Synthesis and antimalarial activity of new nanocopolymer β-lactams and molecular docking study of their monomers
详细信息    查看全文
  • 作者:Edris Ebrahimi ; Aliasghar Jarrahpour ; Nahid Heidari…
  • 关键词:β ; Lactams ; Nanoparticles ; Polyacrylates ; Emulsion polymerization ; Molecular docking
  • 刊名:Medicinal Chemistry Research
  • 出版年:2016
  • 出版时间:February 2016
  • 年:2016
  • 卷:25
  • 期:2
  • 页码:247-262
  • 全文大小:2,012 KB
  • 参考文献:Abeylath SC, Turos E (2007) Glycosylated polyacrylate nanoparticles by emulsion polymerization. Carbohydr Polym 70:32–37PubMed PubMedCentral CrossRef
    Abeylath SC, Turos E, Dickey S, Lim DV (2008) Glyconanobiotics: novel carbohydrated nanoparticle antibiotics for MRSA and Bacillus anthracis. Bioorg Med Chem 16:2412–2418PubMed PubMedCentral CrossRef
    Alcaide B, Almendros P, Aragoncillo C (2007) β-Lactams: versatile building blocks for the stereoselective synthesis of non-β-lactam products. Chem Rev 107:4437–4492PubMed CrossRef
    Alcaide B, Aragoncillo C, Almendros P (2008) Comprehensive heterocyclic chemistry III. Elsevier, Oxford
    Antony E, Weiland EA, Korolev S, Lohman TM (2012) Plasmodium falciparum SSB tetramer wraps single-stranded DNA with similar topology but opposite polarity to E. coli SSB. J Mol Biol 420:269–283PubMed PubMedCentral CrossRef
    Atioglu Z, Akkurt M, Jarrahpour A, Ebrahimi E, Büyükgüngör O (2015) Crystal structure of 4-[(E)-(4-nitrobenzylidene) amino] phenol. Acta Cryst E 71:o113–o114CrossRef
    Bae SJ, Ha YM, Park YJ, Park JY, Song YM, Ha TK, Chun P, Moon HR, Chung HY (2012) Design, synthesis, and evaluation of (E)-N-substituted benzylidene—aniline derivatives as tyrosinase inhibitors. Eur J Med Chem 57:383–390PubMed CrossRef
    Borthwick AD, Weingarten G, Haley TM, Tomaszewski M, Wang W, Hu Z, Bedard J, Jin H, Yuen L, Mansour TS (1998) Design and synthesis of monocyclic β-lactams as mechanism-based inhibitors of human cytomegalovirus protease. Bioorg Med Chem Lett 8:365–370PubMed CrossRef
    Cavalcanti LP, Konovalov O, Torriani IL, Haas H (2005) Drug loading to lipid-based cationic nanoparticles. Nucl Instrum Meth B 238:290–293CrossRef
    Chackalamannil S, Chan T-Y, Chelliah MV, Clasby MC, Dwyer M, Greenlee WJ, Hirabayashi T, Neelamkavil S, Nishida H, Saitoh F (2010) U.S. patent application publications: Google Patents
    Cossfo FP, Aizpurua JM, Palomo C (1986) Synthetic applications of chromium (VI) reagents in combination with chlorotrimethylsilane. Can J Chem 64:225–231CrossRef
    Ebrahimi E, Jarrahpour A (2014) Thionyl chloride (or oxalyl chloride) as an efficient acid activator for one-pot synthesis of β-lactams. Iran J Sci Technol A 38:49–53
    El-Ansary A, Al-Daihan S (2009) On the toxicity of therapeutically used nanoparticles: an overview. J Toxicol 2009:1–10CrossRef
    Fisher JF, Meroueh SO, Mobashery S (2005) Bacterial resistance to β-lactam antibiotics: compelling opportunism, compelling opportunity. Chem Rev 105:395–424PubMed CrossRef
    Fontana G, Pitarresi G, Tomarchio V, Carlisi B, San Biagio PL (1998) Preparation, characterization and in vitro antimicrobial activity of ampicillin-loaded polyethylcyanoacrylate nanoparticles. Biomaterials 19:1009–1017PubMed CrossRef
    Fontana G, Licciardi M, Mansueto S, Schillaci D, Giammona G (2001) Amoxicillin-loaded polyethylcyanoacrylate nanoparticles: influence of PEG coating on the particle size, drug release rate and phagocytic uptake. Biomaterials 22:2857–2865PubMed CrossRef
    Frisch MJ, Trucks GW, Schlegel HB, Scuseria, GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian, Inc., Wallingford, CT
    Garay-Jimenez JC, Turos E (2011) A convenient method to prepare emulsified polyacrylate nanoparticles from for drug delivery applications. Bioorg Med Chem Lett 21:4589–4591PubMed CrossRef
    George G (1992) The organic chemistry of β-lactams. VCH, New York
    Gerona-Navarro G, García-López MT, González-Muñiz R (2003) Easy access to orthogonally protected α-alkyl aspartic acid and α-alkyl asparagine derivatives by controlled opening of β-lactams. Tetrahedron Lett 44:6145–6148CrossRef
    Goel RK, Mahajan MP, Kulkarni SK (2004) Evaluation of anti-hyperglycemic activity of some novel monocyclic beta lactams. J Pharm Pharm Sci 7:80–83PubMed
    Greenhalgh K, Turos E (2009) In vivo studies of polyacrylate nanoparticle emulsions for topical and systemic applications. Nanomed Nanotechnol 5:46–54CrossRef
    Halve AK, Bhadauria D (2007) N/C-4 substituted azetidin-2-ones: synthesis and preliminary evaluation as new class of antimicrobial agents. Bioorg Med Chem Lett 17:341–345PubMed CrossRef
    Han WT, Trehan AK, Wright JK, Federici ME, Seiler SM, Meanwell NA (1995) Azetidin-2-one derivatives as inhibitors of thrombin. Bioorg Med Chem Lett 3:1123–1143CrossRef
    Han G, Ghosh P, Rotello VM (2007) Functionalized gold nanoparticles for drug delivery. Nanomedicine 2:113–123PubMed CrossRef
    Henry-Michelland S, Alonso M, Andremont A, Maincen P, Sauzieres J, Couvreur P (1987) Attachment of antibiotics to nanoparticles: preparation, drug-release and antimicrobial activity in vitro. Int J Pharm 35:121–127CrossRef
    Hosseini-Sarvari M (2011) Nano-tube TiO2 as a new catalyst for eco-friendly synthesis of imines in sunlight. Chin Chem Lett 22:547–550CrossRef
    Jain NK, Asthana A (2007) Dendritic systems in drug delivery applications. Expert Opin Drug Deliv 4:495–512PubMed CrossRef
    Jarrahpour A, Heiran R (2014) Synthesis of new nanocopolymer containing β-lactams. J Iran Chem Soc 11:75–83CrossRef
    Jarrahpour A, Doroodmand MM, Ebrahimi E (2012) The first report of [2 + 2] ketene-imine cycloaddition reactions (Staudinger) on carbon nanotubes. Tetrahedron Lett 53:2797–2801CrossRef
    Jarrahpour A, Ebrahimi E, Sinou V, Latour C, Brunel JM (2014) Diastereoselective synthesis of potent antimalarial cis-β-lactam agents through a [2 + 2] cycloaddition of chiral imines with a chiral ketene. Eur J Med Chem 87:364–371PubMed CrossRef
    Kaddouri H, Nakache S, Houzé S, Mentré F, Le Bras J (2006) Assessment of the drug susceptibility of Plasmodium falciparum clinical isolates from Africa by using a Plasmodium lactate dehydrogenase immunodetection assay and an inhibitory maximum effect model for precise measurement of the 50-percent inhibitory concentration. Antimicrob Agents Chemother 50:3343–3349PubMed PubMedCentral CrossRef
    Konaklieva M (2002) Beta-lactams as inhibitors of serine enzymes. Curr Med Chem: Anti-Infect Agents 1:215–238
    Langer R (1998) Drug delivery and targeting. Nature 392:5–10PubMed
    Le Nagard H, Vincent C, Mentré F, Le Bras J (2011) Online analysis of in vitro resistance to antimalarial drugs through nonlinear regression. Comput Methods Programs Biomed 104:10–18PubMed CrossRef
    Lee AL, Venkataraman S, Sirat SB, Gao S, Hedrick JL, Yang YY (2012) The use of cholesterol-containing biodegradable block copolymers to exploit hydrophobic interactions for the delivery of anticancer drugs. Biomaterials 33:1921–1928PubMed CrossRef
    Lemkul JA, Bevan DR (2012) The role of molecular simulations in the development of inhibitors of amyloid β-peptide aggregation for the treatment of Alzheimer’s disease. ACS Chem Neurosci 3:845–856PubMed PubMedCentral CrossRef
    Marchand-Brynaert J, Brulé C (2008) Comprehensive heterocyclic chemistry III. Elsevier, Oxford
    McCarthy JR, Kelly KA, Sun EY, Weissleder R (2007) Targeted delivery of multifunctional magnetic nanoparticles. Nanomedicine 2:153–167PubMed CrossRef
    Müller IA, Kratz F, Jung M, Warnecke A (2010) Schiff bases derived from p-aminobenzyl alcohol as trigger groups for pH-dependent prodrug activation. Tetrahedron Lett 51:4371–4374CrossRef
    Murphy-Jolly MB, Owens SB, Freeman JL, Gray GM, Lawson CM, Shelton DP (2010) Syntheses, crystal structures and photophysical measurements of phosphite-substituted schiff base and Azobenzene ligands. Eur J Inorg Chem 2010:5263–5271CrossRef
    Noedl H, Bronnert J, Yingyuen K, Attlmayr B, Kollaritsch H, Fukuda M (2005) Simple histidine-rich protein 2 double-site sandwich enzyme-linked immunosorbent assay for use in malaria drug sensitivity testing. Antimicrob Agents Chemother 49:3575–3577PubMed PubMedCentral CrossRef
    Ojima I, Delaloge F (1997) Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon method. Chem Soc Rev 26:377–386CrossRef
    Peer D, Karp JM, Hong S, Farokhzad OC, Margalit R, Langer R (2007) Nanocarriers as an emerging platform for cancer therapy. Nat Nanotechnol 2:751–760PubMed CrossRef
    Peng L-J, Liu Z-Q, Wang J-T, Wu L-M (2007) N-Nitrosation of (E)-2-(benzylidene-amino) ethanols. Tetrahedron Lett 48:7418–7421CrossRef
    Rosenblum SB, Huynh T, Afonso A, Davis HR, Yumibe N, Clader JW, Burnett DA (1998) Discovery of 1-(4-fluorophenyl)-(3 R)-[3-(4-fluorophenyl)-(3 S)-hydroxypropyl]-(4 S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): a designed, potent, orally active inhibitor of cholesterol absorption. J Med Chem 41:973–980PubMed CrossRef
    RSCB Protein Data Bank. http://​www.​rcsb.​org/​pdb/​
    Saturnino C, Fusco B, Saturnino P, De Martino G, Rocco F, Lancelot J-C (2000) Evaluation of analgesic and anti-inflammatory activity of novel beta-lactam monocyclic compounds. Biol Pharm Bull 23:654–656PubMed CrossRef
    Singh P, Destito G, Schneemann A, Manchester M (2006) Canine parvovirus-like particles, a novel nanomaterial for tumor targeting. J Nanobiotechnol 4:1–11CrossRef
    Smith AM, Gao X, Nie S (2004) Quantum dot nanocrystals for in vivo molecular and cellular imaging. Photochem Photobiol 80:377–385PubMed CrossRef
    Sperka T, Pitlik J, Bagossi P, Tözsér J (2005) Beta-lactam compounds as apparently uncompetitive inhibitors of HIV-1 protease. Bioorg Med Chem Lett 15:3086–3090PubMed CrossRef
    Staudinger H (1907) Zur kenntniss der Ketene. Diphenylketen. Liebigs Ann Chem 356:51–123CrossRef
    Thakur A, Walia MK, Kumar S (2013) Nanoemulsion in enhancement of bioavailability of poorly soluble drugs: a review. Pharmacophore 4:15–25
    Trott O, Olson AJ (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 31:455–461PubMed PubMedCentral
    Turos E, Shim J-Y, Wang Y, Greenhalgh K, Reddy GSK, Dickey S, Lim DV (2007) Antibiotic-conjugated polyacrylate nanoparticles: new opportunities for development of anti-MRSA agents. Bioorg Med Chem Lett 17:53–56PubMed PubMedCentral CrossRef
    Veinberg G, Shestakova I, Vorona M, Kanepe I, Lukevics E (2004) Synthesis of antitumor 6-alkylidenepenicillanate sulfones and related 3-alkylidene-2-azetidinones. Bioorg Med Chem Lett 14:147–150PubMed CrossRef
    Verkhivker GM, Bouzida D, Gehlhaar DK, Rejto PA, Freer ST, Rose PW (2002) Complexity and simplicity of ligand–macromolecule interactions: the energy landscape perspective. Curr Opin Struct Biol 12:197–203PubMed CrossRef
    Yevdokimov YM, Skuridin SG, Nechipurenko YD, Zakharov MA, Salyanov VI, Kurnosov AA, Kuznetsov VD, Nikiforov VN (2005) Nanoconstructions based on double-stranded nucleic acids. Int J Biol Macromol 36:103–115PubMed CrossRef
    Zarei M, Mohamadzadeh M (2011) 3-Thiolated 2-azetidinones: synthesis and in vitro antibacterial and antifungal activities. Tetrahedron 67:5832–5840CrossRef
  • 作者单位:Edris Ebrahimi (1)
    Aliasghar Jarrahpour (1)
    Nahid Heidari (1)
    Véronique Sinou (2)
    Christine Latour (2)
    Jean M. Brunel (3)
    Amin R. Zolghadr (1)
    Edward Turos (4)

    1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71946-84795, Iran
    2. UMR-MD3 Relation hôte-parasites, Physiopathologie and Pharmacologie, Faculté de pharmacie, Aix-Marseille Université, Bd Jean Moulin, 13385, Marseille, France
    3. Centre de Recherche en Cancérologie de Marseille (CRCM), UM 105, CNRS, UMR7258, Institut Paoli Calmettes, Inserm, U1068, Faculté de pharmacie, Aix-Marseille Université, Bd Jean Moulin, 13385, Marseille, France
    4. Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, CHE 205, Tampa, FL, USA
  • 刊物主题:Pharmacology/Toxicology; Biochemistry, general; Cell Biology;
  • 出版者:Springer US
  • ISSN:1554-8120
文摘
This report describes the preparation of some new β-lactam nanocopolymers. These nanoparticles are synthesized in water by emulsion polymerization of an acrylate β-lactam pre-dissolved in a mixture of co-monomers in the presence of sodium dodecyl sulfate as a surfactant and potassium persulfate as a radical initiator. Dynamic light scattering analysis and electron microscopy images of these emulsions show that the nanoparticles are approximately 30–70 nm in diameter. These compounds have been evaluated for their antimalarial activities against chloroquine-resistant Plasmodium faliparum K1 strain demonstrating IC50 varying from 14 to 50 µM. The interactions between these β-lactam nanocopolymers and the P. falciparum single-stranded DNA-binding proteins have been studied by molecular docking calculations.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700