Eledoisin acetate | CAS#69-25-0 | neuropeptide tachykinin

MedKoo Cat#: 326642 | Name: Eledoisin acetate

Description:

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

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

Eledoisin acetate

CAS#Eledoisin acetate

Theoretical Analysis

MedKoo Cat#: 326642

Name: Eledoisin acetate

CAS#: Eledoisin acetate

Chemical Formula: C56H89N13O17S

Exact Mass: 0.0000

Molecular Weight: 1248.46

Elemental Analysis: C, 53.88; H, 7.19; N, 14.59; O, 21.79; S, 2.57

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

69-25-0 (free base) 16679-58-6 (free base) 62357-86-2 (acetate trihydrate); Eledoisin acetate

Synonym

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

IUPAC/Chemical Name

acetic acid;(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

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

Instruction

View handling instruction

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.

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: 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.