Ac-SDKP

Ac-SDKP
Identifiers
	IUPAC name (2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-6-aminohexanoyl]pyrrolidine-2-carboxylic acid;
CAS Number	120081-14-3;
PubChem CID	65938;
IUPHAR/BPS	10060;
ChemSpider	59343;
UNII	H041538E9P;
ChEBI	CHEBI:191178;
ChEMBL	ChEMBL420741;
Chemical and physical data
Formula	C20H33N5O9
Molar mass	487.510 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O;
	InChI InChI=1S/C20H33N5O9/c1-11(27)22-14(10-26)18(31)24-13(9-16(28)29)17(30)23-12(5-2-3-7-21)19(32)25-8-4-6-15(25)20(33)34/h12-15,26H,2-10,21H2,1H3,(H,22,27)(H,23,30)(H,24,31)(H,28,29)(H,33,34)/t12-,13-,14-,15-/m0/s1; Key:HJDRXEQUFWLOGJ-AJNGGQMLSA-N;

Ac-SDKP (Thymosin Beta 4 Fragment (1–4), Goralatide) is an endogenous tetrapeptide derivative that is the N-acetylated derivative of the fragment composed of amino acids 1-4 derived from cleavage of the N-terminus of the signalling factor thymosin beta-4 by the enzyme prolyl oligopeptidase. It is a selective inhibitor of haematopoietic cell proliferation and has antiinflammatory, anti-fibrotic, and pro-angiogenic properties, with particular applications in preventing the development of kidney fibrosis and cardiac fibrosis following injury to these organs.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]

References

↑ Guigon M, Bonnet D (June 1995). "Inhibitory peptides in hematopoiesis". Experimental Hematology. 23 (6): 477–481. PMID 7768302.
↑ Cavasin MA (2006). "Therapeutic potential of thymosin-beta4 and its derivative N-acetyl-seryl-aspartyl-lysyl-proline (Ac-SDKP) in cardiac healing after infarction". American Journal of Cardiovascular Drugs. 6 (5): 305–311. doi:10.2165/00129784-200606050-00003. PMID 17083265.
↑ Sosne G, Qiu P, Goldstein AL, Wheater M (July 2010). "Biological activities of thymosin beta4 defined by active sites in short peptide sequences". FASEB Journal. 24 (7): 2144–2151. doi:10.1096/fj.09-142307. PMID 20179146.
↑ Douglas RG, Ehlers MR, Sturrock ED (August 2013). "Antifibrotic peptide N-acetyl-Ser-Asp-Lys-Pro (Ac-SDKP): opportunities for angiotensin-converting enzyme inhibitor design". Clinical and Experimental Pharmacology & Physiology. 40 (8): 535–541. doi:10.1111/1440-1681.12062. PMID 23351021.
↑ Hrenak J, Paulis L, Simko F (2015). "N-acetyl-seryl-aspartyl-lysyl-proline (Ac-SDKP): Potential target molecule in research of heart, kidney and brain". Current Pharmaceutical Design. 21 (35): 5135–5143. doi:10.2174/1381612821666150909093927. PMID 26350537.
↑ Mnguni AT, Engel ME, Borkum MS, Mayosi BM (2015). "The Effects of Angiotensin Converting Enzyme Inhibitors (ACE-I) on Human N-Acetyl-Seryl-Aspartyl-Lysyl-Proline (Ac-SDKP) Levels: A Systematic Review and Meta-Analysis". PLOS ONE. 10 (12) e0143338. Bibcode:2015PLoSO..1043338M. doi:10.1371/journal.pone.0143338. PMC 4686106. PMID 26656271.
↑ Kumar N, Yin C (August 2018). "The anti-inflammatory peptide Ac-SDKP: Synthesis, role in ACE inhibition, and its therapeutic potential in hypertension and cardiovascular diseases". Pharmacological Research. 134: 268–279. doi:10.1016/j.phrs.2018.07.006. PMID 29990624.
↑ Wang W, Jia W, Zhang C (October 2022). "The Role of Tβ4-POP-Ac-SDKP Axis in Organ Fibrosis". International Journal of Molecular Sciences. 23 (21) 13282. doi:10.3390/ijms232113282. PMC 9655242. PMID 36362069.
↑ Liu AD, Yang F (February 2023). "[Review on biological effects and mechanism of Ac-SDKP]". Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi = Zhonghua Laodong Weisheng Zhiyebing Zazhi = Chinese Journal of Industrial Hygiene and Occupational Diseases. 41 (2): 149–155. doi:10.3760/cma.j.cn121094-20220506-00238. PMID 36882283.

[1] Guigon M, Bonnet D (June 1995). "Inhibitory peptides in hematopoiesis". Experimental Hematology. 23 (6): 477–481. PMID 7768302.

[2] Cavasin MA (2006). "Therapeutic potential of thymosin-beta4 and its derivative N-acetyl-seryl-aspartyl-lysyl-proline (Ac-SDKP) in cardiac healing after infarction". American Journal of Cardiovascular Drugs. 6 (5): 305–311. doi:10.2165/00129784-200606050-00003. PMID 17083265.

[3] Sosne G, Qiu P, Goldstein AL, Wheater M (July 2010). "Biological activities of thymosin beta4 defined by active sites in short peptide sequences". FASEB Journal. 24 (7): 2144–2151. doi:10.1096/fj.09-142307. PMID 20179146.

[4] Douglas RG, Ehlers MR, Sturrock ED (August 2013). "Antifibrotic peptide N-acetyl-Ser-Asp-Lys-Pro (Ac-SDKP): opportunities for angiotensin-converting enzyme inhibitor design". Clinical and Experimental Pharmacology & Physiology. 40 (8): 535–541. doi:10.1111/1440-1681.12062. PMID 23351021.

[5] Hrenak J, Paulis L, Simko F (2015). "N-acetyl-seryl-aspartyl-lysyl-proline (Ac-SDKP): Potential target molecule in research of heart, kidney and brain". Current Pharmaceutical Design. 21 (35): 5135–5143. doi:10.2174/1381612821666150909093927. PMID 26350537.

[6] Mnguni AT, Engel ME, Borkum MS, Mayosi BM (2015). "The Effects of Angiotensin Converting Enzyme Inhibitors (ACE-I) on Human N-Acetyl-Seryl-Aspartyl-Lysyl-Proline (Ac-SDKP) Levels: A Systematic Review and Meta-Analysis". PLOS ONE. 10 (12) e0143338. Bibcode:2015PLoSO..1043338M. doi:10.1371/journal.pone.0143338. PMC 4686106. PMID 26656271.

[7] Kumar N, Yin C (August 2018). "The anti-inflammatory peptide Ac-SDKP: Synthesis, role in ACE inhibition, and its therapeutic potential in hypertension and cardiovascular diseases". Pharmacological Research. 134: 268–279. doi:10.1016/j.phrs.2018.07.006. PMID 29990624.

[8] Wang W, Jia W, Zhang C (October 2022). "The Role of Tβ4-POP-Ac-SDKP Axis in Organ Fibrosis". International Journal of Molecular Sciences. 23 (21) 13282. doi:10.3390/ijms232113282. PMC 9655242. PMID 36362069.

[9] Liu AD, Yang F (February 2023). "[Review on biological effects and mechanism of Ac-SDKP]". Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi = Zhonghua Laodong Weisheng Zhiyebing Zazhi = Chinese Journal of Industrial Hygiene and Occupational Diseases. 41 (2): 149–155. doi:10.3760/cma.j.cn121094-20220506-00238. PMID 36882283.

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Ac-SDKP

See also

References