MedKoo Cat#: 574089 | Name: Eledoisin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eledoisin is an undecapeptide tachykinin that acts as a potent agonist of neurokinin receptors, especially NK1 and NK2, which mediate smooth muscle contraction and sensory neurotransmission. It binds these G protein-coupled receptors, activating phospholipase C and increasing intracellular calcium, leading to vasodilation, pain signaling, and muscle contraction. Isolated from the octopus Eledone moschata, eledoisin is widely used in research on neuropeptide signaling, inflammation, and pain.

Chemical Structure

Eledoisin
Eledoisin
CAS#69-25-0 (free base)

Theoretical Analysis

MedKoo Cat#: 574089

Name: Eledoisin

CAS#: 69-25-0 (free base)

Chemical Formula: C54H85N13O15S

Exact Mass: 1187.6009

Molecular Weight: 1188.41

Elemental Analysis: C, 54.58; H, 7.21; N, 15.32; O, 20.19; S, 2.70

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 Weeks
10mg USD 600.00 2 Weeks
25mg USD 1,000.00 2 Weeks
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Related CAS #
69-25-0 (free base) 16679-58-6 (free base) 62357-86-2 (acetate trihydrate); Eledoisin acetate
Synonym
Eledoisin, ELD 950, ELD950, ELD-950, Moschatin; Eledone peptide; Eledoisinum; Eledoisina; Eledoisine
IUPAC/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
InChi Key
AYLPVIWBPZMVSH-FCKMLYJASA-N
InChi Code
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
SMILES Code
O=C([C@H]1N(C([C@H]2NC(CC2)=O)=O)CCC1)N[C@@H](CO)C(N[C@@H](CCCCN)C(N[C@@H](CC(O)=O)C(N[C@@H](C)C(N[C@@H](CC3=CC=CC=C3)C(N[C@@H]([C@H](CC)C)C(NCC(N[C@@H](CC(C)C)C(N[C@@H](CCSC)C(N)=O)=O)=O)=O)=O)=O)=O)=O)=O
Appearance
A crystalline solid
Purity
>98% (or refer to the Certificate of Analysis)
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.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,188.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: STUERMER E, FANCHAMPS A. ELEDOISIN. CHEMIE, PHARMAKOLOGIE, KLINISCH- EXPERIMENTELLE UND VORLAEUFIGE THERAPEUTISCHE ERFAHRUNGEN [ELEDOISIN. CHEMISTRY, PHARMACOLOGY CLINICO-EXPERIMENTAL AND PRELIMINARY THERAPEUTICAL EXPERIENCES]. Dtsch Med Wochenschr. 1965 May 28;90:1012-20. German. doi: 10.1055/s-0028-1111460. PMID: 14286221. 2: SANDRIN E, BOISSONNAS RA. Synthesis of eledoisin. Experientia. 1962 Feb 15;18:59-61. doi: 10.1007/BF02138251. PMID: 14496888. 3: Erdös EG. Hypotensive peptides: bradykinin, kallidin, and eledoisin. Adv Pharmacol (1962). 1966;4:1-90. doi: 10.1016/s1054-3589(08)60097-6. PMID: 5333768. 4: Rossi SR, Dartt DA, Gilbard JP. Eledoisin and lacrimal secretion in the rabbit. Curr Eye Res. 1990 Mar;9(3):273-6. doi: 10.3109/02713689009044523. PMID: 2347204. 5: Beleslin DB. The action of eledoisin on the peristaltic reflex of guinea-pig isolated ileum. Br J Pharmacol. 1969 Sep;37(1):234-44. doi: 10.1111/j.1476-5381.1969.tb09540.x. PMID: 4390482; PMCID: PMC1703768. 6: Terragno NA, Malik KU, Nasjletti A, Terragno DA, McGiff JC. Renal prostaglandins. Adv Prostaglandin Thromboxane Res. 1976;2:561-71. PMID: 824936. 7: Erspamer V, Glaesser A. The action of eledoisin on the systemic arterial blood pressure of some experimental animals. Br J Pharmacol Chemother. 1963 Jun;20(3):516-27. doi: 10.1111/j.1476-5381.1963.tb01488.x. PMID: 19108179; PMCID: PMC1703815. 8: ANASTASI A, ERSPAMER V. Occurrence and some properties of eledoisin in extracts of posterior salivary glands of Eledone. Br J Pharmacol Chemother. 1962 Oct;19(2):326-36. doi: 10.1111/j.1476-5381.1962.tb01197.x. PMID: 14012711; PMCID: PMC1482152. 9: Ferreira SH, Vane JR. The disappearance of bradykinin and eledoisin in the circulation and vascular beds of the cat. Br J Pharmacol Chemother. 1967 Jun;30(2):417-24. doi: 10.1111/j.1476-5381.1967.tb02148.x. PMID: 6036419; PMCID: PMC1557274. 10: Nebbioso M, Evangelista M, Librando A, Plateroti AM, Pescosolido N. Iatrogenic dry eye disease: an eledoisin/carnitine and osmolyte drops study. Biomed Pharmacother. 2013 Sep;67(7):659-63. doi: 10.1016/j.biopha.2013.07.001. Epub 2013 Jul 12. PMID: 23906760. 11: Gascon AL. Influence of rat plasma and of various cations on the anti- eledoisin activity of morin. Br J Pharmacol. 1969 Jan;35(1):187-96. doi: 10.1111/j.1476-5381.1969.tb07979.x. PMID: 5762039; PMCID: PMC1703080. 12: Göbbels M, Selbach J, Spitznas M. Effect of eledoisin on tear volume and tear flow in humans as assessed by fluorophotometry. Graefes Arch Clin Exp Ophthalmol. 1991;229(6):549-52. doi: 10.1007/BF00203320. PMID: 1765297. 13: Fitzsimons JT, Evered MD. Eledoisin, substance P and related peptides: intracranial dipsogens in the pigeon and antidipsogens in the rat. Brain Res. 1978 Jul 21;150(3):533-42. doi: 10.1016/0006-8993(78)90818-1. PMID: 678989. 14: Massi M, Micossi LG, de Caro G, Epstein AN. Suppression of drinking but not feeding by central eledoisin and physalaemin in the rat. Appetite. 1986 Mar;7(1):63-70. doi: 10.1016/s0195-6663(86)80042-3. PMID: 3963799. 15: Katsoyannis P, Ginos JZ. Chemical synthesis of peptides. Annu Rev Biochem. 1969;38:881-912. doi: 10.1146/annurev.bi.38.070169.004313. PMID: 4308608. 16: Erspamer V, Erspamer GF. Pharmacological actions of eledoisin on extravascular smooth muscle. Br J Pharmacol Chemother. 1962 Oct;19(2):337-54. doi: 10.1111/j.1476-5381.1962.tb01198.x. PMID: 19108168; PMCID: PMC1482136. 17: Beaujouan JC, Torrens Y, Saffroy M, Glowinski J. Quantitative autoradiographic analysis of the distribution of binding sites for [125I]Bolton Hunter derivatives of eledoisin and substance P in the rat brain. Neuroscience. 1986 Aug;18(4):857-75. doi: 10.1016/0306-4522(86)90105-3. PMID: 2429231. 18: Ferreira SH, Rocha e Silva M. Potentiation of bradykinin and eledoisin by BPF (bradykinin potentiating factor) from Bothrops jararaca venom. Experientia. 1965 Jun 15;21(6):347-9. doi: 10.1007/BF02144709. PMID: 5870517. 19: Lippe C, Bellantuono V, Ardizzone C, Cassano G. Eledoisin and Kassinin, but not Enterokassinin, stimulate ion transport in frog skin. Peptides. 2004 Nov;25(11):1971-5. doi: 10.1016/j.peptides.2004.06.014. PMID: 15501529. 20: Jaeger W. Die Behandlung schwerer Verlaufsformen der Keratoconjunctivitis sicca mit Eledoisin [Treatment of a severe course of keratoconjunctivitis sicca with eledoisin]. Klin Monbl Augenheilkd. 1988 Feb;192(2):163-6. German. doi: 10.1055/s-2008-1050096. PMID: 3283426.