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Lapachone

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https://www.readbyqxmd.com/read/28700690/inactivation-of-human-dgat2-by-oxidative-stress-on-cysteine-residues
#1
Sunhee Jung, Miri Choi, Kwangman Choi, Eun Bin Kwon, Mingu Kang, Dong-Eun Kim, Hyejeong Jeong, Janghwan Kim, Jong Heon Kim, Mun Ock Kim, Sang-Bae Han, Sungchan Cho
Diacylglycerol acyltransferases (DGATs) have a crucial role in the biosynthesis of triacylglycerol (TG), the major storage form of metabolic energy in eukaryotic organisms. Even though DGAT2, one of two distinct DGATs, has a vital role in TG biosynthesis, little is known about the regulation of DGAT2 activity. In this study, we examined the role of cysteine and its oxidation in the enzymatic activity of human DGAT2 in vitro. Human DGAT2 activity was considerably inhibited not only by thiol-modifying reagents (NEM and IA) but also by ROS-related chemicals (H2O2 and β-lapachone), while human DGAT1 and GPAT1 were little affected...
2017: PloS One
https://www.readbyqxmd.com/read/28675505/supramolecular-interactions-between-%C3%AE-lapachone-with-cyclodextrins-studied-using-isothermal-titration-calorimetry-and-molecular-modeling
#2
Francisco H Xavier-Junior, Marcelo M Rabello, Marcelo Z Hernandes, Marília E S Dias, Otoni H M S Andrada, Beatriz P Bezerra, Alejandro P Ayala, Nereide S Santos-Magalhães
Supramolecular interactions between β-lapachone (β-lap) and cyclodextrins (CDs) were investigated by isothermal titration calorimetry. The most favorable host: guest interaction was characterized using X-ray powder diffraction (XRD), differential scanning calorimetry and thermogravimetry (DSC/TG), spectroscopy (FT-IR), spectroscopy (2D ROESY) nuclear magnetic resonance (NMR), and molecular modeling. Phase solubility diagrams showed β-, HP-β-, SBE-β-, γ-, and HP-γ-CDs at 1.5% (w/w) allowed an increase in apparent solubility of β-lap with enhancement factors of 12...
July 4, 2017: Journal of Molecular Recognition: JMR
https://www.readbyqxmd.com/read/28592850/nad-augmentation-ameliorates-acute-pancreatitis-through-regulation-of-inflammasome-signalling
#3
AiHua Shen, Hyung-Jin Kim, Gi-Su Oh, Su-Bin Lee, Seung Hoon Lee, Arpana Pandit, Dipendra Khadka, Seong-Kyu Choe, Sung Chul Kwak, Sei-Hoon Yang, Eun-Young Cho, Hyun-Seok Kim, Hail Kim, Raekil Park, Tae Hwan Kwak, Hong-Seob So
Acute pancreatitis (AP) is a complicated disease without specific drug therapy. The cofactor nicotinamide adenine dinucleotide (NAD(+)) is an important regulator of cellular metabolism and homeostasis. However, it remains unclear whether modulation of NAD(+) levels has an impact on caerulein-induced AP. Therefore, in this study, we investigated the effect of increased cellular NAD(+) levels on caerulein-induced AP. We demonstrated for the first time that the activities and expression of SIRT1 were suppressed by reduction of intracellular NAD(+) levels and the p53-microRNA-34a pathway in caerulein-induced AP...
June 7, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28586252/lapachol-and-lapachone-analogs-a-journey-of-two-decades-of-patent-research-1997-2016
#4
Hidayat Hussain, Ivan R Green
Lapachol (1), β-lapachone (2) and α-lapachone (3) are three well-studied natural products isolated from Tabebuia impetiginosa having most interesting chemodiversity and demonstrating diverse biological effects. Areas covered: The current review summarizes the recent and past discovery of chemotherapeutic agents based on the compounds 1-3. This review presents an overview of patents filed over the past two decades (1997 to 2016) mostly relating to the anticancer effects of these lapachol and lapachone analogues...
June 14, 2017: Expert Opinion on Therapeutic Patents
https://www.readbyqxmd.com/read/28580145/lysosome-oriented-dual-stage-ph-responsive-polymeric-micelles-for-%C3%AE-lapachone-delivery
#5
Yinjian Zhou, Ying Dong, Gang Huang, Yiguang Wang, Xiaonan Huang, Fayun Zhang, David A Boothman, Jinming Gao, Wei Liang
β-Lapachone (β-lap), a novel anticancer agent, is bioactivated by NADP(H):quinone oxidoreductase 1 (NQO1), an enzyme over-expressed in numerous tumors, including lung, pancreas, breast, and prostate cancers. Fast renal clearance and methemaglobinemia / hemolytic side-effects from the clinical formulation (β-lap-hydroxyl propyl-β-cyclodextrin complex) hindered its clinical translation. Here, we investigated a dual model pH responsive polymers for β-lap delivery. Three pH-sensitive linkages, including acylhydrazone, ketal and imine bonds for β-lap prodrug syntheses result in an aryl imine linkage the most optimal linkage...
December 14, 2016: Journal of Materials Chemistry. B, Materials for Biology and Medicine
https://www.readbyqxmd.com/read/28578385/%C3%AE-lapachone-suppresses-tumour-progression-by-inhibiting-epithelial-to-mesenchymal-transition-in-nqo1-positive-breast-cancers
#6
Yang Yang, Xianchun Zhou, Ming Xu, Junjie Piao, Yuan Zhang, Zhenhua Lin, Liyan Chen
NQO1 is a FAD-binding protein that can form homodimers and reduce quinones to hydroquinones, and a growing body of evidence currently suggests that NQO1 is dramatically elevated in solid cancers. Here, we demonstrated that NQO1 was elevated in breast cancer and that its expression level was positively correlated with invasion and reduced disease free survival (DFS) and overall survival (OS) rates. Next, we found that β-lapachone exerted significant anti-proliferation and anti-metastasis effects in breast cancer cell lines due to its effects on NQO1 expression...
June 2, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28481901/%C3%AE-lapachone-suppresses-the-lung-metastasis-of-melanoma-via-the-mapk-signaling-pathway
#7
Ji-Ye Kee, Yo-Han Han, Dae-Seung Kim, Jeong-Geon Mun, Seong-Hwan Park, Hong-Seob So, Sung-Joo Park, Raekil Park, Jae-Young Um, Seung-Heon Hong
β-Lapachone is a natural quinone compound from Lapacho trees, which has various pharmacological effects such as anti-bacterial, anti-fungal, anti-viral, and anti-inflammatory activities. However, the effect of β-lapachone on metastasis of melanoma cells is unclear. In this study, β-lapachone reduced cell viability of metastatic melanoma cancer cell lines B16F10 and B16BL6 through induction of apoptosis via the mitogen-activated protein kinase (MAPK) pathway. Additionally, flow cytometry results showed that β-lapachone increased DNA content in the G0/G1 phase of the cell cycle...
2017: PloS One
https://www.readbyqxmd.com/read/28463406/cpt11-prevents-virus-replication-in-jci-cells-persistently-infected-with-jc-polyomavirus
#8
Souichi Nukuzuma, Chiyoko Nukuzuma, Masanori Kameoka, Shigeki Sugiura, Kazuo Nakamichi, Takafumi Tasaki, Tsutomu Takegami
JC polyomavirus (JCPyV) is the causative agent of the demyelinating disease in the central nervous system, known as PML in immunocompromised patients. Moreover, PML occurred in patients treated with natalizumab for MS or Crohn's disease as natalizumab-related PML. Many antiviral agents are being investigated due to the lack of drugs currently available for PML. The previous study demonstrated that the topoisomerase I inhibitors topotecan and β-lapachone have inhibitory effects on JCPyV replication in IMR-32 cells...
May 2, 2017: Microbiology and Immunology
https://www.readbyqxmd.com/read/28451143/understanding-and-predicting-the-potency-of-ros-based-enzyme-inhibitors-exemplified-by-naphthoquinones-and-ubiquitin-specific-protease-2
#9
Pushparathinam Gopinath, Atif Mahammed, Shimrit Ohayon, Zeev Gross, Ashraf Brik
Recent studies have suggested that selective targeting of overexpressed enzymes in cancer cells by small molecules that induce the formation of reactive oxygen species (ROS) could be a viable approach in cancer therapy. One such example is the inactivation of ubiquitin specific protease-2 (USP2)-an emerging drug target to combat prostate cancer-by β-lapachone, which has been identified to involve oxidation of the catalytic cysteine's thiol residue to sulfinic acid. A rational design of β-lapachone analogs with improved activity requires a much better understanding of the variables that determine ROS production by this class of molecules...
December 1, 2016: Chemical Science
https://www.readbyqxmd.com/read/28433938/imaging-lysosomal-highly-reactive-oxygen-species-and-lighting-up-cancer-cells-and-tumors-enabled-by-a-si-rhodamine-based-near-infrared-fluorescent-probe
#10
Hongxing Zhang, Jing Liu, Chenlu Liu, Pengcheng Yu, Minjia Sun, Xiaohan Yan, Jian-Ping Guo, Wei Guo
Lysosomes have recently been regarded as the attractive pharmacological targets for selectively killing of cancer cells via lysosomal cell death (LCD) pathway that is closely associated with reactive oxygen species (ROS). However, the details on the ROS-induced LCD of cancer cells are still poorly understood, partially due to the absence of a lysosome-targetable, robust, and biocompatible imaging tool for ROS. In this work, we brought forward a Si-rhodamine-based fluorescent probe, named PSiR, which could selectively and sensitively image the pathologically more relavent highly reactive oxygen species (hROS: HClO, HO, and ONOO(-)) in lysosomes of cancer cells...
April 14, 2017: Biomaterials
https://www.readbyqxmd.com/read/28357881/a-new-anthraquinone-and-a-new-naphthoquinone-from-the-whole-plant-of-spermacoce-latifolia
#11
Ying Luo, Hai-Yan Shen, Qing-Xiang Shen, Zhao-Hui Cao, Min Zhang, Shi-Yin Long, Zong-Bao Wang, Jian-Wen Tan
A phytochemical study on the whole plant of Spermacoce latifolia led to the isolation of a new anthraquinone, 1,2,6-trihydroxy-5-methoxy-9,10-anthraquinone (1), and a new naphthoquinone, (2R)-6-hydroxy-7-methoxy-dehydroiso-α-lapachone (2), together with three known anthraquinones (3-5). Their structures were established on the basis of detailed spectroscopic analysis, including one- and two-dimensional NMR, ESI-MS, and HR-ESI-MS techniques. All the compounds were isolated from S. latifolia for the first time...
March 30, 2017: Journal of Asian Natural Products Research
https://www.readbyqxmd.com/read/28346693/using-a-novel-nqo1-bioactivatable-drug-beta-lapachone-arq761-to-enhance-chemotherapeutic-effects-by-metabolic-modulation-in-pancreatic-cancer
#12
Muhammad Shaalan Beg, Xiumei Huang, Molly A Silvers, David E Gerber, Joyce Bolluyt, Venetia Sarode, Farjana Fattah, Ralph J Deberardinis, Matthew E Merritt, Xian-Jin Xie, Richard Leff, Daniel Laheru, David A Boothman
Novel, tumor-selective therapies are needed to increase the survival rate of pancreatic cancer patients. K-Ras-mutant-driven NAD(P)H:quinone oxidoreductase 1 (NQO1) is over-expressed in pancreatic tumor versus associated normal tissue, while catalase expression is lowered compared to levels in associated normal pancreas tissue. ARQ761 undergoes a robust, futile redox cycle in NQO1+ cancer cells, producing massive hydrogen peroxide (H2 O2 ) levels; normal tissues are spared by low NQO1 and high catalase expression...
July 2017: Journal of Surgical Oncology
https://www.readbyqxmd.com/read/28214631/discovery-of-quinone-directed-antitumor-agents-selectively-bioactivated-by-nqo1-over-cpr-with-improved-safety-profile
#13
Jinlei Bian, Xiang Li, Nan Wang, Xingsen Wu, Qidong You, Xiaojin Zhang
In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR...
March 31, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28212345/efficient-catalytic-oxidation-of-3-arylthio-and-3-cyclohexylthio-lapachone-derivatives-to-new-sulfonyl-derivatives-and-evaluation-of-their-antibacterial-activities
#14
Mariana F do C Cardoso, Ana T P C Gomes, Caroline Dos S Moreira, Mário M Q Simões, Maria G P M S Neves, David R da Rocha, Fernando de C da Silva, Catarina Moreirinha, Adelaide Almeida, Vitor F Ferreira, José A S Cavaleiro
New sulfonyl-lapachones were efficiently obtained through the catalytic oxidation of arylthio- and cyclohexylthio-lapachone derivatives with hydrogen peroxide in the presence of a Mn(III) porphyrin complex. The antibacterial activities of the non-oxidized and oxidized lapachone derivatives against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus were evaluated after their incorporation into polyvinylpyrrolidone (PVP) micelles. The obtained results show that the PVP-formulations of the lapachones 4b-g and of the sulfonyl-lapachones 7e and 7g reduced the growth of S...
February 16, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28112927/selective-inhibitors-of-human-liver-carboxylesterase-based-on-a-%C3%AE-lapachone-scaffold-novel-reagents-for-reaction-profiling
#15
M Jason Hatfield, Jingwen Chen, Ellie M Fratt, Liying Chi, John C Bollinger, Randall J Binder, John Bowling, Janice L Hyatt, Jerrod Scarborough, Cynthia Jeffries, Philip M Potter
Carboxylesterases (CEs) are ubiquitous enzymes that are responsible for the metabolism of xenobiotics, including drugs such as irinotecan and oseltamivir. Inhibition of CEs significantly modulates the efficacy of such agents. We report here that β-lapachone is a potent, reversible CE inhibitor with Ki values in the nanomolar range. A series of amino and phenoxy analogues have been synthesized, and although the former are very poor inhibitors, the latter compounds are highly effective in modulating CE activity...
February 23, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28094224/synthesis-of-pharmacologically-important-naphthoquinones-and-anticancer-activity-of-2-benzyllawsone-through-dna-topoisomerase-ii-inhibition
#16
Balagani Sathish Kumar, Kusumoori Ravi, Amit Kumar Verma, Kaneez Fatima, Mohammad Hasanain, Arjun Singh, Jayanta Sarkar, Suaib Luqman, Debabrata Chanda, Arvind S Negi
Naphthoquinones are naturally occurring biologically active entities. Practical de novo syntheses of three naphthoquinones i.e. lawsone (1), lapachol (2), and β-lapachone (3b) have been achieved from commercially available starting materials. The conversion of lapachol (2) to β-lapachone (3b) was achieved through p-TSA/Iodine/BF3-etherate mediated regioselective cyclisation. Further, 2-alkyl and 2-benzyllawsone derivatives have been prepared as possible anticancer agents. Four derivatives exhibited significant anticancer activity and the best analogue i...
December 28, 2016: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/27986568/distinct-responses-of-compartmentalized-glutathione-redox-potentials-to-pharmacologic-quinones-targeting-nqo1
#17
Vladimir L Kolossov, Nagendraprabhu Ponnuraj, Jessica N Beaudoin, Matthew T Leslie, Paul J Kenis, H Rex Gaskins
Deoxynyboquinone (DNQ), a potent novel quinone-based antineoplastic agent, selectively kills solid cancers with overexpressed cytosolic NAD(P)H:quinone oxidoreductase-1 (NQO1) via excessive ROS production. A genetically encoded redox-sensitive probe was used to monitor intraorganellar glutathione redox potentials (EGSH) as a direct indicator of cellular oxidative stress following chemotherapeutic administration. Beta-lapachone (β-lap) and DNQ-induced spatiotemporal redox responses were monitored in human lung A549 and pancreatic MIA-PaCa-2 adenocarcinoma cells incubated with or without dicumarol and ES936, potent NQO1 inhibitors...
January 29, 2017: Biochemical and Biophysical Research Communications
https://www.readbyqxmd.com/read/27974673/mir-218-2-promotes-glioblastomas-growth-invasion-and-drug-resistance-by-targeting-cdc27
#18
Zhuoying Feng, Luping Zhang, Junchen Zhou, Shuai Zhou, Li Li, Xuyan Guo, Guoying Feng, Ze Ma, Wenhua Huang, Fei Huang
Glioma has become a significant global health problem with substantial morbidity and mortality, underscoring the importance of elucidating its underlying molecular mechanisms. Recent studies have identified mir-218 as an anti-oncogene; however, the specific functions of mir-218-1 and mir-218-2 remain unknown, especially the latter. The objective of this study was to further investigate the role of mir-218-2 in glioma. Our results indicated that mir-218-2 is highly overexpressed in glioma. Furthermore, we showed that mir-218-2 is positively correlated with the growth, invasion, migration, and drug susceptibility (to β-lapachone) of glioma cells...
January 24, 2017: Oncotarget
https://www.readbyqxmd.com/read/27960087/leveraging-an-nqo1-bioactivatable-drug-for-tumor-selective-use-of-poly-adp-ribose-polymerase-inhibitors
#19
Xiumei Huang, Edward A Motea, Zachary R Moore, Jun Yao, Ying Dong, Gaurab Chakrabarti, Jessica A Kilgore, Molly A Silvers, Praveen L Patidar, Agnieszka Cholka, Farjana Fattah, Yoonjeong Cha, Glenda G Anderson, Rebecca Kusko, Michael Peyton, Jingsheng Yan, Xian-Jin Xie, Venetia Sarode, Noelle S Williams, John D Minna, Muhammad Beg, David E Gerber, Erik A Bey, David A Boothman
Therapeutic drugs that block DNA repair, including poly(ADP-ribose) polymerase (PARP) inhibitors, fail due to lack of tumor-selectivity. When PARP inhibitors and β-lapachone are combined, synergistic antitumor activity results from sustained NAD(P)H levels that refuel NQO1-dependent futile redox drug recycling. Significant oxygen-consumption-rate/reactive oxygen species cause dramatic DNA lesion increases that are not repaired due to PARP inhibition. In NQO1(+) cancers, such as non-small-cell lung, pancreatic, and breast cancers, cell death mechanism switches from PARP1 hyperactivation-mediated programmed necrosis with β-lapachone monotherapy to synergistic tumor-selective, caspase-dependent apoptosis with PARP inhibitors and β-lapachone...
December 12, 2016: Cancer Cell
https://www.readbyqxmd.com/read/27923905/%C3%AE-lapachone-inhibits-lung-metastasis-of-colorectal-cancer-by-inducing-apoptosis-of-ct26-cells
#20
Ji-Ye Kee, Yo-Han Han, Jinbong Park, Dae-Seung Kim, Jeong-Geon Mun, Kwang Seok Ahn, Hyun-Jung Kim, Jae-Young Um, Seung-Heon Hong
BACKGROUND: β-Lapachone is a quinone-containing compound found in red lapacho (Tabebuia impetiginosa, syn. T avellanedae) trees. Lapacho has been used in traditional medicine by several South and Central American indigenous people to treat various types of cancer. The purpose of this study was to investigate the antimetastatic properties of β-lapachone and the underlying mechanisms using colon cancer cells. METHODS: This research used metastatic murine colon cancer cell lines, colon 26 (CT26) and colon 38 (MC38)...
December 5, 2016: Integrative Cancer Therapies
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