Eledoisin acetate

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MedKoo CAT#: 326642

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

Description: 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. "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.

Chemical Structure

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

Theoretical Analysis

MedKoo Cat#: 326642
Name: Eledoisin acetate
CAS#: 69-25-0 (free base)
Chemical Formula: C56H89N13O17S
Exact Mass: 0.00
Molecular Weight: 1,248.462
Elemental Analysis: C, 53.88; H, 7.19; N, 14.59; O, 21.79; S, 2.57

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 69-25-0 (free base)   16679-58-6   62357-86-2 (acetate trihydrate)  

Synonym: BRN 4796573; BRN4796573; BRN-4796573; ELD 950; ELD-950; ELD950; Eledoisin acetate; Eledone peptide; FI 6225 TF/Ocoa.

IUPAC/Chemical Name: pGlu-Pro-Ser-Lys-Asp-Ala-Phe-Ile-Gly-Leu-Met-NH2

InChi Key: RDMVPYOYHLCAAN-JSMOHVFGSA-N

InChi Code: InChI=1S/C54H85N13O15S.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t30-,31-,33-,34-,35-,36-,37-,38-,39-,40-,44-;/m0./s1

SMILES Code: CSCC[C@@H](C(N)=O)NC([C@H](CC(C)C)NC(CNC([C@H]([C@@H](C)CC)NC([C@H](CC1=CC=CC=C1)NC([C@H](C)NC([C@H](CC(O)=O)NC([C@H](CCCCN)NC([C@H](CO)NC([C@H]2N(C([C@H](CC3)NC3=O)=O)CCC2)=O)=O)=O)=O)=O)=O)=O)=O)=O.CC(O)=O

Appearance: Solid powder

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, not in water

Shelf Life: >2 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,248.46 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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. PubMed PMID: 23906760.

2: 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. PubMed PMID: 15501529.

3: Grace RC, Chandrashekar IR, Cowsik SM. Solution structure of the tachykinin peptide eledoisin. Biophys J. 2003 Jan;84(1):655-64. PubMed PMID: 12524318; PubMed Central PMCID: PMC1302646.

4: Björup P, Torres JL, Adlercreutz P, Clapés P. Reaction medium engineering in enzymatic peptide fragment condensation: synthesis of eledoisin and LH-RH. Bioorg Med Chem. 1998 Jul;6(7):891-901. PubMed PMID: 9730225.

5: Wilson JC, Nielsen KJ, McLeish MJ, Craik DJ. A determination of the solution conformation of the nonmammalian tachykinin eledoisin by NMR and CD spectroscopy. Biochemistry. 1994 Jun 7;33(22):6802-11. PubMed PMID: 8204614.

6: Micossi LG, Tomaszewicz M, Bielarczyk H, Luszawska D, Trognoni A, Szutowicz A. Effect of angiotensin II and eledoisin on cholinergic neurons in rat hippocampus. Neuroreport. 1992 Jan;3(1):36-8. PubMed PMID: 1611032.

7: Geraghty DP, Mussap CJ, Burcher E. Radioiodinated substance P, neurokinin A, and eledoisin bind predominantly in NK1 receptors in guinea pig lung. Mol Pharmacol. 1992 Jan;41(1):147-53. PubMed PMID: 1370705.

8: Beresford IJ, Ireland SJ, Stables J, Hagan RM. Ontogeny and characterization of [125I]Bolton Hunter-eledoisin binding sites in rat spinal cord by quantitative autoradiography. Neuroscience. 1992;46(1):225-32. PubMed PMID: 1317513.

9: Avanov AIa. [Conformational analysis of tachykinins. II. N-terminal fragments of phyllomedusin, eledoisin, kassinin, and neurokinins]. Bioorg Khim. 1991 Jun;17(6):747-55. Russian. PubMed PMID: 1663744.

10: Naukam RJ, Parris WC, Kambam JR, Kruskal JB. The effects of neurokinin A, neurokinin B, and eledoisin on substance P analysis. J Clin Monit. 1991 Apr;7(2):181-5. PubMed PMID: 1712834.

11: Tomaszewicz M, Micossi LG, Bielarczyk H, Luszawska D, Santarelli I, Szutowicz A. Differential effects of angiotensin II and eledoisin on monoamine oxidase A and B activities in rat brain. J Neurochem. 1991 Mar;56(3):729-32. PubMed PMID: 1899693.

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. PubMed PMID: 1765297.

13: Prabhakar NR, Kou YuR, Runold M. Chemoreceptor responses to substance P, physalaemin and eledoisin: evidence for neurokinin-1 receptors in the cat carotid body. Neurosci Lett. 1990 Dec 11;120(2):183-6. PubMed PMID: 1705679.

14: Pompei PL, Massi M, Perfumi M, de Caro G. Spontaneously hypertensive rats are less sensitive than Wistar Kyoto rats to the antidipsogenic action of eledoisin. Pharmacol Res. 1990 Sep-Oct;22 Suppl 1:127-8. PubMed PMID: 2284230.

15: Tarjan E, Blair-West JR, de Caro G, Denton DA, McBurnie MI, Massi M, Szmydynger-Chodobska J, Weisinger RS. Sodium and water intake of sheep, rabbits and cattle during ICV infusion of eledoisin. Pharmacol Biochem Behav. 1990 Apr;35(4):823-8. PubMed PMID: 2345760.

16: Pompei P, Polidori C, Perfumi M, Massi M. Sensitivity of spontaneously hypertensive and of Wistar Kyoto rats to the antidipsogenic action of eledoisin. Regul Pept. 1990 Mar 27;28(1):119-29. PubMed PMID: 2326504.

17: Rossi SR, Dartt DA, Gilbard JP. Eledoisin and lacrimal secretion in the rabbit. Curr Eye Res. 1990 Mar;9(3):273-6. PubMed PMID: 2347204.

18: Perfumi MC, Polidori C, Caraffa E, Cucculelli M, Fede M, Fiorelli A. [Effects of eledoisin on water intake induced by subcutaneous injection of hypertonic NaCl in the rat]. Acta Biomed Ateneo Parmense. 1989;60(1-2):103-11. Italian. PubMed PMID: 2535090.

19: Perfumi M, Sajia A, Costa G, Massi M, Polidori C. Vasopressin release induced by intracranial injection of eledoisin is mediated by central angiotensin II. Pharmacol Res Commun. 1988 Sep;20(9):811-26. PubMed PMID: 3051054.

20: Foster AC, Tridgett R. Comparison of the binding of radiolabelled neurokinin A and eledoisin in rat cortex synaptic membranes. Br J Pharmacol. 1988 Jun;94(2):602-8. PubMed PMID: 2840165; PubMed Central PMCID: PMC1853990.