DOCSLIB.ORG

United States Patent (19) [11] Patent Number: 5,275,626 Grollier 45 Date of Patent: Jan

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent (19) [11] Patent Number: 5,275,626 Grollier 45 Date of Patent: Jan US005275626A United States Patent (19) [11] Patent Number: 5,275,626 Grollier 45 Date of Patent: Jan. 4, 1994 54 METHOD FOR DYEING KERATINOUS 2626173 7/1989 France . FBRESUSING AMONOHYDROXYNDOLE 2093867 9/1982 United Kingdom . OR DHYDROXY NOOLE AND A 2119411 11/1983 United Kingdom . NON-OXIDISTING AROMATIC CARBONYL DERVATIVE AND DYENGAGENT OTHER PUBLICATIONS French Search Report of FR 91 01234 (1991, no month (75) inventor: Jean F. Grollier, Paris, France available). 73) Assignee: L'Oreal, Paris, France Primary Examiner-Paul Lieberman (21) Appl. No.: 831,064 Assistant Examiner-William S. Parks Attorney, Agent, or Firm-Cushman, Darby & Cushman (22 Filed: Feb. 4, 1992 57 ABSTRACT (30) Foreign Application Priority Data The present invention relates to a method for dyeing Feb. 4, 1991 FR France ................................ 91 01234 keratinous fibers, characterized in that the following are 51) Int, C. ................................................ A61K 7/13 applied to the fibers: 52 U.S. C. ........................................... 8/405; 8/406; a) a composition (A) containing, in a medium appro 8/407; 8/409; 8/423; 424/70 priate for dyeing, at least one monohydroxyindole 58 Field of Search ................... 8/405, 406, 407, 409, or dihydroxyindole, this application being pre ceded or followed by the application of 8/423, 634; 424/70 b) a composition (B) containing, in a medium appro (56) References Cited priate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, U.S. PATENT DOCUMENTS hydroxybenzophenones, 2-hydroxy-1,4-benzoqui 5,034,015 7/1991 Junino et al. ........................... 8/405 nones, hydroxy-1,4-naphthoquinones,amino-1,4- 5,053,053 10/1991. De Labbey et al. naphthoquinones,hydroxy-9,10-anthraquinones 5,064,442 11/1991 Grollier ............. and amino-9,10-anthraquinones. FOREIGN PATENT DOCUMENTS It also relates to the dyeing agents for carrying it out. 0271186 6/1988 European Pat. Off. 0376776 7/1990 European Pat. Off. 19 Claims, No Drawings 5,275,626 2 b) a composition (B) containing, in a medium appro METHOD FOR DYENG KERATINOUSFBRES priate for dyeing, at least one aromatic carbonyl deriva USING AMONOHYDROXY NOOLE OR tive chosen from hydroxyacetophenones, hydroxyben DHYDROXYINDOLE AND ANON-OXIDISTING zophenones, 2-hydroxy-1,4-benzoquinones, hydroxy AROMATIC CARBONYL DERVATIVE AND s 1,4-naphthoquinones,amino-1,4-naphthoquinones, hy DYENGAGENT droxy-9,10-anthraquinones and amino-9,10-anthraqui The present invention relates to a new method for Oes. colouring keratinous fibers, and more particularly Another subject of the invention comprises a multi human keratinous fibers, such as the hair, using at least 10 component dyeing agent, preferably in the form of a one monohydroxyindole or dihydroxyindole and at "dyeing kit" or "dyeing set" for carrying out the least one non-oxidizing aromatic carbonyl derivative. There has in the past already been proposed dyeing of method according to the invention. keratinous fibers, and in particular the hair, with the aid The following are used as monohydroxyindole or of hydroxyl derivatives of indole. In fact, it is known 15 dihydroxyindole, according to the invention: the com that the natural synthesis of eumelanins from tyrosine pounds of formula (I): proceeds in several steps, one of which consists in the formation of 5,6-dihydroxyindole, which oxidizes to form a pigment which is one of the main constituents of RO R3 eumelanin. 20 Thus, French Patents Nos. 1,166,172 and 1,264,707, in particular, propose coloring the hair using aqueous HO R2 compositions containing 5,6-dihydroxyindole. Using compositions of this type it is possible to dye the hair in light shades by an application of the product or in in 25 in which: creasingly lasting shades by superimposition of the ap plication. R1, R3 and R4, which may be identical or different, However, these methods do not make it possible to represent a hydrogen atom or a C1-C4 alkyl group; obtain a sufficiently wide range of varied shades, in R2 denotes a hydrogen atom, a C1-C4 alkyl group or particular the shades known as "with glints', which are 30 a carboxyl group; and the corresponding alkali particularly desired in hair coloring. metal, alkaline earth metal, ammonium and amine Methods for hair dyeing using indole derivatives, in salts of these compounds. which methods the color is developed by means of The redox potential of the indole derivatives of for oxidizing systems, have also been described. Oxidizing mula (I), measured at pH 7 on a vitreous carbon elec systems of this type are described, in particular, in Euro 35 trode by voltammetry, is, according to the invention, pean. Patent Application No. 376,776 and other known oxidizing agents comprise hydrogen peroxide, on its less than 200 mV. own or in combination with an iodide, periodates, bro Amongst these indoles, the preferred compounds mates, persulphates, perborates and nitrites, in particu according to the invention are chosen from: lar. 5,6-dihydroxyindole, The applicant has now demonstrated that it was pos 2-methyl-5,6-dihydroxyindole, sible to obtain, in a method which does not require 3-methyl-5,6-dihydroxyindole, oxidizing development other than that by atmospheric 1-methyl-5,6-dihydroxyindole, oxygen, varied shades which are very natural or rich in 2,3-dimethyl-5,6-dihydroxyindole, glints, without having the disadvantages of the prior art. 45 5-methoxy-6-hydroxyindole and In fact, in hair dyeing it is generally difficult to obtain natural shades and a uniformity of color on hair which 2-carboxy-5,6-dihydroxyindole. is long and/or sensitized by permanent waving, dyeing The non-oxidizing aromatic carbonyl derivatives are or bleaching, and over its entire length. in particular chosen from the following compounds: The method according to the invention is a method 50 hydroxyacetophenones or hydroxybenzophenones for dyeing keratinous fibers, in particular the hair, using, which are chosen from the compounds of formula in a two-stage process, the application of at least one (II): indole derivative, this application being preceded or followed by the application of at least one non-oxidizing aromatic carbonyl derivative. 55 (II) This method makes it possible to obtain a good cover ing of white hair in a uniform natural shade over the entire head of hair without altering the mechanical properties of the hair. These dyeings are of low selectiv ity and also have a good resistance to perspiration, to washing, to light and to chemical and atmospheric at tack. The method for dyeing keratinous fibers is character in which: ized in that the following are applied to the fibers: R5, R6 and R7, which may be identical or different, a) a composition (A) containing, in a medium appro 65 denote a hydrogen atom or a hydroxyl or methoxy priate for dyeing, at least one monohydroxyindole or group, at least one of R5, R6 and R7 denoting hy dihydroxyindole, this application being preceded or droxyl, and R represents a methyl group or R8, R8 followed by the application of representing a 5,275,626 4. R29, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl or C1-C4 monohydroxyalkyl group, at least one of R21 to R27 representing a hydroxyl or NR28R29 group. Amongst these non-oxidizing carbonyl derivatives, according to the invention, the following compounds may be mentioned: 2-hydroxyacetophenone, radical, where R9, Rio and R1, which may be identical 2,5-dihydroxyacetophenone, or different, represent a hydrogen atom or a hydroxyl 10 2,6-dihydroxyacetophenone, or methoxy group; 4-hydroxy-3-methoxyacetophenone, 2-hydroxy-1,4-benzoquinones which are chosen form 3,4,5-trihydroxyacetophenone, the compounds of formula (III): 2,2'-dihydroxybenzophenone, 2-hydroxybenzophenone, (III) 15 2,2',4,4-tetrahydroxybenzophenone and 3,4,2',4',6'-pentahydroxybenzophenone; 2,5-dihydroxy-1,4-benzoquinone, 2,5-dihydroxy-3-ethyl-1,4-benzoquinone, 2,5-dihydroxy-3,6-dimethoxy-1,4-benzoquinone, 20 2,5-dihydroxy-3-methyl-6-isopropyl-1,4-benzoquinone, 2,5-dihydroxy-3,6-bis-p-hydroxyphenyl-1,4-benzoqui in which: none, R2, R13 and R4, which may be identical or different, 2-hydroxy-3-methyl-6-methoxy-1,4-benzoquinone, represent a hydrogen atom or a C1-C4 alkoxy, hy 2-hydroxy-3-methyl-5,6-dimethoxy-1,4-benzoquinone, droxyl, C1-C4 alkyl, amino, C1-C4 aminoalkyl or 25 2-hydroxy-3-methoxy-6-methyl-1,4-benzoquinone and parahydroxyphenyl group; 2,3,5,6-tetrahydroxy-1,4-benzoquinone; hydroxy-1,4-naphthoquinones or amino-1,4-naph 2-hydroxy-3-isopentenyl-1,4-naphthoquinone, thoquinones which are chosen from the compounds 2-hydroxy-3-amino-7-methoxy-1,4-naphthoquinone, of formula (IV): 2-hydroxy-3-N-methylamino-1,4-naphthoquinone, 30 2-hydroxy-6-methoxy-1,4-naphthoquinone, 2-hydroxy-5-methoxy-1,4-naphthoquinone, (IV) 2-hydroxy-8-methoxy-1,4-naphthoquinone, 2-hydroxy-5,8-dimethoxy-1,4-naphthoquinone, 2-hydroxy-3-acetyl-1,4-naphthoquinone, 35 5-hydroxy-2-methoxy-1,4-naphthoquinone, 5-hydroxy-3-dimethylamino-1,4-naphthoquinone, 5-hydroxy-3-methoxy-1,4-naphthoquinone, 5-hydroxy-2-methyl-1,4-naphthoquinone, in which: 5-hydroxy-2-methyl-3-chloro-1,4-naphthoquinone, R1s and R16, which may be identical or different, represent a hydrogen or chlorine atom or a hy 5-hydroxy-2-carboxymethylthio-1,4-naphthoquinone, droxyl, methoxy, methyl, isopentenyl, acetyl or 5-hydroxy-3-carboxymethylthio-1,4-naphthoquinone, -SCH2COOH group, or a -NR19R20 group, 5,8-dihydroxy-1,4-naphthoquinone, where R19 and R20, which may be identical or 5,8-dihydroxy-2-chloro-1,4-naphthoquinone, different,
Load more

Recommended publications
  • Separation of Hydroxyanthraquinones by Chromatography
    Separation of hydroxyanthraquinones by chromatography B. RITTICH and M. ŠIMEK* Research Institute of Animal Nutrition, 691 23 Pohořelice Received 6 May 1975 Accepted for publication 25 August 1975 Chromatographic properties of hydroxyanthraquinones have been examined. Good separation was achieved using new solvent systems for paper and thin-layer chromatography on common and impregnated chromatographic support materials. Commercial reagents were analyzed by the newly-developed procedures. Было изучено хроматографическое поведение гидроксиантрахинонов. Хорошее разделение было достигнуто при использовании предложенных новых хроматографических систем: бумажная хроматография смесью уксусной кислоты и воды на простой бумаге или бумаге импрегнированной оливковым мас­ лом, тонкослойная хроматография на целлюлозе импрегнированной диметилфор- мамидом и на силикагеле без или с импрегнацией щавелевой или борной кислотами. Anthraquinones constitute an important class of organic substances. They are produced industrially as dyes [1] and occur also in natural products [2]. The fact that some hydroxyanthraquinones react with metal cations to give colour chelates has been utilized in analytical chemistry [3]. Anthraquinone and its derivatives can be determined spectrophotometrically [4—6] and by polarography [4]. The determination of anthraquinones is frequently preceded by a chromatographic separation the purpose of which is to prepare a chemically pure substance. For chromatographic separation of anthraquinone derivatives common paper [7—9] and paper impregnated with dimethylformamide or 1-bromonaphthalene has been used [10, 11]. Dyes derived from anthraquinone have also been chromatographed on thin layers of cellulose containing 10% of acetylcellulose [12]. Thin-layer chromatography on silica gel has been applied in the separation of dihydroxyanthraquinones [13], di- and trihydroxycarbox- ylic acids of anthraquinones [14] and anthraquinones occurring in nature [15].
    [Show full text]
  • United States Patent (19) 11 Patent Number: 4,746,461 Zielske (45) Date of Patent: May 24, 1988
    United States Patent (19) 11 Patent Number: 4,746,461 Zielske (45) Date of Patent: May 24, 1988 54 METHOD FOR PREPARING 4,041,051 8/1977 Yamado et al. ..................... 260/371 1,4-DIAMINOANTHRAQUINONES AND 4,661,293 4/1987 Zielske ................................ 260/377 INTERMEDIATES THEREOF FOREIGN PATENT DOCUMENTS 75 Inventor: Alfred G. Zielske, Pleasanton, Calif. 2014178 8/1979 United Kingdom................ 260/377 2019870 1 1/1979 United Kingdom ..... ... 260/377 73 Assignee: The Clorox Company, Oakland, Calif. 2100307A 5/1980 United Kingdom ................ 260/377 (21) Appl. No.: 945,906 OTHER PUBLICATIONS 22 Filed: Dec. 23, 1986 Morrison & Boyd, Organic Chemistry, 3rd ed., 1973, pp. 458, 456,527, 528. s Related U.S. Application Data Chemical Abstract, vol. 88, #10498g&h, Schultz et al., 60 Division of Ser. No. 868,884, May 23, 1986, Pat. No. 1978, "Synthesis of Meso-Substituted Hydroxyantha 4,661,293, which is a continuation of Ser. No. 556,835, rones with Laxative Activity Parts I & II' Arch. Dec. 1, 1983, abandoned. Pharm, vol. 310, No. 10, pp. 769-780, 1977. 51 Int. Cl." ...................... C11D 15/02; C11D 13/00 Primary Examiner-Glennon H. Hollrah 52 U.S. C. .................................... 260/370; 260/371; Assistant Examiner-Raymond Covington 260/374 Attorney, Agent, or Firm-Majestic, Gallagher, Parsons 58 Field of Search ............... 260/370, 371, 377, 378, & Siebert 260/374 (57) ABSTRACT (56) References Cited Aminoanthraquinones are generally useful as dyes and U.S. PATENT DOCUMENTS coloring agents. But known methods of synthesizing 2,174,751 10/1939 Koerberle ........................... 260/367 unsymmetrically substituted 1,4-diaminoanthraquinones 2,183,652 12/1939 Lord ............
    [Show full text]
  • Anthraquinones Mireille Fouillaud, Yanis Caro, Mekala Venkatachalam, Isabelle Grondin, Laurent Dufossé
    Anthraquinones Mireille Fouillaud, Yanis Caro, Mekala Venkatachalam, Isabelle Grondin, Laurent Dufossé To cite this version: Mireille Fouillaud, Yanis Caro, Mekala Venkatachalam, Isabelle Grondin, Laurent Dufossé. An- thraquinones. Leo M. L. Nollet; Janet Alejandra Gutiérrez-Uribe. Phenolic Compounds in Food Characterization and Analysis , CRC Press, pp.130-170, 2018, 978-1-4987-2296-4. hal-01657104 HAL Id: hal-01657104 https://hal.univ-reunion.fr/hal-01657104 Submitted on 6 Dec 2017 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Anthraquinones Mireille Fouillaud, Yanis Caro, Mekala Venkatachalam, Isabelle Grondin, and Laurent Dufossé CONTENTS 9.1 Introduction 9.2 Anthraquinones’ Main Structures 9.2.1 Emodin- and Alizarin-Type Pigments 9.3 Anthraquinones Naturally Occurring in Foods 9.3.1 Anthraquinones in Edible Plants 9.3.1.1 Rheum sp. (Polygonaceae) 9.3.1.2 Aloe spp. (Liliaceae or Xanthorrhoeaceae) 9.3.1.3 Morinda sp. (Rubiaceae) 9.3.1.4 Cassia sp. (Fabaceae) 9.3.1.5 Other Edible Vegetables 9.3.2 Microbial Consortia Producing Anthraquinones,
    [Show full text]
  • Fundamentals of Natural Dyes and Its Application on Textile Substrates Virendra Kumar Gupta
    Chapter Fundamentals of Natural Dyes and Its Application on Textile Substrates Virendra Kumar Gupta Abstract The meticulous environmental standards in textiles and garments imposed by countries cautious about nature and health protection are reviving interest in the application of natural dyes in dyeing of textile materials. The toxic and allergic reactions of synthetic dyes are compelling the people to think about natural dyes. Natural dyes are renewable source of colouring materials. Besides textiles it has application in colouration of foods, medicine and in handicraft items. Though natural dyes are ecofriendly, protective to skin and pleasing colour to eyes, they are having very poor bonding with textile fibre materials, which necessitate mordant- ing with metallic mordants, some of which are not eco friendly, for fixation of natural dyes on textile fibres. So the supremacy of natural dyes is somewhat sub- dued. This necessitates newer research on application of natural dyes on different natural fibres for completely eco friendly textiles. The fundamentals of natural dyes chemistry and some of the important research work are therefore discussed in this review article. Keywords: colour fastness, dyeing, extraction of natural dyes, natural dyes 1. Introduction After the advent of mauveine by Henry Perkin in 1856 and subsequent commer- cialization of synthetic dyes had replaced natural dyes, and since then consumption and application of natural dyes for textiles got reduced substantially. In present scenario environmental consciousness of people about natural products, renewable nature of materials, less environmental damage and sustainability of the natural products has further revived the use of natural dyes in dyeing of textile materials.
    [Show full text]
  • Helicopter Transmission Oil Discolouration
    UNCLASSIFIED Helicopter Transmission Oil Discolouration Andrew Becker and Paul Rawson Air Vehicles Division Defence Science and Technology Organisation DSTO-TR-2672 ABSTRACT An increase in the incidence of abnormal discolouration of oil in ADF helicopter tail rotor transmissions has been observed and reported over the last eight years. Aircraft maintainers have initially attributed the discolouration to a range of contamination modes including incorrect fluid addition, hydraulic fluid contamination and degraded fluid. A program of work was conducted at DSTO to identify and characterise the cause of the abnormal discolouration. This report details the identification of a coloured metal quinizarate salt which forms in the aircraft transmissions under normal operating conditions and describes the mechanism of formation and some characteristics of the quinizarate salt to assist in developing maintenance programs to manage the coloured salt when observed in service conditions. RELEASE LIMITATION Approved for public release UNCLASSIFIED UNCLASSIFIED Published by Air Vehicles Division DSTO Defence Science and Technology Organisation 506 Lorimer St Fishermans Bend, Victoria 3207 Australia Telephone: (03) 9626 7000 Fax: (03) 9626 7999 © Commonwealth of Australia 2012 AR-015-243 February 2012 APPROVED FOR PUBLIC RELEASE UNCLASSIFIED UNCLASSIFIED Helicopter Transmission Oil Discolouration Executive Summary Effective lubrication of modern military aircraft transmissions requires the use of highly specified synthetic polyol ester lubricants. Significant effort can be expended in ensuring serviceability of these oils through a range of oil condition monitoring programs. The current oil used in many ADF helicopter transmissions meets the MIL-PRF-23699 specification and a number of specific brands of oil meeting this specification are in routine service within the ADF.
    [Show full text]
  • PROVISIONAL PEER REVIEWED TOXICITY VALUES for ALIZARIN RED COMPOUNDS (VARIOUS CASRNS) Derivation of Subchronic and Chronic Oral Rfds
    EPA/690/R-04/001F l Final 12-20-2004 Provisional Peer Reviewed Toxicity Values for Alizarin Red Compounds (Various CASRNs) Derivation of Subchronic and Chronic Oral RfDs Superfund Health Risk Technical Support Center National Center for Environmental Assessment Office of Research and Development U.S. Environmental Protection Agency Cincinnati, OH 45268 Acronyms and Abbreviations bw body weight cc cubic centimeters CD Caesarean Delivered CERCLA Comprehensive Environmental Response, Compensation and Liability Act of 1980 CNS central nervous system cu.m cubic meter DWEL Drinking Water Equivalent Level FEL frank-effect level FIFRA Federal Insecticide, Fungicide, and Rodenticide Act g grams GI gastrointestinal HEC human equivalent concentration Hgb hemoglobin i.m. intramuscular i.p. intraperitoneal i.v. intravenous IRIS Integrated Risk Information System IUR inhalation unit risk kg kilogram L liter LEL lowest-effect level LOAEL lowest-observed-adverse-effect level LOAEL(ADJ) LOAEL adjusted to continuous exposure duration LOAEL(HEC) LOAEL adjusted for dosimetric differences across species to a human m meter MCL maximum contaminant level MCLG maximum contaminant level goal MF modifying factor mg milligram mg/kg milligrams per kilogram mg/L milligrams per liter MRL minimal risk level i MTD maximum tolerated dose MTL median threshold limit NAAQS National Ambient Air Quality Standards NOAEL no-observed-adverse-effect level NOAEL(ADJ) NOAEL adjusted to continuous exposure duration NOAEL(HEC) NOAEL adjusted for dosimetric differences across species
    [Show full text]
  • Isolation and Synthesis of Anthraquinones and Related Compounds of Rubia Cordifolia
    J. Serb. Chem. Soc. 70 (7) 937–942 (2005) UDC 633.863:547.263:542.913 JSCS – 3329 Original scientific paper Isolation and synthesis of anthraquinones and related compounds of Rubia cordifolia RAM SINGHa,b* and GEETANJALIb aCentre for Environmental Management of Degraded Ecosystems, School of Environmental Studies, University of Delhi, Delhi – 110 007 and bDepartment of Chemistry, University of Delhi, Delhi – 110 007, India (e-mail: [email protected]) (Received 17 August 2004) Abstract: Anthraquinones and their glycosides, along with other compounds, have been isolated and characterized from the acetone:water (1:1) percolation of dried roots of Rubia cordifolia. Selected anthraquinones were synthesized using montmo- rillonite clays under solventless condition in 75 to 85 % yield. Keywords: Anthraquinones, Rubia cordifolia, montmorillonite clays. INTRODUCTION The family Rubiaceae comprises about 450 genera and 6500 species and in- cludes trees, shrubs and infrequently herbs. Rubia cordifolia is a perennial, herba- ceous climbing plant, with very long roots, cylindrical, flexuous, with a thin red bark.1 Stems often have a long, rough, grooved, woody base. Plants belonging to this family are known to contain substantial amounts of anthraquinones, especially in the roots.2,3 The traditional therapeutic use of the plant has been for skin disorders and for anticancer activity.3–5 Furthermore, the anthraquinones of the Rubiaceae family exhibit some interesting in vivo biological activities, such as antimicrobial,6 antifungal,7 hypotensive,8 analgesic,8 antimalarial,5,9 antioxidant,10 antileukemic and mutagenic functions.11,12 Apart from its medicinal value, this plant has also been used as natural food colourants and as natural hair dyes.13 The interest in the isolation of natural dyes and colouring matters is increasing due to their applica- tions in food, drugs and other human consumptions.
    [Show full text]
  • Suppression Effect of Purpurin Derivatives on Nitric Oxide Synthase
    J. Korean Soc. Appl. Biol. Chem. 54(2), 302-307 (2011) Short Communication Suppression Effect of Purpurin Derivatives on Nitric Oxide Synthase Hoi-Seon Lee* Department of Bioenvironmental Chemistry and Institute of Agricultural Science & Technology, College of Agriculture & Life Science, Chonbuk National University, Jeonju 561-756, Republic of Korea Received September 1, 2010; Accepted September 9, 2010 The inhibitory effects of Rubia tinctorum root-derived materials against nitric oxide (NO) production were assessed by evaluation of NO production and inducible NO synthase (iNOS) expression, and compared to those of trihydroxyanthraquinone derivatives. The inhibitory effect of 1,2,4-trihydroxyanthraquinone (purpurin) from R. tinctorum roots against NO production was 60.7 and 38.5% at 2.5 and 1.25 μg/mL, respectively. Inhibitory effect of 1,2,7-trihydroxy- anthraquinone was 52.5% at 2.5 μg/mL. Suppression effects of 1,2,4-trihydroxyanthraquinone on iNOS expression were confirmed by western blot analysis. Key words: functional foods, inducible nitric oxide synthase, NO production, Rubia tinctorum, 1,2,4-trihydroxyanthraquinone Medicinal plants may prove to be an alternative to the murine peritoneal macrophages following stimulation inducible nitric oxide synthase (iNOS) inhibitors presently with LPS. in use, as the plants constitute a rich source of active Acrylamide, ε-amino-n-caproic acid, bovine serum chemicals [Lee et al., 2000; 2002; Lee, 2011]. Because albumin, brilliant blue G-250, 1,3,8-trihydroxyanthraquinone, these plant-derived compounds are largely free from 6-methyl-1,3,8-trihydroxyanthraquinone, ethylene diamine adverse effects, studies may facilitate the development of acid, leupeptin, lipopolysaccharide, N,N'-methylene-bis- safer iNOS inhibitors.
    [Show full text]
  • New Insights in Alzheimer's Disease
    pharmaceuticals Review Journey on Naphthoquinone and Anthraquinone Derivatives: New Insights in Alzheimer’s Disease Marta Campora † , Valeria Francesconi †, Silvia Schenone, Bruno Tasso and Michele Tonelli * Dipartimento di Farmacia, Università degli Studi di Genova, Viale Benedetto XV, 3, 16132 Genova, Italy; [email protected] (M.C.); [email protected] (V.F.); [email protected] (S.S.); [email protected] (B.T.) * Correspondence: [email protected] † These authors equally contributed to the study and both should be considered as first author. Abstract: Alzheimer’s disease (AD) is a progressive neurodegenerative disease that is characterized by memory loss, cognitive impairment, and functional decline leading to dementia and death. AD imposes neuronal death by the intricate interplay of different neurochemical factors, which continue to inspire the medicinal chemist as molecular targets for the development of new agents for the treatment of AD with diverse mechanisms of action, but also depict a more complex AD scenario. Within the wide variety of reported molecules, this review summarizes and offers a global overview of recent advancements on naphthoquinone (NQ) and anthraquinone (AQ) derivatives whose more relevant chemical features and structure-activity relationship studies will be discussed with a view to providing the perspective for the design of viable drugs for the treatment of AD. In particular, cholinesterases (ChEs), β-amyloid (Aβ) and tau proteins have been identified as key targets of these classes of compounds, where the NQ or AQ scaffold may contribute to the biological effect against AD as main unit or significant substructure. The multitarget directed ligand (MTDL) strategy will be described, as a chance for these molecules to exhibit significant potential on the road to therapeutics for AD.
    [Show full text]
  • Influence of Structural Characteristics of Substituents on the Antioxidant
    Computational and Theoretical Chemistry xxx (2015) xxx–xxx Contents lists available at ScienceDirect Computational and Theoretical Chemistry journal homepage: www.elsevier.com/locate/comptc Influence of structural characteristics of substituents on the antioxidant activity of some anthraquinone derivatives ⇑ Zoran Markovic´ a, , Svetlana Jeremic´ a, Jasmina Dimitric´ Markovic´ b, Marijana Stanojevic´ Pirkovic´ c, Dragan Amic´ d a Department of Chemical-Technological Sciences, State University of Novi Pazar, Vuka Karadzˇic´a bb, 36300 Novi Pazar, Serbia b Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia c Faculty of Medical Sciences, University of Kragujevac, Svetozara Markovic´a 69, 34000 Kragujevac, Serbia d Faculty of Agriculture, The Josip Juraj Strossmayer University, Kralja Petra Svacˇic´a 1d, HR-31000 Osijek, Croatia article info abstract Article history: The antioxidant activity of chrysophanol (CH), emodin (EM), aloe-emodin (AE), and 1,3,8- Received 31 August 2015 trihydroxyanthraquinone (THA) was examined in water and pentyl ethanoate by using the M052X/ Received in revised form 4 October 2015 6-311++G(d,p) level of theory. It was shown that hydrogen bonds are of significant importance for the Accepted 4 October 2015 stability of the radical and anionic species obtained in the HAT and SPLET mechanisms. Consequently, Available online xxxx all radicals and anions formed with retention of O9ÁÁÁH1–O1 and O9ÁÁÁH8–O8 hydrogen bonds are more stable than those where the hydrogen bonds are disturbed. The exceptions are the radical and anion of Keywords: AE, the unpaired electron or negative charge is poorly delocalized. Anthraquinones The high IP values for all investigated compounds undoubtedly discredit the SET-PT mechanism.
    [Show full text]
  • Anthraquinones As Inhibitors of Sulfide Production from Sulfate-Reducing Bacteria
    Europaisches Patentamt 19 European Patent Office Office europeen des brevets © Publication number: 0 525 073 B1 12 EUROPEAN PATENT SPECIFICATION © Date of publication of patent specification © int. ci.5: A01N 35/06, C12Q 1/04, 25.05.94 Bulletin 94/21 C12Q 1/18 © Application number : 91908405.3 © Date of filing : 19.03.91 © International application number : PCT/US91/01734 @ International publication number : WO 91/15954 31.10.91 Gazette 91/25 @ ANTHRAQUINONES AS INHIBITORS OF SULFIDE PRODUCTION FROM SULFATE-REDUCING BACTERIA. © Priority: 18.04.90 US 510763 © Proprietor : E.I. DU PONT DE NEMOURS AND 07.02.91 US 652406 COMPANY 1007 Market Street Wilmington Delaware 19898 (US) @ Date of publication of application 03.02.93 Bulletin 93/05 © Inventor : ANDERSON, Albert Gordon 2410 St. Francis Street (45) Publication of the grant of the patent : Wilmington, DE 19808 (US) 25.05.94 Bulletin 94/21 Inventor : COOLING, Frederick Beiswanger, III 521 Cabot Drive @ Designated Contracting States : Hockessin, DE 19707-0731 (US) AT BE CH DE ES FR GB GR IT LI NL Inventor : ODOM, James Martin 28 Hilltop Road Avondale, PA 19311 (US) © References cited : Inventor : WEIMER, Paul James EP-A- 0 094 721 14 Oxwood Circle CH-A- 505 900 Madison, Wl 53717 (US) CH-A- 614 466 GB-A- 2 155 453 US-A- 4 532 117 © Representative : Jones, Alan John et al CHEMICAL ABSTRACTS, vol. 43, no. 7, 10 April CARPMAELS & RANSFORD 1949, Columbus, Ohio, US; M. ANCHEL: 43 Bloomsbury Square "Identification of the antibiotic substance London, WC1A 2RA (GB) from cassia reticulata as 4,5-dihydroxyanthra- CO quinone-2-carboxylic acid", abstract no.
    [Show full text]
  • MEDICINAL CHEMISTRY a Series of Monographs a Complete List of Titles in This Series Appears at the End of This Volume
    MEDICINAL CHEMISTRY A Series of Monographs A complete list of titles in this series appears at the end of this volume. DOXORUBICIN Anticancer Antibiotics FEDERICO ARCAMONE Farmitalia Carlo Erba Ricerca e Sviluppo Chimico Milano, Italy 1981 ACADEMIC PRESS A Subsidiary of Har court Brace Jovanovich, Publishers New York London Toronto Sydney San Francisco COPYRIGHT © 1981, BY ACADEMIC PRESS, INC. ALL RIGHTS RESERVED. NO PART OF THIS PUBLICATION MAY BE REPRODUCED OR TRANSMITTED IN ANY FORM OR BY ANY MEANS, ELECTRONIC OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT PERMISSION IN WRITING FROM THE PUBLISHER. ACADEMIC PRESS, INC. Ill Fifth Avenue, New York, New York 10003 United Kingdom Edition published by ACADEMIC PRESS, INC. (LONDON) LTD. 24/28 Oval Road, London NW1 7DX Library of Congress Cataloging in Publication Data Arcamone, Federico. Doxorubicin. (Medicinal chemistry, a series of monographs) Includes bibliographies and index. 1. Adriamycin. 2. Cancer—Chemotheraphy. 3. Anti­ neoplastic agents. I. Title. II. Series. [DNLM: 1. Doxorubicin. 2. Doxorubicin—Analogs and derivatives. 3. Antibiotics, Antineoplastic. Wl ME64 / 0V 269 A668d] RC271.A37A72 616.99Ά061 80-1106 ISBN 0-12-059280-0 PRINTED IN THE UNITED STATES OF AMERICA 81 82 83 84 9 8 7 6 5 4 3 2 1 To my Wife and Children Preface The successful development of doxorubicin as a wide-spectrum antitumor an­ tibiotic was the result of a systematic search of the most effective chemical species within a group of biologically active microbial metabolites, namely the anthracycline glycosides. Starting from the classical rhodomycins, an inter­ mediate step was represented by the study of the first S.
    [Show full text]