111)(H,86,90)(H,87,91)(H,88,92)(H,93,122)(H,94,128)(H,95,121)(H,96,125)(H,97,127)(H,98,129)(H,99,130)(H,100,123)(H,101,126)(H,102,132)(H,103,134)(H,104,133)(H,105,124)(H,106,120)(H,107,131)(H,112,113)(H,114,115)(H,116,117)(H,118,119)(H,135,136)(H4,84,85,89)/t37-,38-,39+,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,63-,64-/m0/s1 | StdInChIKey = GHPHCEQEWSDUET-MMXWBEGUSA-N | SMILES = CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC2=CN=CN2)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC4=CN=CN4)NC(=O)[C@H](CC(=O)O)N }}

'''Link-N''' ('''DHLSDNYTLDHDRAIH''') is a naturally occurring 16-amino acid peptide which is the N-terminal fragment derived from enzymatic cleavage of cartilage link protein.

It has antiinflammatory effects and stimulates cartilage regrowth in both ''in vitro'' cultures of human cartilage tissue<ref name = "McKenna_1998">{{cite journal | vauthors = McKenna LA, Liu H, Sansom PA, Dean MF | title = An N-terminal peptide from link protein stimulates proteoglycan biosynthesis in human articular cartilage in vitro | journal = Arthritis and Rheumatism | volume = 41 | issue = 1 | pages = 157–162 | date = January 1998 | pmid = 9433881 | doi = 10.1002/1529-0131(199801)41:1<157::AID-ART19>3.0.CO;2-J }}</ref><ref name = "Liu_2000">{{cite journal | vauthors = Liu H, McKenna LA, Dean MF | title = An N-terminal peptide from link protein can stimulate biosynthesis of collagen by human articular cartilage | journal = Archives of Biochemistry and Biophysics | volume = 378 | issue = 1 | pages = 116–122 | date = June 2000 | pmid = 10871051 | doi = 10.1006/abbi.2000.1758 }}</ref><ref name = "Petit_2011">{{cite journal | vauthors = Petit A, Yao G, Rowas SA, Gawri R, Epure L, Antoniou J, Mwale F | title = Effect of synthetic link N peptide on the expression of type I and type II collagens in human intervertebral disc cells | journal = Tissue Engineering. Part A | volume = 17 | issue = 7–8 | pages = 899–904 | date = April 2011 | pmid = 21067464 | doi = 10.1089/ten.TEA.2010.0494 }}</ref><ref name = "He_2018">{{cite journal | vauthors = He R, Wang B, Cui M, Xiong Z, Lin H, Zhao L, Li Z, Wang Z, Peggrem S, Xia Z, Shao Z | title = Link Protein N-Terminal Peptide as a Potential Stimulating Factor for Stem Cell-Based Cartilage Regeneration | journal = Stem Cells International | date = 2018 | volume = 2018 | article-number = 3217895 | pmid = 29531532 | doi = 10.1155/2018/3217895 | doi-access = free | pmc = 5831317 }}</ref> and animal models of arthritis,<ref = "Noorwali_2018">{{cite journal | vauthors = Noorwali H, Grant MP, Epure LM, Madiraju P, Sampen HJ, Antoniou J, Mwale F | title = Link N as a therapeutic agent for discogenic pain | journal = JOR Spine | volume = 1 | issue = 1 | article-number = e1008 | date = March 2018 | pmid = 31463438 | doi = 10.1002/jsp2.1008 | pmc = 6686832 }}</ref><ref = "Antoniou_2019">{{cite journal | vauthors = Antoniou J, Epure LM, Grant MP, Richard H, Sampalis J, Roughley PJ, Laverty S, Mwale F | title = Short link N acts as a disease modifying osteoarthritis drug | journal = European Cells & Materials | volume = 37 | pages = 347–359 | date = May 2019 | pmid = 31044415 | doi = 10.22203/eCM.v037a21 | doi-access = free }}</ref><ref = "Alaqeel_2020">{{cite journal | vauthors = Alaqeel M, Grant MP, Epure LM, Salem O, AlShaer A, Huk OL, Bergeron SG, Zukor DJ, Kc R, Im HJ, Anbazhagan AN, Antoniou J, Mwale F | title = Link N suppresses interleukin-1β-induced biological effects on human osteoarthritic cartilage | journal = European Cells & Materials | volume = 39 | pages = 65–76 | date = January 2020 | pmid = 31939630 | doi = 10.22203/eCM.v039a04 | doi-access = free }}</ref><ref = "Liao_2024">{{cite journal | vauthors = Liao HJ, Chen HT, Chang CH | title = Peptides for Targeting Chondrogenic Induction and Cartilage Regeneration in Osteoarthritis | journal = Cartilage | article-number = 19476035241276406 | date = September 2024 | pmid = 39291443 | doi = 10.1177/19476035241276406 | pmc = 11556548 }}</ref><ref = "Shih_2024">{{cite journal | vauthors = Shih SY, Grant MP, Epure LM, Alad M, Lerouge S, Huk OL, Bergeron SG, Zukor DJ, Merle G, Im HJ, Antoniou J, Mwale F | title = Advances in the Regulation of Periostin for Osteoarthritic Cartilage Repair Applications | journal = Biomolecules | volume = 14 | issue = 11 | date = November 2024 | page = 1469 | pmid = 39595645 | doi = 10.3390/biom14111469 | pmc = 11592007 | doi-access = free }}</ref><ref = "Grant_2025">{{cite journal | vauthors = Grant MP, Alad M, Yousef F, Epure LM, Antoniou J, Mwale F | title = Link N Directly Targets IL-1β to Suppress Inflammation and Regulate Sensory Pain in Intervertebral Disc Degeneration | journal = Biomolecules | volume = 15 | issue = 4 | date = April 2025 | page = 603 | pmid = 40305345 | doi = 10.3390/biom15040603 | pmc = 12024905 | doi-access = free }}</ref> but is not known to have been tested in humans.

== See also == * B7-33 * BPC-157 * Cartalax * Mechano growth factor * PEPITEM * TB-500 * Teriparatide * Tertomotide

== References == {{Reflist}}

Category:Hexadecapeptides