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Synthesis and evaluation of 2-phenylamino-1, 4-naphthoquinones derivatives as potential hypoglycaemic agents / Síntese e avaliação de derivados de 2-fenilamino-1, 4-naftoquinonas como potenciais agentes hipoglicemiantes
Razaque, R; Raza, A. R; Irshad, M; Rubab, S. L; Batool, S; Nisar, B; Akram, Z; Akhtar, M. T; Qadir, R; Siddique, Abu Bakar; Siddique, Farzana; Saadia, M.
  • Razaque, R; University of Sargodha. Institute of Chemistry. Sargodha. PK
  • Raza, A. R; University of Sargodha. Institute of Chemistry. Sargodha. PK
  • Irshad, M; University of Education Lahore. Department of Chemistry. Division of Science and Technology. Lahore. PK
  • Rubab, S. L; University of Education. Department of Chemistry. Jauharabad. PK
  • Batool, S; University of Sargodha. Department of Zoology. Sargodha. PK
  • Nisar, B; University of Lahore. Department of Chemistry. Sargodha. PK
  • Akram, Z; Griffith University. Health Institute Queensland. School of Medical Sciences. Queensland. AU
  • Akhtar, M. T; University of Sargodha. Institute of Chemistry. Sargodha. PK
  • Qadir, R; University of Sargodha. Institute of Chemistry. Sargodha. PK
  • Siddique, Abu Bakar; University of Sargodha. Institute of Chemistry. Sargodha. PK
  • Siddique, Farzana; University of Sargodha. Insititute of Food Science and Nutrition. Sargodha. PK
  • Saadia, M; Ghazi University. Department of Chemistry. Dera Ghazi Khan. PK
Braz. j. biol ; 84: e254234, 2024. tab, graf, ilus
Article in English | LILACS, VETINDEX | ID: biblio-1364499
ABSTRACT
Due to the severe side effects revealed by most of the currently used antidiabetic medicines, search for finding new and safe drugs to manage diabetes is continued. Naphthoquinones possessing strong antioxidant properties have been employed as candidates for diabetes therapy. Present study is aimed at finding the antioxidant and hypoglycaemic potential of some novel derivatives of 2-phenylamino-1,4-naphthoquinones (PAN) including chloro, nitro, methyl and bromo (5a-d) derivatives synthesized by single pot experiment. Product crystals were purified by TLC and characterized by FT-IR. The antioxidant potential of the compounds was assayed through DPPH radical scavenging and reducing power activities noted as UV-vis. absorbance. The DPPH assay has showed the powerful antioxidant activity of nitro and bromo derivatives, while the nitro derivative showed the significant reduction potential towards FRAP assay. Hypoglycaemic potential of the compounds was studied in rat animal model. All synthesized compounds revealed better hypoglycaemic activity; however, the chloro-derivative exhibited the more potent hypoglycaemic activity showing about 43% reduction in the mean blood glucose levels of the treated animals. As the bioreduction of naphthoquinones may be influenced by changing its redox properties, it has been noticed that the e-donating resonance effect (+R) of 'chloro' group has shown the significant effects on biological activity through stabalization of its imine form which limits the potential of generation of free radicals during bioreduction of quinones and thus has been proposed as the reason of its hypoglycaemic activity. Future studies employing the properties of e-donating groups of PAN may optimize the drug-receptor interaction for better drug designing and drug development strategies against diabetes and also for the clinical trials.
RESUMO
Em razão dos graves efeitos colaterais causados pela maioria dos medicamentos antidiabéticos atualmente utilizados, continua a busca por novos medicamentos seguros para o controle do diabetes. As naftoquinonas, que possuem fortes propriedades antioxidantes, têm sido empregadas como candidatas à terapia do diabetes. O presente estudo visa encontrar o potencial antioxidante e hipoglicemiante de alguns novos derivados de 2-fenilamino-1,4-naftoquinonas (PAN), incluindo derivados de cloro, nitro, metil e bromo (5a-d) sintetizados por experimento em pote único. Os cristais do produto foram purificados por TLC e caracterizados por FT-IR. O potencial antioxidante dos compostos foi testado por meio de atividades de sequestro de radicais DPPH e redução de energia observada como absorção no UV-vis. O ensaio DPPH mostrou a poderosa atividade antioxidante dos derivados nitro e bromo, enquanto o derivado nitro mostrou o potencial de redução significativo para o ensaio FRAP. O potencial hipoglicêmico dos compostos foi estudado em modelo animal de rato. Todos os compostos sintetizados revelaram melhor atividade hipoglicemiante; no entanto, o derivado cloro apresentou atividade hipoglicêmica mais potente, com redução de 43% nos níveis médios de glicose no sangue dos animais tratados. Como a biorredução de naftoquinonas pode ser influenciada pela alteração de suas propriedades redox, notou-se que o efeito da doação eletrônica por ressonância (+R) do grupo "cloro" tem sido significativo na atividade biológica por meio da estabilização de sua forma imina, que limita o potencial de geração de radicais livres durante a biorredução de quinonas, e, portanto, tem sido proposto como a razão de sua atividade hipoglicemiante. Estudos futuros empregando as propriedades de grupos de doação eletrônica de PAN podem otimizar a interação droga-receptor para melhor planejamento de medicamentos e estratégias de desenvolvimento de medicamentos contra o diabetes e também para os ensaios clínicos.

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Full text: Available Index: LILACS (Americas) Main subject: Models, Animal / Diabetes Mellitus / Drug Development / Hypoglycemic Agents / Antioxidants Type of study: Prognostic study Limits: Animals Language: English Journal: Braz. j. biol Year: 2024 Type: Article Institution/Affiliation country: Ghazi University/PK / Griffith University/AU / University of Education Lahore/PK / University of Education/PK / University of Lahore/PK / University of Sargodha/PK

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Full text: Available Index: LILACS (Americas) Main subject: Models, Animal / Diabetes Mellitus / Drug Development / Hypoglycemic Agents / Antioxidants Type of study: Prognostic study Limits: Animals Language: English Journal: Braz. j. biol Year: 2024 Type: Article Institution/Affiliation country: Ghazi University/PK / Griffith University/AU / University of Education Lahore/PK / University of Education/PK / University of Lahore/PK / University of Sargodha/PK