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Scyliorhinin II

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Scyliorhinin II, a cyclic Tachykinin peptide, is a potent NK3 receptor agonist.

Category

Peptide Inhibitors

Catalog number

BAT-009341

CAS number

112748-19-3

Molecular Formula

C77H119N21O26S3

Molecular Weight

1851.09

Specification
Reference Reading

IUPAC Name

2-[15-[[6-amino-2-[[2-[[4-amino-2-[[2-[[1-(2-amino-3-hydroxypropanoyl)pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-20-[[1-[[1-[[2-[[1-[(1-amino-4-methylsulfanyl-1-oxobutan-2-yl)amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]-23-(carboxymethyl)-2,5,8,14,22,25-hexaoxo-17,18-dithia-1,4,7,13,21,24-hexazatricyclo[24.3.0.09,13]nonacosan-6-yl]acetic acid

Synonyms

L-Methioninamide, L-seryl-L-prolyl-L-seryl-L-asparaginyl-L-seryl-L-lysyl-L-cysteinyl-L-prolyl-L-α-aspartylglycyl-L-prolyl-L-α-aspartyl-L-cysteinyl-L-phenylalanyl-L-valylglycyl-L-leucyl-, cyclic(7→13)-disulfide; Ser-Pro-Ser-Asn-Ser-Lys-Cys-Pro-Asp-Gly-Pro-Asp-Cys-Phe-Val-Gly-Leu-Met-NH2

Appearance

White or Off-white Lyophilized Powder

Purity

≥98%

Density

1.47±0.1 g/cm3

Boiling Point

2202.7±65.0 °C at 760 mmHg

Sequence

SPSNSKCPDGPDCFVGLM

Storage

Store at -20°C

Solubility

Soluble in DMSO

InChI

InChI=1S/C77H119N21O26S3/c1-38(2)26-44(65(112)85-42(62(81)109)20-25-125-5)84-57(103)31-82-75(122)61(39(3)4)95-68(115)45(27-40-14-7-6-8-15-40)87-71(118)51-36-126-127-37-52(77(124)98-24-13-19-55(98)73(120)89-47(29-59(105)106)63(110)83-32-58(104)96-22-11-17-53(96)72(119)90-48(30-60(107)108)67(114)93-51)94-64(111)43(16-9-10-21-78)86-69(116)49(34-100)91-66(113)46(28-56(80)102)88-70(117)50(35-101)92-74(121)54-18-12-23-97(54)76(123)41(79)33-99/h6-8,14-15,38-39,41-55,61,99-101H,9-13,16-37,78-79H2,1-5H3,(H2,80,102)(H2,81,109)(H,82,122)(H,83,110)(H,84,103)(H,85,112)(H,86,116)(H,87,118)(H,88,117)(H,89,120)(H,90,119)(H,91,113)(H,92,121)(H,93,114)(H,94,111)(H,95,115)(H,105,106)(H,107,108)/t41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,61-/m0/s1

InChI Key

BIVHHUZLTJIRQO-UHFFFAOYSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(CCSC)C(=O)N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CC1=CC=CC=C1)NC(=O)C2CSSCC(C(=O)N3CCCC3C(=O)NC(C(=O)NCC(=O)N4CCCC4C(=O)NC(C(=O)N2)CC(=O)O)CC(=O)O)NC(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C(CC(=O)N)NC(=O)C(CO)NC(=O)C5CCCN5C(=O)C(CO)N

1. Scyliorhinin I and II: two novel tachykinins from dogfish gut

C F Deacon, L Thim, L O'Toole, J M Conlon FEBS Lett . 1986 May 5;200(1):111-6. doi: 10.1016/0014-5793(86)80521-x.

Two peptides with tachykinin-like ability to contract longitudinal muscle from the guinea pig ileum were isolated from the intestine of the common dogfish, Scyliorhinus caniculus. The amino acid sequence of scyliorhinin I was established as Ala-Lys-Phe-Asp-Lys-Phe-Tyr-Gly-Leu-Met-NH2 and this peptide cross-reacted with antisera directed against the C-terminal region fo substance P. The amino acid sequence of scyliorhinin II was established as Ser-Pro-Ser-Asn-Ser-Lys-Cys-Pro-Asp-Gly-Pro-Asp-Cys-Phe-Val-Gly-Leu-Met- NH2 and this peptide cross-reacted with antisera directed against the C-terminal region of neurokinin A. The mammalian peptides substance P and neurokinin A were absent from the dogfish intestinal tissue.

2. Isolation of the tachykinin, des[Ser1Pro2]scyliorhinin II from the intestine of the ray, Torpedo marmorata

L Thim, J M Conlon Gen Comp Endocrinol . 1988 Sep;71(3):383-8. doi: 10.1016/0016-6480(88)90266-3.

A peptide with neurokinin A-like immunoreactivity was isolated from an extract of the intestine of an elasmobranch fish, Torpedo marmorata. The primary structure of the peptide was established as Ser-Asn-Ser-Lys-Cys-Pro-Asp-Gly-Pro-Asp-Cys-Phe-Val-Gly-Leu-Met.NH2. This amino acid sequence is identical to that of residues (3-18) of scyliorhinin II previously isolated from the intestine of the common dogfish (Scyliorhinus canicula). The presence of the truncated peptide, lacking Ser-Pro, in the Torpedo gut suggests that scyliorhinin II may be a substrate for an enzyme with dipeptidylpeptidase IV-like specificity. The data support previous assertions that strong evolutionary pressure has acted within the elasmobranch subclass of chondrichthyean fish to conserve the structures of regulatory peptides.

3. Binding sites for tachykinin peptides in the brain and stomach of the dogfish, Scyliorhinus canicula

S H Buck, J M Conlon, P L Van Giersbergen Peptides . 1991 Sep-Oct;12(5):1161-3. doi: 10.1016/0196-9781(91)90075-z.

In membranes of dogfish brain and stomach, two binding sites for tachykinins were identified. One site specifically bound [125I]-Bolton-Hunter substance P (BH-SP) and the rank potency of tachykinins to compete for BH-SP binding revealed similarities with the rank potency of an NK1 receptor. The pharmacology of the other site, which specifically bound [125I]-Bolton-Hunter scyliorhinin II (BH-Scy II), did not resemble any of the mammalian tachykinin receptors. The rank potency to inhibit BH-Scy II binding to this second site was: scyliorhinin II approximately scyliorhinin I greater than eledoisin approximately substance P approximately neurokinin A greater than phyllomedusin approximately physalaemin greater than [Sar9Met(O2)11]substance P. Neurokinin B and senktide did not displace BH-Scy II binding. In addition, nucleotide analogues inhibited BH-SP binding but not BH-Scy II binding. Our binding data suggest the existence of a mammalian-like NK1 receptor and of a nonmammalian tachykinin receptor in the dogfish.