Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, cancer-associated isozyme IX with lipophilic sulfonamides

被引:29
|
作者
Franchi, M
Vullo, D
Gallori, E
Pastorek, J
Russo, A
Scozzafava, A
Pastorekova, S
Supuran, CT
机构
[1] Univ Florence, Lab Chim Bioinorgan, I-50019 Florence, Italy
[2] Univ Florence, Dipartimento Biol Anim & Genet, I-50122 Florence, Italy
[3] Slovak Acad Sci, Inst Virol, Bratislava 84245, Slovakia
关键词
carbonic anhydrase; isozyme I; II; IX; lipophilic; sulfonamide; anticancer drug;
D O I
10.1080/1475636031000138778
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of new compounds was obtained by reaction of aromatic/heterocyclic sulfonamides incorporating amino groups with N , N -diphenylcarbamoyl chloride and diphenylacetyl chloride. These sulfonamides were assayed for the inhibition of three carbonic anhydrase (CA, EC 4.2.1.1) isozymes: the cytosolic CA I and CA II, and the transmembrane, cancer-associated isozyme CA IX. Good inhibitors against all these isoforms were detected, and the inhibition profile of the newly investigated isozyme IX was observed to be different from that of the cytosolic isozymes, I and II. This may lead to the development of novel anticancer therapies based on the selective inhibition of CA IX.
引用
收藏
页码:333 / 338
页数:6
相关论文
共 50 条
  • [41] Carbonic anhydrase inhibitors. Inhibition of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II, and IX with a series of 1,3,4-thiadiazole- and 1,2,4-triazole-thiols
    Almajan, GL
    Innocenti, A
    Puccetti, L
    Manole, G
    Barbuceanu, S
    Saramet, I
    Scozzafava, A
    Supuran, CT
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (09) : 2347 - 2352
  • [42] Carbonic anhydrase inhibitors. Inhibition of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II and IX with some 1,3,4-oxadiazole- and 1,2,4-triazole-thiols
    Almajan, Gabriela Laura
    Barbuceanu, Stefania-Felicia
    Innocenti, Alessio
    Scozzafava, Andrea
    Supuran, Claudiu T.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2008, 23 (01) : 101 - 107
  • [43] Carbonic anhydrase inhibitors.: Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors
    Cecchi, A
    Hulikova, A
    Pastorek, J
    Pastoreková, S
    Scozzafava, A
    Winum, JY
    Montero, JL
    Supuran, CT
    JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) : 4834 - 4841
  • [44] Carbonic anhydrase inhibitors:: Inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides
    Wilkinson, Brendan L.
    Bornaghi, Laurent F.
    Houston, Todd A.
    Innocenti, Alessio
    Vullo, Daniela
    Supuran, Claudiu T.
    Poulsen, Sally-Ann
    JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (07) : 1651 - 1657
  • [45] Carbonic anhydrase inhibitors.: Part 591 inhibition of carbonic anhydrase isozymes I, II and IV with arsanilic acid derivatives
    Scozzafava, A
    Briganti, F
    Supuran, CT
    MAIN GROUP METAL CHEMISTRY, 1998, 21 (06): : 357 - 364
  • [46] Carbonic anhydrase inhibitors. Cloning, characterization and inhibition studies of the cytosolic isozyme III with anions
    Nishimori, Isao
    Minakuchi, Tomoko
    Onishi, Saburo
    Vullo, Daniela
    Cecchi, Alessandro
    Scozzafava, Andrea
    Supuran, Claudiu T.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2009, 24 (01) : 70 - 76
  • [47] Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with organic phosphates and phosphonates
    Winum, JY
    Innocenti, A
    Gagnard, V
    Montero, JL
    Scozzafava, A
    Vullo, D
    Supuran, CT
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (06) : 1683 - 1686
  • [48] Carbonic anhydrase inhibitors. Part 76 - Inhibition of isozyme I, II and IV by sulfacetamide derivatives
    Scozzafava, A
    Briganti, F
    Supuran, CT
    REVUE ROUMAINE DE CHIMIE, 1999, 44 (09) : 895 - 906
  • [49] Carbonic anhydrase inhibitors:: Inhibition of the tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamides
    Özensoy, Ö
    Puccetti, L
    Fasolis, G
    Arslan, O
    Scozzafava, A
    Supuran, CT
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (21) : 4862 - 4866
  • [50] Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozymes IX and XII with polyfluorinated aromatic/heterocyclic sulfonamides
    Pastorekova, S
    Vullo, D
    Casini, A
    Scozzafava, A
    Pastorek, J
    Nishimori, I
    Supuran, CT
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2005, 20 (03) : 211 - 217