当前位置： SCI文献检索 > BIOORGANIC CHEMISTRY期刊下所有文献 > Pyridinium derivatives of 3-aminobenzenesulfonamide are nanomolar-potent inhibitors of tumor-expressed carbonic anhydrase isozymes CA IX and CA XII.

Pyridinium derivatives of 3-aminobenzenesulfonamide are nanomolar-potent inhibitors of tumor-expressed carbonic anhydrase isozymes CA IX and CA XII.

Abstract：

:Building on the conclusions of previous inhibition studies with pyridinium-benzenesulfonamides from our team and on the X-ray crystal structure of the lead compound identified, a series of 24 pyridinium derivatives of 3-aminobenzenesulfonamide was synthesized and investigated for carbonic anhydrase inhibition. The new pyridinium-sulfonamides were evaluated as inhibitors of four human carbonic anhydrase (CA, EC 4.2.1.1) isoforms, namely CA I, CA II (cytosolic), CA IX and XII (transmembrane, tumor-associated forms). Excellent inhibitory activity in the nanomolar range was observed against CA IX with most of these sulfonamides, and against CA XII (nanomolar/sub-nanomolar) with some of the new compounds. These sulfonamides were generally potent inhibitors of CA II and CA I too. Docking studies revealed a preference of these compounds to bind the P1 hydrophobic site of CAs, supporting the observed inhibition profile. The salt-like nature of these positively charged sulfonamides can further focus the inhibitory ability on membrane-bound CA IX and CA XII and could efficiently decrease the viability of three human carcinomas under hypoxic conditions where these isozymes are over-expressed, thus recommending the new compounds as potential diagnostic tools or therapeutic agents.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Akocak S,Güzel-Akdemir Ö,Kishore Kumar Sanku R,Russom SS,Iorga BI,Supuran CT,Ilies MA

doi

10.1016/j.bioorg.2020.104204

subject

Has Abstract

pub_date

2020-10-01 00:00:00

pages

104204

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(20)31501-7

journal_volume

103

pub_type

杂志文章

相关文献

BIOORGANIC CHEMISTRY文献大全
  • Benzopyrone represents a privilege scaffold to identify novel adenosine A1/A2A receptor antagonists.

    abstract：:Adenosine receptor antagonists are under investigation as potential drug candidates for the treatment of certain cancers, neurological disorders, depression and potentially improve tumour immunotherapy. The benzo-γ-pyrone scaffold is well-known in medicinal chemistry with diverse pharmacological activities attributed ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.01.004

    authors： van der Walt MM,Terre'Blanche G

    更新日期：2018-04-01 00:00:00

  • Synthesis, inhibition properties against xanthine oxidase and molecular docking studies of dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives.

    abstract：:This study focused on synthesis various dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives under the conditions of green chemistry without the use of solvent and catalysts. Their inhibition properties were also investigated on xanthine oxidase (XO) act...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2021.104654

    authors： Yagiz G,Noma SAA,Altundas A,Al-Khafaji K,Taskin-Tok T,Ates B

    更新日期：2021-01-12 00:00:00

  • Design and synthesis of novel 4-thiazolidinone derivatives with promising anti-breast cancer activity: Synthesis, characterization, in vitro and in vivo results.

    abstract：:Novel lead compounds as anticancer agents with the ability to circumvent emerging drug resistance have recently gained a great deal of interest. Thiazolidinones are among such compounds with well-established biological activity in the field of oncology. Here, we designed, synthesized and characterized a series of thia...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104276

    authors： Tahmasvand R,Bayat P,Vahdaniparast SM,Dehghani S,Kooshafar Z,Khaleghi S,Almasirad A,Salimi M

    更新日期：2020-11-01 00:00:00

  • Esterification of all four monoribonucleotides with acetyl-D-L-valine proceeds with a preference for the D-isomer but the D/L ratio in the products declines as a function of the hydrophobicity of the nucleotide.

    abstract：:We recently reported that esterification of 5'-AMP with N-acetyl amino acids proceeds with a preference for D-amino acids, and the D/L ratio in products declines as the hydrophobicity of the amino acid declines. Using one amino acid, Ac-Val, we now show that esterification of all four nucleotides proceeds with a pref...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/0045-2068(92)90019-y

    authors： Wickramasinghe NS,Lacey JC Jr

    更新日期：1992-01-01 00:00:00

  • Flurbiprofen derivatives as novel α-amylase inhibitors: Biology-oriented drug synthesis (BIODS), in vitro, and in silico evaluation.

    abstract：:Novel derivatives of flurbiprofen 1-18 including flurbiprofen hydrazide 1, substituted aroyl hydrazides 2-9, 2-mercapto oxadiazole derivative 10, phenacyl substituted 2-mercapto oxadiazole derivatives 11-15, and benzyl substituted 2-mercapto oxadiazole derivatives 16-18 were synthesized and characterized by EI-MS, 1H ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.07.038

    authors： Khan M,Alam A,Khan KM,Salar U,Chigurupati S,Wadood A,Ali F,Mohammad JI,Riaz M,Perveen S

    更新日期：2018-12-01 00:00:00

  • Structural optimization of imidazothiazole derivatives affords a new promising series as B-Raf V600E inhibitors; synthesis, in vitro assay and in silico screening.

    abstract：:BRAF mutation is commonly known in a number of human cancer types. It is counted as a potential component in treating cancer. In this study, based on structural optimization of previously reported inhibitors (3-fluro substituted derivatives of imidazo[2,1-b]thiazole-based scaffold), we designed and synthesized sixteen...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103967

    authors： Ammar UM,Abdel-Maksoud MS,Ali EMH,Mersal KI,Ho Yoo K,Oh CH

    更新日期：2020-07-01 00:00:00

  • Synthesis, DNA/RNA-interaction and biological activity of benzo[k,l]xanthene lignans.

    abstract：:Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104190

    authors： Tumir LM,Zonjić I,Žuna K,Brkanac SR,Jukić M,Huđek A,Durgo K,Crnolatac I,Glavaš-Obrovac L,Cardullo N,Pulvirenti L,Muccilli V,Tringali C,Stojković MR

    更新日期：2020-11-01 00:00:00

  • Synthesis and DNase I inhibitory properties of some 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines.

    abstract：:A series of six novel and six known thieno[2,3-d]pyrimidin-4-amines 2-13 were synthesized, and further were used as a starting material for preparation of a small series of eight novel thieno[2,3-d]pyrimidin-4-phthalimides 14-21. Eight compounds, five amine and three phthalimide derivatives, inhibited bovine pancreati...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.07.009

    authors： Ts Mavrova A,Dimov S,Yancheva D,Kolarević A,Ilić BS,Kocić G,Šmelcerović A

    更新日期：2018-10-01 00:00:00

  • Structure-activity relationship studies of prostate-specific membrane antigen (PSMA) inhibitors derived from α-amino acid with (S)- or (R)-configuration at P1' region.

    abstract：:Prostate-specific membrane antigen (PSMA), a type II membrane glycoprotein, is considered an excellent target for the diagnosis or treatment of prostate cancer. We previously investigated the effect of β- and γ-amino acids with (S)- or (R)-configuration in the S1 pocket on the binding affinity for PSMA. However, compr...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104304

    authors： Kwon H,Lim H,Ha H,Choi D,Son SH,Nam H,Minn I,Byun Y

    更新日期：2020-11-01 00:00:00

  • Antitrypanosomal activity of epi-polygodial from Drimys brasiliensis and its effects in cellular membrane models at the air-water interface.

    abstract：:Epi-polygodial, a drimane sesquiterpene was isolated from Drimys brasiliensis (Winteraceae). This compound demonstrated high parasite selectivity towards Trypanosoma cruzi trypomastigotes (IC50 = 5.01 μM) with a selectivity index higher than 40. These results were correlated with the effects observed when this compoun...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.11.048

    authors： Gonçalves GEG,Morais TR,Gomes KS,Costa-Silva TA,Tempone AG,Lago JHG,Caseli L

    更新日期：2019-03-01 00:00:00

  • Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity.

    abstract：:A library of 33 polymethoxylated flavones (PMF) was evaluated for heme-binding affinity by biomimetic MS assay and in vitro antiplasmodial activity on two strains of P. falciparum. Stability of heme adducts was discussed using the dissociation voltage at 50% (DV50). No correlation was observed between the methoxylatio...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104243

    authors： Ortiz S,Vásquez-Ocmín PG,Cojean S,Bouzidi C,Michel S,Figadère B,Grougnet R,Boutefnouchet S,Maciuk A

    更新日期：2020-11-01 00:00:00

  • Extraction, isolation and in vitro evaluation of affinisine from Tabernaemontana catharinensis in human melanoma cells.

    abstract：:Plant compounds have been identified as new drug prototypes. In this line, this work aimed to isolate the indole alkaloid affinisine from Tabernaemontana catharinensis and test its antitumor activity. The alkaloid was isolated by silica gel open column chromatography from the ethanolic extract of the stem of T. cathar...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103079

    authors： Fagundes Rosales P,Gower A,Lucia Ruiz Benitez M,Silveira Pacheco B,Vieira Segatto N,Roesch-Ely M,Collares T,Kömmling Seixas F,Moura S

    更新日期：2019-09-01 00:00:00

  • Potent human dihydroorotate dehydrogenase inhibitory activity of new quinoline-4-carboxylic acids derived from phenolic aldehydes: Synthesis, cytotoxicity, lipophilicity and molecular docking studies.

    abstract：:A series of novel 2-substituted quinoline-4-carboxylic acids was synthesized by Doebner reaction starting from freely available protocatechuic aldehyde and vanillin precursors. Human dihydroorotate dehydrogenase (hDHODH) was recognised as a clear molecular target for these heterocycles. All compounds were also tested ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104373

    authors： Petrović MM,Roschger C,Chaudary S,Zierer A,Mladenović M,Jakovljević K,Marković V,Botta B,Joksović MD

    更新日期：2020-12-01 00:00:00

  • Probing the high potency of pyrazolyl pyrimidinetriones and thioxopyrimidinediones as selective and efficient non-nucleotide inhibitors of recombinant human ectonucleotidases.

    abstract：:With the aim to discover novel, efficient and selective inhibitors of human alkaline phosphatase and nucleotide pyrophosphatase enzymes, two new series of pyrazolyl pyrimidinetriones (PPTs) (6a-g) and thioxopyrimidinediones (PTPs) (6h-n) were synthesized in good chemical yields using Knoevenagel condensation reaction ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.03.067

    authors： Andleeb H,Hameed S,Ejaz SA,Khan I,Zaib S,Lecka J,Sévigny J,Iqbal J

    更新日期：2019-07-01 00:00:00

  • Synthesis of oxazolidinone from enantiomerically enriched allylic alcohols and determination of their molecular docking and biologic activities.

    abstract：:Enantioselective synthesis of functionalized cyclic allylic alcohols via kinetic resolution in transesterifcation with different lipase enzymes has been developed. The influence of the enzymes and temperature activity was studied. By determination of ideal reaction conditions, byproduct formation is minimized; this ma...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.102980

    authors： Atmaca U,Kaya R,Karaman HS,Çelik M,Gülçin İ

    更新日期：2019-07-01 00:00:00

  • Compounds from the fruits of mangrove Sonneratia apetala: Isolation, molecular docking and antiaging effects using a Caenorhabditis elegans model.

    abstract：:The chemical investigation of the fruits of a mangrove Sonneratia apetala collected from the Beibu Gulf led to the isolation of four new compounds, sonneradons A-D (1-4), as well as 18 known compounds (5-22). The structures of the new compounds were elucidated based on extensive spectroscopic analysis, and the structu...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103813

    authors： Yi X,Jiang S,Qin M,Liu K,Cao P,Chen S,Deng J,Gao C

    更新日期：2020-06-01 00:00:00

  • Design and synthesis of new benzoxazole/benzothiazole-phthalimide hybrids as antitumor-apoptotic agents.

    abstract：:Herein, we synthesized a series of twelve benzoxazole and benzothiazole derivatives incorporated with phthalimide core as anticancer agents. The most active compounds were 5a and 5g against HepG2 and MCF7 cell lines with IC50 = 0.011 and 0.006 μM, respectively. They evaluated against EGFR and HER2 enzymes. From cell c...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.102978

    authors： Philoppes JN,Lamie PF

    更新日期：2019-08-01 00:00:00

  • New bisphosphorothioates and bisphosphoroamidates: synthesis, molecular modeling and determination of insecticide and toxicological profile.

    abstract：:A series of new compounds, N,N'-bis(dialkylphosphoryl)diamines and S,S'-bis(dialkylphosphoryl)-1,3-propanedithiols were prepared by a Todd-Atherton like reaction of dialkylphosphites with symmetrical diamines and 1,3-propanedithiols in a biphasic system [F.R. Athertoon, H.T. Howard, A.R. Todd, J. Chem. Soc. (1948) 110...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2006.08.006

    authors： dos Santos VM,Sant'Anna CM,Moya Borja GE,Chaaban A,Côrtes WS,DaCosta JB

    更新日期：2007-02-01 00:00:00

  • Novel carbazole-stilbene hybrids as multifunctional anti-Alzheimer agents.

    abstract：:Molecules capable of engaging with multiple targets associated with pathological condition of Alzheimer's disease have proved to be potential anti-Alzheimer's agents. In our goal to develop multitarget-directed ligands for the treatment of Alzheimer's disease, a novel series of carbazole-based stilbene derivatives wer...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103977

    authors： Patel DV,Patel NR,Kanhed AM,Teli DM,Patel KB,Joshi PD,Patel SP,Gandhi PM,Chaudhary BN,Prajapati NK,Patel KV,Yadav MR

    更新日期：2020-08-01 00:00:00

  • An NMR spectroscopy study of bendaline-albumin interactions.

    abstract：:The complete assignment of the 1H and 13C NMR spectra of bendaline (BNDL) was performed by mono-dimensional and homo- and hetero-correlated two-dimensional NMR experiments. The interaction between bendaline and albumin was also studied by the analysis of the motional parameters spin-lattice relaxation times, allowing ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/s0045-2068(03)00078-6

    authors： Delfini M,Bianchetti C,Di Cocco ME,Pescosolido N,Porcelli F,Rosa R,Rugo G

    更新日期：2003-10-01 00:00:00

  • Design, synthesis, in vitro and in silico investigation of aldose reductase inhibitory effects of new thiazole-based compounds.

    abstract：:Aldose reductase (AR) catalyzes the NADPH-dependent reduction of glucose to sorbitol in the polyol pathway, which plays an important role in the development of diabetic complications including cataract, retinopathy, nephropathy, and neuropathy. AR has been considered as an important target to heal these long-term diab...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104110

    authors： Sever B,Altıntop MD,Demir Y,Akalın Çiftçi G,Beydemir Ş,Özdemir A

    更新日期：2020-09-01 00:00:00

  • Synthesis and evaluation of redox-sensitive gonadotropin-releasing hormone receptor-targeting peptide conjugates.

    abstract：:Lytic peptides have been demonstrated to exhibit obvious advantages in cancer therapy with binding ability toward tumor cells via electrostatic attractions, which are lack of active targeting and aggregation to tumor tissue. In the present study, five conjugated lytic peptides were redesigned and constructed to target...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.102945

    authors： Dai Y,Yue N,Liu C,Cai X,Su X,Bi X,Li Q,Li C,Huang W,Qian H

    更新日期：2019-07-01 00:00:00

  • Design, synthesis and biological evaluation of some novel benzothiazole/benzoxazole and/or benzimidazole derivatives incorporating a pyrazole scaffold as antiproliferative agents.

    abstract：:In an aim at developing new antiproliferative agents, new series of benzothiazole/benzoxazole and/or benzimidazole substituted pyrazole derivatives 11a-c, 12a-c and 13a-c were prepared and evaluated for their antiproliferative activity against breast carcinoma (MCF-7) and non-small cell lung cancer (A549) cell lines. ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2017.07.007

    authors： Abdelgawad MA,Bakr RB,Omar HA

    更新日期：2017-10-01 00:00:00

  • Current development of 5-nitrofuran-2-yl derivatives as antitubercular agents.

    abstract：:Pulmonary tuberculosis (TB) is an infectious disease caused by Mycobacterium tuberculosis (MTB) and still remains one of the foremost fatal infectious diseases, infecting nearly a third of the worldwide population. The emergencies of multidrug-resistant and extensively drug-resistant tuberculosis (MDR and XDR-TB) prom...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.bioorg.2019.102969

    authors： Elsaman T,Mohamed MS,Mohamed MA

    更新日期：2019-07-01 00:00:00

  • Design, synthesis and biological evaluation of N-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-4-oxo-3,4-dihydrophthalazine-1-carboxamide derivatives as novel P-glycoprotein inhibitors reversing multidrug resistance.

    abstract：:The overexpression of P-glycoprotein plays an important role in the process of multidrug resistance (MDR). P-gp inhibitors are one of the effective strategies to reverse tumor MDR. Novel P-gp inhibitors with phthalazinone scaffolds were designed, synthesized and evaluated. Compound 26 was found to be the most promisin...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.01.039

    authors： Qiu Q,Zhou J,Shi W,Kairuki M,Huang W,Qian H

    更新日期：2019-05-01 00:00:00

  • Antimalarial activity of HIV-1 protease inhibitor in chromone series.

    abstract：:Increasing parasite resistance to nearly all available antimalarial drugs becomes a serious problem to human health and necessitates the need to continue the search for new effective drugs. Recent studies have shown that clinically utilized HIV-1 protease (HIV-1 PR) inhibitors can inhibit the in vitro and in vivo grow...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2014.10.006

    authors： Lerdsirisuk P,Maicheen C,Ungwitayatorn J

    更新日期：2014-12-01 00:00:00

  • Eight new glycosides with hepatoprotective activity isolated from the aerial parts of Morinda parvifolia.

    abstract：:Eight new glycosides, morindaparvins P-W, were isolated from the butanol extract of the aerial parts of Morinda parvifolia. These new structures were elucidated by comprehensive spectroscopic analysis and by comparing the experimental and calculated electronic circular dichroism spectra. The butanol extract was observ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.11.055

    authors： Su X,Li L,Sun H,Zhang F,Li C,Li F,Wang H,Li B,Chen R,Kang J

    更新日期：2019-06-01 00:00:00

  • In vitro study and structure-activity relationship analysis of stilbenoid derivatives as powerful vasorelaxants: Discovery of new lead compound.

    abstract：:The development of vasorelaxant as the antihypertensive drug is important as it produces a rapid and direct relaxation effect on the blood vessel muscles. Resveratrol (RV), as the most widely studied stilbenoid and the lead compound, inducing the excellent vasorelaxation effect through the multiple signalling pathways...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104239

    authors： Chan SY,Loh YC,Oo CW,Yam MF

    更新日期：2020-11-01 00:00:00

  • How the surface functionalized nanoparticles affect conformation and activity of proteins: Exploring through protein-nanoparticle interactions.

    abstract：:To understand the effect of counter ions (Na+) on the secondary conformation and functionality of the lysozyme, we have studied the interaction of lysozyme with counterion associated iron oxide nanoparticles (IONPs). The investigation was carried out at pH 7.4 and 9.0, with three different types of NPs, namely, bare I...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.09.020

    authors： Dyawanapelly S,Mehrotra P,Ghosh G,Jagtap DD,Dandekar P,Jain R

    更新日期：2019-02-01 00:00:00

  • Evaluation of angularly condensed diquinothiazines as potential anticancer agents.

    abstract：:We present efficient synthesis of isomeric types of angularly fused diquinothiazines in the reactions of 2,2'-dichloro-3,3'-diquinolinyl disulfide and diquinodithiin with 3-, 5-, 6- and 8-aminoquinolines. The pentacyclic diquinothiazine ring systems were identified as diquino[3,2-b;3',4'-e][1,4]thiazine, diquino[3,2-b...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.04.005

    authors： Jeleń M,Pluta K,Latocha M,Morak-Młodawska B,Suwińska K,Kuśmierz D

    更新日期：2019-06-01 00:00:00