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1.
Sci Rep ; 14(1): 13201, 2024 06 08.
Artigo em Inglês | MEDLINE | ID: mdl-38851845

RESUMO

Sugar esters display surface-active properties, wetting, emulsifying, and other physicochemical phenomena following their amphipathic nature and recognize distinct biological activity. The development of nutritional pharmaceuticals and other applications remains of great interest. Herein, three novel homologous series of several N-mono-fatty acyl amino acid glucosyl esters were synthesized, and their physicochemical properties and biological activities were evaluated. The design and preparation of these esters were chemically performed via the reaction of glucose with different fatty acyl amino acids as renewable starting materials, with the suggestion that they would acquire functional characteristics superior and competitive to certain conventional surfactants. The synthesized products are characterized using FTIR, 1H-NMR, and 13C-NMR spectroscopy. Further, their physicochemical properties, such as HLB, CMC, Γmax, γCMC, and Amin, were determined. Additionally, their antimicrobial and anticancer efficiency were assessed. The results indicate that the esters' molecular structure, including the acyl chain length and the type of amino acid, significantly influences their properties. The measured HLB ranged from 8.84 to 12.27, suggesting their use as oil/water emulsifiers, wetting, and cleansing agents. All esters demonstrate promising surface-active characteristics, with moderate to high foam production with good stability. Notably, compounds 6-O-(N-dodecanoyl, tetradecanoyl cysteine)-glucopyranose (34, 35), respectively and 6-O-(N-12-hydroxy-9-octadecenoyl cysteine)-glucopyranose (38) display superior foamability. Wetting efficiency increased with decreasing the chain length of the acyl group. The storage results reveal that increasing the fatty acyl hydrophobe length enhances the derived emulsion's stability for up to 63 days. Particularly, including cysteine in these glucosyl esters improves wetting, foaming, and emulsifying potentialities. Furthermore, the esters exhibit antibacterial activity against several tested Gram-positive and Gram-negative bacteria and fungi. On the other hand, they show significant antiproliferative effects on some liver tumor cell lines. For instance, compounds 6-O-(N-12-hydroxy-9-octadecenoylglycine)-glucopyranose (28), 6-O-(N-dodecanoyl, hexadecanoyl, 9-octadecenoyl and 12-hydroxy-9-octadecenoylvaline)- glucopyranose (29, 31, 32 and 33), respectively in addition to the dodecanoyl, hexadecanoyl, 9-octadecenoyl and 12-hydroxy-9-octadecenoyl cysteine glucopyranose (34, 36, 37 and 38), respectively significantly inhibit the examined cancer cells.


Assuntos
Anti-Infecciosos , Antineoplásicos , Tensoativos , Antineoplásicos/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Tensoativos/química , Tensoativos/síntese química , Tensoativos/farmacologia , Humanos , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Anti-Infecciosos/síntese química , Relação Estrutura-Atividade , Testes de Sensibilidade Microbiana , Ésteres/química , Ésteres/farmacologia , Ésteres/síntese química , Linhagem Celular Tumoral , Aminoácidos/química
2.
Bioorg Chem ; 93: 103332, 2019 12.
Artigo em Inglês | MEDLINE | ID: mdl-31593885

RESUMO

A series of some new tetrahydroindolocarbazole derivatives has been synthesized. The structure of the synthesized compounds has been confirmed by different spectroscopic techniques such as IR, NMR, elemental analysis and mass spectrometry. The target compounds were evaluated for their antitumor activity against breast cancer cell line MCF-7, their GI% and their LC50 have been determined. Six of the synthesized compounds exhibited GI% values against MCF-7 cell lines exceeding 70% ranging from 71.9 to 85.0% in addition that compound 11 expressed GI% values of 99.9% and considered the most active derivatives among the synthesized ones. Compound 11 showed a remarkable decrease of u PA level to 3.5 ng/ml compared to DOX. Compound 5, 11 and 15 showed significant decrease in expression of MTAP and CDKN2A, in addition to a remarkable decrease in DNA damage comet assay method. Molecular modeling studies were performed to interpretate the behavior of active ligands as uPA inhibitors.


Assuntos
Antineoplásicos/farmacologia , Neoplasias da Mama/patologia , Doxorrubicina/farmacologia , Ativador de Plasminogênio Tipo Uroquinase/antagonistas & inibidores , Sítios de Ligação , Neoplasias da Mama/enzimologia , Neoplasias da Mama/genética , Feminino , Humanos , Células MCF-7 , Modelos Moleculares , Ativador de Plasminogênio Tipo Uroquinase/metabolismo
3.
Bioorg Chem ; 80: 545-554, 2018 10.
Artigo em Inglês | MEDLINE | ID: mdl-30014922

RESUMO

Tetrahydroindolocarbazoles (THICZs) with versatile substituents, have been designed, synthesized, structure characterized, then investigated for their in-vitro anticancer screening, urokinase inhibition (uPA) evaluated, DNA-damage determination was further explored. Compounds 5, 8, 10 and 17 displayed the most promising antitumor activities against the breast cancer cell line as compared to the standard drug, doxorubicin with IC50 = 5.24 ±â€¯0.37, 4.00 ±â€¯0.52, 7.20 ±â€¯0.90 and 9.60 ±â€¯1.10 µg/ml (versus 3.30 ±â€¯0.48 µg/ml for doxorubicin). Compounds 5, 8, 10 and 17 represents the most significant uPA inhibitors of our study with IC50 of 3.80, 2.70. 4.75, 10.80 (ng/ml) respectively. The expression levels of CDKN2A gene were decreased in 8, 10 and 17 cell lines as compared to those in positive control samples. Cell lines treated with 5, 8, 10 and 17 clearly observed a high score of damaged DNA cells. A deeper examination revealed that our hetroaromatics showed an extensive hydrogen bonding interactions that is required in the S pocket which is important for activity Arg 217, Gly 219, Gly 216, Lys 143 and Ser 190. So we present THICZs as promising uPA inhibitors expected as significant promise for further development as anti-invasiveness drugs.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Carbazóis/química , Carbazóis/farmacologia , Neoplasias/tratamento farmacológico , Ativador de Plasminogênio Tipo Uroquinase/antagonistas & inibidores , Antineoplásicos/síntese química , Neoplasias da Mama/tratamento farmacológico , Neoplasias da Mama/genética , Neoplasias da Mama/metabolismo , Carbazóis/síntese química , Linhagem Celular Tumoral , Dano ao DNA/efeitos dos fármacos , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Feminino , Humanos , Indóis/síntese química , Indóis/química , Indóis/farmacologia , Células MCF-7 , Modelos Moleculares , Neoplasias/genética , Neoplasias/metabolismo , Ativador de Plasminogênio Tipo Uroquinase/metabolismo
4.
Acta Pol Pharm ; 73(5): 1163-1180, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-29638057

RESUMO

In this study, [4-(N-substituted sulfamoyl)phenyl]carbonohydrazonoy dicyanides 3a-c were synthesized and condensed with various hydrazine hydrate derivatives to produce the corresponding 3,5-diaminopyrazole derivatives 4-9, respectively. Furthermore, condensation of 3b with ax-naphthol, urea and thiourea yielded the pyrimidine derivatives 10 and 11a,b, respectively. Also, condensation of 3b with hydroxylamine hydrochloride produced the isoxazole derivative 12. Treatment of 3b with different secondary amines afforded the piperidine and piperazine derivatives 13a-c, respectively, while its condensation with diamines yielded the corresponding diazepine, benzodiazepine and benzooxazepine derivatives 14-16. Reaction of 3b with malononitrile or diazonium salt 2b with MND followed by treatment with malononitrile afforded the pyrido-pyridazine derivative 18. Anti-inflammatory and analgesic evaluation of some of the synthesized compounds as representative examples exhibited equipotent activity to that of the reference drug celecoxib. The ulcerogenic potential of the tested derivatives showed a complete safety profile on G.I.T. system. Molecular docking studies showed that the tested compounds induced good fitting and forming different hydrogen bonds with the amino acid residues at the active sites of COX-2 enzyme.


Assuntos
Analgésicos/síntese química , Anti-Inflamatórios/síntese química , Simulação de Acoplamento Molecular , Sulfonamidas/síntese química , Analgésicos/química , Analgésicos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Masculino , Ratos , Ratos Wistar , Sulfonamidas/química , Sulfonamidas/farmacologia
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