13139-14-5Relevant articles and documents
Synthesis and biological evaluation of novel 1-Alkyl-tryptophan analogs as potential antitumor agents
Sun, Ting,Li, Zhao-Long,Tian, Hua,Wang, Shih-Chen,Cai, Jiong
, p. 5339 - 5348 (2009)
To seek novel antitumor agents, we designed and synthesized new 1-tryptophan analogs based on tryptophan catabolism. 1-Alkyl-tryptophan analogues including 1-ethyl-tryptophan (1-ET), 1-propyltryptophan (1-PT), 1-isopropyltryptophan (1-isoPT) and 1-butyltryptophan (1-BT) were synthesized from tryptophan. We examined whether those compounds had the antiproliferative effects on SGC7901 and HeLa cells line by using MTT assay in vitro, respectively. Compared to tryptophan, all targeted compounds efficiently inhibited proliferation of two cancer cell lines at 2 mmol/L for 48 hours. Among these tryptophan analogs, 1-BT showed the most powerful cytotoxicity against SGC7901 and HeLa cells at 1 mmol/L and 2 mmol/L concentration. These data suggest that some specific tryptophan analogs could be developed as potential anti-neoplastic agents.
Supramolecular helix of an amphiphilic pyrene derivative induced by chiral tryptophan through electrostatic interactions
Xiao, Jinchong,Xu, Jialiang,Cui, Shuang,Liu, Huibiao,Wang, Shu,Li, Yuliang
, p. 645 - 648 (2008)
An amphophilic pyrene derivative (PyDNH3) bearing positively charged ammonium cations has been synthesized and characterized. Self-assembly of PyDNH3 in the presence of chiral tryptophan derivatives was investigated in ethanol/water by optical and chiroptical spectra, indicating the formation of helical aggregates. Scanning electron microscope (SEM) images showed the formation of ring-shape structures.
Soluble non-cross-linked poly(norbornene) supports for peptide synthesis with minimal reagents
Naganna, Nimmashetti,Madhavan, Nandita
, p. 11549 - 11557 (2014)
Solid-phase peptide synthesis has been an attractive method for synthesizing peptides because it is quick and can be automated. The heterogeneous reaction medium in solid-phase peptide synthesis necessitates the use of large equivalents of reagents to drive the reactions to completion. Peptide synthesis using soluble, yet isolable, supports is an attractive alternative to solid-phase peptide synthesis. Reported herein is a soluble poly(norbornene)-derived support containing multiple attachment sites for high loading capacities and solubilizing oligoether/alkyl groups. The Ala-attached support has been used to synthesize tri- to octapeptides in 28 to 97% yields using only 1.2 equiv of amino acids and coupling reagents. The acyclic hexapeptide precursor to natural product segatalin A was synthesized in 41% yield on the support using one-eighth of the equivalents of coupling reagents compared to that in reported procedures. The support could be recovered in up to 98% yield after peptide synthesis, and the recovered support was utilized to synthesize tri- and tetrapeptides that contain amino acids other than Ala at the C-terminus in ca. 80% yields.
Development of N-hydroxybenzamide derivatives with indole-containing cap group as histone deacetylases inhibitors
Li, Xiaoyang,Wu, Jingde,Li, Xiaoguang,Mu, Weiwei,Liu, Xueliang,Jin, Yiming,Xu, Wenfang,Zhang, Yingjie
, p. 6258 - 6270 (2015)
Histone deacetylases inhibitors (HDACIs) have captured more and more attention in many diseases therapies, of which cancer is the most intractable. A novel series of N-hydroxybenzamide derivatives containing indole cap group was designed and synthesized. Most compounds exhibited excellent HDACs inhibitory activity, especially 8q-8v with low nanomolar IC50 values (1.5-13.0 nM), which were much more potent than the positive control SAHA. The most potent compound 8r showed slightly higher growth inhibitory activity than SAHA in multiple tumor cell lines, even though, antiproliferative activity of 8r seemed inferior to its HDAC inhibition activity. Poor transcellular permeability obtained from the result of HDAC class I cellular assay could explain the inferior antiproliferative activity. In addition, 8r displayed similar HDAC IIa cellular activity to class I, which indicated 8r might be a potent pan-HDAC inhibitor.
Lead discovery of a guanidinyl tryptophan derivative on amyloid cascade inhibition
Jiaranaikulwanitch, Jutamas,Suwanttananuruk, Piyapan,Vajragupta, Opa,Waiwut, Pornthip
, p. 546 - 558 (2020)
Amyloid cascade, one of pathogenic pathways of Alzheimer's disease (AD), was focused as one of drug discovery targets. In this study, β-secretase (BACE1) inhibitors were designed aiming at the development of multifunctional compounds targeting amyloid pathogenic cascade. Tryptophan was used as a core structure due to its properties of the central nervous system (CNS) penetration and BACE1 inhibition activity. Three amino acid residues and guanidine were selected as linkers to connect the tryptophan core structure and the extended aromatic moieties. The distance between the aromatic systems of the core structure and the extended moieties was kept at the optimal length for amyloid-β (Aβ) peptide binding to inhibit its fibrillation and aggregation. Sixteen designed compounds were evaluated in silico. Eight hit compounds of TSR and TGN series containing serine and guanidine linkers, respectively, were identified and synthesized based on docking results. TSR2 and TGN2 were found to exert strong actions as BACE1 (IC50 24.18 μM and 22.35 μM) and amyloid aggregation inhibitors (IC50 37.06 μM and 36.12 μM). Only TGN2 demonstrated a neuroprotective effect in SH-SY5Y cells by significantly reducing Aβ-induced cell death at a concentration of 2.62 μM. These results support the validity of multifunctional approaches to inhibition of the β-amyloid cascade.
The (+/-)-1-(4-Methoxyphenyl)ethyl Ester as a Carboxyl Protecting Group
Bernatowicz, Michael S.,Chao, Hann-Guang,Matsueda, Gary R.
, p. 1651 - 1652 (1994)
Unhindered carboxylic acids were converted to their (+/-)-1-(4-methoxyphenyl)ethyl (MPe) esters in good yields by condensation with (+/-)-1-(4-methoxyphenyl)ethanol under mild conditions.The Mpe esters were rapidly and quantitatively cleavable by either 1percent TFA in CH2Cl2 or 10percent DCA in CH2Cl2, conditions which leave Boc, t-butyl ester and either intact.An Mpe ester was removed by hydrogenolysis much more slowsly than the analogous benzyl ester.
Conditional changes enhanced production of bioactive metabolites of marine derived fungus Eurotium rubrum
Kamauchi, Hitoshi,Kinoshita, Kaoru,Sugita, Takashi,Koyama, Kiyotaka
, p. 4911 - 4914 (2016)
Metabolites of marine derived fungus Eurotium rubrum MPUC136 differed between cultivation on wheat medium and Czapek-Dox agar medium. Melanin synthesis inhibitory activity of crude extract of culture on wheat medium showed stronger activity than that of crude extract of culture on Czapek-Dox agar medium. A new diketopiperazine compound isoechinulin D (1) and eight reported diketopiperazines (2–9) were isolated from the crude extract of wheat medium. The structure of 1 was established using NMR, MS and IR methods. 2–5 inhibited melanogenesis using B16 melanoma cells (IC50?=?68, 2.4, 83, 9.1?μM each). Structure–Activity-Relationships of diketopiperazines (1–10) indicated the importance of the prenyl groups at C-2, C-5 and C-7, the vinyl group at C-12 to C-25 and the sp2carbons at C-8 and C-9. Isolated compounds (1–9) were not or slightly observed from the extracts of Czapek-Dox agar medium by HPLC analysis, suggesting that different cultivation processes could affect metabolism and enhance bioactivities.
Pseudo-peptides as novel antileptospiral agents: Synthesis and spectral characterization
Shivamallu, Chandan,Sharanaiah, Umesha,Kollur, Shiva Prasad,Mallesh, Naveen Kumar R.,Hosakere, Revanasiddappa D.,Balamurugan
, p. 1152 - 1157 (2014)
In this paper, we describe the synthesis of novel class of pseudo-peptides derived by coupling an amino acid with a heterocyclic moiety containing free amine group using suitable coupling agents. The synthesized compounds were characterized using spectral (1H NMR, 13C NMR and MS) techniques. Preliminary pharmacological assays for Leptospirosis were studied by test tube dilution (TDT) and micro dilution technique (MDT). In particular, all the analyses led to the conclusion that the synthesized compound inhibiting the Leptospira a causal organism of Leptospirosis.
L-Proline induced self-assembly of indolicidin derived palindromic tripeptide
Joshi, Khashti Ballabh,Singh, Prabhpreet
, p. 3534 - 3537 (2014)
We describe the synthesis, crystal structure, and various microscopic studies of the palindromic tripeptide WPW derived from antimicrobial peptide indolicidin. The present study reveals that tripeptide 1 and 2 undergo self-assembly to form vesicular structures after prolonged incubation, thus giving an interesting insight into the contribution of l-proline and flanking tryptophan residues in the self-assembly process. These vesicles were also amenable to simple focused ion beam (FIB)-aided bisection and thus possible to mill these vesicles to create different shapes. The circular dichroism (CD) analysis indicates that incubation promotes and stabilizes the more favorable secondary structures for 1 and 2. Preliminary result shows that tripeptide 1 exhibits appreciable interaction with Tb3+ as determined by quenching in tryptophan fluorescence.
Enantioselective recognition by optically active chiral fluorescence sensors bearing amino acid units
Xu, Kuo-Xi,He, Yong-Bing,Qin, Hai-Juan,Qing, Guang-Yan,Liu, Shun-Ying
, p. 3042 - 3048 (2005)
Chiral fluorescence receptors 1 and 2 were synthesized and their structures characterized by IR, 1H NMR, 13C NMR, MS spectra, and elemental analysis. The chiral recognition abilities of 1 and 2 were studied by 1H NMR and fluorescence spectra. The results demonstrate that receptors 1 and 2 with bis(tetrabutylammonium) dibenzoyl tartrate formed a 1:1 complex. Receptor 2 exhibits an excellent enantioselective recognition ability toward the enantiomers of bis(tetrabutylammonium) dibenzoyl tartrate.
