DOCSLIB.ORG

Photoactivatable, and Cleavable Through an Azo Linkage

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Photoactivatable, and Cleavable Through an Azo Linkage Proc. Nad. Acad. Sci. USA Vol. 81, pp. 5286-5290, September 1984 Biochemistry "25I-labeled crosslinking reagent that is hydrophilic, photoactivatable, and cleavable through an azo linkage (heterobifunctional reagent/carrier-free specific activity/sulfosuccinimide ester/aryl azide/transfer of radioactive label from derivatized protein A to serum IgG) JOHN B. DENNY AND GUNTER BLOBEL Laboratory of Cell Biology, The Rockefeller University, New York, NY 10021 Contributed by Gunter Blobel, March 7, 1984 ABSTRACT A radioactive crosslinking reagent, N-[4-(P- protein-SH groups (13, 14). In addition, they cannot be used azido-m-[1251]iodophenylazo)benzoyl]-3-aminopropyl- in the presence of thiol reducing agents. We therefore have N'-oxysulfosuccinimide ester, has been synthesized. The rea- prepared a photoactivatable crosslinker that is cleavable gent is photoactivatable, water-soluble, cleavable through an through an azo linkage, as in reagents described previously azo linkage, and labeled with 125I at the carrier-free specific (15-17), but with the added advantages of the high specific activity of 2000 Ci/mtnol. Any protein derivatized with the radioactivity of 125I and a sulfonate group to render the com- reagent is thus converted into an '251-labeled photoaffinity pound water-soluble. Photoactivatable crosslinking reagents probe. Crosslinks are formed following photolysis with 366- have been prepared that contain 35S (18) and 125I (19), but in nm light, and cleavage by sodium dithionite results in the do- the latter case the reagents were not cleavable and were not nation of radioactivity to the distal partner in crosslinked com- prepared at the carrier-free specific activity of 2000 Ci/mmol plexes. The newly labeled proteins are then analyzed by gel (1 Ci = 37 GBq). electrophoresis and autoradiography. The compound was pre- In this paper we have selected the protein A-IgG interac- pared by iodination of N-[4-(p-aminophenylazo)benzoylJ-3- tion (20) as a model system with which to test the crosslink- aminopropionic acid using carrier-free Na'25I and chlora- ing reagent. We show that radioactive label is transferred to mine-T, followed by azide formation and conversion to the wa- the heavy chain of IgG when derivatized protein A-Sepha- ter-soluble sulfosuccinimide ester. As a model system, protein rose is photolyzed in the presence of human serum and sub- A-Sepharose was derivatized with the reagent under subdued sequently treated with sodium dithionite. In addition, the ra- light. Each derivatized protein A molecule contained only one dioactive labeling that occurs following photolysis with 366- crosslinker. The derivatized protein A-Sepharose was then nm light is due to reactions mediated by the aryl nitrene and photolyzed in the presence of human serum and subsequently is not due to the incorporation of free 125I. This latter result treated with sodium dithionite. Analysis of the serum by gel is in agreement with those of others (19, 21-24). electrophoresis revealed that 1.1% of the radioactive label originally present on the protein A-Sepharose was transferred MATERIALS AND METHODS to the heavy chain of IgG, which was the most intensely labeled Aniline was purchased from Aldrich and was vacuum-dis- protein in the gel. The next most intensely labeled protein was tilled at 78°C prior to use. Tetrahydrofuran (gold label), diox- IgG light chain, which incorporated radioactivity that was ane (gold label), formaldehyde sodium bisulfite addition lowver by a factor of 3.6 than that of the heavy chain. These compound, p-aminobenzoic acid, sodium nitrite, and sodium results demonstrated the specificity of the derivatized protein azide were purchased from Aldrich and used without further A-Sepharose as a photoaffinity probe. Photolabeling of IgG purification. Dicyclohexylcarbodiimide and N-hydroxysuc- was the result ofnitrene-mediated reactions and was not due to cinimide were from Pierce, Na 251 was from Amersham, so- the incorporation of free 1251. dium dithionite and chloramine-T were from Fisher, TLC plates were from EM Laboratories (Elmsford, NY), and pro- Photoactivatable crosslinking reagents have been success- tein A-Sepharose CL-4B and f-alanine were from Sigma. fully used to detect plasma membrane receptors for insulin NMR spectra were obtained on a Nicolet Fourier trans- (1), epidermal growth factor (2), human choriogonadotropin form spectrometer at 300 MHz. Chemical shifts were rela- (3), and the N-formyl chemotactic peptide (4) and to identify tive to an internal tetramethylsilane standard. IR spectra the nearest neighbors of many proteins, including fibronec- were obtained on a Perkin-Elmer model 237 B spectropho- tin (5), calmodulin (6), fibrinogen (7), glycopeptides (8), and tometer. ribosomal proteins (9) (for other previous studies, see refs. Preparation of N-[4-(p-Aminophenylazo)benzdyl]-3-gmino- 10-12). In some cases (1-4, 6, 8) relatively small proteins propionic Acid (VII). The reaction scheme for the prepara- and peptides were labeled with 125I, derivatized with a pho- tion of compound VII is shown in Fig. 1. toactivatable reagent, and crosslinked to their putative re- Sodium anilino N-methylenesulfohate (III) was prepared ceptors. However, crosslinks were not cleaved and high mo- by mixing 22 g (0.231 mol) of aniline (I) with 33.3 g (0.237 lecular weight complexes were assumed to contain the 125I- mol) of formaldehyde sodium bisulfite addition compound labeled peptide and its receptor. The above approach is more (II) in 100 ml of water at 70°C for 20 min with constant stir- difficult when used to detect receptors for larger pro- ring. The solution was then cooled on ice and the white crys- teins, due to the inability of crosslinked complexes to enter tals were collected by filtration, washed with ether, and vac- polyacrylamide gels. Cleavable, photoactivatable crosslink- uum-dried (yield, 66%). The N-methylenesulfonate group ing reagents were therefore developed (10-12), but most of protected the amino group from unwanted side reactions the reagents are cleavable through a disulfide bond and are during subsequent steps. therefore subject to mercaptan-disulfide interchange with A solution of diazotized p-aminobenzoic acid (IV) was prepared by dropwise addition of 3.6 g of sodium nitrite in 10 The publication costs of this article were defrayed in part by page charge ml of cold (4°C) water to an ice-cold suspension of 6.5 g payment. This article must therefore be hereby marked "advertisement" (0.047 mol) of p-aminobenzoic acid in 27.5 ml of 5.5 M HCl. in accordance with 18 U.S.C. §1734 solely to indicate this fact. After 15 min at 0°C, all of the above solution was added with 5286 Downloaded by guest on September 28, 2021 Biochemistry: Denny and Blobel Proc. Natl. Acad ScL USA 81 (1984) 5287 aminophenylazo)benzoyl]-3-aminopropionic acid (VII), was Ki6@> INH2 + HOCH2SO3 Na+ collected by centrifugation, washed with water, and vacu- (II) um-dried. The yield was 0.163 g (0.52 mmol) or 13% based (I) on the amount of compound VI used. The product at this stage was contaminated with 1-2% of @" NHcH2SO3 Na+ (III) compound VI. TLC on silica gel 60 in chloroform/methanol, 2:1 (vol/vol), was used to purify the desired compound VII (Rf = 0.45) from the contaminant VI (Rf = 0.66). NMR (com- HOOC A g2 i pound VII) (dimethyl-d6 sulfoxide): 2.52 (t, 2H, CH2), 3.49 (IV) /A (q, 2H, CH2), 6.25 (s, 2H, aromatic NH2), 6.71 (d, 2H, aro- HOOC N-N j NHCH2SO3 Na+ (V) matic H), 7.71 (d, 2H, aromatic H), 7.81 (d, 2H, aromatic H), 7.99 (d, 2H, aromatic H), 8.65 (s, 1H, amide-NH) ppm (s = 1 1. NaOH 2. HC1 singlet, d = doublet, t = triplet, q = quartet). IR (compound VII) (potassium bromide): 3460 cm-' (N-H stretch of CONH), 3405 and 3375 cm-' (N-H HOOC ( >)N-N < NH2 (VI) stretch of NH2), 1760 cm-' (C==O stretch of COOH), 1605 cm'1 (N-H bend of NH2). | 1. DCC/POSu Preparation of N-[4-(p-Azido-m-[125I~iodophenylazo)ben- 2. P-alanine (pH 9.5) 3. HC1 zoyl]-3-aminopropyl-N'-oxysulfosuccinimide Ester (X). The reaction scheme for the preparation of the final crosslinker, compound X, is shown in Fig. 2. HOOCCH2CH2HN8 N-N NH2 (VII) To iodinate compound VII, 150 ,ul of a 5 mM solution of the compound in dioxane/water, 2:1 (vol/vol), was mixed FIG. 1. Preparation of N-[4-(p-aminophenylazo)benzoyl]-3- with 10 ,ul (1 mCi, 0.5 nmol) of carrier-free Na1251, 89 ,ul of aminopropionic acid (VII). Aniline (I) reacts with formaldehyde so- water, 30 Al of 0.3 M H2SO4, and 31 ,ul of chloramine-T at 40 dium bisulfite addition compound (II) to give the adduct III. Reac- mg/ml in water (final pH = 1.9). The solution was centri- tion of III with diazotized p-aminobenzoic acid (IV) gives the azo fuged vigorously in a vortex for 5 sec and was then incubated compound (V), which is treated with NaOH to remove the N-methyl for 30 sec at room temperature, followed by the addition of sulfonate group. The resulting azo compound (VI) is converted to an 31 ,ul of NaHSO3 at 30 mg/ml in water. The solution was active ester by using N-hydroxysuccinimide (HOSu) and dicyclo- then immediately extracted three times with 0.5-ml portions hexylcarbodiimide (DCC) and then reacts with 18-alanine to give of ether. The ether extracts were combined and concentrat- compound VII. ed to 50 ,ul with a stream of N2, and the concentrate was then applied to a 0.2-mm-thick silica gel 60 plate with plastic stirring to an ice-cold solution of compound III (13.1 g, 0.063 backing (20 x 20 cm).
Load more

Recommended publications
  • Synthesis and in Vitro Antimicrobial and Anthelminthic Evaluation of Naphtholic and Phenolic Azo Dyes
    Hindawi Journal of Tropical Medicine Volume 2020, Article ID 4850492, 8 pages https://doi.org/10.1155/2020/4850492 Research Article Synthesis and In Vitro Antimicrobial and Anthelminthic Evaluation of Naphtholic and Phenolic Azo Dyes Joseph Kwasi Adu ,1 Cedric Dzidzor Kodjo Amengor ,2 Nurudeen Mohammed Ibrahim ,1 Cynthia Amaning-Danquah,3 Charles Owusu Ansah,1 Dorcas Dzifa Gbadago,1 and Joseph Sarpong-Agyapong1 1Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences, College of Health Sciences, Kwame Nkrumah University of Science and Technology (KNUST), Kumasi, Ghana 2Department of Pharmaceutical Chemistry, School of Pharmacy, University of Health and Allied Sciences, Ho, Ghana 3Department of Pharmacology, Faculty of Pharmacy and Pharmaceutical Sciences, College of Health Sciences, Kwame Nkrumah University of Science and Technology (KNUST), Kumasi, Ghana Correspondence should be addressed to Joseph Kwasi Adu; [email protected] Received 29 February 2020; Accepted 11 May 2020; Published 1 June 2020 Academic Editor: Sukla Biswas Copyright © 2020 Joseph Kwasi Adu et al. *is 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. *e antimicrobial activity of 2-naphtholic and phenolic azo compounds was determined against seven microbial species, Staphylococcus aureus (ATCC 25923), Streptococcus pyrogenes (clinical), and Enterococcus faecalis (ATCC 29212), Salmonella typhi (clinical), Pseudomonas aeruginosa (ATCC 27853), Escherichia coli (ATCC 251922), and Candida albicans (ATCC 10231), using the high-throughput spot culture growth inhibition assay (HT-SPOTi). *e minimum inhibitory concentrations (MIC) were determined for the active azo dyes. All the azo compounds (A1–B4) were screened for anthelmintic activity against adult Ghanaian earthworms, Hyperiodrilus spp.
    [Show full text]
  • Experiment 19: Combinatorial Synthesis of Azo Dyes
    1 Experiment 19: Combinatorial Synthesis of Azo Dyes When a new pharmaceutical is needed to treat a medical condition, modern chemists sometimes utilize a research technique known as combinatorial chemistry to find molecules that have the necessary biological activity. In combinatorial chemistry, a large number of structurally related compounds, called a library, is generated using a single common reaction. The diversity of the compounds in the library can arise from varying the substituents of the molecule, the functional groups or both. For instance, a library of esters can be generated by reacting a variety of different alcohols and carboxylic acids together. Once a library has been generated, the compounds must be screened for the desired activity. An example of a class of drugs that was explored using combinatorial methods are the benzodiazepines, which are used to treat anxiety disorders. Two approaches to combinatorial syntheses are employed. In a parallel synthesis, each compound is prepared individually, and the tests are performed separately on each compound. In a split synthesis, the library of compounds is both prepared and tested in mixtures of the compounds. In the latter case, the results of the tests are complex and usually require deconvolution, although a savings is realized in terms of time and materials. In either case, combinatorial chemistry allows the researcher to draw conclusions about the relationship between structure and function in molecules. The technique has been so successfully exploited that it is now utilized in other areas of chemistry besides pharmaceutical research, including catalysis and materials research. In this experiment, your lab section will generate a library of dye compounds using a parallel synthesis.
    [Show full text]
  • United States Patent Office 2,083,691 Method of Producing a Kama, Perg)
    Patented June 15, 1937 2,083,691 UNITED STATES PATENT OFFICE 2,083,691 METHOD OF PRODUCING A KAMA, PERG). Ot - George Lewis Cunningham, Niagara Falls, N. Y. assignor to The Mathieson Alkali Works, no, New York, N. Y., a corporation of Virginia No Drawing. Application 29, 1988 serial No. 105,103 6 Claims. (C123-184) This invention relates to the production of than about 2:1 and the proportion of benzene anhydrous sodium peroxide, Na2O. The inven being sufficient to maintain the hydrazo and azo tion provides a process for manufacturing an compounds in solution. The alcohols and alco hydrous sodium peroxide producing a product of. holates of the alcohols having not more than 4 5 high purity with good economy, with respect both carbon atoms are useful in the process of the to material costs and operating costs. - invention. The oxidation reaction may be typi The generally practiced processes for the pro fled as follows: duction of sodium peroxide all involve the use of metallic sodium and the use of rather high 10 temperatures, and consequently involve high 0. The process is made cyclic by regenerating the costs in both of these respects. The process of hydrazo benzene by reducing the azo benzene re temperaturesthis invention, unnecessary however, makes and, theinstead use ofof high re sulting from the oxidation with a sodium amal quiring metallic sodium, is applicable to the sodi gam, this reaction also producing the sodium . 5 um amalgam produced in conventional mercury alcoholate consumed in the oxidation. This re 5 cathode electrolytic cells. duction reaction may be typified as follows: Manchot & Herzog have hitherto described the production of sodium peroxide by reaction be tween oxygen and a methyl alcohol solution of 20 hydrazo benzene and sodium methylate (Anna For the complete cylic process, the reaction ma 20 len, 1901, 316, 331).
    [Show full text]
  • Synthesis of New Azo Compounds Based on N-(4- Hydroxypheneyl)Maleimide and N-(4-Methylpheneyl)Maleimide
    Molecules 2010, 15, 7498-7508; doi:10.3390/molecules15107498 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Synthesis of New Azo Compounds Based on N-(4- Hydroxypheneyl)maleimide and N-(4-Methylpheneyl)maleimide Issam Ahmed Mohammed * and Asniza Mustapha School of Industrial Technology, Universiti Sains Malaysia, 11800 Penang, Malaysia Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +604-6533888; Fax: +604-6573678. Received: 1 October 2010; in revised form: 14 October 2010 / Accepted: 18 October 2010 / Published: 25 October 2010 Abstract: Maleic anhydride was reacted with p-aminophenol and p-toluidine in the presence of di-phosphorus pentoxide (P2O5) as a catalyst to produce two compounds: N-(4-hydroxy- phenyl)maleimide (I) and N-(4-methylphenyl)maleimide (II). The new azo compounds I(a-c) and II(a-c) were prepared by the reaction of I and II with three different aromatic amines, namely aniline, p-aminophenol and p-toluidine. The structures of these compounds were confirmed by CHN, FT-IR, 1H-NMR, 13C-NMR, mass spectrum and UV/Vis spectroscopy. Keywords: synthesis; azo compounds; aromatic amines; N-(4-hydroxylpheneyl)maleimide 1. Introduction Small molecules and macromolecules containing imide groups exhibit great electrical properties, good solubility in polar media, resistance to hydrolysis and high thermal stability [1-8]. Due to their excellent properties many efforts have been made to produce different compounds containing imide groups consisting of two carbonyl groups bound to nitrogen. The most common unsubstituted cyclic imides were prepared by heating dicarboxylic acids or their anhydrides with reactants including ammonia, urea, formamide lithium nitride or primary amines [9-12], but the reaction needs to be carried out at high temperatures for efficient ring closure.
    [Show full text]
  • Reduction of Nitro to Azo Compounds
    Singh, V. P. , Gates, P., & Engman, L. (2017). Nitro-, Azo- and Amino Derivatives of Ebselen: Synthesis, Structure and Cytoprotective Effects. Journal of Organic Chemistry, 82(1), 313. https://doi.org/10.1021/acs.joc.6b02418 Peer reviewed version Link to published version (if available): 10.1021/acs.joc.6b02418 Link to publication record in Explore Bristol Research PDF-document This is the accepted author manuscript (AAM). The final published version (version of record) is available online via American Chemical Society at http://doi.org/10.1021/acs.joc.6b02418. Please refer to any applicable terms of use of the publisher. University of Bristol - Explore Bristol Research General rights This document is made available in accordance with publisher policies. Please cite only the published version using the reference above. Full terms of use are available: http://www.bristol.ac.uk/red/research-policy/pure/user-guides/ebr-terms/ Nitro-, Azo- and Amino Derivatives of Ebselen: Synthesis, Structure and Cytoprotective Effects Vijay P. Singh,*,† Jia-fei Poon,† Jiajie Yan,† Xi Lu,‡ Marjam Karlsson Ott,‡ Ray J. Butcher,§ Paul J. Gates¶ and Lars Engman*,† †Department of Chemistry – BMC, Uppsala University, Box 576, SE-751 23 Uppsala, Sweden ‡Division of Applied Materials Science, Department of Engineering Sciences, Uppsala University, Sweden §Department of Chemistry, Howard University, Washington D.C. 20059, United States ¶University of Bristol, School of Chemistry, Bristol, BS8 1TS, United Kingdom Abstract: Novel azo-bis-ebselen compounds 7 were prepared by reduction of 7-nitro-2-aryl-1,2- benzisoselenazol-3(2H)-ones 3 and 6 with sodium benzenetellurolate, NaTeC6H5, and by reaction of 2-bromo-3-nitrobenzamides with Na2Se2.
    [Show full text]
  • Azo Polymerization Initiators Comprehensive Catalog
    Azo Polymerization Initiators Comprehensive Catalog FUJIFILM Wako Pure Chemical Corporation 4-1 Nihonbashi Honcho 2-Chome, Japan Chuo-Ku, Tokyo 103-0023, Japan TEL+81-3-3244-0305 FUJIFILM Wako Chemicals U.S.A. Corporation 1600 Bellwood Road Richmond, USA VA 23237, U.S.A. TEL+1-804-271-7677 FUJIFILM Wako Chemicals Europe GmbH Fuggerstrasse 12 D-41468 Neuss GERMANY Germany TEL+49-2131-311-0 Wako Chemicals (Shanghai) Co., Ltd. C1-C2, 26F, Junyao International Plaza, China 789 Zhaojiabang Road, Shanghai 200032, China TEL+86-21-6407-0511 Specialty Chemicals Web Site http://www.wako-chem.co.jp/kaseihin_en/ 180401 K2 SI 01 Introduction/What is Radical Polymerization? What is Azo Polymerization Initiator? Radical Formation Mechanism 01 INDEX 01 Introduction/What is Radical Polymerization? P1 07 Detailed Explanations 1. Azo Nitrile P11-14 What are Azo Polymerization Initiator? What are Azo Polymerization Initiator? Radical Formation Mechanism P2 2. Azo Ester P15-16 An azo polymerization initiator is a compound having an azo group (R-N=N-R’), which decomposes with heat 3. Azo Amide P17-18 Characteristics of Azo Polymerization Initiators and Comparison with Peroxides P3 02 4. Azo Imidazoline P19-20 and/or light, and forms carbon radical. The formed carbon radical is excellent in reactivity, and progresses polym- Examples of radical reactions using Azo Polymerization Initiators P4 5. Azo Amidine P21-22 erization and halogenation reactions of different types of vinyl monomers. 03 Selection Guide P5-6 6. Macro Azo Initiator P23-26 04 Decomposition
    [Show full text]
  • Aromatic Amines from Azo Dye Reduction: Status Review with Emphasis on Direct UV Spectrophotometric Detection in Textile Industry Wastewaters
    Dyes and Pigments 61 (2004) 121–139 www.elsevier.com/locate/dyepig Aromatic amines from azo dye reduction: status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters H.M. Pinheiroa, E. Touraudb,*, O. Thomasb aCentro de Engenharia Biolo´gica e Quı´mica, Instituto Superior Te´cnico, Avenida Rovisco Pais, 1049-001 Lisboa, Portugal bLaboratoire de Ge´nie de l’Environnement Industriel, Ecole des Mines d’Ale`s, 6 Avenue de Clavie`res, 30319 Ale`s Cedex, France Received 28 July 2003; received in revised form 10 October 2003; accepted 17 October 2003 Abstract The present status of origins, known hazards, release restrictions and environmental fate of aromatic amines is reviewed. The specific case of aromatic amines arising from the reduction of the azo bond of azo colorants is addressed, with emphasis on the recalcitrance of azo dyes, their demonstrated vulnerability to azo bond reduction through dif- ferent mechanisms and the lack of data on the biodegradability of the resulting amines. The evolution and present array of analysis methods for aromatic amines in water samples is reviewed, highlighting the increased sophistication and sensitivity attained, and referring a few efforts towards fast analysis methodologies. The case for the application of direct ultraviolet spectral analysis with advanced deconvolution techniques for the monitoring of aromatic amines in textile effluent treatment is presented. # 2003 Elsevier Ltd. All rights reserved. Keywords: Aromatic amines; Azo dyes; Hazards; Textile wastewater; Analysis; UV spectra 1. Origin and types of aromatic amines in the some examples of environmentally or health-rela- environment ted important amines together with their major origins and potential impact.
    [Show full text]
  • Wo 2008/056828 A2
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date PCT 15 May 2008 (15.05.2008) WO 2008/056828 A2 (51) International Patent Classification: (74) Agents: TAKAMATSU, Takeshi et al; Koh-Ei Patent C07D 231/38 (2006.01) Firm, Kawabe Bldg., 7-9, Shimbashi 3-chome, Minato-ku, Tokyo 1050004 (JP). (21) International Application Number: PCT/JP2007/072240 (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (22) International Filing Date: AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, 9 November 2007 (09.1 1.2007) CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, (25) Filing Language: English IN, IS, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, (26) Publication Language: English RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW (30) Priority Data: 2006-304998 10 November 2006 (10.11.2006) JP (84) Designated States (unless otherwise indicated, for every 2006-304999 10 November 2006 (10.11.2006) JP kind of regional protection available): ARIPO (BW, GH, 2007-211816 15 August 2007 (15.08.2007) JP GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (71) Applicant (for all designated States except US): FUJI- European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FILM Corporation [JP/JP]; 26-30, Nishiazabu 2-chome, FR, GB, GR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, PL, Minato-ku, Tokyo, 1060031 (JP).
    [Show full text]
  • Synthesis, Antibacterial and Antifungal Activities of Some New Azo Anils Containing Pyrazole Moiety
    Indian Journal of Chemistry Vol. 53B, February 2014, pp 227-237 Synthesis, antibacterial and antifungal activities of some new azo anils containing pyrazole moiety S Sharma*a, Jasvir Kaurb, Sandeep Kaurb & Poonam Sharmaa aDepartment of Plant Breeding & Genetics, Punjab Agricultural University, Ludhiana 141 004, India bDepartment of Chemistry, Punjab Agricultural University, Ludhiana 141 004, India E-mail: [email protected] Received 11 February 2013; accepted (revised) 31 October 2013 A series of azo compounds namely 3-(Phenylazo) benzaldehyde 1a-f, 3-(4-Nitrophenylazo) benzaldehyde 3a-f and 3- (1,5-Dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl-azo) benzaldehyde 6 were synthesized and then azo anils viz. 3-(Phenylazo)-1,5 dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H pyrazol-4-yl imino methyl benzene 2a-f, 4a-f and 7-9 have been synthesized from azo compounds by reacting with corresponding amines. All the compounds synthesized by conventional method are also prepared by using microwave irradiation method and are characterized by spectroscopic techniques (UV, FTIR and 1H NMR). The synthesized compounds have been screened for antimicrobial activity against bacteria viz. Mesorhizobium sp., Bacillus sp. and Pseudomonas sp., fungus (Ascochyta blight) and yeast (Sacchromycis cerevisiae). The azo anils show minor to moderate activity against bacteria and no activity against fungus and yeast. The activity shown by some compounds is due to substitution of chloro, methoxy or nitro group on phenyl ring or due to some heterocyclic moiety. Keywords: Azo anils, azo compounds, microwave irradiation, Mesorhizobium sp., Bacillus sp., Pseudomonas sp. Azo anil formation is of major importance in and pharmaceutical chemistry with several biological biological processes as many of these involve the applications.
    [Show full text]
  • Characterising Particulate Organic Nitrogen at a Savannah-Grassland Region in South Africa
    atmosphere Article Characterising Particulate Organic Nitrogen at A Savannah-Grassland Region in South Africa Wanda Booyens 1, Pieter G. Van Zyl 1,* , Johan P. Beukes 1, Jose Ruiz-Jimenez 2, Matias Kopperi 2, Marja-Liisa Riekkola 2 , Ville Vakkari 1,3, Miroslav Josipovic 1, Markku Kulmala 4 and Lauri Laakso 1,3 1 Unit for Environmental Science and Management, North-West University, Private Bag X6001, Potchefstroom 2520, South Africa 2 Department of Chemistry, University of Helsinki, PO Box 55, 00014 Helsinki, Finland 3 Finnish Meteorological Institute, PO Box 503, 00101 Helsinki, Finland 4 Department of Physical Sciences, University of Helsinki, P.O. Box 64, 00014 Helsinki, Finland * Correspondence: [email protected]; Tel.: +27-18-299-2353 Received: 29 July 2019; Accepted: 20 August 2019; Published: 26 August 2019 Abstract: Although atmospheric organic N compounds are considered to be important, especially in new particle formation and their contribution to brown carbon, these species are not that well understood. This can be partially attributed to their chemical complexity. Therefore, the aim of this study was to assess the characteristics of organic N compounds utilising comprehensive two-dimensional gas chromatography coupled with a time-of-flight mass spectrometer (GCxGC-TOFMS) in aerosol samples that were collected at a savanna-grassland background region and to determine the possible sources. 135 atmospheric organic N compounds were tentatively characterised and semi-quantified, which included amines, nitriles, amides, urea, pyridine derivatives, amino acids, nitro-and nitroso compounds, imines, cyanates and isocyanates, and azo compounds. Amines contributed to 51% of the semi-quantified concentrations, while nitriles, pyridine derivatives, and amides comprised 20%, 11%, and 8%, respectively, of the semi-quantified concentrations.
    [Show full text]
  • Synthesis and Characterization of Azo Compounds and Study of the Effect of Substituents on Their Liquid Crystalline Behavior
    Molecules 2010, 15, 5620-5628; doi:10.3390/molecules15085620 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Synthesis and Characterization of Azo Compounds and Study of the Effect of Substituents on Their Liquid Crystalline Behavior Uhood J. Al-Hamdani *, Tarik E. Gassim and Howraa H. Radhy Department of Chemistry, College of Education, Basrah University, Basrah, Iraq ∗ Author to whom correspondence should be addressed; E-Mail:[email protected]; Tel.: +9647712616545. Received: 1 July 2010; in revised form: 4 August 2010 / Accepted: 12 August 2010 / Published: 13 August 2010 Abstract: In this paper we present six select mesomorphic azo compounds distinguished by the presence of diverse substituents on a central benzene nucleus. All the synthesized compounds exhibit enantiotropic mesophases. The mesomorphic properties of the substituted compounds were compared with those of the unsubstituted parent compound to evaluate the effect of the nature and position of the substituents on mesomorphism. Keywords: azo; lateral group; liquid crystal Introduction Until 1983 it was generally accepted that substituents diminish the mesogenic properties of a compound, with the extent of the effect depending on their size. Cox et al. [1] synthesized nematogens in which a phenyl side group was attached without a spacer. Mesogens with aromatic substituents have been prepared [2-7]. Recently a homologous series of mesogenic azo compounds containing three rings in the main core and substituted with aromatic or hydroxyl groups on the central benzene nucleus was reported [8,9]. The mesogenic homologous series with hydroxyl group substituents exhibited nematic mesomorphism, whereas the homologous series with aromatic branches exhibited smectogenic tendencies.
    [Show full text]
  • Azo Compound, Aqueous Solution, Ink Composition, Ink for Inkjet Recording, Inkjet Recording Method, Ink Cartridge for Inkjet Recording, and Inkjet Recorded Material
    (19) TZZ _ _T (11) EP 2 712 894 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 02.04.2014 Bulletin 2014/14 C09B 31/153 (2006.01) C09D 11/00 (2014.01) (21) Application number: 13185960.5 (22) Date of filing: 25.09.2013 (84) Designated Contracting States: • Hayashi, Shinya AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Kanagawa 258-8577 (JP) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • Iizumi, Takashi PL PT RO RS SE SI SK SM TR Kanagawa 258-8577 (JP) Designated Extension States: • Yamada, Hiroshi BA ME Kanagawa 258-8577 (JP) • Norizuki, Yutaro (30) Priority: 26.09.2012 JP 2012212754 Kanagawa 258-8577 (JP) 14.03.2013 JP 2013051807 • Amasaki, Ichiro 20.09.2013 JP 2013196181 Kanagawa 258-8577 (JP) • Tanaka, Shigeaki (71) Applicant: Fujifilm Corporation Kanagawa 258-8577 (JP) Minato-ku Tokyo (JP) (74) Representative: Morpeth, Fraser Forrest Fujifilm Imaging Colorants Limited (72) Inventors: Intellectual Property Group • Yagi, Kazunari P.O. Box 42 Kanagawa 258-8577 (JP) Hexagon Tower Blackley, Manchester M9 8ZS (GB) (54) Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded material (57) There is provided a compound represented by the following formula (1): wherein each of R1a to R1k independently represents a hydrogen atom or a monovalent substituent, the substituents may combine with each other to form a ring, each of M1a and M1b independently represents a hydrogen atom or a monovalent counter cation, Y1 represents a nitrogen atom or a carbon atom having a hydrogen atom or monovalent substituent,1 A represents an aromatic group, and the aromatic group represented by A 1 may contain a heteroatom or may have a substituent.
    [Show full text]