Article
Chemistry, Organic
Mladena Glavas, Matija Gredicak, Zoran Stefanic, Ivanka Jeric
Summary: A concise and practical strategy was described for the synthesis of a novel class of 14-membered macrocycles containing an enediyne structural unit. The highly modular assembly of enediyne-peptide macrocycles was achieved through sequential Ugi/Sonogashira reactions. These macrocyclic compounds exhibited moderate antiproliferative activity and can serve as templates for further diversification in terms of ring size, shape, and stereochemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jian Pan, Qingwen Tan, Saibin Zhu, Xiaohui Yan, Yu Li, Zhoukang Zhuang, Xiangcheng Zhu, Yanwen Duan, Yong Huang
Summary: The identification and characterization of enediyne polyketide synthases (PKSEs) have revealed that polyene is a common intermediate produced by PKSEs, but the pathway for formation of enediyne cores remains unclear. In this study, we report the biosynthesis of pentaene polyols and cinnamic acid derivatives from an activated enediyne biosynthetic gene cluster. We found that increasing the cellular pool of (L)-Phe improved the yields of polyene polyols, and a flexible ammonia lyase was responsible for biosynthesis of cinnamic acid derivatives. Our findings also suggest a possible role of a polyene epoxide intermediate in the construction of 9-membered enediyne macrocycles.
Article
Chemistry, Multidisciplinary
Chun Gui, Edward Kalkreuter, Yu-Chen Liu, Ajeeth Adhikari, Christiana N. Teijaro, Dong Yang, Changsoo Chang, Ben Shen
Summary: This study investigates the biosynthetic mechanism of anthraquinone-fused enediynes. By identifying and characterizing the enzyme TnmK1, it reveals a new way of forming chemical bonds in these molecules. Additionally, an intermediate with potential anti-cancer activity was discovered. These findings are important for enzymology, natural product biosynthesis, and drug development.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Annadka Shrinidhi, Charles L. Perrin
Summary: The newly synthesized cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene can serve as a convenient model substrate for studying the reactivity of enediynes, with its p-dehydrobenzene diradical being trapable by nucleophiles in solution. The cyclization is the rate-limiting step, with a speed slightly slower than the parent substrate but faster than its benzene analogue.
Article
Biochemistry & Molecular Biology
Esther J. J. Han, Seoung Rak Lee, Craig A. A. Townsend, Mohammad R. R. Seyedsayamdost
Summary: Researchers have discovered new antibiotics and metabolites in previously unexplored Streptomyces clavuligerus strains using a fluorescence-based DNA cleavage assay and high-throughput elicitor screening. These compounds, called clavulynes A-J, have unique carbonate and terminal olefin functionalities, and contribute to the growing repertoire of enediynes.
ACS CHEMICAL BIOLOGY
(2023)
Article
Food Science & Technology
Ziying Yang, Yajie Hu, Panpan Yue, Rui Tian, Huiling Li, Baozhong Lu, Gegu Chen, Feng Peng
Summary: In this study, amorphous selenium nanoparticles were prepared by decorating them with lichenan, and their potential anticancer efficacy was demonstrated through ROS-triggered selenium release.
Article
Oncology
Mostafa M. El-Sheekh, Mohamed Nassef, Eman Bases, Shimaa El Shafay, Rania El-Shenody
Summary: This study evaluated the antitumor and antitumor immunological potentials of extracts from brown alga Padinapavonica and red alga Janiarubens. The extracts showed effective inhibition of liver cancer cells in vitro and enhanced antitumor immunity in vivo. They also reduced tumor cell viability and increased lymphocyte count while decreasing neutrophils and monocytes. These extracts have potential antitumor and immunological effects with low toxicity, suggesting further investigation into their mechanisms.
CANCER CELL INTERNATIONAL
(2022)
Article
Chemistry, Multidisciplinary
Prabuddha Bhattacharya, Soham Chakraborty, Ashwin Balaji, Amit Basak
Summary: This study investigates the kinetics of Bergman cyclization reaction and finds that the structural features of enediynes affect their reaction rates. The cd-distance model and the transition state model are proposed based on the analysis of experimental data. Recently, a distortion model is introduced to explain the regioselectivity of nucleophilic addition to unsymmetrical enediynes. The study also reveals that larger interior angles at the proximal alkyne carbons in enediynes lead to lower activation barriers and faster reaction rates.
Article
Engineering, Biomedical
Qin Wang, Firdoz Shaik, Xiuxin Lu, Wenhao Zhang, Yafei Wu, Haisheng Qian, Weiqing Zhang
Summary: A novel nanozyme, A-NiB@C-IrOx, consisting of amorphous NiB alloy core completely coated with an ultrathin layer of IrOx shell, demonstrates efficient self-cascade catalysis for continuous generation of ROS and depletion of GSH, leading to high therapeutic efficiency.
ACTA BIOMATERIALIA
(2023)
Article
Pharmacology & Pharmacy
Sajid Jalal, Ting Zhang, Jia Deng, Jie Wang, Ting Xu, Tianhua Zhang, Chuanxin Zhai, Ruqiang Yuan, Hongming Teng, Lin Huang
Summary: This study found that LXX-8250 treatment can induce apoptosis in melanoma cells by inhibiting autophagic flux and glycolysis. This effect is mediated by suppression of PFKFB4 expression. The research provides a novel strategy for the treatment of melanoma.
FRONTIERS IN PHARMACOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Chun Gui, Edward Kalkreuter, Yu-Chen Liu, Gengnan Li, Andrew D. Steele, Dong Yang, Changsoo Chang, Ben Shen
Summary: In this study, two cofactorless oxygenases were characterized for their biochemical and structural properties, revealing their roles in catalyzing deformylation, ring cleavage, and epoxidation in the biosynthesis of tiancimycin A. These oxygenases are rare in nature and play important roles in natural product biosynthesis.
NATURE CHEMICAL BIOLOGY
(2023)
Article
Food Science & Technology
Yangyang Liu, Yonglu Li, Wen Chen, Xiang Ye, Ruoyi Jia, Lushuang Yu, Qiong Tang, Pengcheng Tu, Yong Jiang, Qiang Chu, Xiaodong Zheng
Summary: This study investigated the antitumor activity of the flavones-rich fraction of Tetrastigma hemsleyanum root in vitro and in vivo. The results showed that this fraction inhibited proliferation and migration of HepG2 cells through the PI3K/AKT pathway. It also induced changes in cellular oxidative stress levels and mitochondrial membrane potential. In vivo experiments demonstrated that the treatment suppressed tumor growth and regulated the expression of proteins involved in tumor growth and apoptosis. These findings suggest Tetrastigma hemsleyanum as a promising candidate for liver cancer treatment.
FOOD QUALITY AND SAFETY
(2021)
Article
Chemistry, Medicinal
Liwei Ma, Jinling Zhang, Xuemei Wang, Jifang Yang, Lina Guo, Xiaoli Wang, Bo Song, Wei Dong, Wenbao Wang
Summary: DSG-amino acid ester derivatives showed cytotoxic activities against various human cancer cell lines, with compound 7g exhibiting the most significant cytotoxicity against the K562 cell line. Mechanistic studies revealed that compound 7g induced mitochondrial-related apoptosis in K562 cells, highlighting its potential as a promising scaffold for the development of more potent anticancer agents.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Lan-Shan Liao, Lin-Jie Tan, Yin Chen, Qi-Yuan Yang, Muhammad Iqbal Choudhary, Ying-Ming Pan, Hai-Tao Tang, Gui-Fa Su, Hong Liang, Zhen-Feng Chen
Summary: An efficient one-pot reaction for the synthesis of oxoaporphine alkaloids has been developed, and their antitumor activities have been evaluated. Compound 4B exhibited the most potent activity, inhibiting the growth of T-24 tumor cells effectively and showing significant tumor growth inhibition in a mouse model. Substitution at the C3-position of the oxoaporphine core with -NO2 significantly enhanced the anticancer activity.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Xin Zhang, Tingting Yang, Xin Jin, Kaige Lin, Xiling Dai, Ting Gao, Guozheng Huang, Minghui Fan, Liang Ma, Zi Liu, Jianguo Cao
Summary: In this study, podophyllotoxin derivatives incorporating piperazinyl-cinnamic amide moieties at the 4-position were synthesized. Compound 6e showed the best anti-proliferative properties and inhibited mitochondria-associated apoptosis in MCF-7 cells.
BIOORGANIC CHEMISTRY
(2022)