64605-37-4Relevant articles and documents
4-Chloro-l-kynurenine as fluorescent amino acid in natural peptides
Alferova, Vera A.,Shuvalov, Maxim V.,Suchkova, Taisiya A.,Proskurin, Gleb V.,Aparin, Ilya O.,Rogozhin, Eugene A.,Novikov, Roman A.,Solyev, Pavel N.,Chistov, Alexey A.,Ustinov, Alexey V.,Tyurin, Anton P.,Korshun, Vladimir A.
, p. 1697 - 1705 (2018/09/21)
4-Chloro-l-kynurenine (3-(4-chloroanthraniloyl)-l-alanine, l-4-ClKyn), an amino acid known as a prospective antidepressant, was recently for the first time found in nature in the lipopeptide antibiotic taromycin. Here, we report another instance of its identification in a natural product: 4-chloro-l-kynurenine was isolated from acidic hydrolysis of a new complex peptide antibiotic INA-5812. l-4-ClKyn is a fluorescent compound responsible for the fluorescence of the above antibiotic. Whereas fluorescence of 4-chlorokynurenine was not reported before, we synthesized the racemic compound and studied its emission in various solvents. Next, we prepared conjugates of dl-4-ClKyn with two suitable energy acceptors, BODIPY FL and 3-(phenylethynyl)perylene (PEPe), and studied fluorescence of the derivatives. 4-Chloro-dl-kynurenine emission is not detected in both conjugates, thus evidencing effective energy transfer. However, BODIPY FL emission in the conjugate is substantially reduced, probably due to collisional or photoinduced charge-transfer-mediated quenching. The intrinsic fluorescence of l-4-ClKyn amino acid in antibiotics paves the way for spectral studies of their mode of action.
METHODS FOR THE SYNTHESIS OF CHIRAL KYNURENINE COMPOUNDS
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Paragraph 0036, (2014/10/04)
Provided are methods for synthesizing compounds, including chiral kynurenine compounds. The methods are suitable for large-scale manufacture and produce the chiral kynurenines compounds in high chemical purity and high chiral purity.
New homocamptothecins: Synthesis, antitumor activity, and molecular modeling
Miao, Zhenyuan,Sheng, Chunquan,Zhang, Wannian,Ji, Haitao,Zhang, Jing,Shao, Luecheng,You, Liang,Zhang, Min,Yao, Jianzhong,Che, Xiaoyin
, p. 1493 - 1510 (2008/09/17)
Homocamptothecins (hCPTs) represent a class of new emerging antitumor agents, which contains a seven-membered β-hydroxylactone in place of the conventional six-membered α-hydroxylactone ring (E ring) of camptothecins. Some novel 7-substituted hCPTs were designed and synthesized based on a newly developed synthetic route which couples ring A with ring C, E and D. Most of the synthesized compounds exhibit very high cytotoxic activity on tumor cell line A549. Some compounds, such as 9b, 9l, and 9y, show broad in vitro antitumor spectrum and are more potent than topotecan. Three-dimensional quantitative structure-activity relationship (3D-QSAR) methods, CoMFA and CoMSIA, were applied to explain the structure-activity relationship (SAR) of the synthesized compounds. Furthermore, molecular docking was used to clarify the binding mode of the synthesized compounds to human DNA topoisomerase I. The important hydrophobic, base-pair stacking, and hydrogen-bonding interactions were observed between the hCPT derivatives and their receptor. The results from molecular modeling will guide the design of novel hCPTs with higher antitumor activity.
