N-hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8

Campestre C, Agamennone M, Tortorella P, Preziuso S, Biasone A, Gavuzzo E, Pochetti G, Mazza F, Hiller O, Tschesche H, Consalvi V, et al. (2006)
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 16(1): 20-24.

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DOI
Autor*in
Campestre, C; Agamennone, M; Tortorella, P; Preziuso, S; Biasone, A; Gavuzzo, E; Pochetti, G; Mazza, F; Hiller, O; Tschesche, HaraldUniBi; Consalvi, V; Gallina, C
Einrichtung
Fakultät für Chemie > Biochemie I
Abstract / Bemerkung
The first crystallographic structure of an N-hydroxyurea inhibitor bound into the active site of a matrix metalloproteinase is reported. The ligand and three other analogues were prepared and studied as inhibitors of MMP-2, MMP-3, and MMP-8. The crystal structure of the complex with MMP-8 shows that the N-hydroxyurea, contrary to the analogous hydroxamate, binds the catalytic zinc ion in a monodentate rather than bidentate mode and with high out-of-plane distortion of the amide bonds. (c) 2005 Elsevier Ltd. All rights reserved.
Stichworte
N-hydroxyurea mode of binding; N-hydroxyurea inhibitors; X-ray crystal structure; molecular modeling; MMPs inhibitors; zinc binding groups
Erscheinungsjahr
2006
Zeitschriftentitel
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Band
16
Ausgabe
1
Seite(n)
20-24
ISSN
0960-894X
Page URI
https://pub.uni-bielefeld.de/record/1601428

Zitieren

Campestre C, Agamennone M, Tortorella P, et al. N-hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. 2006;16(1):20-24.
Campestre, C., Agamennone, M., Tortorella, P., Preziuso, S., Biasone, A., Gavuzzo, E., Pochetti, G., et al. (2006). N-hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 16(1), 20-24. https://doi.org/10.1016/j.bmcl.2005.09.057
Campestre, C, Agamennone, M, Tortorella, P, Preziuso, S, Biasone, A, Gavuzzo, E, Pochetti, G, et al. 2006. “N-hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8”. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 16 (1): 20-24.
Campestre, C., Agamennone, M., Tortorella, P., Preziuso, S., Biasone, A., Gavuzzo, E., Pochetti, G., Mazza, F., Hiller, O., Tschesche, H., et al. (2006). N-hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 16, 20-24.
Campestre, C., et al., 2006. N-hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 16(1), p 20-24.
C. Campestre, et al., “N-hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8”, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 16, 2006, pp. 20-24.
Campestre, C., Agamennone, M., Tortorella, P., Preziuso, S., Biasone, A., Gavuzzo, E., Pochetti, G., Mazza, F., Hiller, O., Tschesche, H., Consalvi, V., Gallina, C.: N-hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. 16, 20-24 (2006).
Campestre, C, Agamennone, M, Tortorella, P, Preziuso, S, Biasone, A, Gavuzzo, E, Pochetti, G, Mazza, F, Hiller, O, Tschesche, Harald, Consalvi, V, and Gallina, C. “N-hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8”. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 16.1 (2006): 20-24.

23 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Identification of drug-target interaction from interactome network with 'guilt-by-association' principle and topology features.
Li ZC, Huang MH, Zhong WQ, Liu ZQ, Xie Y, Dai Z, Zou XY., Bioinformatics 32(7), 2016
PMID: 26614126
Catechol-based matrix metalloproteinase inhibitors with additional antioxidative activity.
Tauro M, Laghezza A, Loiodice F, Piemontese L, Caradonna A, Capelli D, Montanari R, Pochetti G, Di Pizio A, Agamennone M, Campestre C, Tortorella P., J Enzyme Inhib Med Chem 31(sup4), 2016
PMID: 27556138
The Cell Killing Mechanisms of Hydroxyurea.
Singh A, Xu YJ., Genes (Basel) 7(11), 2016
PMID: 27869662
Ribonucleotide reductase metallocofactor: assembly, maintenance and inhibition.
Zhang C, Liu G, Huang M., Front Biol (Beijing) 9(2), 2014
PMID: 24899886
Dual carbonic anhydrase/matrix metalloproteinase inhibitors incorporating bisphosphonic acid moieties targeting bone tumors.
Tauro M, Loiodice F, Ceruso M, Supuran CT, Tortorella P., Bioorg Med Chem Lett 24(12), 2014
PMID: 24813742
Insight towards the conserved water mediated recognition of catalytic and structural Zn(+2) ions in human Matrix Metalloproteinase-8 enzyme: A study by MD-simulation methods.
Chakrabarti B, Bairagya HR, Mishra DK, Chatterjee PK, Mukhopadhyay BP., Bioinformation 9(3), 2013
PMID: 23423544
Matrix metalloproteinases as potential targets in the venous dilation associated with varicose veins.
Kucukguven A, Khalil RA., Curr Drug Targets 14(3), 2013
PMID: 23316963
Arylamino methylene bisphosphonate derivatives as bone seeking matrix metalloproteinase inhibitors.
Tauro M, Laghezza A, Loiodice F, Agamennone M, Campestre C, Tortorella P., Bioorg Med Chem 21(21), 2013
PMID: 24071448
Matrix metalloproteinase inhibitors as investigative tools in the pathogenesis and management of vascular disease.
Benjamin MM, Khalil RA., EXS 103(), 2012
PMID: 22642194
Synthesis and evaluation of inhibitors of E. coli PgaB, a polysaccharide de-N-acetylase involved in biofilm formation.
Chibba A, Poloczek J, Little DJ, Howell PL, Nitz M., Org Biomol Chem 10(35), 2012
PMID: 22855025
Biphenyl sulfonylamino methyl bisphosphonic acids as inhibitors of matrix metalloproteinases and bone resorption.
Rubino MT, Agamennone M, Campestre C, Campiglia P, Cremasco V, Faccio R, Laghezza A, Loiodice F, Maggi D, Panza E, Rossello A, Tortorella P., ChemMedChem 6(7), 2011
PMID: 21714093
Pyrone-based inhibitors of metalloproteinase types 2 and 3 may work as conformation-selective inhibitors.
Durrant JD, de Oliveira CA, McCammon JA., Chem Biol Drug Des 78(2), 2011
PMID: 21609408
Identification of novel matrix metalloproteinase inhibitors by screening of phenol fragments library.
Rubino MT, Maggi D, Laghezza A, Loiodice F, Tortorella P., Arch Pharm (Weinheim) 344(9), 2011
PMID: 21695711
Covalent inhibitors of fatty acid amide hydrolase: a rationale for the activity of piperidine and piperazine aryl ureas.
Palermo G, Branduardi D, Masetti M, Lodola A, Mor M, Piomelli D, Cavalli A, De Vivo M., J Med Chem 54(19), 2011
PMID: 21830831
Including receptor flexibility and induced fit effects into the design of MMP-2 inhibitors.
Durrant JD, de Oliveira CA, McCammon JA., J Mol Recognit 23(2), 2010
PMID: 19882751
Keloids: a new challenge for nutrition.
Ferreira AC, Hochman B, Furtado F, Bonatti S, Ferreira LM., Nutr Rev 68(7), 2010
PMID: 20591108
Zinc-binding groups modulate selective inhibition of MMPs.
Agrawal A, Romero-Perez D, Jacobsen JA, Villarreal FJ, Cohen SM., ChemMedChem 3(5), 2008
PMID: 18181119
Carbonic anhydrase inhibitors: inhibition of cytosolic/tumor-associated isoforms I, II, and IX with iminodiacetic carboxylates/hydroxamates also incorporating benzenesulfonamide moieties.
Santos MA, Marques S, Vullo D, Innocenti A, Scozzafava A, Supuran CT., Bioorg Med Chem Lett 17(6), 2007
PMID: 17251018
The design of inhibitors for medicinally relevant metalloproteins.
Jacobsen FE, Lewis JA, Cohen SM., ChemMedChem 2(2), 2007
PMID: 17163561
Phosph(on)ate as a zinc-binding group in metalloenzyme inhibitors: X-ray crystal structure of the antiviral drug foscarnet complexed to human carbonic anhydrase I.
Temperini C, Innocenti A, Guerri A, Scozzafava A, Rusconi S, Supuran CT., Bioorg Med Chem Lett 17(8), 2007
PMID: 17314045
Crystal structure of human arginase I complexed with thiosemicarbazide reveals an unusual thiocarbonyl mu-sulfide ligand in the binuclear manganese cluster.
Di Costanzo L, Pique ME, Christianson DW., J Am Chem Soc 129(20), 2007
PMID: 17469833
N-hydroxyurea--a versatile zinc binding function in the design of metalloenzyme inhibitors.
Temperini C, Innocenti A, Scozzafava A, Supuran CT., Bioorg Med Chem Lett 16(16), 2006
PMID: 16759856
Synthesis of bicyclic molecular scaffolds (BTAa): an investigation towards new selective MMP-12 inhibitors.
Mannino C, Nievo M, Machetti F, Papakyriakou A, Calderone V, Fragai M, Guarna A., Bioorg Med Chem 14(22), 2006
PMID: 16899369

34 References

Daten bereitgestellt von Europe PubMed Central.


Woessner, 2000
Matrix metalloproteinase inhibitors: applications in oncology.
Yip D, Ahmad A, Karapetis CS, Hawkins CA, Harper PG., Invest New Drugs 17(4), 1999
PMID: 10759405
Matrix metalloproteinases: biologic activity and clinical implications.
Nelson AR, Fingleton B, Rothenberg ML, Matrisian LM., J. Clin. Oncol. 18(5), 2000
PMID: 10694567

Clark, Expert Opin. Anti-Inflammatory Immunomodulatory Invest. Drugs 2(), 2000
Matrix metalloproteinase inhibitors in arthritis.
Bottomley KM, Johnson WH, Walter DS., J. Enzym. Inhib. 13(2), 1998
PMID: 9629530
Matrix metalloproteinases: multifunctional effectors of inflammation in multiple sclerosis and bacterial meningitis.
Leppert D, Lindberg RL, Kappos L, Leib SL., Brain Res. Brain Res. Rev. 36(2-3), 2001
PMID: 11690622
Protease inhibitors: current status and future prospects.
Leung D, Abbenante G, Fairlie DP., J. Med. Chem. 43(3), 2000
PMID: 10669559
The design, structure, and clinical update of small molecular weight matrix metalloproteinase inhibitors.
Skiles JW, Gonnella NC, Jeng AY., Curr. Med. Chem. 11(22), 2004
PMID: 15544483
Molecular Recognition of Proteinminus signLigand Complexes: Applications to Drug Design.
Babine RE, Bender SL., Chem. Rev. 97(5), 1997
PMID: 11851455
The 1.8-A crystal structure of a matrix metalloproteinase 8-barbiturate inhibitor complex reveals a previously unobserved mechanism for collagenase substrate recognition.
Brandstetter H, Grams F, Glitz D, Lang A, Huber R, Bode W, Krell HW, Engh RA., J. Biol. Chem. 276(20), 2001
PMID: 11278347
New beginnings for matrix metalloproteinase inhibitors: identification of high-affinity zinc-binding groups.
Puerta DT, Lewis JA, Cohen SM., J. Am. Chem. Soc. 126(27), 2004
PMID: 15237990
A bioinorganic perspective on matrix metalloproteinase inhibition.
Puerta DT, Cohen SM., Curr Top Med Chem 4(15), 2004
PMID: 15579096
Hydroxamic acids as pharmacological agents.
Muri EM, Nieto MJ, Sindelar RD, Williamson JS., Curr. Med. Chem. 9(17), 2002
PMID: 12171558
The design and synthesis of aryl hydroxamic acid inhibitors of MMPs and TACE.
Levin JI., Curr Top Med Chem 4(12), 2004
PMID: 15320727
Structure determination and analysis of human neutrophil collagenase complexed with a hydroxamate inhibitor.
Grams F, Crimmin M, Hinnes L, Huxley P, Pieper M, Tschesche H, Bode W., Biochemistry 34(43), 1995
PMID: 7577999

Sing, Bioorg. Med. Chem. Lett. 5(), 1995
N-(Hydroxyaminocarbonyl)phenylalanine: a novel class of inhibitor for carboxypeptidase A.
Chung SJ, Kim DH., Bioorg. Med. Chem. 9(1), 2001
PMID: 11197339
Hydroxyurea is a carbonic anhydrase inhibitor.
Scozzafava A, Supuran CT., Bioorg. Med. Chem. 11(10), 2003
PMID: 12713833
Biaryl ether retrohydroxamates as potent, long-lived, orally bioavailable MMP inhibitors.
Michaelides MR, Dellaria JF, Gong J, Holms JH, Bouska JJ, Stacey J, Wada CK, Heyman HR, Curtin ML, Guo Y, Goodfellow CL, Elmore IB, Albert DH, Magoc TJ, Marcotte PA, Morgan DW, Davidsen SK., Bioorg. Med. Chem. Lett. 11(12), 2001
PMID: 11412979
Structure-activity relationships of N-hydroxyurea 5-lipoxygenase inhibitors.
Stewart AO, Bhatia PA, Martin JG, Summers JB, Rodriques KE, Martin MB, Holms JH, Moore JL, Craig RA, Kolasa T, Ratajczyk JD, Mazdiyasni H, Kerdesky FA, DeNinno SL, Maki RG, Bouska JB, Young PR, Lanni C, Bell RL, Carter GW, Brooks CD., J. Med. Chem. 40(13), 1997
PMID: 9207936

Hajduk, J. Am. Chem. Soc. 119(), 1997

Bryde, Acta Chrystallogr. C 49(), 1993

AUTHOR UNKNOWN, 0

Dhanaraj, Croat. Chem. Acta 72(), 1999
X-ray structure of human stromelysin catalytic domain complexed with nonpeptide inhibitors: implications for inhibitor selectivity.
Pavlovsky AG, Williams MG, Ye QZ, Ortwine DF, Purchase CF 2nd, White AD, Dhanaraj V, Roth BD, Johnson LL, Hupe D, Humblet C, Blundell TL., Protein Sci. 8(7), 1999
PMID: 10422833
Matrilysin-inhibitor complexes: common themes among metalloproteases.
Browner MF, Smith WW, Castelhano AL., Biochemistry 34(20), 1995
PMID: 7756291
Design, synthesis, and biological evaluation of matrix metalloproteinase inhibitors derived from a modified proline scaffold.
Cheng M, De B, Almstead NG, Pikul S, Dowty ME, Dietsch CR, Dunaway CM, Gu F, Hsieh LC, Janusz MJ, Taiwo YO, Natchus MG, Hudlicky T, Mandel M., J. Med. Chem. 42(26), 1999
PMID: 10639284
Two crystal structures of human neutrophil collagenase, one complexed with a primed- and the other with an unprimed-side inhibitor: implications for drug design.
Gavuzzo E, Pochetti G, Mazza F, Gallina C, Gorini B, D'Alessio S, Pieper M, Tschesche H, Tucker PA., J. Med. Chem. 43(18), 2000
PMID: 10978185
The application of x-ray, NMR, and molecular modeling in the design of MMP inhibitors.
Rush TS 3rd, Powers R., Curr Top Med Chem 4(12), 2004
PMID: 15320728
Recent developments in the design of specific Matrix Metalloproteinase inhibitors aided by structural and computational studies.
Rao BG., Curr. Pharm. Des. 11(3), 2005
PMID: 15723627

Remko, Struct. Chem. 15(), 2004
QXP: powerful, rapid computer algorithms for structure-based drug design.
McMartin C, Bohacek RS., J. Comput. Aided Mol. Des. 11(4), 1997
PMID: 9334900

AUTHOR UNKNOWN, 0
Metal complexes of 1-substituted 3-hydroxyureas.
Harmon RE, Dabrowiak JC, Brown DJ, Gupta SK, Herbert M, Chitharanjan D., J. Med. Chem. 13(3), 1970
PMID: 5441147
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