keyword
https://read.qxmd.com/read/33022012/evaluation-of-the-anti-inflammatory-effects-of-synthesised-tanshinone-i-and-isotanshinone-i-analogues-in-zebrafish
#1
JOURNAL ARTICLE
Matthew J Foulkes, Faith H Tolliday, Katherine M Henry, Stephen A Renshaw, Simon Jones
During inflammation, dysregulated neutrophil behaviour can play a major role in a range of chronic inflammatory diseases, for many of which current treatments are generally ineffective. Recently, specific naturally occurring tanshinones have shown promising anti-inflammatory effects by targeting neutrophils in vivo, yet such tanshinones, and moreover, their isomeric isotanshinone counterparts, are still a largely underexplored class of compounds, both in terms of synthesis and biological effects. To explore the anti-inflammatory effects of isotanshinones, and the tanshinones more generally, a series of substituted tanshinone and isotanshinone analogues was synthesised, alongside other structurally similar molecules...
2020: PloS One
https://read.qxmd.com/read/32985744/natural-compounds-against-doxorubicin-induced-cardiotoxicity-a-review-on-the-involvement-of-nrf2-are-signaling-pathway
#2
REVIEW
Fatemeh Yarmohammadi, Ramin Rezaee, Gholamreza Karimi
Cardiotoxicity is the main concern for long-term use of the doxorubicin (DOX). Reactive oxygen species (ROS) generation leads to oxidative stress that significantly contributes to the cardiac damage induced by DOX. The nuclear factor erythroid 2-related factor (Nrf2) acts as a protective player against DOX-induced myocardial oxidative stress. Several natural compounds (NCs) with anti-oxidative effects, were examined to suppress DOX cardiotoxicity such as asiatic acid, α-linolenic acid, apigenin, baicalein, β-lapachone, curdione, dioscin, ferulic acid, Ganoderma lucidum polysaccharides, genistein, ginsenoside Rg3, indole-3-carbinol, naringenin-7-O-glucoside, neferine, p-coumaric acid, pristimerin, punicalagin, quercetin, sulforaphane, and tanshinone IIA...
March 2021: Phytotherapy Research: PTR
https://read.qxmd.com/read/32974194/targeting-base-excision-repair-in-cancer-nqo1-bioactivatable-drugs-improve-tumor-selectivity-and-reduce-treatment-toxicity-through-radiosensitization-of-human-cancer
#3
REVIEW
Colton L Starcher, S Louise Pay, Naveen Singh, I-Ju Yeh, Snehal B Bhandare, Xiaolin Su, Xiumei Huang, Erik A Bey, Edward A Motea, David A Boothman
Ionizing radiation (IR) creates lethal DNA damage that can effectively kill tumor cells. However, the high dose required for a therapeutic outcome also damages healthy tissue. Thus, a therapeutic strategy with predictive biomarkers to enhance the beneficial effects of IR allowing a dose reduction without losing efficacy is highly desirable. NAD(P)H:quinone oxidoreductase 1 (NQO1) is overexpressed in the majority of recalcitrant solid tumors in comparison with normal tissue. Studies have shown that NQO1 can bioactivate certain quinone molecules (e...
2020: Frontiers in Oncology
https://read.qxmd.com/read/32963735/naphthoquinones-from-handroanthus-impetiginosus-promote-skin-wound-healing-through-sirt3-regulation
#4
JOURNAL ARTICLE
Fayyaz Ahmad, Shaheen Bibi, Mincheol Kang, Mariam Anees, Muhammad Ansar, Muhammad Rizwan Alam, Sun Yeou Kim, Hussain Mustatab Wahedi
Objectives: Lapachone is a natural naphthoquinone-derived compound found in Tabebuia avellanedae . It is well-known for its analgesic, anti-inflammatory, anti-microbial, diuretic, and anti-cancerous effects. However, the wound-healing effects of this compound are not known yet. The aim of this study was to investigate the wound healing activity of naphthoquinones (α-lapachone and β-lapachone) from Handroanthus impetiginosus . Materials and Methods: Expression of Sirt3, migration-related proteins (Rac1, Cdc42, α-Pak) and angiogenesis-related protein of vascular endothelial growth factor (VEGF) was monitored using western blot analysis...
September 2020: Iranian Journal of Basic Medical Sciences
https://read.qxmd.com/read/32922184/nad-p-h-quinone-oxidoreductase-1-determines-radiosensitivity-of-triple-negative-breast-cancer-cells-and-is-controlled-by-long-non-coding-rna-neat1
#5
JOURNAL ARTICLE
Li-Ching Lin, Hsueh-Te Lee, Peng-Ju Chien, Yu-Hao Huang, Mu-Ya Chang, Yueh-Chun Lee, Wen-Wei Chang
Radioresistant cells cause recurrence in patients with breast cancer after they undergo radiation therapy. The molecular mechanisms by which cancer cells obtain radioresistance should be understood to develop radiation-sensitizing agents. Results showed that the protein expression and activity of NAD(P)H:quinone oxidoreductase 1 (NQO1) were upregulated in radioresistant MDA-MB-231 triple-negative breast cancer (TNBC) cells. NQO1 knockdown inhibited the proliferation of NQO1 expressing Hs578t TNBC cells or the radioresistant MDA-MB-231 cells, whereas NOQ1 overexpression increased the survival of MDA-MB-231 cells, which lack of NQO1 expression originally, under irradiation...
2020: International Journal of Medical Sciences
https://read.qxmd.com/read/32807066/naphthoquinone-based-hydrazone-hybrids-synthesis-and-potent-activity-against-cancer-cell-lines
#6
JOURNAL ARTICLE
Délis Galvão Guimarães, Arlan de Assis Gonsalves, Larissa Araújo Rolim, Edigênia Cavalcante Araújo, Victória Laysna Dos Anjos Santos, Maria Francilene Souza Silva, Fátima de Cássia Evangelista de Oliveira, Marcília Pinheiro da Costa, Claudia Pessoa, Marília Oliveira Fonseca Goulart, Thaissa Lucio Silva, Danyelle Cândido Santos, Cleônia Roberta Melo Araújo
BACKGROUND: Natural naphthoquinones have shown diversified biological activities including antibacterial, antifungal, antimalarial, and cytotoxic activities. However, they are also compounds with acute cytotoxicity, immunotoxicity, carcinogenesis, and cardio- and hepatotoxicity, then the modification at their redox center is an interesting strategy to overcome such harmful activity. OBJECTIVE: In this study, four novel semisynthetic hydrazones, derived from the isomers α- and β-lapachones (α and β, respectively) and coupled with the drugs hydralazine (HDZ) and isoniazid (ACIL), were prepared, evaluated by electrochemical methods and assayed for anticancer activity...
August 17, 2020: Medicinal Chemistry
https://read.qxmd.com/read/32789798/%C3%AE-lapachone-induces-acute-oxidative-stress-in-rat-primary-astrocyte-cultures-that-is-terminated-by-the-nqo1-inhibitor-dicoumarol
#7
JOURNAL ARTICLE
Johann Steinmeier, Sophie Kube, Gabriele Karger, Eric Ehrke, Ralf Dringen
β-lapachone (β-lap) is reduced in tumor cells by the enzyme NAD(P)H: quinone acceptor oxidoreductase 1 (NQO1) to a labile hydroquinone which spontaneously reoxidises to β-lap, thereby generating reactive oxygen species (ROS) and oxidative stress. To test for the consequences of an acute exposure of brain cells to β-lap, cultured primary rat astrocytes were incubated with β-lap for up to 4 h. The presence of β-lap in concentrations of up to 10 µM had no detectable adverse consequences, while higher concentrations of β-lap compromised the cell viability and the metabolism of astrocytes in a concentration- and time-dependent manner with half-maximal effects observed for around 15 µM β-lap after a 4 h incubation...
August 13, 2020: Neurochemical Research
https://read.qxmd.com/read/32761734/self-amplified-apoptosis-targeting-nanoplatform-for-synergistic-magnetic-thermal-chemo-therapy-in-vivo
#8
JOURNAL ARTICLE
Wei Liu, Li Chen, Ming Chen, Wu Wang, Xiaoling Li, Hong Yang, Shiping Yang, Zhiguo Zhou
The low efficiency homing of nanomaterials in tumors remains a major challenge in nanomedicine. Inspired by the apoptosis targeting properties of phosphatidylserine (PS), a self-amplified apoptosis targeting nanoplatform (MNPs-ZnDPA/β-Lap) is fabricated combining Zn0.4 Co0.6 Fe2 O4 @Zn0.4 Mn0.6 Fe2 O4 nanoparticles (MNPs) with an excellent magnetic hyperthermia effect, a chemotherapeutic drug of β-lapachone (β-Lap) with the promotion of cell apoptosis, and the good apoptosis targeting moiety of Zn(II)-bis(dipicolylamine) (bis-ZnDPA) for PS...
September 2020: Advanced Healthcare Materials
https://read.qxmd.com/read/32753868/ultrasound-combined-with-core-cross-linked-nanosystem-for-enhancing-penetration-of-doxorubicin-prodrug-beta-lapachone-into-tumors
#9
JOURNAL ARTICLE
Qianyan Li, Wei Hou, Meixuan Li, Hemin Ye, Huanan Li, Zhibiao Wang
Background: Nanosized drug delivery systems (NDDSs) have shown excellent prospects in tumor therapy. However, insufficient penetration of NDDSs has significantly impeded their development due to physiological instability and low passive penetration efficiency. Methods: Herein, we prepared a core cross-linked pullulan-modified nanosized system, fabricated by visible-light-induced diselenide bond cross-linked method for transporting β-Lapachone and doxorubicin prodrug (boronate-DOX, BDOX), to improve the physiological stability of the NDDSs for efficient passive accumulation in tumor blood vessels (β-Lapachone/BDOX-CCS)...
2020: International Journal of Nanomedicine
https://read.qxmd.com/read/32707497/an-evaluation-on-potential-anti-inflammatory-effects-of-%C3%AE-lapachone
#10
REVIEW
Narmin Mokarizadeh, Pouran Karimi, Hamid Kazemzadeh, Nazila Fathi Maroufi, Saeed Sadigh-Eteghad, Saba Nikanfar, Nadereh Rashtchizadeh
Inflammation plays a significant role in the pathogenesis of chronic diseases. Inflammatory diseases such as bacterial diseases, Alzheimer's disease, rheumatoid arthritis, multiple sclerosis, and so on, impose huge costs on the health systems. On the other hand, some side effects have been reported for the classic drugs used to treat these diseases. Plants phytochemicals have revealed important prospects in the handling and controlling of human diseases. β-lapachone, is a derivative of the naturally occurring element lapachol, from Tabebuia avellanedae and its anti-inflammatory effects have been reported in several reports...
October 2020: International Immunopharmacology
https://read.qxmd.com/read/32682198/synthesis-and-biological-evaluation-of-%C3%AE-lapachone-monastrol-hybrids-as-potential-anticancer-agents
#11
JOURNAL ARTICLE
Liqiang Wu, Xin Ma, Xiaojuan Yang, Chong Zhang
A series of novel β-lapachone analogs was designed and synthesized by replacing pyran ring of β-lapachone with tetrahydropyrimidinethione moiety of monastrol. These hybrids had potent antiproliferative activity against NQO1-rich cell lines (HepG2 and A549), while NQO1-defficient cell lines (H596 and LO2) were less sensitive to these hybrids. Dicoumarol partially inhibited the activity of these compounds against A549 cell lines, indicating that the activation of biological reduction mediated by NQO1 might partly affect the antiproliferative effects...
July 12, 2020: European Journal of Medicinal Chemistry
https://read.qxmd.com/read/32668395/bioanalytical-method-development-and-validation-of-a-liquid-chromatography-tandem-mass-spectrometry-method-for-determination-of-%C3%AE-lapachone-in-human-plasma
#12
JOURNAL ARTICLE
William C Putnam, Raja Reddy Kallem, Indhumathy Subramaniyan, M Shaalan Beg, Vindhya Edpuganti
The purpose of this work was to develop and validate a rapid, sensitive and robust liquid chromatography tandem mass spectrometric method for the quantification of β-lapachone in human plasma and to use that method to analyze human clinical samples. Sample preparation for the developed method involved liquid-liquid extraction using ethyl acetate for extraction of β-lapachone and cryptotanshinone (internal standard) from human plasma. Chromatographic resolution was achieved on a Kinetex C18 column using a gradient elution and a chromatographic flow rate of 0...
July 8, 2020: Journal of Pharmaceutical and Biomedical Analysis
https://read.qxmd.com/read/32627387/dual-ph-ros-responsive-nanoplatform-with-deep-tumor-penetration-and-self-amplified-drug-release-for-enhancing-tumor-chemotherapeutic-efficacy
#13
JOURNAL ARTICLE
Yongfei Li, Mie Chen, Bowen Yao, Xun Lu, Boyang Song, Shauna N Vasilatos, Xiang Zhang, Xiaomei Ren, Chang Yao, Weihe Bian, Lizhu Sun
Poor deep tumor penetration and incomplete intracellular drug release remain challenges for antitumor nanomedicine application in clinical settings. Herein, a nanomedicine (RLPA-NPs) is developed that can achieve prolonged blood circulation, deep tumor penetration, active-targeting of cancer cells, endosome/lysosome escape, and intracellular selectivity self-amplified drug release for effective drug delivery. The RLPA-NPs are constructed by encapsulation of a pH-sensitive polymer octadecylamine-poly(aspartate-1-(3-aminopropyl) imidazole) (OA-P(Asp-API)) and a ROS-generation agent, β-Lapachone (Lap), in micelles assembled by the tumor-penetration peptide internalizing RGD (iRGD)-modified ROS-responsive paclitaxel (PTX)-prodrug...
August 2020: Small
https://read.qxmd.com/read/32592323/novel-%C3%AE-carboline-based-indole-4-7-quinone-derivatives-as-nqo1-inhibitor-with-potent-antitumor-activities-by-inducing-ros-apoptosis-and-dna-damage
#14
JOURNAL ARTICLE
Yibing Guo, Liancheng Xu, Changchun Ling, Tao Yang, Wenjie Zheng, Jin Lv, Qingsong Guo, Bohua Chen
Eighteen new β-carboline-based indole-4,7-quinone derivatives (12a-i and 13a-i) were designed and synthesized, and their in vitro and in vivo antiproliferative activities were studied. Most of target compounds showed strong inhibition on three human tumor cells' proliferation. In particular, the most active compound 13g not only displayed more prominent antiproliferative activities than β-lapachone, a clinical antitumor candidate, but also exerted significant NAD(P)H: quinone-oxidoreductase-1 (NQO1) inhibitory activity and NQO1-dependent cytotoxicity in HT29 cells...
June 26, 2020: Chemical Biology & Drug Design
https://read.qxmd.com/read/32501667/acidity-triggered-tumor-targeted-nanosystem-for-synergistic-therapy-via-a-cascade-of-ros-generation-and-no-release
#15
JOURNAL ARTICLE
Yufei Cao, Mingsheng Liu, Ju Cheng, Juanjuan Yin, Congshu Huang, Haiyan Cui, Xiangdong Zhang, Guanghui Zhao
Nitric oxide (NO) gas therapy has aroused intense interest in recent years. L-Arginine (L-Arg) reacts with ROS in tumor cells to generate NO. This phenomenon represents an effective method for tumor therapy. However, endogenous ROS levels in most types of tumor cells cannot enable an effective reaction. β-Lapachone is generally used to increase H2O2, which can oxidize guanidine derivatives to form nitric oxide in tumor cells. In addition, based on ferrocene (Fc) catalyzed Fenton reaction, ·OH is generated from H2O2, and the ONOO- could be generated from an interaction between ·O2- (generated through the Haber-Weiss reaction) and NO...
June 5, 2020: ACS Applied Materials & Interfaces
https://read.qxmd.com/read/32464425/design-synthesis-and-biological-evaluation-of-4-substituted-3-4-dihydrobenzo-h-quinoline-2-5-6-1h-triones-as-nqo1-directed-antitumor-agents
#16
JOURNAL ARTICLE
Li-Qiang Wu, Xin Ma, Chong Zhang, Zhao-Peng Liu
A novel series of 4-substituted-3,4-dihydrobenzo[h]quinoline-2,5,6(1H)-triones as NQO1-directed antitumor agents were designed, synthesized, biologically evaluated. Compounds 3n, 3o and 3j proved to be good NQO1 substrates that showed increased metabolic rates relative to that of β-lapachone. In addition, 3n, 3o and 3j potently inhibited the growth of NQO1-rich breast cancer MCF-7 cell, liver hepatocellular HepG2 cell, and lung cancer A549 cell. In cellular mechanistic studies, the representative compound 3o triggered ROS generation depending on the NQO1 dose, and induce HepG2 cell apoptosis by the generated oxidative stress...
May 1, 2020: European Journal of Medicinal Chemistry
https://read.qxmd.com/read/32464218/in-silico-in-vitro-and-in-vivo-evaluation-of-natural-bignoniaceous-naphthoquinones-in-comparison-with-atovaquone-targeting-the-selection-of-potential-antimalarial-candidates
#17
JOURNAL ARTICLE
Maria Fernanda Alves do Nascimento, Tatiane Freitas Borgati, Larissa Camila Ribeiro de Souza, Carlos Alberto Tagliati, Alaíde Braga de Oliveira
The natural naphthoquinones lapachol, α- and β-lapachone are found in Bignoniaceous Brazilian plant species of the Tabebuia genus (synonym Handroanthus) and are recognized for diverse bioactivities, including as antimalarial. The aim of the present work was to perform in silico, in vitro and in vivo studies to evaluating the antimalarial potential of these three naphthoquinones in comparison with atovaquone, a synthetic antimalarial. The ADMET properties of these compounds were predicted in silico by the preADMET program...
May 25, 2020: Toxicology and Applied Pharmacology
https://read.qxmd.com/read/32418514/facile-synthesis-of-naphtha-quinoxaline-derivatives-from-%C3%AE-lapachone-using-graphene-oxide-as-catalyst
#18
JOURNAL ARTICLE
Pooja Vyas, Barkha Darra Wadhwani, Ravindra Singh Rao, Poonam Khandelwal
OBJECTIVE: To develop efficient method for the synthesis of naphtha-quinoxaline derivatives via the reaction of β-lapachone with various 1,2-diamines. METHODS: A mixture of β-lapachone (1mmol), 1,2-diamine (1mmol) and graphene oxide (20mg) in methanol (3mL) was heated at 60°C, under constant stirring for appropriate time. After completion of the reaction, the catalyst was filtered off, washed with ethyl acetate (3x3mL) and the combined filtrate was washed with H2O, dried (anhy...
2020: Current Organic Synthesis
https://read.qxmd.com/read/32369362/hetero-diels-alder-reactions-of-quinone-methides-the-origin-of-the-%C3%AE-regioselectivity-of-3-methylene-1-2-4-naphthotriones
#19
JOURNAL ARTICLE
Maicon Delarmelina, Sabrina B Ferreira, Fernando de C da Silva, Vitor F Ferreira, José Walkimar de M Carneiro
The regioselective formation of α- and β-lapachone via Hetero-Diels-Alder reactions was investigated by experimental and computational approaches. The experimentally observed α-selectivity was explored in detail, revealing that lower energy barrier for formation of α-lapachone is a result of lower Pauli repulsion throughout the reaction path, when compared to the β-isomer. By comparing equivalent points on both α- and β-lapachone Potential Energy Surfaces (PES) according to the Activation Strain Model (ASM) and Energy Decomposition Analysis (EDA), we were able to demonstrate that the Pauli repulsion term increases more significantly when going from reactants to TSβ than to TSα, resulting in lower interaction energy in the early stages of the reaction path and in a later transition state for β-lapachone...
May 5, 2020: Journal of Organic Chemistry
https://read.qxmd.com/read/32203888/kl1333-a-derivative-of-%C3%AE-lapachone-protects-against-cisplatin-induced-ototoxicity-in-mouse-cochlear-cultures
#20
JOURNAL ARTICLE
Han-Sol Lee, Ye-Ri Kim, In-Kyu Lee, Un-Kyung Kim, Jeong-In Baek, Kyu-Yup Lee
Cisplatin (CP) is a chemotherapeutic drug used to treat cancerous solid tumors, but it causes serious side effects, including ototoxicity. The major cause of CP-induced ototoxicity is increased levels of mitochondrial reactive oxygen species (ROS). In this study, we examined the effect of 2-Isopropyl-3H-naphtho(1,2-d)imidazole-4,5-dione (KL1333), a β-lapachone derivative, on CP-induced ototoxicity using ex vivo organotypic culture system of cochlea. Hair cell damages in CP-treated cochlear explants with or without KL1333 were compared by immunohistochemistry...
March 20, 2020: Biomedicine & Pharmacotherapy
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