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Farnesylation

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https://www.readbyqxmd.com/read/28547322/metabolic-engineering-of-saccharomyces-cerevisiae-for-production-of-germacrene-a-a-precursor-of-beta-elemene
#1
Yating Hu, Yongjin J Zhou, Jichen Bao, Luqi Huang, Jens Nielsen, Anastasia Krivoruchko
Beta-elemene, a sesquiterpene and the major component of the medicinal herb Curcuma wenyujin, has antitumor activity against various types of cancer and could potentially serve as a potent antineoplastic drug. However, its current mode of production through extraction from plants has been inefficient and suffers from limited natural resources. Here, we engineered a yeast cell factory for the sustainable production of germacrene A, which can be transformed to beta-elemene by a one-step chemical reaction in vitro...
May 25, 2017: Journal of Industrial Microbiology & Biotechnology
https://www.readbyqxmd.com/read/28544034/knock-down-of-farnesyl-pyrophosphate-synthase-protects-heart-derived-h9c2-cells-against-hypoxia-reoxygenation-induced-injury
#2
Dong-Pu Dai, Huan-Dong Wu, Jian Yang, Shi-Zhen Shen, Chen-Ze Zhao, Jie Ding, Shen-Jiang Hu
Farnesyl pyrophosphate synthase (FPPS) is a key enzyme in the mevalonate pathway. Our previous studies have indicated that cardiac-specific overexpression of FPPS induces cardiac hypertrophy and dysfunction in mice, and inhibition of FPPS prevents angiotensin (Ang) II-induced hypertrophy in cardiomyocytes. However, the role for FPPS in myocardial ischemia/reperfusion (MIR) injury is still not clear. The objective of this work was to investigate the effect of FPPS on MIR injury in H9c2 cells which were subjected to hypoxia/reoxygenation (HR) to mimic MIR...
May 24, 2017: Cell Biology International
https://www.readbyqxmd.com/read/28540724/pde%C3%AE-binding-to-ras-isoforms-provides-a-route-to-proper-membrane-localization
#3
Serena Muratcioglu, Hyunbum Jang, Attila Gursoy, Ozlem Keskin, Ruth Nussinov
To signal, Ras isoforms must be enriched at the plasma membrane (PM). It was suggested that phosphodiesterase-δ (PDEδ) can bind and shuttle some farnesylated Ras isoforms to the PM - but not all. Among these, interest focused on K-Ras4B, the most abundant oncogenic Ras isoform. To study PDEδ/Ras interactions, we modeled and simulated the PDEδ/K-Ras4B complex. We obtained structures which were similar to two subsequently determined crystal structures. We next modeled and simulated complexes of PDEδ with the farnesylated hypervariable regions (HVRs) of K-Ras4A and N-Ras...
May 25, 2017: Journal of Physical Chemistry. B
https://www.readbyqxmd.com/read/28527898/triterpenes-and-meroterpenes-from-ganoderma-lucidum-with-inhibitory-activity-against-hmgs-reductase-aldose-reductase-and-%C3%AE-glucosidase
#4
Baosong Chen, Jin Tian, Jinjin Zhang, Kai Wang, Li Liu, Bo Yang, Li Bao, Hongwei Liu
Seven new compounds including four lanostane triterpenoids, lucidenic acids Q-S (1-3) and methyl ganoderate P (4), and three triterpene-farnesyl hydroquinone conjugates, ganolucinins A-C (5-7), one new natural product ganomycin J (8), and 73 known compounds (9-81) were isolated from fruiting bodies of Ganoderma lucidum. The structures of the compounds 1-8 were determined by spectroscopic methods. Bioactivities of compounds isolated were assayed against HMG-CoA reductase, aldose reductase, α-glucosidase, and PTP1B...
May 17, 2017: Fitoterapia
https://www.readbyqxmd.com/read/28521569/exploring-the-biochemistry-of-the-prenylome-and-its-role-in-disease-through-proteomics-progress-and-potential
#5
Maura Brioschi, Alma Martinez Fernandez, Cristina Banfi
Protein prenylation is a ubiquitous covalent post-translational modification characterized by the addition of farnesyl or geranylgeranyl isoprenoid groups to a cysteine residue located near the carboxyl terminal of a protein. It is essential for the proper localization and cellular activity of numerous proteins, including Ras family GTPases and G-proteins. In addition to its roles in cellular physiology, the prenylation process has important implications in human diseases and in the recent years, it has become attractive target of inhibitors with therapeutic potential...
May 26, 2017: Expert Review of Proteomics
https://www.readbyqxmd.com/read/28520394/in-vitro-metabolic-engineering-of-amorpha-4-11-diene-biosynthesis-at-enhanced-rate-and-specific-yield-of-production
#6
Xixian Chen, Congqiang Zhang, Ruiyang Zou, Gregory Stephanopoulos, Heng-Phon Too
In vitro metabolic engineering is an alternative approach to cell-based biosynthesis. It offers unprecedented flexibility for the study of biochemical pathways, thus providing useful information for the rational design and assembly of reaction modules. Herein, we took the advantage of in vitro metabolic engineering to initially gain insight into the regulatory network of a reconstituted amorpha-4,11-diene (AD) synthetic pathway. Guided by lin-log approximation, we rapidly identified the hitherto unrecognized inhibition of adenosine triphosphate (ATP) on both farnesyl pyrophosphate synthase (FPPS) and amorpha-4,11-diene synthase (ADS)...
May 25, 2017: ACS Synthetic Biology
https://www.readbyqxmd.com/read/28515154/progerin-sequestration-of-pcna-promotes-replication-fork-collapse-and-mislocalization-of-xpa-in-laminopathy-related-progeroid-syndromes
#7
Benjamin A Hilton, Ji Liu, Brian M Cartwright, Yiyong Liu, Maya Breitman, Youjie Wang, Rowdy Jones, Hui Tang, Antonio Rusinol, Phillip R Musich, Yue Zou
Hutchinson-Gilford progeria syndrome (HGPS) is a rare genetic disorder that is caused by a point mutation in the LMNA gene resulting in production of a truncated farnesylated-prelamin A protein (progerin). We previously reported that XPA mislocalized to the progerin-induced DNA double-strand break (DSB) sites, blocking DSB repair, which led to DSB accumulation, DNA damage responses, and early replication arrest in HGPS. In this study, the XPA mislocalization to DSBs occurred at stalled or collapsed replication forks, concurrent with a significant loss of PCNA at the forks, whereas PCNA efficiently bound to progerin...
May 17, 2017: FASEB Journal: Official Publication of the Federation of American Societies for Experimental Biology
https://www.readbyqxmd.com/read/28508733/synthesis-of-aurachins-b-and-h
#8
Kazuki Takahashi, Shigefumi Kuwahara, Masaru Enomoto
The synthesis of aurachin B, an antibiotic that features a C3-oxygen-substituted quinoline N-oxide nucleus bearing a farnesyl side chain at C4, was accomplished in 60% overall yield from o-nitrotoluene by a concise five-step sequence. An enantioselective synthesis of aurachin H was also achieved for the first time in only two steps from an optically active epoxy iodide.
May 16, 2017: Bioscience, Biotechnology, and Biochemistry
https://www.readbyqxmd.com/read/28489963/the-aspergillus-fumigatus-farnesyltransferase-%C3%AE-subunit-rama-mediates-growth-virulence-and-antifungal-susceptibility
#9
Tiffany S Norton, Qusai Al Abdallah, Amy M Hill, Rachel V Lovingood, Jarrod R Fortwendel
Post-translational prenylation mechanisms, including farnesylation and geranylgeranylation, mediate both subcellular localization and protein-protein interaction in eukaryotes. The prenyltransferase complex is an αβ heterodimer in which the essential α-subunit is common to both the farnesyltransferase and the geranylgeranyltransferase type-I enzymes. The β-subunit is unique to each enzyme. Farnesyltransferase activity is an important mediator of protein localization and subsequent signaling for multiple proteins, including Ras GTPases...
May 10, 2017: Virulence
https://www.readbyqxmd.com/read/28484475/de-novo-sequencing-and-transcriptome-analysis-reveal-key-genes-regulating-steroid-metabolism-in-leaves-roots-adventitious-roots-and-calli-of-periploca-sepium-bunge
#10
Jian Zhang, Xinglin Li, Fuping Lu, Shanying Wang, Yunhe An, Xiaoxing Su, Xiankuan Li, Lin Ma, Guangjian Han
Periploca sepium Bunge is a traditional medicinal plant, whose root bark is important for Chinese herbal medicine. Its major bioactive compounds are C21 steroids and periplocin, a kind of cardiac glycoside, which are derived from the steroid synthesis pathway. However, research on P. sepium genome or transcriptomes and their related genes has been lacking for a long time. In this study we estimated this species nuclear genome size at 170 Mb (using flow cytometry). Then, RNA sequencing of four different tissue samples of P...
2017: Frontiers in Plant Science
https://www.readbyqxmd.com/read/28483909/progerin-induced-replication-stress-facilitates-premature-senescence-in-hutchinson-gilford-progeria-syndrome
#11
Keith Wheaton, Denise Campuzano, Weili Ma, Michal Sheinis, Brandon Ho, Grant W Brown, Samuel Benchimol
Hutchinson-Gilford progeria syndrome (HGPS) is caused by a mutation in LMNA that produces an aberrant lamin A protein, progerin. The accumulation of progerin in HGPS cells leads to an aberrant nuclear morphology, genetic instability and p53-dependent premature senescence. How p53 is activated in response to progerin production is unknown. Here, we show that young, cycling HGPS fibroblasts, exhibit chronic DNA damage primarily in S phase as well as delayed replication fork progression. We demonstrate that progerin binds to PCNA altering its distribution away from replicating DNA in HGPS cells leading to γH2AX formation, ATR activation and RPA Ser33 phosphorylation...
May 8, 2017: Molecular and Cellular Biology
https://www.readbyqxmd.com/read/28471077/total-syntheses-of-aurachins%C3%A2-a-and-b
#12
Haruhiko Hattori, Satoshi Yokoshima, Tohru Fukuyama
Aurachins A and B are alkaloids having 3-hydroxyquinoline N-oxide cores. An efficient method for the synthesis of 3-hydroxyquinoline N-oxides was established and is amenable to the total syntheses of aurachins A and B. Alkylation of 1-(2-nitrophenyl)butan-2-one with farnesyl bromide took place selectively at the benzylic position, and subsequent treatment of the alkylated product with sodium tert-butoxide in dimethyl sulfoxide gave aurachin B. Alkylation of 1-(2-nitrophenyl)butan-2-one with an epoxy iodide derived from farnesol was used to access aurachin A...
May 4, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28469964/comprehensive-pharmacological-profiling-of-neurofibromatosis-cell-lines
#13
Jianman Guo, Michael R Grovola, Hong Xie, Grace E Coggins, Patrick Duggan, Rukhsana Hasan, Jiale Huang, Danny W Lin, Claire Song, Gabriela M Witek, Simon Berritt, David C Schultz, Jeffrey Field
Patients with Neurofibromatosis type 1 (NF1) and Neurofibromatosis type 2 (NF2) are predisposed to tumors of the nervous system. NF1 patients predominantly develop neurofibromas, and Malignant Peripheral Nerve Sheath Tumors (MPNST) while NF2 patients develop schwannomas and meningiomas. Here we quantified the drug sensitivities of NF1 and NF2 tumor cell lines in a high throughput platform. The platform contained a comprehensive collection of inhibitors of MEK, RAF, RAS, farnesyl transferase, PAK and ERK, representative drugs against many other cancer pathways including Wnt, Hedgehog, p53, EGF, HDAC, as well as classical cytotoxic agents recommended for treating MPNST, such as doxorubicin and etoposide...
2017: American Journal of Cancer Research
https://www.readbyqxmd.com/read/28450026/formation-of-e-nerolidol-in-tea-camellia-sinensis-leaves-exposed-to-multiple-stresses-during-tea-manufacturing
#14
Ying Zhou, Lanting Zeng, Xiaoyu Liu, Jiadong Gui, Xin Mei, Xiumin Fu, Fang Dong, Jingchi Tang, Lingyun Zhang, Ziyin Yang
(E)-Nerolidol is a volatile sesquiterpene that contributes to the floral aroma of teas (Camellia sinensis). The unique manufacturing process for oolong tea involves multiple stresses, resulting in a high content of (E)-nerolidol, which is not known to form in tea leaves. This study aimed to determine the formation mechanism of (E)-nerolidol in tea exposed to multiple stresses during tea manufacture. C. sinensis (E)-nerolidol synthase (CsNES) recombinant protein, found in the cytosol, was found to transform farnesyl diphosphate into (E)-nerolidol...
September 15, 2017: Food Chemistry
https://www.readbyqxmd.com/read/28448716/phosphorylation-weakens-but-does-not-inhibit-membrane-binding-and-clustering-of-k-ras4b
#15
Si-Yu Zhang, Benjamin Sperlich, Fang-Yi Li, Samy Al-Ayoubi, Hong-Xue Chen, YuFen Zhao, Yan-Mei Li, Katrin Weise, Roland Winter, Yong-Xiang Chen
K-Ras4B is one of the most frequently mutated Ras isoforms in cancers. The signaling activity of K-Ras4B depends on its localization to the plasma membrane (PM), which is mainly mediated by its polybasic farnesylated C-terminus. On top of the constitutive cycles that maintain the PM enrichment of K-Ras4B, conditional phosphorylation at Ser181 located within this motif has been found to be involved in regulating K-Ras4B's cell distribution and signaling activity. However, discordant observations have undermined our understanding of the role this phosphorylation plays...
April 27, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28423648/polyisoprenylated-cysteinyl-amide-inhibitors-disrupt-actin-cytoskeleton-organization-induce-cell-rounding-and-block-migration-of-non-small-cell-lung-cancer
#16
Elizabeth Ntantie, Jerrine Fletcher, Felix Amissah, Olufisayo O Salako, Augustine T Nkembo, Rosemary A Poku, Francis O Ikpatt, Nazarius S Lamango
The malignant potential of Non-Small Cell Lung Cancer (NSCLC) is dependent on cellular processes that promote metastasis. F-actin organization is central to cell migration, invasion, adhesion and angiogenesis, processes involved in metastasis. F-actin remodeling is enhanced by the overexpression and/or hyper-activation of some members of the Rho family of small GTPases. Therefore, agents that mitigate hyperactive Rho proteins may be relevant for controlling metastasis. We previously reported the role of polyisoprenylated cysteinyl amide inhibitors (PCAIs) as potential inhibitors of cancers with hyperactive small GTPases...
May 9, 2017: Oncotarget
https://www.readbyqxmd.com/read/28419419/the-isoprenoid-derivative-n6-benzyladenosine-cm223-exerts-antitumor-effect-in-glioma-patient-derived-primary-cells-through-the-mevalonate-pathway
#17
Elena Ciaglia, Manuela Grimaldi, Mario Abate, Mario Scrima, Manuela Rodriquez, Chiara Laezza, Roberta Ranieri, Simona Pisanti, Pierangela Ciuffreda, Clementina Manera, Patrizia Gazzerro, Anna Maria D'Ursi, Maurizio Bifulco
BACKGROUND AND PURPOSE: N6-Isopentenyladenosine (i6A) is a modified nucleoside exerting in vitro and in vivo antiproliferative effects. We previously demonstrated that the i6A action is correlated to farnesyl pyrophosphate synthase (FPPS) expression and activity, a key enzyme involved in the mevalonate (MVA) pathway, which is found aberrant in brain cancer. To develop new anti-glioma strategies, we looked for other valuable compounds exhibiting improved activity as compared to i6A. EXPERIMENTAL APPROACH: we designed and synthesized i6A derivatives characterized by the introduction of diverse chemical moieties in the N6 position of adenosine and tested for their efficacy in U87 and primary derived patient's glioma cell model...
April 18, 2017: British Journal of Pharmacology
https://www.readbyqxmd.com/read/28419130/virus-induced-down-regulation-of-gmera1a-and-gmera1b-genes-enhances-the-stomatal-response-to-abscisic-acid-and-drought-resistance-in-soybean
#18
Takuya Ogata, Yukari Nagatoshi, Noriko Yamagishi, Nobuyuki Yoshikawa, Yasunari Fujita
Drought is a major threat to global soybean production. The limited transformation potential and polyploid nature of soybean have hindered functional analysis of soybean genes. Previous research has implicated farnesylation in the plant's response to abscisic acid (ABA) and drought tolerance. We therefore used virus-induced gene silencing (VIGS) to evaluate farnesyltransferase genes, GmERA1A and GmERA1B (Glycine max Enhanced Response to ABA1-A and -B), as potential targets for increasing drought resistance in soybean...
2017: PloS One
https://www.readbyqxmd.com/read/28418649/nature-s-selection-of-geranyl-group-as-a-trna-modification-the-effects-of-chain-length-on-base-pairing-specificity
#19
Phensinee Haruehanroengra, Sweta Vangaveti, Srivathsan V Ranganathan, Rui Wang, Alan Chen, Jia Sheng
The recently discovered geranyl modification on the 2-thio position of wobble U34 residues in tRNA(Glu), tRNA(Lys), and tRNA(Gln) in several bacteria has been found to enhance the U:G pairing specificity and reduce the frameshifting error during translation. It is a fundamentally interesting question why nature chose a C10 terpene group in tRNA systems. In this study, we explore the significance of the terpene length on base-paring stability and specificity using a series of 2-thiouridine analogues containing different lengths of carbon chains, namely, methyl- (C1), dimethylallyl- (C5), and farnesyl-modified (C15) 2-thiothymidines in a DNA duplex...
April 18, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28404524/concise-synthesis-of-artemisinin-from-a-farnesyl-diphosphate-analogue
#20
Xiaoping Tang, Melodi Demiray, Thomas Wirth, Rudolf K Allemann
Artemisinin is one of the most potent anti-malaria drugs and many often-lengthy routes have been developed for its synthesis. Amorphadiene synthase, a key enzyme in the biosynthetic pathway of artemisinin, is able to convert an oxygenated farnesyl diphosphate analogue directly to dihydroartemisinic aldehyde, which can be converted to artemisinin in only four chemical steps, resulting in an efficient synthetic route to the anti-malaria drug.
April 4, 2017: Bioorganic & Medicinal Chemistry
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