M.W=400-450 | - Page 3 of 13 - Indole Building Blocks

Shortridge, Matthew D.’s team published research in Journal of Proteome Research in 10 | CAS: 2854-32-2

Journal of Proteome Research published new progress about 2854-32-2. 2854-32-2 belongs to indole-building-block, auxiliary class GPCR/G Protein,Cannabinoid Receptor, name is 2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-1-morpholinoethanone, and the molecular formula is C7H6Cl2, Quality Control of 2854-32-2.

Shortridge, Matthew D. published the artcileCorrelation between protein function and ligand binding profiles, Quality Control of 2854-32-2, the publication is Journal of Proteome Research (2011), 10(5), 2538-2545, database is CAplus and MEDLINE.

The authors report that proteins with the same function bind the same set of small mols. from a standardized chem. library. This observation led to a quantifiable and rapidly adaptable method for protein functional anal. using exptl. derived ligand binding profiles. Ligand binding is measured using a high-throughput NMR ligand affinity screen with a structurally diverse chem. library. The method was demonstrated using a set of 19 proteins with a range of functions. A statistically significant similarity in ligand binding profiles was only observed between the two functionally identical albumins and between the five functionally similar amylases. This new approach is independent of sequence, structure, or evolutionary information and, therefore, extends the ability to analyze and functionally annotate novel genes.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Di Nicolantonio, Federica’s team published research in Proceedings of the National Academy of Sciences of the United States of America in 105 | CAS: 2854-32-2

Proceedings of the National Academy of Sciences of the United States of America published new progress about 2854-32-2. 2854-32-2 belongs to indole-building-block, auxiliary class GPCR/G Protein,Cannabinoid Receptor, name is 2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-1-morpholinoethanone, and the molecular formula is C23H23ClN2O4, SDS of cas: 2854-32-2.

Di Nicolantonio, Federica published the artcileReplacement of normal with mutant alleles in the genome of normal human cells unveils mutation-specific drug responses, SDS of cas: 2854-32-2, the publication is Proceedings of the National Academy of Sciences of the United States of America (2008), 105(52), 20864-20869, database is CAplus and MEDLINE.

Mutations in oncogenes and tumor suppressor genes are responsible for tumorigenesis and represent favored therapeutic targets in oncol. The authors exploited homologous recombination to knock-in individual cancer mutations in the genome of nontransformed human cells. Sequential introduction of multiple mutations was also achieved, demonstrating the potential of this strategy to construct tumor progression models. Knock-in cells displayed allele-specific activation of signaling pathways and mutation-specific phenotypes different from those obtainable by ectopic oncogene expression. Profiling of a library of pharmacol. agents on the mutated cells showed striking sensitivity or resistance phenotypes to pathway-targeted drugs, often matching those of tumor cells carrying equivalent cancer mutations. Thus, knock-in of single or multiple cancer alleles provides a pharmacogenomic platform for the rational design of targeted therapies.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Muldoon, Pretal P.’s team published research in Neuropharmacology in 176 | CAS: 2854-32-2

Neuropharmacology published new progress about 2854-32-2. 2854-32-2 belongs to indole-building-block, auxiliary class GPCR/G Protein,Cannabinoid Receptor, name is 2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-1-morpholinoethanone, and the molecular formula is C23H23ClN2O4, Product Details of C23H23ClN2O4.

Muldoon, Pretal P. published the artcileInhibition of monoacylglycerol lipase reduces nicotine reward in the conditioned place preference test in male mice, Product Details of C23H23ClN2O4, the publication is Neuropharmacology (2020), 108170, database is CAplus and MEDLINE.

Nicotine, the primary psychoactive component in tobacco, plays a major role in the initiation and maintenance of tobacco dependence and addiction, a leading cause of preventable death worldwide. In this study, we utilized complementary genetic and pharmacol. approaches to test the hypothesis that increasing the levels of the endocannabinoid 2-arachindonoylglycerol (2-AG), will enhance nicotine reward by stimulating neuronal CB1 receptors. Contrary to our hypothesis, we found that inhibition of monoacylglycerol lipase (MAGL), the primary catabolic enzyme of 2-AG, attenuates nicotine conditioned place preference (CPP) in mice, through a non-CB1 receptor-mediated mechanism. In support of our findings, repeated MAGL inhibition did not induce a reduction in CB1 brain receptor levels or hinder function. To explore the potential mechanism of action, we investigated if MAGL inhibition affected other fatty acid levels in our CPP paradigm. Indeed, MAGL inhibition caused a concomitant decrease in arachidonic acid (AA) levels in various brain regions of interest, suggesting an AA cascade-dependent mechanism. This idea is supported by dose-dependent attenuation of nicotine preference by the selective COX-2 inhibitors valdecoxib and LM-4131. Collectively, these findings, along with our reported studies on nicotine withdrawal, suggest that inhibition of MAGL represents a promising new target for the development of pharmacotherapies to treat nicotine dependence.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhao, Liang team published research on Advanced Healthcare Materials in 2022 | 35737-15-6

Reference of 35737-15-6, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., 35737-15-6.

Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. 35737-15-6, formula is C26H22N2O4, Name is Fmoc-Trp-OH. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings. Reference of 35737-15-6.

Zhao, Liang;Chen, Junyi;Tian, Long;Zhang, Yahan;Chen, Longming;Du, Xinbei;Ma, Mengke;Li, Jian;Meng, Qingbin;Li, Chunju research published 《 Supramolecular Detoxification of Macromolecular Biotoxin through the Complexation by a Large-Sized Macrocycle》, the research content is summarized as follows. Biotoxins are diverse, complex, and hypertoxic, ultimately serving as grave and lasting menaces to humanity. Here, it is aimed to introduce a new detoxification methodol. for macromol. biotoxin through complexation by a very large macrocycle. A 25-mer peptide isolated from Lycosa erythrognatha spider venom (LyeTxI) is selected as the model macromol. biotoxin. Quaterphen[4]arene, with a side length of ≈1.6 nm, has a sufficient cavity to bind LyeTxI. Hence, the water-soluble derivative of Quaterphen[4]arene (H) is designed and synthesized. H exhibits an overall host-guest complexation toward LyeTxI, resulting in a considerably high association constant of (7.01 ± 0.18) x 10⁷ M^-1. This encapsulation of peptide is interesting as traditional macrocycles can only engulf the amino acid residues of peptides due to their limited cavity size. In vitro assay verifies that complexation by H inhibits the interactions of LyeTxI with cell membranes, thereby reducing its cytotoxicity, suppressing hemolysis, and decreasing the release of lactate dehydrogenase. Notably, the i.v. administration of H has a significant therapeutic effect on LyeTxI-poisoned mice, alleviating inflammation and tissue damage, and markedly improving the survival rate from 10% to 80%. An efficient and potentially versatile approach is provided to detoxify macromol. biotoxins, with giant macrocycle serving as an antidote.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhu, Han-Ying team published research on Tetrahedron Letters in 2021 | 35737-15-6

Electric Literature of 35737-15-6, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., 35737-15-6.

Zhu, Han-Ying;Wu, Meng;Yu, Fei-Qiang;Zhang, Yan-Ni;Xi, Tong-Kuai;Chen, Kai;Fang, Ge-Min research published 《 Chemical synthesis of thioether-bonded bicyclic peptides using tert-butylthio and Trt-protected cysteines》, the research content is summarized as follows. Thioether-bonded bicyclic peptide can resist proteolytic degradation and become a promising scaffold for peptide-based inhibitor discovery. Chem. synthesis of thioether-bonded bicyclic peptide usually requires two orthogonal Cys protecting groups. Here, we report an efficient strategy for its preparation by using the commonly used Trt-protected and StBu-protected cysteines. Due to the thiol-disulfide exchange, S-StBu group is generally considered incompatible with sulfhydryl group under neutral conditions. We find that, in DIPEA-containing DMF solution, the peptide that contains both sulfhydryl and S-StBu groups can undergo selective thiol bisalkylation while maintaining the integrity of the S-StBu groups. In our strategy, the formation of two thioether bonds are both conducted in solution, and can be easily tracked by HPLC, which may be beneficial for the chem. synthesis of thioether-bonded bicyclic peptides.

Yang, Su team published research on ChemBioChem in 2021 | 35737-15-6

Related Products of 35737-15-6, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., 35737-15-6.

Indole, first isolated in 1866, has the molecular formula C8H7N, and it is commonly synthesized from phenylhydrazine and pyruvic acid, 35737-15-6, formula is C26H22N2O4, Name is Fmoc-Trp-OH. although several other procedures have been discovered.Indole is a colourless solid having a pleasant fragrance in highly dilute solutions. It melts at 52.5° C (126.5° F). Related Products of 35737-15-6.

Yang, Su;Chang, Yan;Hazoor, Shan;Brautigam, Chad;Foss, Frank W. Jr.;Pan, Zui;Dong, He research published 《 Modular Design of Supramolecular Ionic Peptides with Cell-Selective Membrane Activity》, the research content is summarized as follows. The rational design of materials with cell-selective membrane activity is an effective strategy for the development of targeted mol. imaging and therapy. Here we report a new class of cationic multidomain peptides (MDPs) that can undergo enzyme-mediated mol. transformation followed by supramol. assembly to form nanofibers in which cationic clusters are presented on a rigid β-sheet backbone. This structural transformation, which is induced by cells overexpressing the specific enzymes, led to a shift in the membrane perturbation potential of the MDPs, and consequently enhanced cell uptake and drug delivery efficacy. We envision the directed self-assembly based on modularly designed MDPs as a highly promising approach to generate dynamic supramol. nanomaterials with emerging membrane activity for a range of disease targeted mol. imaging and therapy applications.

Yang, Yi team published research on Organic Process Research & Development in 2021 | 35737-15-6

Safety of Fmoc-Trp-OH, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., 35737-15-6.

In addition to indoleacetic acid, indigo, and tryptophan, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. 35737-15-6, formula is C26H22N2O4, Name is Fmoc-Trp-OH. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families. Safety of Fmoc-Trp-OH.

Yang, Yi;Hansen, Lena;Fraczek, Aleksandra;Badalassi, Fabrizio;Kjellstrom, Johan research published 《 DMF-assisted iodination side reaction during the preparation of disulfide peptides, its substrate/solvent/Ph dependence, and implications on disulfide-peptide production》, the research content is summarized as follows. Severe iodination of a disulfide peptide mol. (peptide D) was detected from the on-resin disulfide cyclization process. LC/MS/MS results indicated that iodination occurred on the Thi (thienylalanine) residue. Systematic investigation revealed that the iodination reaction occurred predominantly in the I₂/DMF-mediated on-resin disulfide formation reaction. The iodination side reaction was strongly solvent-dependent and favored in DMF and NMP. A tentative mechanism similar to that of the Vilsmeier-Haack reaction was proposed. A variety of amino acid/peptide substrates were tested as iodination substrates. The results indicated the susceptibility of amino acids with electron-rich aromatic groups to iodination. Addnl., various solutions were proposed for preventing peptide iodination based on the findings in this study. This study demonstrates the applicability of the on-resin disulfide production of peptides bearing electron-rich aromatic residues.

Yao, Guiyang team published research on Journal of the American Chemical Society in 2021 | 35737-15-6

35737-15-6, Nalpha-FMOC-L-Tryptophan,also known as Fmoc-Trp-OH， is a useful research compound. Its molecular formula is C26H22N2O4 and its molecular weight is 426.5 g/mol. The purity is usually 95%.
Nα-Fmoc-L-Tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.
Fmoc-Trp-OH is an amino acid derivative
Fmoc-L-Trp-OH is an amide that contains a low bioavailability and inhibits the transfer of amino acids to ribosomes. It has been shown to inhibit the growth of cancer cells in cell culture and to have antimicrobial activity. Fmoc-L-Trp-OH is synthesized by reacting Naphthalene with glycine, followed by hydrolysis of the ester group under trifluoroacetic acid. The product is then conjugated with a polypeptide. This method of synthesis was developed as a way to produce peptides that are difficult to synthesize using solid-phase chemistry., Computed Properties of 35737-15-6

Yao, Guiyang;Knittel, Caroline H.;Kosol, Simone;Wenz, Marius T.;Keller, Bettina G.;Gruss, Hendrik;Braun, Alexandra C.;Lutz, Christian;Hechler, Torsten;Pahl, Andreas;Suessmuth, Roderich D. research published 《 Iodine-mediated tryptathionine formation facilitates the synthesis of amanitins》, the research content is summarized as follows. Synthetic methods on the macrocyclization of peptides are of high interest since they facilitate the synthesis of various types of potentially bioactive compounds, e.g. addressing targets like protein-protein-interactions. Herein, we report on an efficient method to construct tryptathionine-cross-links in peptides between the amino acids Trp and Cys. This reaction not only is the basis for the total synthesis of the death cap toxin α-amanitin but also provides rapid access to various new amanitin analogs. This study for the first time presents a systematic compilation of structure-activity relations (SAR) of amatoxins with regard to RNA polymerase II inhibition and cytotoxicity with one amanitin derivative of superior RNAP II inhibition. The present approach paves the way for the synthesis of structurally diverse amatoxins as future payloads for antibody-toxin conjugates in cancer therapy.

Yin, Huawu team published research on Journal of the American Chemical Society in 2021 | 35737-15-6

Yin, Huawu;Zhou, Xiuman;Huang, Yen-Hua;King, Gordon J.;Collins, Brett M.;Gao, Yanfeng;Craik, David J.;Wang, Conan K. research published 《 Rational Design of Potent Peptide Inhibitors of the PD-1:PD-L1 Interaction for Cancer Immunotherapy》, the research content is summarized as follows. Peptides have potential to be developed into immune checkpoint inhibitors, but the target interfaces are difficult to inhibit. Here, we explored an approach to mimic the binding surface of PD-1 to design inhibitors. Mimicking native PD-1 resulted in a mimetic with no activity. However, mimicking an affinity-optimized PD-1 resulted in the peptide mimetic MOPD-1 that displayed nanomolar affinity to PD-L1 and could inhibit PD-1:PD-L1 interactions in both protein- and cell-based assays. Mutagenesis and structural characterization using NMR spectroscopy and X-ray crystallog. revealed that binding residues from the high affinity PD-1 are crucial for the bioactivity of MOPD-1. Furthermore, MOPD-1 was extremely stable in human serum and inhibited tumor growth in vivo, suggesting it has potential for use in cancer immunotherapy. The successful design of an inhibitor of PD-1:PD-L1 using the mimicry approach described herein illustrates the value of placing greater emphasis on optimizing the target interface before inhibitor design and is an approach that could have broader utility for the design of peptide inhibitors for other complex protein-protein interactions.

Yuan, Zhenbo team published research on Green Chemistry in 2022 | 35737-15-6

Yuan, Zhenbo;Lu, Liushen;Liu, Meiling;Liu, Xuanzhong;Liu, Changmei;Yin, Dejing;Zhang, Yan;Rao, Yijian research published 《 Natural product cercosporin as a bioinspired photocatalyst for the synthesis of peptides containing kynurenine via an energy transfer mechanism》, the research content is summarized as follows. Cercosporin-catalyzed photo-mediated oxidation for the rapid and efficient synthesis of kynurenine (Kyn) derivatives as well as Kyn-containing peptides under mild conditions was developed, exhibiting great functional group tolerance and broad substrate scope to produce various nonproteinogenic peptides. This environmentally friendly process utilized the natural product cercosporin (CP) as a metal-free photocatalyst, visible light as a sustainable energy source, and oxygen as a green oxidant. Moreover, the synthetic utility of this photooxidation reaction was exemplified by the gram-scale synthesis employing crude CP conveniently obtained from the fermentation broth of Cercospora, and the successive transformation to kynurenine. Finally, preliminary mechanistic studies revealed that an energy transfer pathway was involved in the reaction.