DOCSLIB.ORG

Studies on the Protective Effects of Scutellarein Against Neuronal Injury

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Studies on the Protective Effects of Scutellarein Against Neuronal Injury Hindawi Publishing Corporation Journal of Chemistry Volume 2015, Article ID 497842, 7 pages http://dx.doi.org/10.1155/2015/497842 Research Article Studies on the Protective Effects of Scutellarein against Neuronal Injury by Ischemia through the Analysis of Endogenous Amino Acids and Ca2+ Concentration Together with Ca2+-ATPase Activity Hao Tang, Ze-Xi Dong, Ting Gu, Nian-Guang Li, Yu-Ping Tang, Qian-Ping Shi, Jian-Ming Guo, Peng-Xuan Zhang, and Jin-Ao Duan Jiangsu Collaborative Innovation Center of Chinese Medicine Resources Industrialization, Jiangsu Key Laboratory for High Technology Research of TCM Formulae, and National and Local Collaborative Engineering Center of Chinese Medicine Resources, Nanjing University of Chinese Medicine, Nanjing 210023, China Correspondence should be addressed to Nian-Guang Li; [email protected] and Yu-Ping Tang; [email protected] Received 21 January 2015; Revised 24 May 2015; Accepted 28 May 2015 Academic Editor: Patricia Valentao Copyright © 2015 Hao Tang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Scutellarin, which is extracted from the dried plant of Erigeron breviscapus, has been reported to protect the neural injury against excitotoxicity induced by ischemia. However, there are a few studies on the protective effects of scutellarein, which is the main metabolite of scutellarin in vivo. Thus, this study investigated the neuroprotective effects of scutellarein on cerebral ischemia/reperfusion in rats by bilateral common carotid artery occlusion (BCCAO) model, through the analysis of endogenous 2+ 2+ amino acids using HILIC-MS/MS, and evaluation of Ca concentration together with Ca -ATPase activity. The results showed that scutellarein having good protective effects on cerebral ischemia/reperfusion might by decreasing the excitatory amino acids, 2+ 2+ increasing the inhibitory amino acids, lowing intracellular Ca level, and improving Ca -ATPase activity, which suggested that scutellarein might be a promising potent agent for the therapy of ischemic cerebrovascular disease. 1. Introduction aminoacid,playsaneuroprotectiveroleinvivo[6, 7]. Thus, the determination of these amino acid neurotransmitters is Ischemic cerebrovascular disease is the main cause of disabil- very important to evaluate the global cerebral ischemic injury. ity and death among the elderly people [1]. The increasing Erigeron breviscapus (Vant.) Hand.-Mazz., which mainly evidences showed that the excessive release of various amino growsinYunnanprovinceofChina,hasbeenusedforcen- acid neurotransmitters is one pathogenesis during ischemia turies as an important Chinese traditional herbal medicine reperfusion [2], indicating that the amino acid levels could to treat ischemic cerebrovascular diseases. Previous studies be diagnostic markers. The depolarization is mediated by have demonstrated that breviscapine, which is extracted from the metabolic failure which is caused by ischemia, and the thedriedwholeplantofErigeron breviscapus,hasneu- 2+ results indicate that there is an influx of Ca via voltage- roprotective effect against glutamate-induced excitotoxicity, 2+ 2+ sensitive Ca channels, thus initiate a flood of amino acid by inhibiting the accumulation of intracellular Ca and neurotransmitters, especially glutamate and aspartic acid [3], upregulating X-linked inhibitor of apoptosis protein (XIAP) release into the synaptic cleft. The excitatory amino acids, expression in hippocampal neurons [8]. Tao et al. found that which are the most important amino acid neurotransmitters, the breviscapus ethanol extract could inhibit GABA transam- couldinduceacascadeofeventsleadingtocelldeath[4, inase (GABA-T) and succinic semialdehyde dehydrogenase 5]. However, -aminobutyric acid (GABA), as an inhibitory (SSADH)inthebraintissuetoincreasetheGABAlevel 2 Journal of Chemistry OH O OH OH O HO O O HO O HO OH HO HO OH O OH O Scutellarin Scutellarein Figure 1: The chemical structures of scutellarin and scutellarein. [9]. Scutellarin (Figure 1), the major bioactive constituent in for the Care and Use of Laboratory Animals (US National breviscapine, possesses potent pharmacological effects similar Research Council, 1996) and the related ethics regulations of to those of the herb. Many studies showed that scutellarin our university. had a markedly neuroprotective activity against ischemia- 2+ induced injury by its anti-excitotoxicity, blocking Ca chan- 2.2. Drug Administration and Surgery. The rats were ran- nels, scavenging of reactive oxygen species, and so forth domly divided into six groups (=6/group) including sham- [10, 11]. Interestingly, some researchers found that scutellarin operation group, bilateral common carotid artery occlu- wasmainlyabsorbedintheformofitshydrolyzedproduct sion (BCCAO) rats without pretreatment (model group), scutellarein (Figure 1)byintestines[12], and scutellarein was and BCCAO rats pretreated with scutellarein (0.09, 0.17, mucheasiertobeabsorbedwiththetriplebioavailability,after 0.35 mmol/kg). The rats in the treatment groups were intra- oral administration of these two compounds in equal amount gastrically administrated with scutellarein under body weight [13]. A recent research indicated that scutellarein had better for 6 consecutive days, while the rats in the sham-operated protective effect than scutellarin in rat cerebral ischemia10 [ ]. and model group were intragastrically administrated with However, there are a few studies on the protective effect equal volume of 0.25% CMC-Na; 10% of choral hydrate of scutellarein against excitotoxicity, which is induced by (350 mg/kg ip) was used for anesthesia on the seventh day. excitatory neurotransmitters. Therefore, the aim of this study The bilateral common carotid arteries were exposed and was to evaluate the possible protective effect of scutellarein ligated with 0 thread for 30 min to induce cerebral ischemia; against neuronal injury, through the analysis of endogenous 2+ 2+ following cerebral ischemia, reperfusion was achieved by amino acids, and Ca concentration together with Ca - declamping the arteries for 15 min. Then repeated ischemia ATPase activity. was allowed for 30 min and reperfusion was allowed for 22 h. While the rats which only had the bilateral isolation of bilat- 2. Materials and Methods eral common carotid arteries (without occlusion) served as the sham-operated group. Anesthetized rats were placed on a 2.1. Materials. Scutellarein was prepared according to our heating pad during recovery from anesthesia to maintain the ∘ previous procedure [14–16]. Chemicals standards of pheny- body temperature at 37.0 ± 0.5 Caftersurgery[17, 18]. lalanine (Phe), -aminobutyric acid (GABA), leucine (Leu), valine (Val), methionine (Met), taurine (Tau), alanine (Ala), 2.3. Preparation of Standard Solutions. Amixedstandard hydroxyproline (H-pro), glycine (Gly), glutamic acid (Glu), solution containing 17 analytes was dissolved in water, and glutamine (Gln), serine (Ser), asparagines (Asn), citrulline the concentrations of these analytes were shown as follows: (Cit), aspartic acid (Asp), arginine (Arg), and lysine (Lys) GABA, 23.2 g/mL; Gly, 51.6 g/mL; Glu, 158 g/mL; Tau, were purchased from Sigma-Aldrich (St. Louis, MO). The 20.4 g/mL; Asp, 16.8 g/mL; Leu, 172.0 g/mL; Met, 20.0 g/ acetonitrile and formic acid were all of HPLC grade and mL; Phe, 21.6 g/mL; Ala, 122.0 g/mL; Cit, 24.0 g/mL; Gln, purchased from Merck (Darmstadt, Germany). Ammonium 19.2 g/mL; Asn, 31.6 g/mL; Ser, 233.6 g/mL; Val, 21.6 g/ formate (analytical grade) was purchased from the Shanghai mL; H-pro, 32.8 g/mL; Lys, 22.4 g/mL; Arg, 22.8 g/mL. Chemical Reagent Factory (Shanghai, China). Pure water Thesemixedstandardsolutionswerethendilutedtoappro- for UHPLC analysis was purified using a Milli-Q water priate concentration for building calibration curves. The purification system (Millipore, Billerica, MA) and used for all standard solutions were filtered through a 0.22 mmembrane solutions and dilutions. Other reagents and chemicals were of prior to injection. analytical grade. All male Wister rats (240±20 g, clean grade, Certification SCXK 2009-0001) were obtained from Shanghai SLAC Labo- 2.4. Preparation of Sample Solutions. All rats were anes- ratory Animal Co. Ltd. (Shanghai, China). All rats were bred thetized with 10% choral hydrate and then sacrificed by ∘ on 12 h dark-light cycle, with temperature of 23 ± 2 Cand decapitation. The complete cerebrum was removed from the humidity of 60 ± 5%,andtheyhavefreeaccesstothefood skull, and the hippocampus tissue was carefully isolated; ∘ and water. The rats were cared in accordance with the Guide subsequently, the tissues were stored at −80 C. 0.1 g ischemia Journal of Chemistry 3 tissue was homogenized in appropriate cold normal saline. diversity, high polarity, and the absence of specific chro- The obtained supernatants were centrifuged at 3000 rpm for mophores. In the past decade, many analytical methods ∘ 10 min at 4 C. After vortex for 2 min and centrifugation at have been used and they can be classified into two cate- 13000 rpm for 10 min, the upper layer was transferred into gories, the first approach for analysis of amino acids was another tube, and was then added 3 times of methanol. The the derivation method applying the reversed-phase high- concentrate was evaporated to dryness in a rotary evaporator performance liquid chromatography (RP-HPLC) or capillary
Load more

Recommended publications
  • Hydroxylation of the Eukaryotic Ribosomal Decoding Center Affects Translational Accuracy
    Hydroxylation of the eukaryotic ribosomal decoding center affects translational accuracy Christoph Loenarza,1, Rok Sekirnika,2, Armin Thalhammera,2, Wei Gea, Ekaterina Spivakovskya, Mukram M. Mackeena,b,3, Michael A. McDonougha, Matthew E. Cockmanc, Benedikt M. Kesslerb, Peter J. Ratcliffec, Alexander Wolfa,4, and Christopher J. Schofielda,1 aChemistry Research Laboratory and Oxford Centre for Integrative Systems Biology, University of Oxford, Oxford OX1 3TA, United Kingdom; bTarget Discovery Institute, University of Oxford, Oxford OX3 7FZ, United Kingdom; and cCentre for Cellular and Molecular Physiology, University of Oxford, Oxford OX3 7BN, United Kingdom Edited by William G. Kaelin, Jr., Harvard Medical School, Boston, MA, and approved January 24, 2014 (received for review July 31, 2013) The mechanisms by which gene expression is regulated by oxygen Enzyme-catalyzed hydroxylation of intracellularly localized are of considerable interest from basic science and therapeutic proteins was once thought to be rare, but accumulating recent perspectives. Using mass spectrometric analyses of Saccharomyces evidence suggests it is widespread (11). Motivated by these cerevisiae ribosomes, we found that the amino acid residue in findings, we investigated whether the translation of mRNA to closest proximity to the decoding center, Pro-64 of the 40S subunit protein is affected by oxygen-dependent modifications. A rapidly ribosomal protein Rps23p (RPS23 Pro-62 in humans) undergoes growing eukaryotic cell devotes most of its resources to the tran- posttranslational hydroxylation. We identify RPS23 hydroxylases scription, splicing, and transport of ribosomal proteins and rRNA as a highly conserved eukaryotic subfamily of Fe(II) and 2-oxoglu- (12). We therefore reasoned that ribosomal modification is a tarate dependent oxygenases; their catalytic domain is closely re- candidate mechanism for the regulation of protein expression.
    [Show full text]
  • Significance of Urinary Hydroxyproline in Man
    SIGNIFICANCE OF URINARY HYDROXYPROLINE IN MAN Darwin J. Prockop, Albert Sjoerdsma J Clin Invest. 1961;40(5):843-849. https://doi.org/10.1172/JCI104318. Find the latest version: https://jci.me/104318/pdf SIGNIFICANCE OF URINARY HYDROXYPROLINE IN MAN By DARWIN J. PROCKOP AND ALBERT SJOERDSMA (From the Section of Experimental Therapeutics, National Heart Institute, Bethesda, Md.) (Submitted for publication September 27, 1960; accepted January 12, 1961) Since nearly all of the hydroxyproline of the of Marfan's syndrome (2) reflect a rapid rate of body is found in collagen, it has been suggested collagen degradation. (1, 2) that the urinary excretion of this imino An incidental discovery in the study was that acid may be an important index of collagen me- the increase in urinary hydroxyproline after in- tabolism. The origin of urinary hydroxyproline, gestion of gelatin represents an increased excre- however, is not definitely established. The iso- tion of hydroxyproline peptides. This appears to topic studies of Stetten (3) in rats indirectly sug- be the first demonstration that significant amounts gested that most of the free and peptide hydroxy- of peptides can be excreted following ingestion of proline in the body arises from the breakdown of a protein. collagen, since she found that hydroxyproline-N'5 was not significantly incorporated into collagen. MATERIALS AND METHODS Ziff, Kibrick, Dresner and Gribetz (1), on the The 8 subjects utilized in the study were hospitalized other hand, observed an increased excretion of for periods of 3 to 12 weeks; 3 were patients with Mar- hydroxyproline when it was added to the diet of fan's syndrome, 2 of whom were previously shown to have elevated excretions of hydroxyproline (2).
    [Show full text]
  • (12) Patent Application Publication (10) Pub. No.: US 2007/0254315 A1 Cox Et Al
    US 20070254315A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2007/0254315 A1 Cox et al. (43) Pub. Date: Nov. 1, 2007 (54) SCREENING FOR NEUROTOXIC AMINO (60) Provisional application No. 60/494.686, filed on Aug. ACID ASSOCATED WITH NEUROLOGICAL 12, 2003. DSORDERS Publication Classification (75) Inventors: Paul A. Cox, Provo, UT (US); Sandra A. Banack, Fullerton, CA (US); Susan (51) Int. Cl. J. Murch, Cambridge (CA) GOIN 33/566 (2006.01) GOIN 33/567 (2006.01) Correspondence Address: (52) U.S. Cl. ............................................................ 435/721 PILLSBURY WINTHROP SHAW PITTMAN LLP (57) ABSTRACT ATTENTION: DOCKETING DEPARTMENT Methods for screening for neurological disorders are dis P.O BOX 105OO closed. Specifically, methods are disclosed for screening for McLean, VA 22102 (US) neurological disorders in a Subject by analyzing a tissue sample obtained from the subject for the presence of (73) Assignee: THE INSTITUTE FOR ETHNO elevated levels of neurotoxic amino acids or neurotoxic MEDICINE, Provo, UT derivatives thereof associated with neurological disorders. In particular, methods are disclosed for diagnosing a neu (21) Appl. No.: 11/760,668 rological disorder in a subject, or predicting the likelihood of developing a neurological disorder in a Subject, by deter (22) Filed: Jun. 8, 2007 mining the levels of B-N-methylamino-L-alanine (BMAA) Related U.S. Application Data in a tissue sample obtained from the subject. Methods for screening for environmental factors associated with neuro (63) Continuation of application No. 10/731,411, filed on logical disorders are disclosed. Methods for inhibiting, treat Dec. 8, 2003, now Pat. No. 7,256,002.
    [Show full text]
  • Interpretive Guide for Amino Acids
    Interpretive Guide for Amino Acids Intervention Options LOW HIGH Essential Amino Acids Arginine (Arg) Arg Mn Histidine (His) Folate, His Isoleucine (Ile) * B6, Check for insulin insensitivity Leucine (Leu) * B6, Check for insulin insensitivity Lysine (Lys) Carnitine Vitamin C, Niacin, B6, Iron, a-KG Methionine(Met) * B6, á-KG, Mg, SAM Phenylalanine (Phe) * Iron,VitaminC,Niacin,LowPhediet Threonine(Thr) * B6, Zn Tryptophan(Trp) Trpor5-HTP Niacin, B6 Valine (Val) * B6, Check for insulin insensitivity Essential Amino Acid Derivatives Neuroendocrine Metabolism y-Aminobutyric Acid (GABA) a-KG, B6 Glycine (Gly) Gly Folate, B6,B2,B5 Serine (Ser) B6, Mn, Folate * Taurine (Tau) Tau, B6 Vit. E, Vit. C, B-Carotene, CoQ10, Lipoate Tyrosine(Tyr) Iron,Tyr,VitaminC,Niacin Cu, Iron, Vitamin C, B6 Ammonia/Energy Metabolism a-Aminoadipic Acid B6, a-KG Asparagine (Asn) Mg Aspartic Acid (Asp) a-KG, B6 Mg, Zn Citrulline (Cit) Mg, Aspartic acid Glutamic Acid (Glu) B6, a-KG Niacin, B6 Glutamine (Gln) a-KG, B6 Ornithine (Orn) Arg Mg, a-KG, B6 Sulfur Metabolism Cystine (Cys) NAC B2 Cystathionine B6 Homocystine (HCys) B6, Folate, B12, Betaine Additional Metabolites a-Amino-N-Butyric Acid a-KG, B6 B6, a-KG Alanine (Ala) * B6 Anserine Zn n-Alanine Lactobacillus and Bifidobacteria, B6 n-Aminoisobutyric Acid B6 Carnosine Zn Ethanolamine Mg Hydroxylysine (HLys) Vitamin C, Iron, a-KG Hydroxyproline (HPro) Vitamin C, Iron, a-KG 1-Methylhistidine Vitamin E, B12, Folate 3-Methylhistidine BCAAs, Vit. E, Vit. C, n-Carotene, CoQ10, Lipoate Phosphoethanolamine (PE) SAM, B12, Folate, Betaine Phosphoserine Mg Proline (Pro) a-KG Vitamin C, Niacin Sarcosine B2 * Use balanced or custom mixtures of essential amino acids Nordic Laboratiroes∙ Nygade 6, 3.sal ∙ 1164 Copenhagen K ∙ DenmarkTel: +45 33 75 1000 ∙ e-mail: [email protected] In association with ©Metametrix, Inc.
    [Show full text]
  • Ratio of Phosphate to Amino Acids
    National Institute for Health and Care Excellence Final Neonatal parenteral nutrition [D10] Ratio of phosphate to amino acids NICE guideline NG154 Evidence reviews February 2020 Final These evidence reviews were developed by the National Guideline Alliance which is part of the Royal College of Obstetricians and Gynaecologists FINAL Error! No text of specified style in document. Disclaimer The recommendations in this guideline represent the view of NICE, arrived at after careful consideration of the evidence available. When exercising their judgement, professionals are expected to take this guideline fully into account, alongside the individual needs, preferences and values of their patients or service users. The recommendations in this guideline are not mandatory and the guideline does not override the responsibility of healthcare professionals to make decisions appropriate to the circumstances of the individual patient, in consultation with the patient and/or their carer or guardian. Local commissioners and/or providers have a responsibility to enable the guideline to be applied when individual health professionals and their patients or service users wish to use it. They should do so in the context of local and national priorities for funding and developing services, and in light of their duties to have due regard to the need to eliminate unlawful discrimination, to advance equality of opportunity and to reduce health inequalities. Nothing in this guideline should be interpreted in a way that would be inconsistent with compliance with those duties. NICE guidelines cover health and care in England. Decisions on how they apply in other UK countries are made by ministers in the Welsh Government, Scottish Government, and Northern Ireland Executive.
    [Show full text]
  • Article the Bee Hemolymph Metabolome: a Window Into the Impact of Viruses on Bumble Bees
    Article The Bee Hemolymph Metabolome: A Window into the Impact of Viruses on Bumble Bees Luoluo Wang 1,2, Lieven Van Meulebroek 3, Lynn Vanhaecke 3, Guy Smagghe 2 and Ivan Meeus 2,* 1 Guangdong Provincial Key Laboratory of Insect Developmental Biology and Applied Technology, Institute of Insect Science and Technology, School of Life Sciences, South China Normal University, Guangzhou, China; [email protected] 2 Department of Plants and Crops, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium; [email protected], [email protected] 3 Laboratory of Chemical Analysis, Department of Veterinary Public Health and Food Safety, Faculty of Vet- erinary Medicine, Ghent University, Merelbeke, Belgium; [email protected]; [email protected] * Correspondence: [email protected] Selection of the targeted biomarker set: In total we identified 76 metabolites, including 28 amino acids (37%), 11 carbohy- drates (14%), 11 carboxylic acids, 2 TCA intermediates, 4 polyamines, 4 nucleic acids, and 16 compounds from other chemical classes (Table S1). We selected biologically-relevant biomarker candidates based on a three step approach: (1) their expression profile in stand- ardized bees and its relation with viral presence, (2) pathways analysis on significant me- tabolites; and (3) a literature search to identify potential viral specific signatures. Step (1) and (2), pathways analysis on significant metabolites We performed two-way ANOVA with Tukey HSD tests for post-hoc comparisons and used significant metabolites for metabolic pathway analysis using the web-based Citation: Wang, L.L.; Van platform MetaboAnalyst (http://www.metaboanalyst.ca/) in order to get insights in the Meulebroek, L.; Vanhaecke.
    [Show full text]
  • Schneider-Dissertation-2019
    Biosynthetic Investigation, Synthesis, and Bioactivity Evaluation of Putative Peptide Aldehyde Natural Products From the Human Gut Microbiota The Harvard community has made this article openly available. Please share how this access benefits you. Your story matters Citation Schneider, Benjamin Aaron. 2019. Biosynthetic Investigation, Synthesis, and Bioactivity Evaluation of Putative Peptide Aldehyde Natural Products From the Human Gut Microbiota. Doctoral dissertation, Harvard University, Graduate School of Arts & Sciences. Citable link http://nrs.harvard.edu/urn-3:HUL.InstRepos:42029686 Terms of Use This article was downloaded from Harvard University’s DASH repository, and is made available under the terms and conditions applicable to Other Posted Material, as set forth at http:// nrs.harvard.edu/urn-3:HUL.InstRepos:dash.current.terms-of- use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
    [Show full text]
  • Proposal of the Annotation of Phosphorylated Amino Acids and Peptides Using Biological and Chemical Codes
    molecules Article Proposal of the Annotation of Phosphorylated Amino Acids and Peptides Using Biological and Chemical Codes Piotr Minkiewicz * , Małgorzata Darewicz , Anna Iwaniak and Marta Turło Department of Food Biochemistry, University of Warmia and Mazury in Olsztyn, Plac Cieszy´nski1, 10-726 Olsztyn-Kortowo, Poland; [email protected] (M.D.); [email protected] (A.I.); [email protected] (M.T.) * Correspondence: [email protected]; Tel.: +48-89-523-3715 Abstract: Phosphorylation represents one of the most important modifications of amino acids, peptides, and proteins. By modifying the latter, it is useful in improving the functional properties of foods. Although all these substances are broadly annotated in internet databases, there is no unified code for their annotation. The present publication aims to describe a simple code for the annotation of phosphopeptide sequences. The proposed code describes the location of phosphate residues in amino acid side chains (including new rules of atom numbering in amino acids) and the diversity of phosphate residues (e.g., di- and triphosphate residues and phosphate amidation). This article also includes translating the proposed biological code into SMILES, being the most commonly used chemical code. Finally, it discusses possible errors associated with applying the proposed code and in the resulting SMILES representations of phosphopeptides. The proposed code can be extended to describe other modifications in the future. Keywords: amino acids; peptides; phosphorylation; phosphate groups; databases; code; bioinformatics; cheminformatics; SMILES Citation: Minkiewicz, P.; Darewicz, M.; Iwaniak, A.; Turło, M. Proposal of the Annotation of Phosphorylated Amino Acids and Peptides Using 1. Introduction Biological and Chemical Codes.
    [Show full text]
  • Analysis of Amino Acids by HPLC
    Analysis of Amino Acids by HPLC Rita Steed Agilent Technologies, Inc. 800-227-9770 opt 3/opt3/opt 2 Amino Acid Analysis - Agilent Restricted Page 1 June 24, 2010 Outline • Amino Acids – Structure, Chemistry • Separation Considerations • Challenges • Instrumentation • Derivatization – OPA, FMOC • Overview of Separations • Examples Amino Acid Analysis - Agilent Restricted Page 2 June 24, 2010 Amino Acids – Structure, Chemistry CH3 Alanine (()Ala) Glutamic Acid (()Glu) Amino Acid Analysis - Agilent Restricted Page 3 June 24, 2010 Amino Acids – Zwitterionic Amino Acid Analysis - Agilent Restricted Page 4 June 24, 2010 Separation Considerations • Zwitterions - poor solubility near iso- …electric point • Most have poor UV absorbance • Derivatization – OPA, FMOC •Reduce polarity – increases retention in reversed-phase chromatoggpyraphy •Improve sensitivity – UV, Fluorescence • Detector; DAD, FLD, MS, ELSD Amino Acid Analysis - Agilent Restricted Page 5 June 24, 2010 Ortho Phthalaldehyde (OPA) and Fluorenylmethoxy chloroformate (FMOC) Reactions with Amines OPA O SR’ R’SH H NR +RNH2 H Room Temperature O Fluorescence: Ex 340nm, Em 450nm Non-fluorescent DAD: 338 , 10nm; Ref . 390 , 20nm Does not absorb at 338nm FMOC RR’NH - HCl + or Room Temperature RNH2 NRR’ or NHR Fluorescence: Ex 260nm, Em 325nm Fluorescent DAD: 262, 16nm; Ref. 324,8nm Absorbs at 262nm and Fluorescences at 324nm Group/Presentation Title Agilent Restricted Month ##, 200X Names and Order of Elution for OPA and FMOC Derivatives of Amino Acids Peak # AA Name AA Abbreviation Derivative Type Peak # AA Name AA Abbreviation Derivative Type Group/Presentation Title Agilent Restricted Month ##, 200X Agilent AAA Methods - They’ve Evolved • Automated Amino Acid Analysis – AminoQuant I & II (1987) •1090 •1100, Pub.
    [Show full text]
  • Amino Acids and N-Acetyl-Aspartyl-Glutamate As Neurotransmitter Candidates in the Monkey Retinogeniculate Pathways
    City University of New York (CUNY) CUNY Academic Works All Dissertations, Theses, and Capstone Projects Dissertations, Theses, and Capstone Projects 1989 Amino Acids and N-acetyl-aspartyl-glutamate as Neurotransmitter Candidates in the Monkey Retinogeniculate Pathways Ricardo A. Molinar-Rode Graduate Center, City University of New York How does access to this work benefit ou?y Let us know! More information about this work at: https://academicworks.cuny.edu/gc_etds/1641 Discover additional works at: https://academicworks.cuny.edu This work is made publicly available by the City University of New York (CUNY). Contact: [email protected] INFORMATION TO USERS The most advanced technology has been used to photo­ graph and reproduce this manuscript from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are re­ produced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overlaps. Each original is also photographed in one exposure and is included in reduced form at the back of the book.
    [Show full text]
  • Modified Fc Proteins Comprising Site-Specific Non-Natural Amino Acid Residues, Conjugates of the Same, Methods of Their Preparation and Methods of Their Use
    (19) TZZ¥_¥Z_T (11) EP 3 135 690 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 01.03.2017 Bulletin 2017/09 C07K 16/28 (2006.01) A61K 47/50 (2017.01) (21) Application number: 16188712.0 (22) Date of filing: 26.06.2013 (84) Designated Contracting States: • BALIGA, Ramesh AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Foster City, CA 94404 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • BAJAD, Sunil PL PT RO RS SE SI SK SM TR Fremont, CA 94538-3219 (US) • POLLITT, Sonia (30) Priority: 26.06.2012 US 201261664686 P San Mateo, CA 94402 (US) 12.11.2012 US 201261725439 P • MURRAY, Chris Soquel, CA 95073 (US) (62) Document number(s) of the earlier application(s) in •STEINER,Alex accordance with Art. 76 EPC: San Francisco, CA 94107 (US) 13737046.6 / 2 863 955 • GILL, Avinash Emeryville, CA 94608 (US) (71) Applicant: Sutro Biopharma, Inc. South San Francisco, California 94080 (US) (74) Representative: Hutter, Anton et al Venner Shipley LLP (72) Inventors: 200 Aldersgate • THANOS, Christopher London EC1A 4HD (GB) Tiburon, CA 94920 (US) • MCEVOY, Leslie Remarks: Mountain View, CA 94043 (US) This applicationwas filed on 14.9.2016 as a divisional • YIN, Gang application to the application mentioned under INID South San Francisco, CA 94080 (US) code 62. • PENTA, Kalyani Palo Alto, CA 94303 (US) (54) MODIFIED FC PROTEINS COMPRISING SITE-SPECIFIC NON-NATURAL AMINO ACID RESIDUES, CONJUGATES OF THE SAME, METHODS OF THEIR PREPARATION AND METHODS OF THEIR USE (57) Provided herein are modified Fc proteins com- duction and methods of their use.
    [Show full text]
  • Bioactive Peptides Produced by Cyanobacteria of the Genus Nostoc: a Review
    marine drugs Review Bioactive Peptides Produced by Cyanobacteria of the Genus Nostoc: A Review Anna Fidor 1, Robert Konkel 1 and Hanna Mazur-Marzec 1,2,* 1 Division of Marine Biotechnology, Faculty of Oceanography and Geography, University of Gda´nsk, Marszałka J. Piłsudskiego 46, PL-81378 Gdynia, Poland; anna.fi[email protected] (A.F.); [email protected] (R.K.) 2 Institute of Oceanology, Polish Academy of Sciences, Powsta´nców Warszawy 55, PL-81712 Sopot, Poland * Correspondence: [email protected]; Tel.: +48-58-5236621; Fax: 48-58-5236712 Received: 30 August 2019; Accepted: 27 September 2019; Published: 29 September 2019 Abstract: Cyanobacteria of the genus Nostoc are widespread in all kinds of habitats. They occur in a free-living state or in association with other organisms. Members of this genus belong to prolific producers of bioactive metabolites, some of which have been recognized as potential therapeutic agents. Of these, peptides and peptide-like structures show the most promising properties and are of a particular interest for both research laboratories and pharmaceutical companies. Nostoc is a sole source of some lead compounds such as cytotoxic cryptophycins, antiviral cyanovirin-N, or the antitoxic nostocyclopeptides. Nostoc also produces the same bioactive peptides as other cyanobacterial genera, but they frequently have some unique modifications in the structure. This includes hepatotoxic microcystins and potent proteases inhibitors such as cyanopeptolins, anabaenopeptins, and microginins. In this review, we described the most studied peptides produced by Nostoc, focusing especially on the structure, the activity, and a potential application of the compounds. Keywords: cyanobacteria; Nostoc; nonribosomal peptides; bioactivity 1.
    [Show full text]