Cyclo(L-Leu-L-Trp)
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| Category | Bioactive by-products |
| Catalog number | BBF-04418 |
| CAS | 15136-34-2 |
| Molecular Weight | 299.37 |
| Molecular Formula | C17H21N3O2 |
| Purity | ≥95% |
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Description
Cyclo(L-Leu-L-Trp) is a diketopiperazine metabolite originally isolated from Penicillium. It is active against various bacteria and fungi, and it also inhibits the production rate of hydroxy radicals in an electron spin resonance (ESR) spectroscopy-based assay (IC50 = 1.8 µM).
Specification
| Synonyms | 3S-(1H-indol-3-ylmethyl)-6S-(2-methylpropyl)-2,5-piperazinedione; Cyclo(L-leucyl-L-tryptophyl); Cyclo(leu-trp); Cyclo(L-Trp-L-Leu); 2,5-Piperazinedione, 3-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-, (3S-cis)- |
| Storage | Store at -20°C |
| IUPAC Name | (3S,6S)-3-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)piperazine-2,5-dione |
| Canonical SMILES | CC(C)CC1C(=O)NC(C(=O)N1)CC2=CNC3=CC=CC=C32 |
| InChI | InChI=1S/C17H21N3O2/c1-10(2)7-14-16(21)20-15(17(22)19-14)8-11-9-18-13-6-4-3-5-12(11)13/h3-6,9-10,14-15,18H,7-8H2,1-2H3,(H,19,22)(H,20,21)/t14-,15-/m0/s1 |
| InChI Key | BZUNCDPEEKFTCX-GJZGRUSLSA-N |
Properties
| Appearance | Solid Powder |
| Antibiotic Activity Spectrum | Fungi; Bacterial |
| Boiling Point | 635.2°C at 760 mmHg |
| Melting Point | 217.28°C |
| Density | 1.182 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Effect of Neuropeptide Cyclo-L-Prolylglycine on Cell Proliferative Activity
T A Gudasheva, L F Zainullina, Yu V Vakhitova, S B Seredenin, T V Ivanova Bull Exp Biol Med . 2020 Jul;169(3):347-350. doi: 10.1007/s10517-020-04884-9.
Endogenous neuropeptide cyclo-L-prolylglycine possesses mnemotropic and neuroprotective properties, which can result from its positive effect on the level of brain-derived neurotrophic factor and modulation of activity of insulin-like growth factor-1 and AMPA receptors. For detection of possible mitogenic action of cyclo-L-prolylglycine, we analyzed its effect on proliferative activity of HEK293 and SH-SY5Y cells assessed by expression of Ki-67 proliferation marker, cell cycle examination, and incorporation of modified nucleotide analog EdU into DNA. Cyclo-L-prolylglycine did not affect the level of Ki-67 in examined cell lines and distribution of the cells over G1 and G2 phases of the cell cycle, although it insignificantly reduced the percentage of S phase cells, which attested to the absence of intrinsic mitogenic activity of the peptide. At the same time, cyclo-L-prolylglycine reduced the number of the early apoptotic cells, which can be a mechanisms of its protective action.
2. Neuroprotective Effect of Cyclo-(L-Pro-L-Phe) Isolated from the Jellyfish-Derived Fungus Aspergillus flavus
Jee H Jung, Eun La Kim, Ying Wang, Dan-Dan Li, Jongki Hong Mar Drugs . 2021 Jul 26;19(8):417. doi: 10.3390/md19080417.
Peroxisome proliferator-activated receptor (PPAR) expression has been implicated in pathological states such as cancer, inflammation, diabetes, and neurodegeneration. We isolated natural PPAR agonists-eight 2,5-diketopiperazines-from the jellyfish-derived fungusAspergillus flavus. Cyclo-(L-Pro-L-Phe) was the most potent PPAR-γ activator among the eight 2,5-DKPs identified. Cyclo-(L-Pro-L-Phe) activated PPAR-γ in Ac2F rat liver cells and SH-SY5Y human neuroblastoma cells. The neuroprotective effect of this partial PPAR-γ agonist was examined using the 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, lactate dehydrogenase release, and the Hoechst 33342 staining assay in SH-SY5Y cells. Our findings revealed that cyclo-(L-Pro-L-Phe) reduced hydrogen peroxide-induced apoptosis as well as the generation of reactive oxygen species. Rhodamine 123 staining and western blotting revealed that cyclo-(L-Pro-L-Phe) prevented the loss of mitochondrial membrane potential and inhibited the activation of mitochondria-related apoptotic proteins, such as caspase 3 and poly (ADP-ribose) polymerase. Moreover, cyclo-(L-Pro-L-Phe) inhibited the activation and translocation of nuclear factor-kappa B. Thus, the partial PPAR-γ agonist cyclo-(L-Pro-L-Phe) demonstrated potential neuroprotective activity against oxidative stress-induced neurodegeneration in SH-SY5Y cells.
3. The effect of the isomers of cyclo(Trp-Pro) on heart and ion-channel activity
Gareth Kilian, Pieter J Milne, Karin Dyason, Hajierah Jamie J Pharm Pharmacol . 2002 Dec;54(12):1659-65. doi: 10.1211/002235702252.
Cyclo(L-Trp-L-Pro) has shown potential for use in the treatment of cardiovascular dysfunction. The aim of the study was to determine the effects of the isomers of cyclo(Trp-Pro) - cyclo(L-Trp-L-Pro), cyclo(L-Trp-D-Pro), cyclo(D-Trp-L-Pro) and cyclo(D-Trp-D-Pro) - on heart and ion-channel activity. The effects on L-type Ca(2+)-channel, Na(+)-channel and inward rectifier K(+)-channel activity were determined by using the whole-cell patch-clamp technique on myocytes of guinea-pig origin. Dependence on the membrane potential in terms of Ca(2+)-channel activity was also investigated. A modified Langendorff method was used to determine the effects of the isomers on heart rate, coronary flow, duration of ventricular tachycardia and arrhythmia, time to sinus rhythm and QRS interval on the rat isolated heart. Cyclo(L-Trp-L-Pro), cyclo(L-Trp-D-Pro) and cyclo(D-Trp-D-Pro), 100 microM, showed agonism towards Ca(2+)-channel activity, while cyclo(D-Trp-L-Pro) caused a blockage of the current. The action of cyclo(D-Trp-L-Pro) was shown to be independent of membrane potential. No significant effect (P > 0.05) on the inward rectifier K(+) current was observed in the presence of cyclo(L-Trp-D-Pro) and cyclo(D-Trp-D-Pro), while antagonism was noted in the presence of cyclo(L-Trp-L-Pro) and cyclo(D-Trp-L-Pro). All isomers showed antagonist effects on the Na(+) channel. No adverse effects were noted on chronotropic effects in the presence of 200 microM cyclo(L-Trp-L-Pro) and cyclo(D-Trp-D-Pro) (P > 0.05), while cyclo(L-Trp-D-Pro) significantly increased the heart rate. Cyclo(D-Trp-L-Pro) significantly reduced the heart rate (P < 0.05). In addition, no significant effects were observed on the coronary flow rate in the presence of the isomers. All isomers significantly reduced the duration of ventricular tachycardia and arrhythmia, as well as the time to sinus rhythm. Furthermore, no change in the QRS intervals was noted in the presence of the isomers in comparison with the control, with a significant increase being noted for cyclo(D-Trp-D-Pro) (P < 0.05) in reference to the other isomers. The isomers thus show antiarrhythmic potential and may manifest as novel agents in the treatment of cardiovascular dysfunction, since a decrease in ventricular fibrillation may reduce the mortality rates in acute myocardial infarction.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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