Eledoisin

Title: Eledoisin
CAS Registry Number: 69-25-0
Molecular Formula: C54H85N13O15S
Molecular Weight: 1188.40
Percent Composition: C 54.58%, H 7.21%, N 15.32%, O 20.19%, S 2.70%
Literature References: A hendecapeptide from the posterior salivary glands of eledone spp (small octopus spp): Anastasi, Erspamer, Br. J. Pharmacol. 19, 326 (1962); eidem, Experientia 18, 58 (1962). Synthesis: Sandrin, Boissonnas, ibid. 59; eidem, Helv. Chim. Acta 47, 1294 (1964); Lubke et al., Ann. 679, 195 (1964); GB 984810 (1965 to Farmitalia); solid-phase synthesis: P. G. Pietta et al., J. Org. Chem. 39, 44 (1974). Its physiologic action resembles that of the other tachykinins, substance P and physalaemin, q.q.v. Stimulates extravascular smooth muscle, acts as a potent vasodilator and hypotensive agent; in certain species causes salivation, and increases capillary permeability. Pharmacology: Erspamer, Erspamer, Br. J. Pharmacol. 19, 337 (1962); Sicuteri et al., Experientia 19, 44 (1963); G. Bertaccini, Pharmacol. Rev. 28, 127 (1976). Review: Erdös, Adv. Pharmacol. 4, 64-72 (1966).
Derivative Type: Sesquihydrate
Properties: Powder, dec 230°. [a]D22 -44° (c = 1 in 95% acetic acid). Slowly loses activity when incubated in blood.
Optical Rotation: [a]D22 -44° (c = 1 in 95% acetic acid)
Derivative Type: Trifluoroacetate
CAS Registry Number: 10129-92-7
Trademarks: Eloisin (Farmitalia)
Molecular Formula: C54H85N13O15S.C2HF3O2
Molecular Weight: 1302.42
Percent Composition: C 51.64%, H 6.66%, N 13.98%, O 20.88%, S 2.46%, F 4.38%
Therap-Cat: Hypotensive; stimulator of lacrimal secretion.
Keywords: Vasodilator (Peripheral).
Elenolide Eletriptan Eleutherobin Elgodipine Ellagic Acid

Eledoisin
Eledoisin skeletal.svg
PDB 1mxq EBI.jpg
Identifiers
PubChem 10328936
ChemSpider 6006
ChEMBL CHEMBL373569
Jmol-3D images Image 1
Properties
Molecular formula C54H85N13O15S
Molar mass 1188.40 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Eledoisin is an undecapeptide of mollusk origin, belonging to the tachykinin family of neuropeptides.

It was first isolated from the posterior salivary glands of two mollusk species Eledone muschata and Eledone aldovandi, which belong to the octopod order of Cephalopoda. [1]

Other tachykinins from nonmammalian sources include kassinin and physalaemin. The mammalian tachykinins substance P, NKA, and NKB have similar effects as tachykinins of nonmammals and have been more widely studied and characterized. These peptides exhibit a wide and complex spectrum of pharmacological and physiological activities such as vasodilation, hypertension, and stimulation of extravascular smooth muscle.[2]

Eledoisin has the amino acid sequence pGlu-Pro-Ser-Lys-Asp-Ala-Phe-Ile-Gly-Leu-Met-NH. Like all tachykinin peptides, Eledoisin shares the same consensus C-terminal sequence, that is, Phe-Xxx-Gly-Leu-Met-NH. The invariant "Phe7" residue is probably required for receptor binding. "Xxx" is either an aromatic (phenylalanine, tyrosine) or a branched aliphatic (valine, isoleucine) side chain and is thought to be important in receptor selectivity. This common region, often referred to as the "message domain," is believed to be responsible for activating the receptor. The divergent N-terminal region or the "address domain" varies in amino-acid sequence and length and is believed to play a role in determining the receptor subtype specificity. [3]