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Dynorphin (1-17)

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Dynorphin A is a heptadecapeptide derived from the cleavage of prodynorphin and found widely distributed in the central nervous system. It acts as an endogenous kappa receptor agonist with nanomolar binding affinity. It also activates the human novel opioid receptor-like receptor of ORL1. It is resistant to enzymatic degradation and may have antinociceptive functions.

Category

Peptide Inhibitors

Catalog number

BAT-010034

CAS number

80448-90-4

Molecular Formula

C99H155N31O23

Molecular Weight

2147.51

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[[(2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxy-3-phenylpropylidene]amino]-1-hydroxy-4-methylpentylidene]amino]-5-carbamimidamido-1-hydroxypentylidene]amino]-5-carbamimidamido-1-hydroxypentylidene]amino]-1-hydroxy-3-methylpentylidene]amino]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]-hydroxymethylidene]amino]-1-hydroxyhexylidene]amino]-1-hydroxy-4-methylpentylidene]amino]-1-hydroxyhexylidene]amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino]-3-carboxy-1-hydroxypropylidene]amino]-1,4-dihydroxy-4-iminobutylidene]amino]-5-hydroxy-5-iminopentanoic acid

Synonyms

Dynorphin A (swine); Dynorphin A (pig); 1-17-Dynorphin; L-Glutamine, L-tyrosylglycylglycyl-L-phenylalanyl-L-leucyl-L-arginyl-L-arginyl-L-isoleucyl-L-arginyl-L-prolyl-L-lysyl-L-leucyl-L-lysyl-L-tryptophyl-L-α-aspartyl-L-asparaginyl-; Dyn-A17; Dynorphin 17; Dynorphin A; Dynorphin A (1-17); Dynorphin A (human); Dynorphin A (porcine); Dynorphin A (rat); Dynorphin A 1-17; Dynorphin-A (Bos taurus); Porcine dynorphin (1-17); Porcine dynorphin A (1-17); Proteins, Dyn-A17; Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Ile-Arg-Pro-Lys-Leu-Lys-Trp-Asp-Asn-Gln

Related CAS

88161-22-2 (Deleted CAS)

Purity

≥95%

Density

1.46±0.1 g/cm3

Sequence

YGGFLRRIRPKLKWDNQ

Storage

Store at -20°C

Solubility

Soluble in DMSO

InChI

InChI=1S/C99H155N31O23/c1-7-55(6)81(129-86(142)66(28-18-40-112-98(107)108)118-83(139)65(27-17-39-111-97(105)106)120-88(144)70(44-54(4)5)125-89(145)71(46-56-21-9-8-10-22-56)117-79(135)52-115-78(134)51-116-82(138)61(102)45-57-31-33-59(131)34-32-57)94(150)122-67(29-19-41-113-99(109)110)95(151)130-42-20-30-75(130)93(149)121-64(26-14-16-38-101)85(141)124-69(43-53(2)3)87(143)119-63(25-13-15-37-100)84(140)126-72(47-58-50-114-62-24-12-11-23-60(58)62)90(146)128-74(49-80(136)137)92(148)127-73(48-77(104)133)91(147)123-68(96(152)153)35-36-76(103)132/h8-12,21-24,31-34,50,53-55,61,63-75,81,114,131H,7,13-20,25-30,35-49,51-52,100-102H2,1-6H3,(H2,103,132)(H2,104,133)(H,115,134)(H,116,138)(H,117,135)(H,118,139)(H,119,143)(H,120,144)(H,121,149)(H,122,150)(H,123,147)(H,124,141)(H,125,145)(H,126,140)(H,127,148)(H,128,146)(H,129,142)(H,136,137)(H,152,153)(H4,105,106,111)(H4,107,108,112)(H4,109,110,113)/t55-,61-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,81-/m0/s1

InChI Key

JMNJYGMAUMANNW-FIXZTSJVSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)N)C(=O)NC(CCC(=O)N)C(=O)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CC4=CC=CC=C4)NC(=O)CNC(=O)CNC(=O)C(CC5=CC=C(C=C5)O)N

1.Reduced kappa-opioid activity in a rat model of cholestasis.

Inan S;Cowan A Eur J Pharmacol. 2005 Aug 22;518(2-3):182-6.

Increased endogenous opioid activity has been implicated in cholestatic pruritus. In the present study, we have further defined the involvement of opioids in cholestasis. Rats underwent either bile duct ligation or a sham operation. Five days after surgery, brains were removed and agonist-stimulated [35S]GTPgammaS binding was measured in ten brain regions. Serum endomorphin-2, leu-enkephalin and dynorphin A levels were measured using ELISA on day five. Microdialysis to the dorsal hypothalamic area was conducted in the same animal before and after cholestasis. Dialysate endomorphin-1, leu-enkephalin and dynorphin A levels also were measured. Delta- and kappa-stimulated binding was significantly decreased in cholestasic animals compared to controls in the dorsal hypothalamic area. The serum dynorphin A level was lower in the cholestasic group than in controls (2.56+/-0.09 and 3.29+/-0.22 ng/ml, respectively, P<0.01). We propose that pruritus in cholestasis may result from an impaired balance between mu- and kappa-opioid systems.

2.Dynorphin modulates ocular hydrodynamics and releases atrial natriuretic peptide via activation of kappa-Opioid receptors.

Russell KR;Potter DE Exp Eye Res. 2002 Sep;75(3):259-70.

The present study was designed to investigate the effect of the kappa opioid receptor (KOR) agonist, dynorphin A (Dyn), on aqueous humor dynamics (intraocular pressure (IOP), aqueous humor flow rate (AFR)), pupil diameter (PD) and atrial natriuretic peptide (ANP) levels in the aqueous humor of the rabbit. Topical and unilateral application of Dyn caused dose-related, bilateral reductions in IOP and AFR. An intermediate dose of Dyn (33 microg) caused bilateral mydriasis whereas a higher dose (100 microg) caused unilateral miosis. The Dyn-induced reduction in IOP and aqueous flow rate as well as the mydriasis were antagonized by nor-binaltorphimine (nor-BNI), a relatively selective KOR antagonist. In addition to the effects on IOP, PD and AFR, Dyn caused dose-related increases in aqueous ANP levels that was attenuated by nor-BNI. The present study indicates that Dyn reduces IOP, in part, by reducing AFR. Moreover, the increase in ANP levels could be involved in the Dyn-induced reductions in IOP and AFR. Based upon the inhibitory effects of nor-BNI, these Dyn-induced events are due, in part, to the activation of KORs in the ciliary processes of the eye.

3.Separation of dynorphin peptides by capillary electrochromatography using a polydiallyldimethylammonium chloride gold nanoparticle-modified capillary.

Al-Hossaini AM;Suntornsuk L;Lunte SM Electrophoresis. 2016 Sep;37(17-18):2297-304. doi: 10.1002/elps.201600006. Epub 2016 Jun 16.

Dynorphin A (Dyn A) is an endogenous opioid peptide found in blood and central nervous system tissue at very low concentrations. Elevated levels of Dyn A due to different disease states, for example neurodegenerative disease, have been linked to toxic nonopioid activity. CE is a powerful technique that can achieve high-efficiency separations of charged analytes. However, CE has limited use for the analysis of basic proteins and peptides, due to their adsorption onto the inner surface of the fused silica at pHs below their pI. This adsorption can lead to a loss of efficiency, irreproducibility of migration times, and peak tailing. To obviate this problem, a polydiallyldimethylammonium chloride-stabilized gold nanoparticle-coated capillary was investigated for the separation of dynorphin metabolites. The positively charged gold nanoparticles (GNP) minimized unwanted adsorption of the positively charged peptides onto the surface of the fused-silica capillary. Separation efficiency and resolution for opioid peptides Dyn A (1-6), Dyn A (1-7), Dyn A (1-8), Dyn A (1-11), and leu-enkephalin on the GNP-coated capillary column were evaluated under different experimental parameters. The best separation of Dyn A (1-17) and its fragments was achieved using a BGE that consists of 40 mM sodium acetate buffer (pH 5) containing 5% GNP, a field strength of -306 V/cm, and a 75 μm id capillary.