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Prenylation

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https://www.readbyqxmd.com/read/28209709/pathogenic-mutations-in-retinitis-pigmentosa-2-predominantly-result-in-loss-of-rp2-protein-stability-in-human-and-zebrafish
#1
Fei Liu, Yayun Qin, Shanshan Yu, Dinesh C Soares, Lifang Yang, Jun Weng, Chang Li, Meng Gao, Zhaojing Lu, Xuebin Hu, Xiliang Liu, Tao Jiang, Jing Y Liu, Xinhua Shu, Zhaohui Tang, Mugen Liu
Mutations in retinitis pigmentosa 2 (RP2) account for 10-20% of X-linked retinitis pigmentosa (RP) cases. The encoded RP2 protein is implicated in ciliary trafficking of myristoylated and prenylated proteins in photoreceptor cells. To date, over 70 mutations in RP2 have been identified. How these mutations disrupt the function of RP2 is not fully understood. Here, we report a novel in-frame 12-bp deletion (c.357_368del, p.Pro120_Gly123del) in zebrafish rp2 The mutant zebrafish shows reduced rod phototransduction proteins and progressive retinal degeneration...
February 16, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28208018/pharmacophore-mapping-of-thienopyrimidine-based-monophosphonate-thp-mp-inhibitors-of-the-human-farnesyl-pyrophosphate-synthase
#2
Jaeok Park, Chun Yuen Leung, Alexios N Matralis, Cyrus M Lacbay, Michail Tsakos, Guillermo Fernandez De Troconiz, Albert M Berghuis, Youla S Tsantrizos
The human farnesyl pyrophosphate synthase (hFPPS), a key regulatory enzyme in the mevalonate pathway, catalyzes the biosynthesis of the C-15 isoprenoid farnesyl pyrophosphate (FPP). FPP plays a crucial role in the post-translational prenylation of small GTPases that perform a plethora of cellular functions. Although hFPPS is a well-established therapeutic target for lytic bone diseases, the currently available bisphosphonate drugs exhibit poor cellular uptake and distribution into non-skeletal tissues. Recent drug discovery efforts have focused primarily on allosteric inhibition of hFPPS and the discovery of non-bisphosphonate drugs for potentially treating non-skeletal diseases...
February 16, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28202103/deterrent-activity-of-hops-flavonoids-and-their-derivatives-against-stored-product-pests
#3
J Jackowski, J Popłoński, K Twardowska, J Magiera-Dulewicz, M Hurej, E Huszcza
Five flavonoids from hops, two of their derivatives, along with naringenin used as a model compound, were tested for their antifeedant activity against three coleopteran stored product pests: Sitophilus granarius L., Tribolium confusum Duv. and Trogoderma granarium Everts. The introduction, into the tested flavonoid molecules, of additional structural fragments such as prenyl or dimethylpyran moiety, is proposed to significantly alter the deterrent activity of the compounds. The prenyl moiety in flavonoids increased the deterrent activity of these compounds in all three of the grain feeding species used in the tests...
February 16, 2017: Bulletin of Entomological Research
https://www.readbyqxmd.com/read/28195477/enzymatic-n-and-c-protection-in-cyanobactin-ripp-natural-products
#4
Debosmita Sardar, Yue Hao, Zhenjian Lin, Maho Morita, Satish K Nair, Eric W Schmidt
Recent innovations in peptide natural product biosynthesis reveal a surprising wealth of previously uncharacterized biochemical reactions that have potential applications in synthetic biology. Among these, the cyanobactins are noteworthy because these peptides are protected at their N- and C-termini by macrocyclization. Here, we use a novel bifunctional enzyme AgeMTPT to protect linear peptides by attaching prenyl and methyl groups at their free N- and C-termini. Using this peptide protectase in combination with other modular biosynthetic enzymes, we describe the total synthesis of the natural product aeruginosamide B and the biosynthesis of linear cyanobactin natural products...
February 15, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28182779/o-prenylated-3-carboxycoumarins-as-a-novel-class-of-15-lox-1-inhibitors
#5
Atena Jabbari, Mina Mousavian, Seyed Mohamad Seyedi, Mehdi Bakavoli, Hamid Sadeghian
Allyloxy, Isopentenyloxy, geranyloxy and farnesyloxy derivatives of 3-carboxycoumarin, at position 5, 6, 7, and 8, were synthesized and their inhibitory potency against human 15-lipoxygenase-1 (human 15-LOX-1) were determined. Among the synthetic coumarins, O-allyl and O-isopentenyl derivatives demonstrated no considerable lipoxygenase inhibition while O-geranyl and O-farnesyl derivatives demonstrated potent inhibitory activity. 5-farnesyloxy-3-carboxycoumarin demonstrated the most potent inhibitory activity by IC50 = 0...
2017: PloS One
https://www.readbyqxmd.com/read/28181808/versicoamides-f-h-prenylated-indole-alkaloids-from-aspergillus-tennesseensis
#6
Li Liu, Long Wang, Li Bao, Jinwei Ren, Buddha Bahadur Basnet, Ruixing Liu, Luwei He, Junjie Han, Wen-Bing Yin, Hongwei Liu
Three highly modified indole alkaloids, versicoamides F-H (1-3), together with seven known alkaloids (4-10) were isolated from the fungus Aspergillus tennesseensis. The structures of new compounds were determined by analysis of the NMR and MS spectroscopic data. The absolute configurations of 1 and 2 were assigned by single-crystal X-ray diffraction experiments. Compounds 1 and 2 showed weak antiproliferative activity against the H460 cell line. Compounds 1-3 represent a new class of natural product hybrids with new chemical skeletons...
February 9, 2017: Organic Letters
https://www.readbyqxmd.com/read/28172980/prenylated-retinal-ciliopathy-protein-rpgr-interacts-with-pde6%C3%AE-and-regulates-ciliary-localization-of-joubert-syndrome-associated-protein-inpp5e
#7
Kollu N Rao, Wei Zhang, Linjing Li, Manisha Anand, Hemant Khanna
No abstract text is available yet for this article.
October 15, 2016: Human Molecular Genetics
https://www.readbyqxmd.com/read/28168765/prediction-of-anti-alzheimer-s-activity-of-flavonoids-targeting-acetylcholinesterase-in-silico
#8
Subrata Das, Monjur A Laskar, Satyajit D Sarker, Manabendra D Choudhury, Prakash Roy Choudhury, Abhijit Mitra, Shajarahtunnur Jamil, Siti Mariam A Lathiff, Siti Awanis Abdullah, Norazah Basar, Lutfun Nahar, Anupam D Talukdar
INTRODUCTION: Prenylated and pyrano-flavonoids of the genus Artocarpus J. R. Forster & G. Forster are well known for their acetylcholinesterase (AChE) inhibitory, anti-cholinergic, anti-inflammatory, anti-microbial, anti-oxidant, anti-proliferative and tyrosinase inhibitory activities. Some of these compounds have also been shown to be effective against Alzheimer's disease. OBJECTIVE: The aim of the in silico study was to establish protocols to predict the most effective flavonoid from prenylated and pyrano-flavonoid classes for AChE inhibition linking to the potential treatment of Alzheimer's disease...
February 7, 2017: Phytochemical Analysis: PCA
https://www.readbyqxmd.com/read/28167047/lipidated-proteins-spotlight-on-protein-membrane-binding-interfaces
#9
REVIEW
Arjun Ray, Nidhi Jatana, Lipi Thukral
The covalent attachment of lipids to proteins is a fundamental property of all living cells. These lipidated or lipid-modified proteins are directly targeted to the membranes and display diverse functional roles that are critical to cell function, such as membrane signaling and trafficking. All lipidated proteins have been classified by the type of chemical moieties that are attached to them, majorly, palmitoylation, myristoylation, prenylation, cholesterylation, and addition of the Glycosylphosphatidyl inositol (GPI) anchor...
February 3, 2017: Progress in Biophysics and Molecular Biology
https://www.readbyqxmd.com/read/28166207/structure-and-specificity-of-a-permissive-bacterial-c-prenyltransferase
#10
Sherif I Elshahawi, Hongnan Cao, Khaled A Shaaban, Larissa V Ponomareva, Thangaiah Subramanian, Mark L Farman, H Peter Spielmann, George N Phillips, Jon S Thorson, Shanteri Singh
This study highlights the biochemical and structural characterization of the L-tryptophan C6 C-prenyltransferase (C-PT) PriB from Streptomyces sp. RM-5-8. PriB was found to be uniquely permissive to a diverse array of prenyl donors and acceptors including daptomycin. Two additional PTs also produced novel prenylated daptomycins with improved antibacterial activities over the parent drug.
February 6, 2017: Nature Chemical Biology
https://www.readbyqxmd.com/read/28160852/antidiarrhoeal-activity-of-eriosematin-e-isolated-from-the-roots-of-eriosema-chinense-vogel
#11
Satyendra K Prasad, Komal M Parmar, Chhanda C Danta, Damiki Laloo, S Hemalatha
BACKGROUND: Roots of the plant Eriosema chinense Vogel (Fabaceae) is distributed mainly over the Eastern Himalayan region of India and China. The roots of the plant are used as a vegetable by the people of Northern Australia, China and North East India and are used traditionally by the tribal people of Meghalaya (India) for the treatment of diarrhoea. It has been reported to have significant antidiarrhoeal, cytotoxic and antimycobacterial activity. PURPOSE/OBJECTIVE: The present investigation was undertaken to isolate a lead molecule responsible for the observed antidiarrhoeal activity...
January 15, 2017: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
https://www.readbyqxmd.com/read/28147319/mevastatin-blockade-of-autolysosome-maturation-stimulates-lbh589-induced-cell-death-in-triple-negative-breast-cancer-cells
#12
Zhaohu Lin, Zhuqing Zhang, Xiaoxiao Jiang, Xinhui Kou, Yong Bao, Huijuan Liu, Fanghui Sun, Shuang Ling, Ning Qin, Lan Jiang, Yonghua Yang
Histone deacetylase inhibitors (HDACi) are promising anti-cancer agents, and combining a HDACi with other agents is an attractive therapeutic strategy in solid tumors. We report here that mevastatin increases HDACi LBH589-induced cell death in triple-negative breast cancer (TNBC) cells. Combination treatment inhibited autophagic flux by preventing Vps34/Beclin 1 complex formation and downregulating prenylated Rab7, an active form of the small GTPase necessary for autophagosome-lysosome fusion. This means that co-treatment with mevastatin and LBH589 activated LKB1/AMPK signaling and subsequently inhibited mTOR...
January 27, 2017: Oncotarget
https://www.readbyqxmd.com/read/28141896/development-of-the-regiodivergent-asymmetric-prenylation-of-3-substituted-oxindoles
#13
Barry M Trost, Walter Chan, Sushant Malhotra
This paper fully describes our efforts to design a Pd-catalyzed asymmetric prenylation of 3-substituted oxindoles that affords access to both the linear and reverse-prenylated products. Both 3-alkyl- and 3-aryloxindoles performed well under our optimized reaction conditions. The regiodivergent alkylation of monoterpene-derived electrophiles using this methodology was also investigated. The utility of this methodology in natural product synthesis was demonstrated through the efficient total syntheses of four Flustra alkaloids, which also allowed the absolute stereochemistry of the prenylated oxindole products to be assigned...
January 31, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28135865/prenylated-benzoic-acid-derivatives-from-the-stem-of-euodia-lepta
#14
Ming-Bo Zhao, Si-Xiang Zhou, Qing-Ying Zhang, Wei-Feng Wei, Ming-Hui Li, Jian-Yong Xing, Yong Jiang, Peng-Fei Tu
Two new prenylated benzoic acid derivatives, leptoic acid A and (+)-S-anodendroic acid (1-2), along with one known compound, 2,2-dimethyl-2H-1-benzopyran-6-carboxylic acid (3) were isolated from the stem of Euodia lepta (spreng.) Merr. Their structures were elucidated on the basis of the chemical and spectroscopic evidence.
January 30, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28129035/where-no-ras-has-gone-before-vps35-steers-n-ras-through-the-cytosol
#15
Mo Zhou, Mark R Philips
Ras is the best-studied member of the superfamily of small GTPases because of its role in cancer. Ras proteins transmit signals for proliferation, differentiation and survival. Three RAS genes encode 4 isoforms. All Ras isoforms have long been considered membrane bound, a localization required for function. Our recent study revealed that N-Ras differs from all other isoforms in being largely cytosolic even following modification with a prenyl lipid. Endogenous, cytosolic N-Ras chromatographed in both high and low molecular weight pools, a pattern that required prenylation, suggesting prenyl-dependent interaction with other proteins...
January 27, 2017: Small GTPases
https://www.readbyqxmd.com/read/28128488/enolonium-species-umpoled-enolates
#16
Shlomy Arava, Jayprakash N Kumar, Shimon Maksymenko, Mark A Iron, Keshaba N Parida, Peter Fristrup, Alex M Szpilman
Enolonium species/iodo(III)enolates of carbonyl compounds have been suggested to be intermediates in a wide variety of hypervalent iodine induced chemical transformations of ketones, including α-C-O, α-C-N, α-C-C, and α-carbon-halide bond formation, but they have never been characterized. We report that these elusive umpoled enolates may be made as discrete species that are stable for several minutes at -78 °C, and report the first spectroscopic identification of such species. It is shown that enolonium species are direct intermediates in C-O, C-N, C-Cl, and C-C bond forming reactions...
January 27, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28125283/plastoglobuli-plastid-microcompartments-with-integrated-functions-in-metabolism-plastid-developmental-transitions-and-environmental-adaptation
#17
Klaas J van Wijk, Felix Kessler
Plastoglobuli (PGs) are plastid lipoprotein particles surrounded by a membrane lipid monolayer. PGs contain small specialized proteomes and metabolomes. They are present in different plastid types (e.g., chloroplasts, chromoplasts, and elaioplasts) and are dynamic in size and shape in response to abiotic stress or developmental transitions. PGs in chromoplasts are highly enriched in carotenoid esters and enzymes involved in carotenoid metabolism. PGs in chloroplasts are associated with thylakoids and contain ∼30 core proteins (including six ABC1 kinases) as well as additional proteins recruited under specific conditions...
January 25, 2017: Annual Review of Plant Biology
https://www.readbyqxmd.com/read/28122154/protein-kinase-a-inhibition-facilitates-the-antitumor-activity-of-xanthohumol-a-valosin-containing-protein-inhibitor
#18
Yuki Shikata, Tetsuro Yoshimaru, Masato Komatsu, Hiroto Katoh, Reiko Sato, Shuhei Kanagaki, Yasumasa Okazaki, Shinya Toyokuni, Etsu Tashiro, Shumpei Ishikawa, Toyomasa Katagiri, Masaya Imoto
Xanthohumol (XN), a simple prenylated chalcone, can be isolated from hops and has the potential to be a cancer chemopreventive agent against several human tumor cell lines. We previously identified valosin-containing protein (VCP) as a target of XN; VCP can also play crucial roles in cancer progression and prognosis. Therefore, we investigated the molecular mechanisms governing the contribution of VCP to the antitumor activity of XN. Several human tumor cell lines were treated with XN to investigate which human tumor cell lines are sensitive to XN...
January 25, 2017: Cancer Science
https://www.readbyqxmd.com/read/28121714/hepatitis-delta-and-hiv-infection
#19
Vincent Soriano, Kenneth E Sherman, Pablo Barreiro
Viral liver diseases are frequent co-morbidities and major contributors to death in HIV-positive individuals on antiretroviral therapy. Whereas cure of hepatitis C and control of hepatitis B with antivirals avert liver disease progression in most HIV-coinfected patients, the lack of satisfactory treatment for hepatitis delta virus (HDV) infection remains a major threat for developing cirrhosis and liver cancer in this population. In the European Union and North America, sexual contact has replaced injection drug use has major transmission route for HDV in HIV-positive persons...
January 24, 2017: AIDS
https://www.readbyqxmd.com/read/28116998/exploration-of-new-and-potent-lead-molecules-against-caax-prenyl-protease-i-of-leishmania-donovani-through-pharmacophore-based-virtual-screening-approach
#20
Sitrarasu Vijaya Prabhu, Kartikeya Tiwari, Venkatesan Suryanarayanan, Vikash Kumar Dubey, Sanjeev Kumar Singh
AIM AND OBJECTIVE: Visceral leishmaniasis is a deadly disease left untreated in over 95% of cases. It is characterized by irregular bouts of fever, weight loss, enlargement of the spleen and liver, and anemia. It is highly endemic in the Indian subcontinent. CAAX prenyl proteaseI of Leishmania donovani is one of the important targets regulating the post translational modification process. Hence identifying potent drug candidate against the target is essential. This study mainly focuses on developing new and potent inhibitors against CAXX prenyl protease I of Leishmania donovani...
January 20, 2017: Combinatorial Chemistry & High Throughput Screening
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