Eledoisin

Last updated
Eledoisin
Eledoisin skeletal.svg
PDB 1mxq EBI.jpg
Names
IUPAC 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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 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
    Key: AYLPVIWBPZMVSH-FCKMLYJASA-N
  • InChI=1/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)
    Key: AYLPVIWBPZMVSH-UHFFFAOYAZ
  • O=C(NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N)CCSC)CC(C)C)C(C)CC)Cc1ccccc1)C)CC(=O)O)CCCCN)CO)C3N(C(=O)C2NC(=O)CC2)CCC3
Properties
C54H85N13O15S
Molar mass 1188.40 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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-NH2 (qPSKDAFIGLM-NH2) where pGlu and q stand for pyroglutamic acid. 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]

Related Research Articles

Endopeptidase or endoproteinase are proteolytic peptidases that break peptide bonds of nonterminal amino acids, in contrast to exopeptidases, which break peptide bonds from end-pieces of terminal amino acids. For this reason, endopeptidases cannot break down peptides into monomers, while exopeptidases can break down proteins into monomers. A particular case of endopeptidase is the oligopeptidase, whose substrates are oligopeptides instead of proteins.

<i>beta</i>-Endorphin Peptide hormone in Homo sapiens

Beta-Endorphin or β-Endorphin is an endogenous opioid neuropeptide and peptide hormone that is produced in certain neurons within the central nervous system and peripheral nervous system. It is one of three endorphins that are produced in humans, the others of which include α-endorphin and γ-endorphin.

Motilin

Motilin is a 22-amino acid polypeptide hormone in the motilin family that, in humans, is encoded by the MLN gene.

Neurophysin I is a carrier protein with a size of 10 KDa and contains 90 to 97 amino acids. It is a cleavage product of preprooxyphysin. It is a neurohypophysial hormone that is transported in vesicles with oxytocin, the other cleavage product, along axons, from magnocellular neurons of the hypothalamus to the posterior lobe of the pituitary. Although it is stored in neurosecretory granules with oxytocin and released with oxytocin, its biological action is unclear.

Growth hormone–releasing hormone (GHRH), also known as somatocrinin or by several other names in its endogenous forms and as somatorelin (INN) in its pharmaceutical form, is a releasing hormone of growth hormone (GH). It is a 44-amino acid peptide hormone produced in the arcuate nucleus of the hypothalamus.

Tachykinin peptides

Tachykinin peptides are one of the largest families of neuropeptides, found from amphibians to mammals. They were so named due to their ability to rapidly induce contraction of gut tissue. The tachykinin family is characterized by a common C-terminal sequence, Phe-X-Gly-Leu-Met-NH2, where X is either an Aromatic or an Aliphatic amino acid. The genes that produce tachykinins encode precursor proteins called preprotachykinins, which are chopped apart into smaller peptides by posttranslational proteolytic processing. The genes also code for multiple splice forms that are made up of different sets of peptides.

SV40 large T antigen

SV40 large T antigen is a hexamer protein that is a dominant-acting oncoprotein derived from the polyomavirus SV40. TAg is capable of inducing malignant transformation of a variety of cell types. The transforming activity of TAg is due in large part to its perturbation of the retinoblastoma (pRb) and p53 tumor suppressor proteins. In addition, TAg binds to several other cellular factors, including the transcriptional co-activators p300 and CBP, which may contribute to its transformation function.

Kassinin Chemical compound

Kassinin is a peptide derived from the Kassina frog. It belongs to tachykinin family of neuropeptides. It is secreted as a defense response, and is involved in neuropeptide signalling.

A tetrapeptide is a peptide, classified as an oligopeptide, since it only consists of four amino acids joined by peptide bonds. Many tetrapeptides are pharmacologically active, often showing affinity and specificity for a variety of receptors in protein-protein signaling. Present in nature are both linear and cyclic tetrapeptides (CTPs), the latter of which mimics protein reverse turns which are often present on the surface of proteins and druggable targets. Tetrapeptides may be cyclized by a fourth peptide bond or other covalent bonds.

Corticotropin-like intermediate [lobe] peptide (CLIP), also known as adrenocorticotropic hormone fragment 18-39, is a naturally occurring, endogenous neuropeptide with a docosapeptide structure and the amino acid sequence Arg-Pro-Val-Lys-Val-Tyr-Pro-Asn-Gly-Ala-Glu-Asp-Glu-Ser-Ala-Glu-Ala-Phe-Pro-Leu-Glu-Phe. CLIP is generated as a proteolyic cleavage product of adrenocorticotropic hormone (ACTH), which in turn is a cleavage product of proopiomelanocortin (POMC). Its physiological role has been investigated in various tissues, specifically in the central nervous system.

Neurokinin 1 (NK1) antagonists (-pitants) are a novel class of medications that possesses unique antidepressant, anxiolytic, and antiemetic properties. NK-1 antagonists boost the efficacy of 5-HT3 antagonists to prevent nausea and vomiting. The discovery of neurokinin 1 (NK1) receptor antagonists was a turning point in the prevention of nausea and vomiting associated with cancer chemotherapy.

Neurokinin A Chemical compound

Neurokinin A (NKA), formerly known as Substance K, is a neurologically active peptide translated from the pre-protachykinin gene. Neurokinin A has many excitatory effects on mammalian nervous systems and is also influential on the mammalian inflammatory and pain responses.

Neurophysin II

Neurophysin II is a carrier protein with a size of 19,687.3 Da and is made up of a dimer of two virtually identical chains of amino acids. Neurophysin II is a cleavage product of the AVP gene. It is a neurohypophysial hormone that is transported in vesicles with vasopressin, the other cleavage product, along axons, from magnocellular neurons of the hypothalamus to the posterior lobe of the pituitary. Although it is stored in neurosecretory granules with vasopressin and released with vasopressin into the bloodstream, its biological action is unclear. Neurophysin II is also known as a stimulator of prolactin secretion.

Tachykinin receptor 1 Protein-coding gene in the species Homo sapiens

The tachykinin receptor 1 (TACR1) also known as neurokinin 1 receptor (NK1R) or substance P receptor (SPR) is a G protein coupled receptor found in the central nervous system and peripheral nervous system. The endogenous ligand for this receptor is Substance P, although it has some affinity for other tachykinins. The protein is the product of the TACR1 gene.

Big dynorphin is an endogenous opioid peptide of the dynorphin family that is composed of both dynorphin A and dynorphin B. Big dynorphin has the amino acid sequence: Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Ile-Arg-Pro-Lys-Leu-Lys-Trp-Asp-Asn-Gln-Lys-Arg-Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Gln-Phe-Lys-Val-Val-Thr. It has nociceptive and anxiolytic-like properties, as well as effects on memory in mice.

<i>alpha</i>-Endorphin Chemical compound

α-Endorphin is an endogenous opioid peptide with a length of 16 amino acids, and the amino acid sequence: Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr. With the use of mass spectrometry, Nicholas Ling was able to determine the primary sequence of a-endorphin.

Metkefamide

Metkefamide (INN; LY-127,623), or metkephamid acetate (USAN), but most frequently referred to simply as metkephamid, is a synthetic opioid pentapeptide and derivative of [Met]enkephalin with the amino acid sequence Tyr-D-Ala-Gly-Phe-(N-Me)-Met-NH2. It behaves as a potent agonist of the δ- and μ-opioid receptors with roughly equipotent affinity, and also has similarly high affinity as well as subtype-selectivity for the κ3-opioid receptor.

CNMamide (CNMa) is a cyclic neuropeptide identified by computational analysis of Drosophila melanogaster protein sequences and named after its C-terminal ending motif. A gene encoding CNMa was found in most arthropods and comparison among the precursor sequences of several representative species revealed high conservation, particularly in the region of the predicted mature peptide. Two conserved cysteine residues enveloping four amino acids form a disulfide bond and were shown to be important for binding of the peptide to its receptor. Expression of CNMa was confirmed in the larval and adult brain of D. melanogaster but the function of the peptide has not been elucidated yet.

Agelenin, also called U1-agatoxin-Aop1a, is an antagonist of the presynaptic P-type calcium channel in insects. This neurotoxic peptide consists of 35 amino acids and can be isolated from the venom of the spider Allagelena opulenta.

Bulevirtide Antiviral medication

Bulevirtide, sold under the brand name Hepcludex, is an antiviral medication for the treatment of chronic hepatitis D.

References

  1. De Marco, A., and G. Gatti, "1H- and 13C-NMR spectra of eledoisin and intermediate oligopeptides." Int. J. Pep. Pro. Res. 7:437–444, 1975.
  2. R. Christy Rani Grace, Indu R. Chandrashekar and Sudha M. Cowsik, "Solution Structure of the Tachykinin Peptide Eledoisin" Archived 2008-10-11 at the Wayback Machine , Biophysical Journal 84:655-664 (2003), retrieved 05 Dec 2007. This publication has excellent general information on the eledoisin molecule.
  3. Schwyzer, R., "Membrane-assisted molecular mechanism of neurokinin receptor subtype selection." EMBO J. 6:2255–2259, 1987