Anaritide

Anaritide (also known as human atrial natriuretic peptide [102-126])[1] is a synthetic analogue of atrial natriuretic peptide[2] (ANP).

Anaritide
Tertiary structure of Anaritide
Identifiers
  • L-arginyl-L-seryl-L-seryl-L-cysteinyl-L-phenylalanyl-glycyl-glycyl-L-arginyl-L-methionyl-L-alpha-aspartyl-L-arginyl-L-isoleucyl-glycyl-L-alanyl-L-glutaminyl-L-seryl-glycyl-L-leucyl-glycyl-L-cysteinyl-L-asparagyl-L-seryl-L-phenylalanyl-L-arginyl-L-tyrosine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC112H177N39O35S3
Molar mass2726.07 g·mol−1
3D model (JSmol)
  • CCC(C)C(C(=O)NCC(=O)NC(C)C(=O)NC(CCC(=O)N)C(=O)NC(CO)C(=O)NCC(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CS)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(=O)O)NC(=O)C(CCSC)NC(=O)C(CCCNC(=N)N)NC(=O)CNC(=O)CNC(=O)C(CC3=CC=CC=C3)NC(=O)C(CS)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CCCNC(=N)N)N
  • InChI=1S/C112H177N39O35S3/c1-7-56(4)88(151-98(175)65(25-17-36-127-112(122)123)139-101(178)72(43-87(164)165)144-97(174)67(32-37-189-6)140-94(171)63(23-15-34-125-110(118)119)134-84(161)45-128-82(159)44-129-92(169)69(39-58-18-10-8-11-19-58)141-106(183)79(54-188)150-104(181)77(52-155)149-103(180)75(50-153)146-90(167)62(113)22-14-33-124-109(116)117)107(184)132-46-83(160)133-57(5)89(166)137-66(30-31-80(114)157)96(173)147-74(49-152)93(170)131-47-85(162)135-68(38-55(2)3)91(168)130-48-86(163)136-78(53-187)105(182)143-71(42-81(115)158)100(177)148-76(51-154)102(179)142-70(40-59-20-12-9-13-21-59)99(176)138-64(24-16-35-126-111(120)121)95(172)145-73(108(185)186)41-60-26-28-61(156)29-27-60/h8-13,18-21,26-29,55-57,62-79,88,152-156,187-188H,7,14-17,22-25,30-54,113H2,1-6H3,(H2,114,157)(H2,115,158)(H,128,159)(H,129,169)(H,130,168)(H,131,170)(H,132,184)(H,133,160)(H,134,161)(H,135,162)(H,136,163)(H,137,166)(H,138,176)(H,139,178)(H,140,171)(H,141,183)(H,142,179)(H,143,182)(H,144,174)(H,145,172)(H,146,167)(H,147,173)(H,148,177)(H,149,180)(H,150,181)(H,151,175)(H,164,165)(H,185,186)(H4,116,117,124)(H4,118,119,125)(H4,120,121,126)(H4,122,123,127)/t56-,57-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,88-/m0/s1
  • Key:PBSXKCQOTWYLMQ-LWECRCKRSA-N

Structure

Anartidine has the following primary structure:[3]

RSSCFGGRMDRIGAQSGLGCNSFRY

or

H-Arg-Ser-Ser-Cys-Phe-Gly-Gly-Arg-Met-Asp-Arg-Ile-Gly-Ala-Gln-Ser-Gly-Leu-Gly-Cys-Asn-Ser-Phe-Arg-Tyr-OH

This structure is identical to residues 102-126 of human preproANP.[1][4] In comparison, active human ANP comprises resides 99-126 of human preproANP.[5]

Medical uses

Anaritide has been investigated as a potential therapy for acute tubular necrosis but was shown not to improve the dialysis-free survival of these patients.[2] It also appears to exacerbate proteinuria and natriuresis in patients with nephrotic syndrome.[6]

References
  1. Engleback, I. M.; Lappe, R. W.; Hand, J. M. (1988-07-22). "Bronchoprotective and bronchodilator activity of anaritide (human atrial natriuretic factor [102–126]) infusion in the anesthetized guinea pig". Pulmonary Pharmacology. 1 (3): 119–123. doi:10.1016/S0952-0600(88)80009-7. PMID 2980981.
  2. Allgren, Robin L (1997-03-20). "Anaritide in Acute Tubular Necrosis". The New England Journal of Medicine. 336 (12): 828–834. doi:10.1056/NEJM199703203361203. PMID 9062091.
  3. Sato, M.; Anno, I.; Yamaguchi, M.; Iida, H.; Orii, K. (2006). "Anaritide compound summary". CardioVascular and Interventional Radiology. 29 (3): 432–434. doi:10.1007/s00270-005-0036-x. PMID 16132382.
  4. Yandle, Tim; Crozier, Ian; Nicholls, Gary; Espiner, Eric; Carne, Alan; Brennan, Stephen (1987-07-31). "Amino acid sequence of atrial natriuretic peptides in human coronary sinus plasma". Biochemical and Biophysical Research Communications. 146 (2): 832–839. doi:10.1016/0006-291X(87)90606-1. PMID 2956952.
  5. Rosenzweig, Anthony; Seidman, Christine E. (1991). "Atrial Natriuretic Factor and Related Peptide Hormones". Annual Review of Biochemistry. 60: 229–255. doi:10.1146/annurev.bi.60.070191.001305. PMID 1652921.
  6. Zietse, Robert; Schalekamp, Maarten A. (November 1988). "Effect of synthetic human atrial natriuretic peptide (102-126) in nephrotic syndrome". Kidney International. 34 (5): 717–724. doi:10.1038/ki.1988.238. PMID 2974095.
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