Alytesin - CAS 31078-12-3
Category: Inhibitor
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Molecular Formula:
C68H106N22O17S
Molecular Weight:
1535.78
COA:
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Targets:
Bombesin Receptor
Description:
Alytesin is an amphibian bombesin-like peptide originally isolated from the skin of the European amphibian, alytes obstetricans. It has biological activity very similar to bombesin. It could cause rat uterine contraction, intestinal contraction, gastric acid secretion and hypertension in vivo in the dog. It also adjusts thermoregulation following central administration in vivo.
Sequence:
Pyr-Gly-Arg-Leu-Gly-Thr-Gln-Trp-Ala-Val-Gly-His-Leu-Met
MSDS:
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InChIKey:
ISGGITPLKHZHOL-TXYKKBLVSA-N
InChI:
InChI=1S/C68H106N22O17S/c1-33(2)23-46(86-61(101)43(15-12-21-74-68(71)72)82-52(94)29-76-59(99)44-17-19-51(93)81-44)60(100)77-31-54(96)89-56(37(8)91)67(107)85-45(16-18-50(69)92)62(102)88-48(25-38-27-75-41-14-11-10-13-40(38)41)63(103)80-36(7)58(98)90-55(35(5)6)66(106)78-30-53(95)83-49(26-39-28-73-32-79-39)65(105)87-47(24-34(3)4)64(104)84-42(57(70)97)20-22-108-9/h10-11,13-14,27-28,32-37,42-49,55-56,75,91H,12,15-26,29-31H2,1-9H3,(H2,69,92)(H2,70,97)(H,73,79)(H,76,99)(H,77,100)(H,78,106)(H,80,103)(H,81,93)(H,82,94)(H,83,95)(H,84,104)(H,85,107)(H,86,101)(H,87,105)(H,88,102)(H,89,96)(H,90,98)(H4,71,72,74)/t36-,37+,42-,43-,44-,45-,46-,47-,48-,49-,55-,56-/m0/s1
Canonical SMILES:
CC(C)CC(C(=O)NCC(=O)NC(C(C)O)C(=O)NC(CCC(=O)N)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(C)C(=O)NC(C(C)C)C(=O)NCC(=O)NC(CC3=CN=CN3)C(=O)NC(CC(C)C)C(=O)NC(CCSC)C(=O)N)NC(=O)C(CCCN=C(N)N)NC(=O)CNC(=O)C4CCC(=O)N4
1.Central and peripheral alytesin cause short-term anorexigenic effects in neonatal chicks.
Cline MA1, Fouse DN, Prall BC. Neuropeptides. 2008 Jun;42(3):283-91. doi: 10.1016/j.npep.2008.02.004. Epub 2008 Apr 1.
We studied the effects of alytesin, a natural analogue of bombesin, on appetite-related responses and behaviors in neonatal chicks. Chicks responded to both intracerebroventricular (ICV) and peripheral injections of alytesin with short-term reduced feed intake. ICV alytesin caused reduced short-term water intake when feed was present, but we determined this effect was secondary to feed intake since an effect on water intake was not detected in feed-restricted alytesin-treated chicks. The anorexigenic effect of both ICV and peripheral alytesin may be mediated at the hypothalamus, since all hypothalamic nuclei studied; regio lateralis hypothalami, nucleus dorsomedialis hypothalami, nucleus paraventricularis magnocellularis, nucleus perventricularis hypothalami, nucleus infundibuli hypothalami and the nucleus ventromedialis hypothalami, were activated as evident by increased c-Fos immunoreactivity. Central alytesin did not cause increased behaviors that were unrelated to ingestion and did not cause anxiety-related behavior patterns.
2.Antimicrobial peptides and alytesin are co-secreted from the venom of the Midwife toad, Alytes maurus (Alytidae, Anura): implications for the evolution of frog skin defensive secretions.
König E1, Zhou M, Wang L, Chen T, Bininda-Emonds OR, Shaw C. Toxicon. 2012 Nov;60(6):967-81. doi: 10.1016/j.toxicon.2012.06.015. Epub 2012 Jul 16.
The skin secretions of frogs and toads (Anura) have long been a known source of a vast abundance of bioactive substances. In the past decade, transcriptome data of the granular glands of anuran skin has given new impetus to investigations of the putative constituent peptides. Alytes obstetricans was recently investigated and novel peptides with antimicrobial activity were isolated and functionally characterised. However, genetic data for the evolutionarily ancient lineage to which Alytes belongs (midwife toads; Alytidae) remains unavailable. Here we present the first such genetic data for Alytidae, derived via the granular gland transcriptome of a closely-related species of midwife toad, Alytes maurus. First, we present nucleotide sequences of the entire peptide precursors for four novel antimicrobial peptides (AMPs). The two precursors resemble those from Bombinatoridae in both their structural architecture and amino acid sequence. Each precursor comprises two AMPs as tandem repeats, with a member of the alyteserin-1 family (alyteserin-1Ma: GFKEVLKADLGSLVKGIAAHVAN-NH2 or alyteserin-1Mb: GFKEVLKAGLGSLVKGIPAHVAN-NH2) followed by its corresponding member from the alyteserin-2 family (alyteserin-2Ma: FIGKLISAASGLLSHL-NH2 or alyteserin-2Mb: ILGAIIPLVSGLLSHL-NH2).
3.An immunohistochemical demonstration of gastrin-releasing peptide (GRP) in the rat substantia nigra.
Larsen PJ1, Saermark T, Mikkelsen JD. J Chem Neuroanat. 1989 Mar-Apr;2(2):83-93.
The presence of gastrin-releasing peptide-like immunoreactivity in the rat brain was investigated by use of the indirect peroxidase-antiperoxidase technique. A high density of gastrin-releasing peptide-like immunoreactive terminals in the ventral pallidum, the interpenduncular nucleus and in substantia nigra, pars reticulata, was observed. Moreover, gastrin-releasing peptide-like immunoreactive perikarya were observed in the hypothalamic suprachiasmatic nucleus. Antisera raised against gastrin-releasing peptide have been shown to cross-react with substance P, another peptide highly concentrated in the substantia nigra, the ventral pallidum and the interpenduncular nucleus, and gastrin-releasing peptide-immunoreactivity in these areas has therefore been regarded as substance P immunoreactivity. To determine the antigenic epitope recognized by the antiserum raised against gastrin-releasing peptide, specificity studies were performed with known peptides fixed to nitrocellulose filter strips as well as preabsorptions with the same peptides on fixed brain sections containing the substantia nigra.
4.Central neuromodulation of gastric acid secretion by bombesin-like peptides.
Guglietta A, Strunk CL, Irons BJ, Lazarus LH. Peptides. 1985;6 Suppl 3:75-81.
The amphibian skin tetrapeptide bombesin shows potent action in reducing gastric acid secretion by intracerebral ventricular (ICV) administration in rats. In order to establish a relationship between this action and the amino acid composition of the bombesin-like peptides, most of the natural bombesin-like peptides and some synthetic analogues were tested on their ability to reduce gastric acid secretion by ICV administration. The amphibian peptides bombesin, its [Tyr4]-bombesin analogue, alytesin, ranatensin and litorin, and the mammalian peptide GRP significantly reduced gastric acid output 2 hr after peptide administration (p less than 0.01). The data support the following prerequisites for the maximal neuromodulatory role of bombesin-like peptides on gastric secretion: Trp is required at position 8; Gln and His are important at positions 7 and 12, respectively; Leu replacement by Phe, which occurs in the litorin subfamily, modifies the response; and unspecified amino acids or sequences are also involved in the N-terminal region of bombesin-like peptides.
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CAS 31078-12-3 Alytesin

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