Jean Yves Winum

Summary

Country: France

Publications

  1. ncbi Carbonic anhydrase inhibitors: inhibition of transmembrane, tumor-associated isozyme IX, and cytosolic isozymes I and II with aliphatic sulfamates
    Jean-Yves Winum
    , UMR 5032, , , 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
    J Med Chem 46:5471-7. 2003
  2. ncbi New zinc binding motifs in the design of selective carbonic anhydrase inhibitors
    Jean Yves Winum
    Universite Montpellier II, Laboratoire de Chimie Biomoleculaire, UMR 5032, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Mini Rev Med Chem 6:921-36. 2006
  3. ncbi Sulfamates and their therapeutic potential
    Jean Yves Winum
    Laboratoire de Chimie Biomoleculaire, Universite Montpellier II, UMR 5032, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Med Res Rev 25:186-228. 2005
  4. ncbi Synthesis and biological evaluation of Fotemustine analogues on human melanoma cell lines
    Jean Yves Winum
    Laboratoire de Chimie Biomoleculaire, UMR 5032, Université Montpellier II CNRS laboratoires Mayoly Spindler, ENSCM, 8, rue de l Ecole Normale, 34296 cedex, Montpellier, France
    Eur J Med Chem 38:319-24. 2003
  5. ncbi Therapeutic potential of sulfamides as enzyme inhibitors
    Jean Yves Winum
    Universite Montpellier II, Laboratoire de Chimie Biomoleculaire, UMR 5032, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Med Res Rev 26:767-92. 2006
  6. ncbi Carbonic anhydrase IX: a new druggable target for the design of antitumor agents
    Jean Yves Winum
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Med Res Rev 28:445-63. 2008
  7. ncbi Carbonic anhydrase inhibitors. N-cyanomethylsulfonamides--a new zinc binding group in the design of inhibitors targeting cytosolic and membrane-anchored isoforms
    Jean Yves Winum
    Laboratoire de Chimie Biomoleculaire, Universite Montpellier II, UMR 5032, Ecole Nationale Supgrieure de Chimie de Montpellier, 8 rue de l Ecole Normale, Montpellier, France
    J Enzyme Inhib Med Chem 21:477-81. 2006
  8. ncbi Inhibition of carbonic anhydrase IX: a new strategy against cancer
    Jean Yves Winum
    Institut des Biomolécules Max Mousseron IBMM UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Anticancer Agents Med Chem 9:693-702. 2009
  9. ncbi The sulfamide motif in the design of enzyme inhibitors
    Jean Yves Winum
    Assistant Professor, , , UMR 5032, , 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Expert Opin Ther Pat 16:27-47. 2006
  10. ncbi Metal binding functions in the design of carbonic anhydrase inhibitors
    Jean Yves Winum
    Universite Montpellier II, Laboratoire de Chimie Biomoleculaire, UMR 5032, Ecole Nationale Superieure de Chimie de Montpellier, Montpellier Cedex, France
    Curr Top Med Chem 7:835-48. 2007

Collaborators

Detail Information

Publications67

  1. ncbi Carbonic anhydrase inhibitors: inhibition of transmembrane, tumor-associated isozyme IX, and cytosolic isozymes I and II with aliphatic sulfamates
    Jean-Yves Winum
    , UMR 5032, , , 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
    J Med Chem 46:5471-7. 2003
    ..23-0.51). These data are critical for the design of novel antitumor therapies, mainly for hypoxic tumors that overexpress CA IX, which are nonresponsive to radiation or chemotherapy...
  2. ncbi New zinc binding motifs in the design of selective carbonic anhydrase inhibitors
    Jean Yves Winum
    Universite Montpellier II, Laboratoire de Chimie Biomoleculaire, UMR 5032, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Mini Rev Med Chem 6:921-36. 2006
    ..The present review will deal with these different zinc binding functions recently reported in literature...
  3. ncbi Sulfamates and their therapeutic potential
    Jean Yves Winum
    Laboratoire de Chimie Biomoleculaire, Universite Montpellier II, UMR 5032, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Med Res Rev 25:186-228. 2005
    ....
  4. ncbi Synthesis and biological evaluation of Fotemustine analogues on human melanoma cell lines
    Jean Yves Winum
    Laboratoire de Chimie Biomoleculaire, UMR 5032, Université Montpellier II CNRS laboratoires Mayoly Spindler, ENSCM, 8, rue de l Ecole Normale, 34296 cedex, Montpellier, France
    Eur J Med Chem 38:319-24. 2003
    ..Compounds 4 and 8 proved to be more potent than the reference compound on A375 cell line which express the MGMT enzyme involved in the chemoresistance of tumoral cells...
  5. ncbi Therapeutic potential of sulfamides as enzyme inhibitors
    Jean Yves Winum
    Universite Montpellier II, Laboratoire de Chimie Biomoleculaire, UMR 5032, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Med Res Rev 26:767-92. 2006
    ..because of the intrinsic properties of this highly polarized moiety when attached to an organic scaffold. This interesting motif is thus of great value for the design of pharmacological agents with a lot of applications...
  6. ncbi Carbonic anhydrase IX: a new druggable target for the design of antitumor agents
    Jean Yves Winum
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Med Res Rev 28:445-63. 2008
    ....
  7. ncbi Carbonic anhydrase inhibitors. N-cyanomethylsulfonamides--a new zinc binding group in the design of inhibitors targeting cytosolic and membrane-anchored isoforms
    Jean Yves Winum
    Laboratoire de Chimie Biomoleculaire, Universite Montpellier II, UMR 5032, Ecole Nationale Supgrieure de Chimie de Montpellier, 8 rue de l Ecole Normale, Montpellier, France
    J Enzyme Inhib Med Chem 21:477-81. 2006
    ..Thus, the N-cyanomethylsulfonamide zinc binding group is less effective than the sulfonamide, sulfamate or sulfamide ones for the design of effective CA inhibitors...
  8. ncbi Inhibition of carbonic anhydrase IX: a new strategy against cancer
    Jean Yves Winum
    Institut des Biomolécules Max Mousseron IBMM UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Anticancer Agents Med Chem 9:693-702. 2009
    ..This review will focus on the different CA IX inhibitors described in the literature which could represent excellent potential as candidate therapeutic agents in cancer chemotherapy...
  9. ncbi The sulfamide motif in the design of enzyme inhibitors
    Jean Yves Winum
    Assistant Professor, , , UMR 5032, , 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Expert Opin Ther Pat 16:27-47. 2006
    ..due to the intrinsic properties of this highly polarised moiety when attached to an organic scaffold. This interesting motif is, thus, of great value for the design of pharmacological agents with many applications...
  10. ncbi Metal binding functions in the design of carbonic anhydrase inhibitors
    Jean Yves Winum
    Universite Montpellier II, Laboratoire de Chimie Biomoleculaire, UMR 5032, Ecole Nationale Superieure de Chimie de Montpellier, Montpellier Cedex, France
    Curr Top Med Chem 7:835-48. 2007
    ..In the present review we will discuss the different zinc binding function reported in the literature up to now in the design of carbonic anhydrase inhibitors...
  11. ncbi Carbonic anhydrase inhibitors: design of membrane-impermeant copper(II) complexes of DTPA-, DOTA-, and TETA-tailed sulfonamides targeting the tumor-associated transmembrane isoform IX
    Marouan Rami
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier, France
    ChemMedChem 3:1780-8. 2008
    ..Incorporation of radioactive copper isotopes in this type of CA inhibitor may lead to interesting diagnostic/therapeutic applications for such compounds...
  12. ncbi A new β-carbonic anhydrase from Brucella suis, its cloning, characterization, and inhibition with sulfonamides and sulfamates, leading to impaired pathogen growth
    Pascale Joseph
    Centre d Etudes d Agents Pathogenes et Biotechnologies pour la Sante CPBS, UMR 5236 CNRS UM1 UM2, Universite Montpellier II, CC100, Place E Bataillon, 34095 Montpellier, France
    Bioorg Med Chem 19:1172-8. 2011
    ..These promising data on live bacteria allow us to propose bacterial β-CA inhibition as an approach for obtaining anti-infective agents with a new mechanism of action compared to classical antibiotics...
  13. ncbi Brucella suis histidinol dehydrogenase: synthesis and inhibition studies of a series of substituted benzylic ketones derived from histidine
    Marie Rose Abdo
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem 15:4427-33. 2007
    ..Most of the compounds reported here inhibited B. suis HDH in the lower nanomolar range and constitute attractive candidates for the development of novel anti-Brucella agents...
  14. ncbi Targeting of the Brucella suis virulence factor histidinol dehydrogenase by histidinol analogues results in inhibition of intramacrophagic multiplication of the pathogen
    Pascale Joseph
    Centre d Etudes d Agents Pathogenes et Biotechnologies pour la Sante CPBS, CNRS UM1 UM2, UMR 5236, Universite Montpellier II, CC100, Place Eugene Bataillon, 34095, Montpellier Cedex, France
    Antimicrob Agents Chemother 51:3752-5. 2007
    ..These effects have been shown to be correlated with the previously described inhibition of Brucella HDH activity...
  15. ncbi Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isoforms I and II and transmembrane, tumor-associated isoforms IX and XII with boronic acids
    Jean Yves Winum
    Institut des Biomolécules Max Mousseron IBMM UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem 17:3649-52. 2009
    ..The boronic acids probably bind to the Zn(II) ion within the CA active site leading to a tetrahedral geometry of the metal ion and of the B(III) derivative...
  16. ncbi Carbonic anhydrase inhibitors: 2-substituted-1,3,4-thiadiazole-5-sulfamides act as powerful and selective inhibitors of the mitochondrial isozymes VA and VB over the cytosolic and membrane-associated carbonic anhydrases I, II and IV
    Fatma Zohra Smaine
    Institut des Biomolécules Max Mousseron UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 18:6332-5. 2008
    ..2-32 nM and 1.3-74 nM, respectively. Furthermore, the selectivity ratios for inhibiting the mitochondrial enzymes over CA II were in the range of 67.5-415, making these sulfamides the first selective CA VA/VB inhibitors...
  17. ncbi Carbonic anhydrase activators: gold nanoparticles coated with derivatized histamine, histidine, and carnosine show enhanced activatory effects on several mammalian isoforms
    Mohamed Chiheb Saada
    Institut des Biomolécules Max Mousseron, UMR 5247, CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    J Med Chem 54:1170-7. 2011
    ..This is the first example of enzyme activation with nanoparticles and may lead to biomedical applications for conditions in which the CA activity is diminished, such as aging, Alzheimer's disease, or CA deficiency syndrome...
  18. ncbi Carbonic anhydrase inhibitors: copper(II) complexes of polyamino-polycarboxylamido aromatic/heterocyclic sulfonamides are very potent inhibitors of the tumor-associated isoforms IX and XII
    Marouan Rami
    Institut des Biomolécules Max Mousseron UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 18:836-41. 2008
    ..Some Cu(II) complexes showed subnanomolar affinities and some selectivity for the inhibition of the tumor-associated isoforms IX and XII and might be used as PET hypoxia markers of tumors...
  19. ncbi Design of zinc binding functions for carbonic anhydrase inhibitors
    Jean Yves Winum
    Institut des Biomolécules Max Mousseron UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Curr Pharm Des 14:615-21. 2008
    ..In this review, recent studies on the discovery of new zinc binding function will be discussed...
  20. ncbi Anti-virulence strategy against Brucella suis: synthesis, biological evaluation and molecular modeling of selective histidinol dehydrogenase inhibitors
    Marie Rose Abdo
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS Université Montpellier I Université Montpellier II, Ecole Nationale Superieure de Chimie de Montpellier, Montpellier, France
    Org Biomol Chem 9:3681-90. 2011
    ..Experimental data confirmed competition between inhibitors and NAD(+) at this site. Hence, these inhibitors can be considered as promising tools in the development of novel anti-virulence drugs...
  21. ncbi Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis
    Pascale Joseph
    Centre d Etudes d Agents Pathogenes et Biotechnologies pour la Sante, UMR 5236 CNRS UM1 UM2, Universite Montpellier II, CC100, Place E Bataillon, 34095 Montpellier, France
    J Med Chem 53:2277-85. 2010
    ..Whether bsCA 1 inhibitors may have application in the fight against brucellosis, an endemic disease and the major bacterial zoonosis, producing debilitating infection in humans and animals, warrants further studies...
  22. ncbi Carbonic anhydrase inhibitor coated gold nanoparticles selectively inhibit the tumor-associated isoform IX over the cytosolic isozymes I and II
    Maamar Stiti
    Institut des Biomolécules Max Mousseron UMR 5247 CNRS UM1 UM2 Ecole Nationale Supérieure de Chimie de Montpellier, Montpellier Cedex, France
    J Am Chem Soc 130:16130-1. 2008
    ..As CA IX has an extracellular active site, the new nanomaterial which is confined to the extracellular space may be useful for imaging and treatment of hypoxic tumors...
  23. ncbi Carbonic anhydrase inhibitors. Inhibition of isoforms I, II, IV, VA, VII, IX, and XIV with sulfonamides incorporating fructopyranose-thioureido tails
    Jean Yves Winum
    Institut des Biomolécules Max Mousseron IBMM UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 17:2685-91. 2007
    ..Two of the new compounds showed anticonvulsant action in a maximal electroshock seizure test in mice, with the fluorosulfanilamide derivative being a more efficient anticonvulsant than the antiepileptic drug topiramate...
  24. ncbi Carbonic anhydrase inhibitors; fluorinated phenyl sulfamates show strong inhibitory activity and selectivity for the inhibition of the tumor-associated isozymes IX and XII over the cytosolic ones I and II
    Jean Yves Winum
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, Montpellier Cedex, France
    Bioorg Med Chem Lett 19:5082-5. 2009
    ..Some of these compounds were selective CA IX over CA II inhibitors, with selectivity ratios in the range of 11.4-12.1, making them interesting candidates for targeting hypoxic tumors overexpressing CA IX and/or XII...
  25. ncbi Sulfonamides incorporating boroxazolidone moieties are potent inhibitors of the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII
    Marouan Rami
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 21:2975-9. 2011
    ..These boron-containing compounds might be useful for the management of hypoxic tumors overexpressing hCA IX/XII by means of boron neutron capture therapy, a technique not investigated so far with inhibitors of this enzyme...
  26. ncbi Carbonic anhydrase inhibitors: Selective inhibition of the extracellular, tumor-associated isoforms IX and XII over isozymes I and II with glycosyl-thioureido-sulfonamides
    Fatma Zohra Smaine
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 17:5096-100. 2007
    ..The selectivity ratios for the inhibition of the tumor-associated over the cytosolic isozymes were in the range of 107-955 for the most selective such inhibitors...
  27. ncbi Synthesis of rhodamine B-benzenesulfonamide conjugates and their inhibitory activity against human α- and bacterial/fungal β-carbonic anhydrases
    Marouan Rami
    Institut des Biomolecules Max Mousseron, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 21:5210-3. 2011
    ..The β-CAs were inhibited in the micromolar range by these compounds which may have applications for the imaging of hypoxic tumors or bacteria due to their fluorescent moieties...
  28. ncbi Carbonic anhydrase I and II activation with mono- and dihalogenated histamine derivatives
    Mohamed Chiheb Saada
    Institut des Biomolecules Max Mousseron, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 21:4884-7. 2011
    ..Low nanomolar and subnanomolar hCA I and II activators have been detected for the first time, starting from histamine as lead which has an affinity of 2 μM against isoform I and of 125 μM against hCA II...
  29. ncbi Polypharmacology of sulfonamides: pazopanib, a multitargeted receptor tyrosine kinase inhibitor in clinical use, potently inhibits several mammalian carbonic anhydrases
    Jean Yves Winum
    Institut des Biomolecules Max Mousseron, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Chem Commun (Camb) 48:8177-9. 2012
    ..These data indicate that in addition to the TK inhibitory action, pazopanib may exert antitumor/antimetastatic effects also due to the potent inhibition of the tumor-associated, hypoxia-inducible enzymes CA IX and XII...
  30. ncbi Zinc metalloenzymes as new targets against the bacterial pathogen Brucella
    Marie Lopez
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS Université Montpellier I Université Montpellier II, 8 rue de l Ecole Normale, Montpellier Cedex, France
    J Inorg Biochem 111:138-45. 2012
    ..This review illustrates and describes the progress which has been made in the design and the discovery of selective inhibitors of these bacterial enzymes as new potential anti-Brucella agents...
  31. ncbi Therapeutic applications of glycosidic carbonic anhydrase inhibitors
    Jean Yves Winum
    Institut des Biomolécules Max Mousseron IBMM UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, Montpellier, France
    Med Res Rev 29:419-35. 2009
    ..Other carbohydrate-based compounds also demonstrate promising potential for the treatment of ophthalmologic diseases. This review will focus on the development of this emerging sugar-based approach for the development of CAIs...
  32. ncbi Carbonic anhydrase activators: activation of human isozymes I, II and IX with phenylsulfonylhydrazido l-histidine derivatives
    Marie Rose Abdo
    Institut des Biomolécules Max Mousseron IBMM UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 19:2440-3. 2009
    ..The 4-iodophenyl-substituted derivative behaved as a strong and isozyme selective hCA II activator, with an activation constant of 0.21muM. This is the first isoform-selective, potent CA activator reported to date...
  33. ncbi Brucella carbonic anhydrases: new targets for designing anti-infective agents
    Jean Yves Winum
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, EcoleNationale Supérieure de Chimie de Montpellier, 8 rue de l Ecole Normale, Montpellier Cedex, France
    Curr Pharm Des 16:3310-6. 2010
    ..In conclusion, as β-CAs of Brucella are susceptible to inhibition by a wide range of aromatic and heteroaromatic sulfonamides, they may represent novel targets for the development of clinically useful antibacterial agents...
  34. ncbi Carbonic anhydrase inhibitors: glycosylsulfanilamides act as subnanomolar inhibitors of the human secreted isoform VI
    Jean Yves Winum
    Institut des Biomolécules Max Mousseron IBMM UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Chem Biol Drug Des 74:636-9. 2009
    ..11-35.93 for inhibiting the secreted over the cytosolic isozyme. Because of their high water solubility and high affinity for CA VI over CA II, these compounds are useful tools for better understanding the secreted CA isoform CA VI...
  35. ncbi Carbonic anhydrase inhibitors: clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue
    Jean-Yves Winum
    , UMR 5032, , , 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
    J Med Chem 49:7024-31. 2006
    ..Its binding to this isozyme is more similar to that of topiramate and quite different from that of the topiramate cyclic sulfate analogue RWJ-37947...
  36. ncbi Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines
    Jean Yves Winum
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 22:4681-5. 2012
    ..Some of these sulfamates showed significant antiproliferative activity in several breast cancer cell lines, such as SKBR3, MCF10A, ZR75/1, MDA-MB-361 and MCF7, constituting interesting anticancer leads...
  37. ncbi Brucella suis histidinol dehydrogenase: synthesis and inhibition studies of substituted N-L-histidinylphenylsulfonyl hydrazide
    Marie Rose Abdo
    Institut des Biomolécules Max Mousseron IBMM UMR 5247 CNRS UM1 UM2 Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    J Enzyme Inhib Med Chem 23:357-61. 2008
    ..The obtained results demonstrate that modification of the group between the histidinyl moiety and the phenyl ring constitutes an important structural factor for the design of effective HDH inhibitors...
  38. ncbi Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors
    Nadia Touisni
    Institut des Biomolecules Max Mousseron IBMM, UMR 5247 CNRS UM1 UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Superieure de Chimie de Montpellier, 8 rue de l Ecole Normale, 34296 Montpellier Cedex, France
    J Med Chem 54:8271-7. 2011
    ..Because CA IX is overexpressed in hypoxic tumors and exhibits very limited expression in normal tissues, such compounds may be useful for treating cancers not responsive to classic chemo- and radiotherapy...
  39. ncbi Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors
    Jean-Yves Winum
    , , UMR 5032, , 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
    J Med Chem 46:2197-204. 2003
    ..The antitumor properties of the ES/DHEAS inhibitors in clinical trials may on the other hand also be due to their potent inhibitory properties of CA isozymes involved in tumorigenicity, such as CA II and CA IX...
  40. ncbi Carbonic anhydrase inhibitors: aliphatic N-phosphorylated sulfamates--a novel zinc-anchoring group leading to nanomolar inhibitors
    Laurent Bonnac
    , , UMR 5032, UMII, MAYOLY-SPINDLER, CNRS, , 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
    J Enzyme Inhib Med Chem 19:275-8. 2004
    ..The phosphorylated sulfamate moiety represents a novel zinc-binding group for the design of effective CA inhibitors...
  41. ncbi Synthesis and properties of isocannabinoid and cholesterol derivatized rhamnosurfactants: application to liposomal targeting of keratinocytes and skin
    Veronique Barragan-Montero
    Laboratoire de Chimie Biomoleculaire, UMR 5032, Universite Montpellier II, ENSCM, 8, rue de l Ecole Normale, 34296 Montpellier Cedex 5, France
    Eur J Med Chem 40:1022-9. 2005
    ..Skin sections were stained by both liposomal formulations, and different interactions between the liposomes and skin cells according to the surfactant used were noted...
  42. ncbi Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with organic phosphates and phosphonates
    Jean-Yves Winum
    , , UMR 5032, , 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 15:1683-6. 2005
    ..86-2.25 mM). Thus, phosphonates may lead to CA inhibitors with selectivity against two physiologically relevant isozymes, the cytosolic hCA II or the membrane-bound hCA IV...
  43. ncbi Synthesis of new Targretin analogues that induce apoptosis in leukemia HL-60 cells
    Jean-Yves Winum
    , UMR 5032, , ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 12:3529-32. 2002
    ..Compounds 5, 6 and 7 have shown to be more potent than the parent compound to induce apoptosis of HL-60 cells...
  44. ncbi Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits
    Jean-Yves Winum
    , , UMR 5032, , 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
    Bioorg Med Chem Lett 14:225-9. 2004
    ....
  45. ncbi Study on the decomposition of 2-chloroethylnitro- sosulfamides (CENS) in serum using HPLC on-line solid phase extraction
    Achour Seridi
    , , ENSCM, Montpellier, France
    Arch Pharm (Weinheim) 339:521-6. 2006
    ..This study indicates the formation of several metabolites resulting from a mechanism of decomposition more complex than in aqueous phosphate buffer, nevertheless, leading to the same main products...
  46. ncbi Carbonic anhydrase inhibitors: inhibition of cytosolic isozymes I and II with sulfamide derivatives
    Angela Casini
    Dipartimento di Chimica, Laboratorio di Chimica Bioinorganica, , Rm. 188, Via della Lastruccia 3, I-50019 Sesto Fiorentino, Florence, Italy
    Bioorg Med Chem Lett 13:837-40. 2003
    ..This is the first example of CAIs in which low nanomolar inhibitors were generated starting from a very ineffective lead molecule...
  47. ncbi Inclusion complexes of 2-chloroethylnitrososulfamides (CENS) with beta-cyclodextrin
    Mekki Kadri
    , , BP 401, Guelma 24000, Algeria
    Eur J Med Chem 39:79-84. 2004
    ..Characterisation, stoichiometry, solubility, dissociation constants and stability of such complexes were studied, showing that the inclusion with beta-CD appears as a promising mode of formulation of 2-chloroethylnitrososulfamides...
  48. ncbi Carbonic anhydrase inhibitors: the X-ray crystal structure of the adduct of N-hydroxysulfamide with isozyme II explains why this new zinc binding function is effective in the design of potent inhibitors
    Claudia Temperini
    Universita degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm 188, Via della Lastruccia 3, 50019 Sesto Fiorentino Florence, Italy
    Bioorg Med Chem Lett 17:2795-801. 2007
    ....
  49. ncbi Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates
    Jean-Yves Winum
    , Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence, Italy
    Bioorg Med Chem Lett 15:579-84. 2005
    ....
  50. ncbi Design, synthesis, and pharmacological evaluation of pyridinic analogues of nimesulide as cyclooxygenase-2 selective inhibitors
    Fabien Julemont
    Natural and Synthetic Drugs Research Centre, Laboratory of Medicinal Chemistry, Universite de Liege, 1, Avenue de l Hopital, B36, B 4000 Liege, Belgium
    J Med Chem 47:6749-59. 2004
    ..35 microM). Finally, in vivo evaluation of selected compounds showed that they exhibited anti-inflammatory properties similar to that of nimesulide when tested in a carrageenan-induced rat paw oedema model...
  51. ncbi Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides derived from 4-isothiocyanato-benzolamide
    Alessandro Cecchi
    Universita degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm 188, Via della Lastruccia 3, 50019 Sesto Fiorentino Florence, Italy
    Bioorg Med Chem Lett 14:5775-80. 2004
    ..6-62 nM against hCA I, 0.5-1.7 nM against hCA II and 3.2-23 nM against hCA IX, respectively. These derivatives are interesting candidates for the development of novel therapies targeting hypoxic tumors...
  52. ncbi Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating 1,2,4-triazine moieties
    Vladimir Garaj
    , Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence, Italy
    Bioorg Med Chem Lett 14:5427-33. 2004
    ..Clear renal cell carcinoma, which is the most lethal urologic malignancy and is both characterized by very high CA IX expression and chemotherapy unresponsiveness, could be the leading candidate of such novel therapies...
  53. ncbi Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with EMATE, a dual inhibitor of carbonic anhydrases and steroid sulfatase
    Francesco Abbate
    , Polo Scientifico, Dipartimento di Chimica, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, Rm. 188, I-50019 Sesto Fiorentino, Florence, Italy
    Bioorg Med Chem Lett 14:231-4. 2004
    ..In addition, a very short bond of 1.78A between the zinc ion and the coordinated nitrogen atom of the sulfamate moiety is observed, which may explain the high affinity of this inhibitor for hCA II (K(i) of 10nM)...
  54. ncbi Cytotoxicity, DNA damage, and apoptosis induced by new fotemustine analogs on human melanoma cells in relation to O6-methylguanine DNA-methyltransferase expression
    Isabelle Passagne
    School of Pharmacy, Department of Toxicology, Montpellier I University, 15 avenue Charles Flahault BP 14491, 34093 Montpellier Cedex 05, France
    J Pharmacol Exp Ther 307:816-23. 2003
    ..The ability of this compound to induce apoptosis in the absence of BG was confirmed by a specific enzyme-linked immunosorbent assay apoptotic assay using a single-stranded DNA monoclonal antibody...
  55. ncbi Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties
    Jean-Yves Winum
    Polo Scientifico, Laboratorio di Chimica Bioinorganica, , Room 188, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence, Italy
    J Med Chem 48:2121-5. 2005
    ..SAR is discussed for the diverse types of inhibitors and their affinity for different isozymes, with the aim of obtaining isozyme-specific CA IX inhibitors, with putative applications as antitumor drugs...
  56. ncbi Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, IX, and XII with N-hydroxysulfamides--a new zinc-binding function in the design of inhibitors
    Jean-Yves Winum
    , Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy
    Bioorg Med Chem Lett 15:2353-8. 2005
    ....
  57. ncbi Carbonic anhydrase inhibitors: design of spin-labeled sulfonamides incorporating TEMPO moieties as probes for cytosolic or transmembrane isozymes
    Alessandro Cecchi
    Universita degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Room 188, Via della Lastruccia 3, I 50019 Sesto Fiorentino, Firenze, Italy
    Bioorg Med Chem Lett 18:3475-80. 2008
    ....
  58. ncbi Carbonic anhydrase inhibitors: binding of an antiglaucoma glycosyl-sulfanilamide derivative to human isoform II and its consequences for the drug design of enzyme inhibitors incorporating sugar moieties
    Anna Di Fiore
    Istituto di Biostrutture e Bioimmagini CNR, Via Mezzocannone 16, 80134 Naples, Italy
    Bioorg Med Chem Lett 17:1726-31. 2007
    ..Topiramate, another sugar-based CA inhibitor, binds in a completely different manner to CA II as compared to the sulfonamide investigated here. These findings are useful for the design of potent, sugar-derived enzyme inhibitors...
  59. ncbi Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX
    Giuseppina De Simone
    Istituto di Biostrutture e Bioimmagini CNR, Via Mezzocannone 16, 80134 Naples, Italy
    J Med Chem 49:5544-51. 2006
    ....
  60. ncbi Kinetic investigation on aqueous decomposition of 2-chloroethylnitrososulfamide
    Achour Seridi
    , , BP 401, 24000 Guelma, Algeria
    Bioorg Med Chem Lett 16:1021-7. 2006
    ..The results indicate that the mechanism pathway involves a denitrosation of the CENS and competitive hydrolysis with nucleophilic attack on the sulfur atom and formation of sulfamate compounds...
  61. ncbi Carbonic anhydrase inhibitors. Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors
    Alessandro Cecchi
    Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, , Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy
    J Med Chem 48:4834-41. 2005
    ..These inhibitors represent promising candidates for developing anticancer therapies based on tumor-associated CA isozyme inhibition and offer interesting tools for imaging and further investigation of hypoxic tumors...
  62. ncbi Carbonic anhydrase inhibitors. Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with boron-containing sulfonamides, sulfamides, and sulfamates: toward agents for boron neutron capture therapy of hypoxic tumo
    Jean-Yves Winum
    , Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence, Italy
    Bioorg Med Chem Lett 15:3302-6. 2005
    ....
  63. ncbi Carbonic anhydrase inhibitors: novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumour-associated carbonic anhydrase isozymes I, II and IX
    Vladimir Garaj
    , Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence, Italy
    Bioorg Med Chem Lett 15:3102-8. 2005
    ..33-32.00), thus constituting excellent leads for the development of novel approaches for the management of hypoxic tumours...
  64. ncbi Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating thioureido-sulfanilyl scaffolds
    Luca Puccetti
    Ospedale San Lazzaro, Divisione di Urologia, Via Pierino Belli 26, 12051 Alba, Cuneo, Italy
    Bioorg Med Chem Lett 15:2359-64. 2005
    ..Due to the highest expression of CA IX in clear renal cell carcinoma and its chemo/radioresistance, our efforts are first of all directed to generate effective therapeutic strategies for the cure of this malignancy...
  65. ncbi Synthesis and pharmacological evaluation of novel nitrobenzenic thromboxane modulators as antiplatelet agents acting on both the alpha and beta isoforms of the human thromboxane receptor
    Julien Hanson
    Laboratory of Medicinal Chemistry, Department of Pharmacy, Natural and Synthetic Drugs Research Centre, University of Liege, 1, Av de l Hôpital, B 4000 Liege, Belgium
    J Med Chem 49:3701-9. 2006
    ..From the present results, structural features involved in isoform selectivity can be proposed, and thereby several lead compounds have been identified for the further development of selective TP isoform antagonists...
  66. ncbi Inclusion complexes of N-sulfamoyloxazolidinones with beta-cyclodextrin
    Mekki Kadri
    Laboratoire de Chimie Appliquee, Université de Guelma, BP401, Guelma 24000, Algeria
    Bioorg Med Chem Lett 15:889-94. 2005
    ..Hydrophobic properties of N-sulfamoyloxazolidinones are improved following their inclusion into beta-CD...
  67. ncbi Synthesis of substituted N-aryl-N'-Sulfamoyloxazolidin-2-ones with potential antibacterial activity
    Mounir Nessaiba
    Laboratoire de Chimie Appliquee, Université 08 Mai 1945, BP 401 Guelma, Algerie
    Recent Pat Antiinfect Drug Discov 2:131-9. 2007
    ..All the synthesized compounds are characterized by IR, (1)H NMR and mass spectroscopy (ESI-MS)...