Eledoisin

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

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Eledoisin(CAS 69-25-0)

CAT No: 10-101-53

CAS No:69-25-0

Synonyms/Alias:ELEDOISIN;Eledone peptide;69-25-0;Eledoisina;Eledoisine;Eledoisinum;ELD 950;Eledoisin [INN];ELD-950;Eledoisine [INN-French];Eledoisina [INN-Spanish];FI 6225 TF/Ocoa;Eledoisin (INN);UNII-OKY3285J18;DTXSID1046926;Eledoisin Acetate;BRN 4796573;CHEMBL373569;DTXCID9026926;OKY3285J18;Eledoisine (INN-French);Eledoisina (INN-Spanish);ELEDOISIN (MART.);ELEDOISIN [MART.];5-Oxo-L-prolyl-L-prolyl-L-seryl-L-lysyl-L-aspartyl-L-alanyl-L-phenylalanyl-L-isoleucylglycyl-L-leucyl-L-methioninamide;5-oxo-L-prolyl-L-prolyl-L-seryl-L-lysyl-L-alpha-aspartyl-L-alanyl-L-phenylalanyl-L-isoleucylglycyl-L-leucyl-L-methioninamide;ELEDOISIN [MI];ELEDOISIN [WHO-DD];SCHEMBL158143;pGlu-Pro-Ser-Lys-Asp-Ala-Phe-Ile-Gly-Leu-Met-NH2;GTPL2086;CHEBI:135903;Tox21_112815;BDBM50194558;AKOS024456851;CAS-69-25-0;NCGC00167276-01;NTOC00000202-01;C20029;D07936;Q5358600;5-OXOPRO-PRO-SER-LYS-ASP-ALA-PHE-ILE-GLY-LEU-MET-NH2;

Chemical Name:(3S)-3-[[(2S)-6-amino-2-[[(2S)-3-hydroxy-2-[[(2S)-1-[(2S)-5-oxopyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]propanoyl]amino]hexanoyl]amino]-4-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[2-[[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoic acid

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cGMP Peptide
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M.F/Formula
C54H85N13O15S
M.W/Mr.
1188.4
Sequence
One Letter Code:XPSKDAFIGLM
Three Letter Code:H-Pyr-Pro-Ser-Lys-Asp-Ala-Phe-Ile-Gly-Leu-Met-NH2
Labeling Target
Substance-P receptor;
Neuromedin-K receptor
Application
Eledoisin exhibits a wide and complex spectrum of pharmacological and physiological activities such as vasodilation, hypertension, and stimulation of extravascular smooth muscle.
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Areas of Interest
Cardiovascular System & Diseases
Pituitary & Hypothalamic Hormones
Source#
Synthetic
Long-term Storage Conditions
Soluble in DMSO, not in water
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage Conditions
Dry, dark and at 0 - 4 °C
Solubility
-20 °C
InChI
InChI=1S/C54H85N13O15S/c1-7-30(4)44(53(81)57-27-42(70)60-36(24-29(2)3)49(77)61-33(45(56)73)20-23-83-6)66-50(78)37(25-32-14-9-8-10-15-32)63-46(74)31(5)58-48(76)38(26-43(71)72)64-47(75)34(16-11-12-21-55)62-51(79)39(28-68)65-52(80)40-17-13-22-67(40)54(82)35-18-19-41(69)59-35/h8-10,14-15,29-31,33-40,44,68H,7,11-13,16-28,55H2,1-6H3,(H2,56,73)(H,57,81)(H,58,76)(H,59,69)(H,60,70)(H,61,77)(H,62,79)(H,63,74)(H,64,75)(H,65,80)(H,66,78)(H,71,72)/t30-,31-,33-,34-,35-,36-,37-,38-,39-,40-,44-/m0/s1
InChI Key
AYLPVIWBPZMVSH-FCKMLYJASA-N
Canonical SMILES
CCC(C)C(C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(CCSC)C(=O)N)NC(=O)C(CC1=CC=CC=C1)NC(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C2CCCN2C(=O)C3CCC(=O)N3
Isomeric SMILES
CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]3CCC(=O)N3
BoilingPoint
1618.1±65.0 °C at 760 mmHg
ShelfLife
>2 years if stored properly
References

At the end of therapy it was possible to match the beneficial effects of eye drops with carnitin, taurine, sodium hyaluronate and eledoisin. In fact, after 15days of treatment, patients of group 1 showed a decrease of approximately 50% concerning the severity of symptoms and a significant improvement of the tests valued.

Nebbioso, M., Evangelista, M., Librando, A., Plateroti, A. M., & Pescosolido, N. (2013). Iatrogenic dry eye disease: an eledoisin/carnitine and osmolyte drops study. Biomedicine & Pharmacotherapy, 67(7), 659-663.

Both the aqueous and the lipid-induced structure of eledoisin, an undecapeptide of mollusk origin, have been studied by two-dimensional proton nuclear magnetic resonance spectroscopy and distance geometry calculations. Unambiguous nuclear magnetic resonance assignments of protons have been made with the aid of correlation spectroscopy experiments and nuclear Overhauser effect spectroscopy experiments. The distance constraints obtained from the nuclear magnetic resonance data have been utilized in a distance geometry algorithm to generate a family of structures, which have been refined using restrained energy minimization and dynamics.

Grace, R. C. R., Chandrashekar, I. R., & Cowsik, S. M. (2003). Solution structure of the tachykinin peptide eledoisin. Biophysical journal, 84(1), 655-664.

The tachykinin peptide family certainly represents one of the largest peptide families described in the animal organism. So far, more than 40 tachykinins have been isolated from invertebrate (insects, worms, and molluscs), protochordate, and vertebrate (skin, gastrointestinal tract, peripheral and central nervous system) tissues. Substance P (SP), first identified by bioassay as early as 1931 but sequenced only in 1971, several years after the elucidation of the structure of eledoisin from molluscan tissues and of physalaemin from amphibian skin, may be considered as a prototype of the tachykinins.

Severini, C., Improta, G., Falconieri-Erspamer, G., Salvadori, S., & Erspamer, V. (2002). The tachykinin peptide family. Pharmacological reviews, 54(2), 285-322.

Melting Point
N/A

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