Synthesis And Antioxidant Activity Of New Homocarnosine Beta-Cyclodextrin Conjugates

Synthesis And Antioxidant Activity Of New Homocarnosine Beta-Cyclodextrin Conjugates (104 visite)

Amorini AM, Bellia F, Di Pietro V, Giardina B, La Mendola D, Lazzarino G, Sortino S, Tavazzi B, Rizzarelli E, Vecchio G

Eur J Med Chem (ISSN: 0223-5234, 1768-3254, 1768-3254electronic), 2007 Jul; 42(7): 910-920.

Tipo di articolo: Journal Article, Research Support, Non-U. S. Gov'T,

Impact factor: 2.301, Impact factor a 5 anni: 2.548

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-34250160541&partnerID=40&md5=a65d0b29e2713290019cc8a607581f9a

Parole chiave: β-Cylodextrin, Carnosine, Homocarnosine, Low Density Lipoprotein, Pulse Radiolysis, 3a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl)ethyl]amino] 4 Oxobutyl]amino] 3a Deoxy Beta Cyclodextrin, 6a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl)ethyl]amino] 4 Oxobutyl]amino] 6a Deoxy Beta Cyclodextrin, Cupric Ion, Reactive Oxygen Metabolite, Scavenger, Unclassified Drug, Antioxidant Activity, Article, Controlled Study, Drug Activity, Drug Structure, Drug Synthesis, Human, In Vitro Study, In Vivo Study, Nuclear Magnetic Resonance, Oxidation, Beta-Cyclodextrins, Hydrogen-Ion Concentration, Magnetic Resonance Spectroscopy, Molecular Structure, Oxidation-Reduction, 3a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl) Ethyl] Amino] 4 Oxobutyl] Amino] 3a Deoxy Beta Cyclodextrin, 6a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl) Ethyl] Amino] 4 Oxobutyl] Amino] 6a Deoxy Beta Cyclodextrin,

Affiliazioni:

*** IBB - CNR ***
Dipartimento di Scienze Chimiche, Università di Catania, V.le A. Doria 6, 95125 Catania, Italy
Istituto di Biochimica, Biochimica Clinica, Università Cattolica Sacro Cuore, Largo F. Vito 1, 00164 Roma, Italy
Istituto di Biostrutture e Bioimmagini, CNR, Catania, V.le A. Doria 6, 95125 Catania, Italy

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Several in vitro and in vivo studies have suggested that carnosine (β-alanil-l-histidine) and homocarnosine (β-aminobutyril-l-histidine) can act as scavengers of reactive oxygen species. β-Cyclodextrin was functionalized with homocarnosine, obtaining the following new bioconjugate isomers: 6A-[(4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}-4-oxobutyl)amino]-6A-deoxy-β-cyclodextrin and (2AS,3AR)-3A-[(4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}-4-oxobutyl)amino]-3A-deoxy-β-cyclodextrin. Pulse radiolysis investigations show that the β-cyclodextrin homocarnosine bioconjugates are scavengers of {radical dot}OH radicals because of the formation of stable imidazole-centered radicals and the scavenger ability of glucose molecules of the macrocycle. The ability of these new β-cyclodextrin derivatives to inhibit the copper(II) driven LDL oxidation was determined in comparison with that displayed by the analogous carnosine derivatives. Both the β-cyclodextrin carnosine isomers show a higher protective effect than that of free dipeptide and homocarnosine derivatives, bringing into light the role of the β-CD cavity. The ability of these new β-cyclodextrin derivatives to inhibit the copper(II) driven LDL oxidation was determined in comparison with that displayed by the analogous carnosine derivatives. Both the β-cyclodextrin carnosine isomers show a higher protective effect than that of free dipeptide and homocarnosine derivatives, bringing into light the role of the β-CD cavity. © 2007 Elsevier Masson SAS. All rights reserved.

Interrogazione effettuata: [atitle, keywords] "β-Cylodextrin" OR [atitle, keywords] "Carnosine" OR [atitle, keywords] "Homocarnosine" OR [atitle, keywords] "Low Density Lipoprotein" OR [atitle, keywords] "Pulse Radiolysis" OR [atitle, keywords] "3a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl)ethyl]amino] 4 Oxobutyl]amino] 3a Deoxy Beta Cyclodextrin" OR [atitle, keywords] "6a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl)ethyl]amino] 4 Oxobutyl]amino] 6a Deoxy Beta Cyclodextrin"

Nessun risultato.

Interrogazione effettuata: [ptitle] "β-Cylodextrin" OR [ptitle] "Carnosine" OR [ptitle] "Homocarnosine" OR [ptitle] "Low Density Lipoprotein" OR [ptitle] "Pulse Radiolysis" OR [ptitle] "3a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl)ethyl]amino] 4 Oxobutyl]amino] 3a Deoxy Beta Cyclodextrin" OR [ptitle] "6a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl)ethyl]amino] 4 Oxobutyl]amino] 6a Deoxy Beta Cyclodextrin"

Nessun risultato.

Interrogazione effettuata: [btitle, keywords] "β-Cylodextrin" [btitle, keywords] "Carnosine" [btitle, keywords] "Homocarnosine" [btitle, keywords] "Low Density Lipoprotein" [btitle, keywords] "Pulse Radiolysis" [btitle, keywords] "3a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl)ethyl]amino] 4 Oxobutyl]amino] 3a Deoxy Beta Cyclodextrin" [btitle, keywords] "6a [[4 [[1 Carboxy 2 (1h Imidazol 4 Yl)ethyl]amino] 4 Oxobutyl]amino] 6a Deoxy Beta Cyclodextrin"

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La Mendola D, Bonomo RP, Caminati S, Di Natale G, Emmi SS, Hansson O, Maccarrone G, Pappalardo G, Pietropaolo A, Rizzarelli E
* Copper(II) complexes with an avian prion N-terminal region and their potential SOD-like activity (139 visite)
J Chem Res (ISSN: 1873-3344, 0162-0134, 0162-0134print), 2009 Feb; 103(2): 195-204.
Impact Factor: 3.252
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Calabrese V, Cornelius C, Mancuso C, Barone E, Calafato S, Bates T, Rizzarelli E, Kostova AT
* Vitagenes, dietary antioxidants and neuroprotection in neurodegenerative diseases (161 visite)
Frontiers In Bioscience (ISSN: 1093-4715, 1093-9946), 2009 Jan 1; 14: 376-397.
Impact Factor: 3.736
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Calabrese V, Cornelius C, Mancuso C, Pennisi G, Calafato S, Bellia F, Bates TE, Giuffrida Stella AM, Schapira T, Dinkova Kostova AT, Rizzarelli E
* Cellular stress response: a novel target for chemoprevention and nutritional neuroprotection in aging, neurodegenerative disorders and longevity (298 visite)
Neurochemical Research (ISSN: 1573-6903, 0364-3190), 2008 Dec; 33(12): 2444-2471.
Impact Factor: 2.26
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Bellia F, Amorini AM, La Mendola D, Vecchio G, Tavazzi B, Giardina B, Di Pietro V, Lazzarino G, Rizzarelli E
* New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity (130 visite)
Eur J Med Chem (ISSN: 0223-5234, 1768-3254, 1768-3254electronic), 2008 Feb; 43(2): 373-380.
Impact Factor: 2.882
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Calabrese V, Mancuso C, Calvani M, Rizzarelli E, Butterfield DA, Stella AM
* Nitric oxide in the central nervous system: neuroprotection versus neurotoxicity (225 visite)
Nature Reviews Neuroscience (ISSN: 1471-0048), 2007 Oct; 8(10): 766-775.
Impact Factor: 24.52
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Nicoletti VG, Santoro AM, Grasso G, Vagliasindi LI, Giuffrida ML, Cuppari C, Purrello VS, Stella AMG, Rizzarelli E
* Carnosine interaction with nitric oxide and astroglial cell protection (252 visite)
Journal Of Neuroscience Research (ISSN: 0360-4012), 2007 Sep 1; 85(10): 2239-2245.
Impact Factor: 3.268
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Cuzzocrea S, Genovese T, Failla M, Vecchio G, Fruciano M, Mazzon E, Di Paola R, Muià C, La Rosa C, Crimi N, Rizzarelli E, Vancheri C
* Protective effect of orally administered carnosine on bleomycin-induced lung injury (132 visite)
Am J Physiol Lung Cell Mol Physiol (ISSN: 1040-0605), 2007 May; 292(5): L1095-L1095.
Impact Factor: 4.214
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Bellia F, La Mendola D, Maccarrone G, Mineo P, Vitalini D, Scamporrino E, Sortino S, Vecchio G, Rizzarelli E
* Copper(II) Complexes With Beta-Cyclodextrin-Homocarnosine Conjugates And Their Antioxidant Activity (107 visite)
Inorg Chim Acta (ISSN: 0020-1693), 2007 Feb 15; 360(3): 945-954.
Impact Factor: 1.713
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Calabrese V, Colombrita C, Guagliano E, Sapienza M, Ravagna A, Cardile V, Scapagnini G, Santoro AM, Mangiameli A, Butterfield DA, Giuffrida Stella AM, Rizzarelli E
* Protective effect of carnosine during nitrosative stress in astroglial cell cultures (108 visite)
Neurochemical Research (ISSN: 0364-3190, 1573-6903), 2005 Jun; 30(6-7): 797-807.
Impact Factor: 2.187
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La Rosa C, Milardi D, Amato E, Pappalardo M, Grasso D
* Molecular mechanism of the inhibition of cytochrome c aggregation by Phe-Gly (160 visite)
Arch Biochem Biophys (ISSN: 0003-9861), 2005 Mar 1; 435(1): 182-189.
Impact Factor: 3.152
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Giacco R, Clemente G, Luongo D, Lasorella G, Fiume I, Brouns F, Bornet F, Patti L, Cipriano P, Rivellese AA, Riccardi G
* Effects of short-chain fructo-oligosaccharides on glucose and lipid metabolism in mild hypercholesterolaemic individuals (134 visite)
Clin Nutr (ISSN: 0261-5614), 2004 Jun; 23(3): 331-340.
Impact Factor: 2.019
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Mineo P, Vitalini D, La Mendola D, Rizzarelli E, Scamporrino E, Vecchio G
* Coordination Features Of Difunctionalized Beta-Cyclodextrins With Carnosine: Esi-Ms And Spectroscopic Investigations On 6a, 6d-Di-(beta-Alanyl-L-Histidine)-6a, 6d-Dideoxy-Beta-Cyclodextrin And 6a, 6c-Di-(beta-Alanyl-L-Histidine)-6a, 6c-Dideoxy-Beta-Cyclodextrin And Their Copper (ii) Complexes (135 visite)
J Chem Res (ISSN: 1873-3344, 0162-0134, 0162-0134print), 2004 Feb; 98(2): 254-265.
Impact Factor: 2.225
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Pauciullo P, Giannino A, De Michele M, Gentile M, Liguori R, Argiriou A, Carlotto A, Faccenda F, Mancini M, Bond MG, De Simone V, Rubba P
* Increased carotid artery intima-media thickness is associated with a novel mutation of low-density lipoprotein receptor independently of major cardiovascular risk factors (138 visite)
Metab Clin Exp (ISSN: 0026-0495, 1532-8600), 2003; 52(11): 1433-1438.
Impact Factor: 2.013
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Bonomo RP, Bruno V, Conte E, De Guidi G, La Mendola D, Maccarrone G, Nicoletti F, Rizzarelli E, Sortino S, Vecchio G
* Potentiometric, spectroscopic and antioxidant activity studies of SOD mimics containing carnosine (110 visite)
Dalton Trans (ISSN: 1477-9226, 1477-9234, 1477-9234electronic), 2003; (23): 4406-4415.
Impact Factor: 2.908
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Colao A, Di Somma C, Pivonello R, Cuocolo A, Spinelli L, Bonaduce D, Salvatore M, Lombardi G
* The cardiovascular risk of adult GH deficiency (GHD) improved after GH replacement and worsened in untreated GHD: A 12-month prospective study (122 visite)
J Clin Endocrinol Metab (ISSN: 0021-972x), 2002 Mar; 87(3): 1088-1093.
Impact Factor: 5.199
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Mineo P, Vitalini D, La Mendola D, Rizzarelli E, Scamporrino E, Vecchio G
* Electrospray mass spectrometric studies of L-carnosine (β-alanyl-L-histidine) complexes with copper(II) or zinc ions in aqueous solution (117 visite)
Rapid Commun Mass Spectrom (ISSN: 0951-4198, 1097-0231electronic, 0951-4198linking), 2002; 16(7): 722-729.
Impact Factor: 2.372
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La Mendola D, Sortino S, Rizzarelli E, Vecchiog
* Synthesis Of New Carnosine Derivatives Of R-Cyclodextrin And Their Hydroxyl Radical Scavanger Ability (92 visite)
Helvetica Chimica Acta, 2002; 85: 1633-1643.
Impact Factor: 1.394
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Vecchio G, La Mendola D, Rizzarelli E, Sortino S
* SOD-like activity of copper(II) complexes of beta-cyclodextrins functionalized with carnosine (119 visite)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2001 Sep; 86(1): N/D-N/D.
Impact Factor: 1.729
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Tabbì G, Nauser T, Koppenol WH, Reedijk J
A Pulse Radiolysis Study of an Imidazolato-Bridged Asymmetric Dicopper(II) Complex: A Structural and Functional Mimic of Superoxide Dismutase (101 visite)
Eur J Inorg Chem (ISSN: 1434-1948, 1099-0682e), 1998; (12): 1939-1943.
Impact Factor: 2.222
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45 Records (42 escludendo Abstract e Conferenze).
Impact factor totale: 167.327 (157.292 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 176.787 (164.54 escludendo Abstract e Conferenze).

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