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Alytesin

Catalog Number: EVT-242125

CAS Number: 31078-12-3

Molecular Formula: C68H106N22O17S

Molecular Weight: 1535.8 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Alytesin is a bioactive peptide derived from amphibian sources, specifically from the skin exudates of the midwife toad. It has garnered attention due to its diverse biological activities and potential therapeutic applications. The peptide has been studied for its insulinotropic actions, effects on body temperature and pancreatic juice secretion, and antitumor properties. These studies have explored the structure-activity relationships of alytesin and its analogs, aiming to enhance its therapeutic potential and stability for clinical applications.

Mechanism of Action

The insulinotropic actions of alytesin and its analogs have been demonstrated in studies where they stimulate insulin release from clonal β cells. Alyteserin-2a, a specific analog of alytesin, has shown to increase the rate of insulin release at certain concentrations. This effect is mediated through membrane depolarization and an increase in intracellular Ca2+ concentration, which are critical steps in the insulin secretion pathway. Modifications to the peptide structure, such as substitutions with l-lysine or d-lysine, have been found to maintain amphipathicity and enhance its insulinotropic activity. Notably, certain analogs have been shown to significantly improve glucose tolerance in high-fat-fed mice with obesity and insulin resistance, indicating a potential application for alytesin in managing diabetes1.

Applications in Various Fields

Biomedical Applications

Alytesin and its analogs have been synthesized and evaluated for their biomedical applications. The peptides have been found to decrease body temperature and stimulate pancreatic juice secretion, suggesting their role in thermoregulation and digestive processes. The structure of these peptides has been confirmed through high-resolution NMR spectroscopy, ensuring the accuracy of synthesis for further biological studies2.

Antitumor Applications

The structural flexibility of alyteserin-2a has limited its use as an antitumor agent. However, modifications such as hydrocarbon stapling have been employed to enhance its structural integrity. These modifications have led to the discovery of novel stapled peptide antitumor agents with improved helicity levels, protease resistance, and antitumor activity. Among the modified peptides, alyteserin-2a-Sp3 has shown significant potential as a lead compound for the development of new antitumor drugs. This highlights the importance of structural modifications in improving the biological activity and stability of alytesin for therapeutic use3.

Properties

CAS Number

31078-12-3

Product Name

Alytesin

IUPAC Name

(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-2-[[(2S,3R)-2-[[2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]acetyl]amino]pentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]pentanediamide

Molecular Formula

C68H106N22O17S

Molecular Weight

1535.8 g/mol

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

InChI Key

ISGGITPLKHZHOL-TXYKKBLVSA-N

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

Synonyms

alytesin
pGly-Arg-Leu-Gly-Thr-Gln-Trp-Ala-Val-Gly-His-Leu-Met-NH2

Canonical SMILES

Isomeric SMILES

C[C@H]([C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CC3=CN=CN3)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)CNC(=O)[C@@H]4CCC(=O)N4)O

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