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Article ; Online: Synthetic molecules as P2X7 receptor antagonists: A medicinal chemistry update focusing the therapy of inflammatory diseases.

Mafra, João Carlos Martins / Boechat, Nubia / Teixeira, Guilherme Pegas / Faria, Robson Xavier

2023 Volume 957, Page(s) 175999

Abstract: Stimulation of the P2X7 receptor by extracellular adenosine 5'-triphosphate induces a series of responses in the organism, exceptionally protein cascades related to the proinflammatory process. This has made P2X7 a target for research on inflammatory ... ...

Abstract	Stimulation of the P2X7 receptor by extracellular adenosine 5'-triphosphate induces a series of responses in the organism, exceptionally protein cascades related to the proinflammatory process. This has made P2X7 a target for research on inflammatory diseases such as rheumatoid arthritis. Thus, the incessant search for new prototypes that aim to antagonize the action of P2X7 has been remarkable in recent decades, a factor that has already led to numerous clinical studies in humans. In this review, we present the key molecules developed over the years with potential inhibition of P2X7 and inflammation. In addition, an update with newly developed chemical classes with promising activity and results in clinical studies for human pathologies focusing on P2X7 inhibition.
MeSH term(s)	Humans ; Purinergic P2X Receptor Antagonists/pharmacology ; Purinergic P2X Receptor Antagonists/therapeutic use ; Chemistry, Pharmaceutical ; Adenosine Triphosphate ; Arthritis, Rheumatoid ; Inflammation/drug therapy
Chemical Substances	Purinergic P2X Receptor Antagonists ; Adenosine Triphosphate (8L70Q75FXE)
Language	English
Publishing date	2023-08-22
Publishing country	Netherlands
Document type	Journal Article ; Review
ZDB-ID	80121-5
ISSN	1879-0712 ; 0014-2999
ISSN (online)	1879-0712
ISSN	0014-2999
DOI	10.1016/j.ejphar.2023.175999
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Article ; Online: Editorial: new developments in the search for agents to treat tuberculosis.

Boechat, Núbia

Current topics in medicinal chemistry

2013 Volume 13, Issue 22, Page(s) 2807

MeSH term(s)	Antitubercular Agents/pharmacology ; Carcinoma, Hepatocellular/drug therapy ; Cell Proliferation/drug effects ; Humans ; Isoniazid/chemistry ; Liver Neoplasms/drug therapy ; Mycobacterium tuberculosis/drug effects ; Triazoles/pharmacology
Chemical Substances	Antitubercular Agents ; Triazoles ; Isoniazid (V83O1VOZ8L)
Language	English
Publishing date	2013-10-03
Publishing country	United Arab Emirates
Document type	Editorial ; Introductory Journal Article ; Comment
ZDB-ID	2064823-6
ISSN	1873-4294 ; 1568-0266
ISSN (online)	1873-4294
ISSN	1568-0266
DOI	10.2174/15680266113136660200
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Article ; Online: Spirooxadiazoline-oxindoles derived from imatinib show antimyeloproliferative potential in K562 cells.

de Azevedo, Liviane D / Leite, Debora I / de Oliveira, Andressa P / Junior, Floriano P S / Dantas, Rafael F / Bastos, Monica M / Boechat, Nubia / Pimentel, Luiz C F

Archiv der Pharmazie

2024 , Page(s) e2400029

Abstract: Imatinib mesylate was the first representative BCR-ABL1 tyrosine kinase inhibitor (TKI) class for the treatment of chronic myeloid leukemia. Despite the revolution promoted by TKIs in the treatment of this pathology, a resistance mechanism occurs against ...

Abstract	Imatinib mesylate was the first representative BCR-ABL1 tyrosine kinase inhibitor (TKI) class for the treatment of chronic myeloid leukemia. Despite the revolution promoted by TKIs in the treatment of this pathology, a resistance mechanism occurs against all BCR-ABL1 inhibitors, necessitating a constant search for new therapeutic options. To develop new antimyeloproliferative substances, we applied a medicinal chemistry tool known as molecular hybridization to design 25 new substances. These compounds were synthesized and biologically evaluated against K562 cells, which express BCR-ABL1, a constitutively active tyrosine kinase enzyme, as well as in WSS-1 cells (healthy cells). The new compounds are conjugated hybrids that contain phenylamino-pyrimidine-pyridine (PAPP) and an isatin backbone, which are the main pharmacophoric fragments of imatinib and sunitinib, respectively. A spiro-oxindole nucleus was used as a linker because it occurs in many compounds with antimyeloproliferative activity. Compounds 2a, 2b, 3c, 4c, and 4e showed promise, as they inhibited cell viability by between 45% and 61% at a concentration of 10 µM. The CC
Language	English
Publishing date	2024-04-16
Publishing country	Germany
Document type	Journal Article
ZDB-ID	6381-2
ISSN	1521-4184 ; 0365-6233 ; 1437-1014
ISSN (online)	1521-4184
ISSN	0365-6233 ; 1437-1014
DOI	10.1002/ardp.202400029
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Article ; Online: The Use of Zidovudine Pharmacophore in Multi-Target-Directed Ligands for AIDS Therapy.

Bianco, Maria da Conceição Avelino Dias / Inacio Leite, Debora / Silva Castelo Branco, Frederico / Boechat, Nubia / Uliassi, Elisa / Bolognesi, Maria Laura / Bastos, Monica Macedo

Molecules (Basel, Switzerland)

2022 Volume 27, Issue 23

Abstract: The concept of polypharmacology embraces multiple drugs combined in a therapeutic regimen (drug combination or cocktail), fixed dose combinations (FDCs), and a single drug that binds to different targets (multi-target drug). A polypharmacology approach ... ...

Abstract	The concept of polypharmacology embraces multiple drugs combined in a therapeutic regimen (drug combination or cocktail), fixed dose combinations (FDCs), and a single drug that binds to different targets (multi-target drug). A polypharmacology approach is widely applied in the treatment of acquired immunodeficiency syndrome (AIDS), providing life-saving therapies for millions of people living with HIV. Despite the success in viral load suppression and patient survival of combined antiretroviral therapy (cART), the development of new drugs has become imperative, owing to the emergence of resistant strains and poor adherence to cART. 3'-azido-2',3'-dideoxythymidine, also known as azidothymidine or zidovudine (AZT), is a widely applied starting scaffold in the search for new compounds, due to its good antiretroviral activity. Through the medicinal chemistry tool of molecular hybridization, AZT has been included in the structure of several compounds allowing for the development of multi-target-directed ligands (MTDLs) as antiretrovirals. This review aims to systematically explore and critically discuss AZT-based compounds as potential MTDLs for the treatment of AIDS. The review findings allowed us to conclude that: (i) AZT hybrids are still worth exploring, as they may provide highly active compounds targeting different steps of the HIV-1 replication cycle; (ii) AZT is a good starting point for the preparation of co-drugs with enhanced cell permeability.
Language	English
Publishing date	2022-12-03
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules27238502
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Article ; Online: New Imatinib Derivatives with Antiproliferative Activity against A549 and K562 Cancer Cells.

Oliveira, Andressa / Moura, Stefany / Pimentel, Luiz / Neto, João / Dantas, Rafael / Silva-Jr, Floriano / Bastos, Monica / Boechat, Nubia

Molecules (Basel, Switzerland)

2022 Volume 27, Issue 3

Abstract: Tyrosine kinase enzymes are among the primary molecular targets for the treatment of some human neoplasms, such as those in lung cancer and chronic myeloid leukemia. Mutations in the enzyme domain can cause resistance and new inhibitors capable of ... ...

Abstract	Tyrosine kinase enzymes are among the primary molecular targets for the treatment of some human neoplasms, such as those in lung cancer and chronic myeloid leukemia. Mutations in the enzyme domain can cause resistance and new inhibitors capable of circumventing these mutations are highly desired. The objective of this work was to synthesize and evaluate the antiproliferative ability of ten new analogs that contain isatins and the phenylamino-pyrimidine pyridine (PAPP) skeleton, the main pharmacophore group of imatinib. The 1,2,3-triazole core was used as a spacer in the derivatives through a click chemistry reaction and gave good yields. All the analogs were tested against A549 and K562 cells, lung cancer and chronic myeloid leukemia (CML) cell lines, respectively. In A549 cells, the 3,3-difluorinated compound (
MeSH term(s)	A549 Cells ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/therapeutic use ; Apoptosis/drug effects ; Cell Proliferation/drug effects ; Cell Survival/drug effects ; Cells, Cultured ; Drug Resistance, Neoplasm/drug effects ; Drug Screening Assays, Antitumor ; Humans ; Imatinib Mesylate/analogs & derivatives ; Imatinib Mesylate/pharmacology ; Imatinib Mesylate/therapeutic use ; K562 Cells ; Neoplasms/drug therapy ; Neoplasms/pathology ; Protein Kinase Inhibitors/pharmacology ; Protein Kinase Inhibitors/therapeutic use
Chemical Substances	Antineoplastic Agents ; Protein Kinase Inhibitors ; Imatinib Mesylate (8A1O1M485B)
Language	English
Publishing date	2022-01-24
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules27030750
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Article: The cleavage kinetics of hydrazide derivatives of isoniazid by HPLC-UV/DAD and its impact on activity against Mycobacterium tuberculosis

Martins Gouvêa, Marcos / Corrêa de Carvalho, Renata / Silva Castelo-Branco, Frederico / Boechat, Nubia / Duarte Pereira Netto, Annibal / Ferreira de Carvalho Marques, Flávia

Journal of chromatography. 2022 Jan. 01, v. 1188

2022

Abstract: Isoniazid is a first-line drug for the treatment of tuberculosis, a bacterial disease caused by Mycobacterium tuberculosis. Its terminal amino group is highly reactive, leading to significant metabolic deactivation, drug interactions and hepatotoxicity. ... ...

Abstract	Isoniazid is a first-line drug for the treatment of tuberculosis, a bacterial disease caused by Mycobacterium tuberculosis. Its terminal amino group is highly reactive, leading to significant metabolic deactivation, drug interactions and hepatotoxicity. It is speculated that the activity of isoniazid derivatives is, in part, related to the cleavage of the protecting group. Therefore, this study aimed to evaluate the cleavage characteristics of previously developed isoniazid derivatives through kinetic studies by high-performance liquid chromatography with ultraviolet-diode array detectio to establish a comparison between the rates of the process and the respective activities against M. tuberculosis. Chromatographic separations were performed on an XDB C18 column coupled to an XDB C18 precolumn. The mobile phase consisted of ultrapure water and acetonitrile in gradient mode. The flow rate was 1.0 mL/min, the injection volume was 20 μL, and the detection wavelengths were 230 nm (derivatives and isatins) and 270 nm (isoniazid). Incubation of derivatives was carried out for 5 days in 10 mmol/L phosphate buffer solution (pH 3.0, 7.4, 8.0) or in fetal bovine serum at 37 °C. The incubation reduced the concentration of the derivatives and led to the formation of isoniazid in a first-order kinetic reaction. Isoniazid formation was logarithmically correlated with the minimum inhibitory concentration of the derivatives. The results showed that higher cleavage rates are associated with greater activities against M. tuberculosis, providing important information for the development of future generations of isoniazid derivatives and for screening drug candidates for the treatment of tuberculosis.
Keywords	Mycobacterium tuberculosis ; acetonitrile ; fetal bovine serum ; hepatotoxicity ; high performance liquid chromatography ; isoniazid ; minimum inhibitory concentration ; pH ; phosphates ; tuberculosis
Language	English
Dates of publication	2022-0101
Publishing place	Elsevier B.V.
Document type	Article
ISSN	1570-0232
DOI	10.1016/j.jchromb.2021.123080
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Article ; Online: New 2-nitroimidazole-N-acylhydrazones, analogs of benznidazole, as anti-Trypanosoma cruzi agents.

Pitombeira, Marcelly C S R / Júnior, Policarpo A S / Murta, Silvane Maria Fonseca / Romanha, Alvaro / Luccas, Pedro H / Nonato, M Cristina / Rocha, Rafael E O / Ferreira, Rafaela S / da Silveira, Flávia F / Castelo-Branco, Frederico S / Carvalho, Alcione S / Boechat, Nubia

Archiv der Pharmazie

2024 , Page(s) e2400059

Abstract: Chagas disease is a neglected tropical parasitic disease caused by the protozoan Trypanosoma cruzi. Worldwide, an estimated 8 million people are infected with T. cruzi, causing more than 10,000 deaths per year. Currently, only two drugs, nifurtimox and ... ...

Abstract	Chagas disease is a neglected tropical parasitic disease caused by the protozoan Trypanosoma cruzi. Worldwide, an estimated 8 million people are infected with T. cruzi, causing more than 10,000 deaths per year. Currently, only two drugs, nifurtimox and benznidazole (BNZ), are approved for its treatment. However, both are ineffective during the chronic phase, show toxicity, and produce serious side effects. This work aimed to obtain and evaluate novel 2-nitroimidazole-N-acylhydrazone derivatives analogous to BNZ. The design of these compounds used the two important pharmacophoric subunits of the BNZ prototype, the 2-nitroimidazole nucleus and the benzene ring, and the bioisosterism among the amide group of BNZ and N-acylhydrazone. The 27 compounds were obtained by a three-step route in 57%-98% yields. The biological results demonstrated the potential of this new class of compounds, since eight compounds were potent and selective in the in vitro assay against T. cruzi amastigotes and trypomastigotes using a drug-susceptible strain of T. cruzi (Tulahuen) (IC
Language	English
Publishing date	2024-04-16
Publishing country	Germany
Document type	Journal Article
ZDB-ID	6381-2
ISSN	1521-4184 ; 0365-6233 ; 1437-1014
ISSN (online)	1521-4184
ISSN	0365-6233 ; 1437-1014
DOI	10.1002/ardp.202400059
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Article ; Online: Discovery of new piperaquine hybrid analogs linked by triazolopyrimidine and pyrazolopyrimidine scaffolds with antiplasmodial and transmission blocking activities.

Feitosa, Livia M / Franca, Rodolfo Rodrigo F / Ferreira, Maria de Lourdes G / Aguiar, Anna C C / de Souza, Guilherme E / Maluf, Sarah El Chamy / de Souza, Juliana O / Zapata, Luana / Duarte, Denise / Morais, Ines / Nogueira, Fatima / Nonato, M Cristina / Pinheiro, Luiz C S / Guido, Rafael V C / Boechat, Nubia

European journal of medicinal chemistry

2024 Volume 267, Page(s) 116163

Abstract: The World Health Organization (WHO) estimated that there were 247 million malaria cases in 2021 worldwide, representing an increase in 2 million cases compared to 2020. The urgent need for the development of new antimalarials is underscored by specific ... ...

Abstract	The World Health Organization (WHO) estimated that there were 247 million malaria cases in 2021 worldwide, representing an increase in 2 million cases compared to 2020. The urgent need for the development of new antimalarials is underscored by specific criteria, including the requirement of new modes of action that avoid cross-drug resistance, the ability to provide single-dose cures, and efficacy against both assexual and sexual blood stages. Motivated by the promising results obtained from our research group with [1,2,4]triazolo[1,5-a]pyrimidine and pyrazolo[1,5-a]pyrimidine derivatives, we selected these molecular scaffolds as the foundation for designing two new series of piperaquine analogs as potential antimalarial candidates. The initial series of hybrids was designed by substituting one quinolinic ring of piperaquine with the 1,2,4-triazolo[1,5-a]pyrimidine or pyrazolo[1,5-a]pyrimidine nucleus. To connect the heterocyclic systems, spacers with 3, 4, or 7 methylene carbons were introduced at the 4 position of the quinoline. In the second series, we used piperazine as a spacer to link the 1,2,4-triazolo[1,5-a]pyrimidine or pyrazolo[1,5-a]pyrimidine group to the quinoline core, effectively merging both pharmacophoric groups via a rigid spacer. Our research efforts yielded promising compounds characterized by low cytotoxicity and selectivity indices exceeding 1570. These compounds displayed potent in vitro inhibitory activity in the low nanomolar range against the erythrocytic form of the parasite, encompassing both susceptible and resistant strains. Notably, these compounds did not show cross-resistance with either chloroquine or established P. falciparum inhibitors. Even though they share a pyrazolo- or triazolo-pyrimidine core, enzymatic inhibition assays revealed that these compounds had minimal inhibitory effects on PfDHODH, indicating a distinct mode of action unrelated to targeting this enzyme. We further assessed the compounds' potential to interfere with gametocyte and ookinete infectivity using mature P. falciparum gametocytes cultured in vitro. Four compounds demonstrated significant gametocyte inhibition ranging from 58 % to 86 %, suggesting potential transmission blocking activity. Finally, we evaluated the druggability of these new compounds using in silico methods, and the results indicated that these analogs had favorable physicochemical and ADME (absorption, distribution, metabolism, and excretion) properties. In summary, our research has successfully identified and characterized new piperaquine analogs based on [1,2,4]triazolo[1,5-a]pyrimidine and pyrazolo[1,5-a]pyrimidine scaffolds and has demonstrated their potential as promising candidates for the development of antimalarial drugs with distinct mechanisms of action, considerable selectivity, and P. falciparum transmission blocking activity.
MeSH term(s)	Humans ; Antimalarials/pharmacology ; Antimalarials/chemistry ; Plasmodium falciparum ; Quinolines/chemistry ; Malaria, Falciparum/drug therapy ; Pyrimidines/chemistry ; Piperazines
Chemical Substances	Antimalarials ; piperaquine (A0HV2Q956Y) ; Quinolines ; Pyrimidines ; Piperazines
Language	English
Publishing date	2024-01-25
Publishing country	France
Document type	Journal Article
ZDB-ID	188597-2
ISSN	1768-3254 ; 0009-4374 ; 0223-5234
ISSN (online)	1768-3254
ISSN	0009-4374 ; 0223-5234
DOI	10.1016/j.ejmech.2024.116163
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Article ; Online: In silico and in vitro assessment of anti-Trypanosoma cruzi efficacy, genotoxicity and pharmacokinetics of pentasubstituted pyrrolic Atorvastatin-aminoquinoline hybrid compounds

Araujo-Lima, Carlos Fernando / Carvalho, Rita de Cássia Castro / Peres, Raiza Brandão / Fiuza, Ludmila Ferreira de Almeida / Galvão, Bárbara Verena Dias / Castelo-Branco, Frederico S. / Bastos, Mônica Macedo / Boechat, Núbia / Felzenszwalb, Israel / Soeiro, Maria de Nazaré Correia

Acta Tropica. 2023 June, v. 242 p.106924-

2023

Abstract: Atorvastatin (AVA) is a third-generation statin with several pleiotropic effects, considered the last synthetic pharmaceutical blockbuster. Recently, our group described the effects of AVA on DNA damage prevention and against Trypanosoma cruzi infection. ...

Abstract	Atorvastatin (AVA) is a third-generation statin with several pleiotropic effects, considered the last synthetic pharmaceutical blockbuster. Recently, our group described the effects of AVA on DNA damage prevention and against Trypanosoma cruzi infection. In this study, our aim was to evaluate the efficacy, safety, and in silico pharmacokinetic profile of four hybrids of aminoquinolines with AVA 4a-d against T. cruzi using in vitro and in silico models. These synthetic compounds were designed by hybridization of the pentapyrrolic moiety of AVA with the aminoquinolinic unit of chloroquine or primaquine. Pharmacokinetics (ADME) and toxicity parameters were predicted by SwissADME, admetSAR and LAZAR in silico algorithms. The trypanocidal activity of AVA-quinoline hybrids were evaluated in vitro against amastigotes and trypomastigotes of T. cruzi, from Y (Tc II) and Tulahuen (Tc VI) strains. In vitro cardiocytotoxicity was assessed using primary cultures of mouse embryonic cardiac cells and in vitro hepatocytotoxicity on bidimensional and 3D-cultured HepG2 cells. Genotoxicity was evaluated by Ames test and micronucleus assay. Despite the overall good in silico ADMET profile, all tested compounds were predicted to be hepatotoxic. All hybrid derivatives presented high trypanocidal activity, against both trypomastigote and intracellular forms of T. cruzi, presenting EC₅₀’s lower than 1 µM besides superior selectivity than the reference drug, without evidences of cardiotoxicity in vitro. The compounds 4a and 4b presented a time-dependent toxicity in monolayer culture of HepG2 but no detectable toxic effects in their spheroids, opposing to the in silico prediction. We can conclude that the AVA-aminoquinoline hybrids presented a hit profile as antiparasitic agents in synthetic pharmaceutical innovation platforms.
Keywords	Ames test ; DNA damage ; Trypanosoma cruzi ; amastigotes ; atorvastatin ; cardiotoxicity ; chloroquine ; computer simulation ; genotoxicity ; hepatotoxicity ; hybridization ; mice ; micronucleus tests ; moieties ; pharmacokinetics ; prediction ; trypomastigotes ; Chagas disease ; Aminoquinoline ; Hybrid drugs
Language	English
Dates of publication	2023-06
Publishing place	Elsevier B.V.
Document type	Article ; Online
Note	Pre-press version
ZDB-ID	210415-5
ISSN	1873-6254 ; 0001-706X
ISSN (online)	1873-6254
ISSN	0001-706X
DOI	10.1016/j.actatropica.2023.106924
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Article ; Online: A Review of the Development of Multitarget Molecules against HIV-TB Coinfection Pathogens.

Leite, Debora Inacio / de Castro Bazan Moura, Stefany / da Conceição Avelino Dias, Maria / Costa, Carolina Catta Preta / Machado, Gustavo Peixoto / Pimentel, Luiz Claudio Ferreira / Branco, Frederico Silva Castelo / Moreira, Rui / Bastos, Monica Macedo / Boechat, Nubia

Molecules (Basel, Switzerland)

2023 Volume 28, Issue 8

Abstract: The human immunodeficiency virus (HIV) produces the pathologic basis of acquired immunodeficiency syndrome (AIDS). An increase in the viral load in the body leads to a decline in the number of T lymphocytes, compromising the patient's immune system. Some ...

Abstract	The human immunodeficiency virus (HIV) produces the pathologic basis of acquired immunodeficiency syndrome (AIDS). An increase in the viral load in the body leads to a decline in the number of T lymphocytes, compromising the patient's immune system. Some opportunistic diseases may result, such as tuberculosis (TB), which is the most common in seropositive patients. Long-term treatment is required for HIV-TB coinfection, and cocktails of drugs for both diseases are used concomitantly. The most challenging aspects of treatment are the occurrence of drug interactions, overlapping toxicity, no adherence to treatment and cases of resistance. Recent approaches have involved using molecules that can act synergistically on two or more distinct targets. The development of multitarget molecules could overcome the disadvantages of the therapies used to treat HIV-TB coinfection. This report is the first review on using molecules with activities against HIV and
MeSH term(s)	Humans ; HIV ; Antitubercular Agents/pharmacology ; Antitubercular Agents/therapeutic use ; Coinfection/drug therapy ; Coinfection/epidemiology ; Tuberculosis/complications ; Tuberculosis/drug therapy ; Tuberculosis/microbiology ; Mycobacterium tuberculosis ; HIV Infections/complications ; HIV Infections/drug therapy
Chemical Substances	Antitubercular Agents
Language	English
Publishing date	2023-04-10
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules28083342
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