Link-N

Last updated

Link-N
Link-N structure.png
Identifiers
  • (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
CAS Number
PubChem CID
Chemical and physical data
Formula C81H120N26O29
Molar mass 1922.004 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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
  • Key:GHPHCEQEWSDUET-MMXWBEGUSA-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 [1] [2] [3] [4] and animal models of arthritis, [5] [6] [7] [8] [9] [10] but is not known to have been tested in humans.

See also

References

  1. ↑ McKenna LA, Liu H, Sansom PA, Dean MF (January 1998). "An N-terminal peptide from link protein stimulates proteoglycan biosynthesis in human articular cartilage in vitro". Arthritis and Rheumatism. 41 (1): 157–162. doi:10.1002/1529-0131(199801)41:1<157::AID-ART19>3.0.CO;2-J. PMID   9433881.
  2. ↑ Liu H, McKenna LA, Dean MF (June 2000). "An N-terminal peptide from link protein can stimulate biosynthesis of collagen by human articular cartilage". Archives of Biochemistry and Biophysics. 378 (1): 116–122. doi:10.1006/abbi.2000.1758. PMID   10871051.
  3. ↑ Petit A, Yao G, Rowas SA, Gawri R, Epure L, Antoniou J, et al. (April 2011). "Effect of synthetic link N peptide on the expression of type I and type II collagens in human intervertebral disc cells". Tissue Engineering. Part A. 17 (7–8): 899–904. doi:10.1089/ten.TEA.2010.0494. PMID   21067464.
  4. ↑ He R, Wang B, Cui M, Xiong Z, Lin H, Zhao L, et al. (2018). "Link Protein N-Terminal Peptide as a Potential Stimulating Factor for Stem Cell-Based Cartilage Regeneration". Stem Cells International. 2018 3217895. doi: 10.1155/2018/3217895 . PMC   5831317 . PMID   29531532.
  5. ↑ Noorwali H, Grant MP, Epure LM, Madiraju P, Sampen HJ, Antoniou J, et al. (March 2018). "Link N as a therapeutic agent for discogenic pain". JOR Spine. 1 (1) e1008. doi:10.1002/jsp2.1008. PMC   6686832 . PMID   31463438.
  6. ↑ Antoniou J, Epure LM, Grant MP, Richard H, Sampalis J, Roughley PJ, et al. (May 2019). "Short link N acts as a disease modifying osteoarthritis drug". European Cells & Materials. 37: 347–359. doi:10.22203/eCM.v037a21. PMID   31044415.
  7. ↑ Alaqeel M, Grant MP, Epure LM, Salem O, AlShaer A, Huk OL, et al. (January 2020). "Link N suppresses interleukin-1β-induced biological effects on human osteoarthritic cartilage". European Cells & Materials. 39: 65–76. doi:10.22203/eCM.v039a04. PMID   31939630.
  8. ↑ Liao HJ, Chen HT, Chang CH (September 2024). "Peptides for Targeting Chondrogenic Induction and Cartilage Regeneration in Osteoarthritis". Cartilage 19476035241276406. doi:10.1177/19476035241276406. PMC   11556548 . PMID   39291443.
  9. ↑ Shih SY, Grant MP, Epure LM, Alad M, Lerouge S, Huk OL, et al. (November 2024). "Advances in the Regulation of Periostin for Osteoarthritic Cartilage Repair Applications". Biomolecules. 14 (11): 1469. doi: 10.3390/biom14111469 . PMC   11592007 . PMID   39595645.
  10. ↑ Grant MP, Alad M, Yousef F, Epure LM, Antoniou J, Mwale F (April 2025). "Link N Directly Targets IL-1β to Suppress Inflammation and Regulate Sensory Pain in Intervertebral Disc Degeneration". Biomolecules. 15 (4): 603. doi: 10.3390/biom15040603 . PMC   12024905 . PMID   40305345.
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