Corticotropin-like intermediate peptide

Corticotropin-like intermediate [lobe] peptide (CLIP), also known as adrenocorticotropic hormone fragment 18-39 (ACTH(18-39)), is a naturally occurring, endogenous neuropeptide with a docosapeptide structure and the amino acid sequence Arg-Pro-Val-Lys-Val-Tyr-Pro-Asn-Gly-Ala-Glu-Asp-Glu-Ser-Ala-Glu-Ala-Phe-Pro-Leu-Glu-Phe. CLIP is generated as a proteolyic cleavage product of adrenocorticotropic hormone (ACTH),[1][2] which in turn is a cleavage product of proopiomelanocortin (POMC).[3] Its physiological role has been investigated in various tissues,[4][5] specifically in the central nervous system.[6][7][8][9][10]

pro-opiomelanocortin
Identifiers
SymbolPOMC
NCBI gene5443
HGNC9201
OMIM176830
RefSeqNM_000939
UniProtP01189
Other data
LocusChr. 2 p23
Search for
StructuresSwiss-model
DomainsInterPro
Corticotropin-like intermediate peptide
Names
IUPAC name
L-arginyl-L-prolyl-L-valyl-L-lysyl-L-valyl-L-tyrosyl-L-prolyl-L-asparaginyl-L-glycyl-L-alanyl-L-α-glutamyl-L-α-aspartyl-L-α-glutamyl-L-seryl-L-alanyl-L-α-glutamyl-L-alanyl-L-phenylalanyl-L-prolyl-L-leucyl-L-α-glutamyl-L-phenylalanine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C112H165N27O36/c1-56(2)48-72(100(163)125-70(37-41-86(148)149)97(160)133-77(111(174)175)51-63-24-14-11-15-25-63)129-103(166)79-28-20-46-138(79)109(172)75(49-62-22-12-10-13-23-62)131-93(156)61(9)121-95(158)68(35-39-84(144)145)123-92(155)60(8)122-102(165)78(55-140)134-98(161)71(38-42-87(150)151)126-101(164)74(53-88(152)153)128-96(159)69(36-40-85(146)147)124-91(154)59(7)120-83(143)54-119-94(157)73(52-82(115)142)130-104(167)80-29-21-47-139(80)110(173)76(50-64-31-33-65(141)34-32-64)132-107(170)89(57(3)4)135-99(162)67(27-16-17-43-113)127-106(169)90(58(5)6)136-105(168)81-30-19-45-137(81)108(171)66(114)26-18-44-118-112(116)117/h10-15,22-25,31-34,56-61,66-81,89-90,140-141H,16-21,26-30,35-55,113-114H2,1-9H3,(H2,115,142)(H,119,157)(H,120,143)(H,121,158)(H,122,165)(H,123,155)(H,124,154)(H,125,163)(H,126,164)(H,127,169)(H,128,159)(H,129,166)(H,130,167)(H,131,156)(H,132,170)(H,133,160)(H,134,161)(H,135,162)(H,136,168)(H,144,145)(H,146,147)(H,148,149)(H,150,151)(H,152,153)(H,174,175)(H4,116,117,118)/t59-,60-,61-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,89-,90-/m0/s1
    Key: ZYDMZKPAPSZILB-WKNDHWIVSA-N
  • Key: ZYDMZKPAPSZILB-UHFFFAOYAN
SMILES
  • C[C@@H](C(=N[C@@H](CCC(=O)O)C(=N[C@@H](CC(=O)O)C(=N[C@@H](CCC(=O)O)C(=N[C@@H](CO)C(=N[C@@H](C)C(=N[C@@H](CCC(=O)O)C(=N[C@@H](C)C(=N[C@@H](CC1=CC=CC=C1)C(=O)N2CCC[C@H]2C(=N[C@@H](CC(C)C)C(=N[C@@H](CCC(=O)O)C(=N[C@@H](CC3=CC=CC=C3)C(=O)O)O)O)O)O)O)O)O)O)O)O)O)N=C(CN=C([C@H](CC(=N)O)N=C([C@@H]4CCCN4C(=O)[C@H](CC5=CC=C(C=C5)O)N=C([C@H](C(C)C)N=C([C@H](CCCCN)N=C([C@H](C(C)C)N=C([C@@H]6CCCN6C(=O)[C@H](CCCNC(=N)N)N)O)O)O)O)O)O)O
Properties
Chemical formula
 C112H165N27O36
Molar mass 2465.705 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It has been suggested to function as an insulin secretagogue in the pancreas.[11]

References
  1. Gianoulakis C, Seidah NG, Routhier R, Chrétien M (December 1979). "Biosynthesis and characterization of adrenocorticotropic hormone, alpha-melanocyte-stimulating hormone, and an NH2-terminal fragment of the adrenocorticotropic hormone/beta-lipotropin precursor from rat pars intermedia". The Journal of Biological Chemistry. 254 (23): 11903–6. doi:10.1016/S0021-9258(19)86402-5. PMID 227883.
  2. Lloyd D. Fricker (24 July 1991). Peptide biosynthesis and processing. CRC Press. p. 78. ISBN 978-0-8493-8852-1. Retrieved 25 November 2011.
  3. Anthony W. Norman; Gerald Litwack (26 September 1997). Hormones. Academic Press. pp. 12. ISBN 978-0-12-521441-4. Retrieved 25 November 2011.
  4. Marshall JB, Kapcala LP, Manning LD, McCullough AJ (November 1984). "Effect of corticotropin-like intermediate lobe peptide on pancreatic exocrine function in isolated rat pancreatic lobules". The Journal of Clinical Investigation. 74 (5): 1886–9. doi:10.1172/JCI111608. PMC 425369. PMID 6209301.
  5. Zaphiropoulos A, Charnay Y, Vallet P, Constantinidis J, Bouras C (January 1991). "Immunohistochemical distribution of corticotropin-like intermediate lobe peptide (CLIP) immunoreactivity in the human brain". Brain Research Bulletin. 26 (1): 99–111. doi:10.1016/0361-9230(91)90194-O. PMID 1849784. S2CID 556547.
  6. Shojiro Inoué; Shojiro Inoué (1989). Biology of sleep substances. CRC Press. p. 136. ISBN 978-0-8493-4822-8. Retrieved 25 November 2011.
  7. Chastrette N, Cespuglio R, Jouvet M (February 1990). "Proopiomelanocortin (POMC)-derived peptides and sleep in the rat. Part 1--Hypnogenic properties of ACTH derivatives". Neuropeptides. 15 (2): 61–74. doi:10.1016/0143-4179(90)90042-w. PMID 1981927. S2CID 41264103.
  8. Chastrette N, Cespuglio R, Lin YL, Jouvet M (February 1990). "Proopiomelanocortin (POMC)-derived peptides and sleep in the rat. Part 2--Aminergic regulatory processes". Neuropeptides. 15 (2): 75–88. doi:10.1016/0143-4179(90)90043-x. PMID 1964203. S2CID 13731355.
  9. Grigoriev VV, Petrova LN, Ivanova TA, Gabreliyan AV, Serkova TP (March 2009). "Effect of corticotropin-like intermediate lobe peptide on presynaptic and postsynaptic glutamate receptors and postsynaptic GABA receptors in rat brain". Bulletin of Experimental Biology and Medicine. 147 (3): 319–22. doi:10.1007/s10517-009-0499-x. PMID 19529852. S2CID 29237407.
  10. Seidenbecher T, Balschun D, Vogel D, Reymann KG (1993). "Neuronal transmission of hippocampal CA1 neurones is modulated by corticotropin-like intermediate lobe peptide [CLIP; ACTH(18-39)]". Peptides. 14 (6): 1221–4. doi:10.1016/0196-9781(93)90179-K. PMID 8134304. S2CID 7935999.
  11. Marshall, J. B.; Kapcala, L. P.; Manning, L. D.; McCullough, A. J. (November 1984). "Effect of corticotropin-like intermediate lobe peptide on pancreatic exocrine function in isolated rat pancreatic lobules". The Journal of Clinical Investigation. 74 (5): 1886–1889. doi:10.1172/JCI111608. ISSN 0021-9738. PMC 425369. PMID 6209301.
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