Synthesis and Characterization of 3-(1-((3,4-Dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione as a Potential Antitumor Agent
Аутори
Dimić, Dusan S.Marković, Zoran S.
Saso, Luciano
Avdović, Edina H.
Dorović, Jelena R.
Petrović, Isidora
Stanisavljević Ninković, Danijela
Stevanović, Milena
Potocnak, Ivan
Samol'ova, Erika
Trifunović, Srecko R.
Marković, Jasmina M. Dimitric
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
The newly synthesized coumarin derivative with dopamine, 3-(1-((3,4-dihydroxyphenethyDamino)ethylidene)-chroman-2,4-dione, was completely structurally characterized by X-ray crystallography. It was shown that several types of hydrogen bonds are present, which additionally stabilize the structure. The compound was tested in vitro against different cell lines, healthy human keratinocyte HaCaT, cervical squamous cell carcinoma SiHa, breast carcinoma MCF7, and hepatocellular carcinoma HepG2. Compared to control, the new derivate showed a stronger effect on both healthy and carcinoma cell lines, with the most prominent effect on the breast carcinoma MCF7 cell line. The molecular docking study, obtained for ten different conformations of the new compound, showed its inhibitory nature against CDKS protein. Lower inhibition constant, relative to one of 4-OH-coumarine, proved stronger and more numerous interactions with CDKS protein. These interactions were carefully examined for both parent mo...lecule and derivative and explained from a structural point of view.
Извор:
Oxidative Medicine and Cellular Longevity, 2019, 2019Издавач:
- Hindawi Ltd, London
Финансирање / пројекти:
- Operation Program Prague Competitiveness [CZ.2.16/3.1.00/24510]
- Структура и динамика молекулских система у основним и побуђеним електронским стањима (RS-MESTD-Basic Research (BR or ON)-172040)
- Динамика нелинеарних физичкохемијских и биохемијских система са моделирањем и предвиђањем њихових понашања под неравнотежним условима (RS-MESTD-Basic Research (BR or ON)-172015)
- Проучавање сигналних путева и епигенетичких механизама укључених у контролу експресије хуманих SOX гена: даље расветљавање њихове улоге у одређивању судбине и диференцијацији ћелија (RS-MESTD-Basic Research (BR or ON)-173051)
- Синтеза, моделовање, физичко-хемијске и биолошке особине органских једињења и одговарајућих комплекса метала (RS-MESTD-Basic Research (BR or ON)-172016)
- Методе моделирања на више скала са применама у биомедицини (RS-MESTD-Basic Research (BR or ON)-174028)
DOI: 10.1155/2019/2069250
ISSN: 1942-0900
PubMed: 30906500
WoS: 000460379500001
Scopus: 2-s2.0-85062271851
Институција/група
Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Dimić, Dusan S. AU - Marković, Zoran S. AU - Saso, Luciano AU - Avdović, Edina H. AU - Dorović, Jelena R. AU - Petrović, Isidora AU - Stanisavljević Ninković, Danijela AU - Stevanović, Milena AU - Potocnak, Ivan AU - Samol'ova, Erika AU - Trifunović, Srecko R. AU - Marković, Jasmina M. Dimitric PY - 2019 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/1295 AB - The newly synthesized coumarin derivative with dopamine, 3-(1-((3,4-dihydroxyphenethyDamino)ethylidene)-chroman-2,4-dione, was completely structurally characterized by X-ray crystallography. It was shown that several types of hydrogen bonds are present, which additionally stabilize the structure. The compound was tested in vitro against different cell lines, healthy human keratinocyte HaCaT, cervical squamous cell carcinoma SiHa, breast carcinoma MCF7, and hepatocellular carcinoma HepG2. Compared to control, the new derivate showed a stronger effect on both healthy and carcinoma cell lines, with the most prominent effect on the breast carcinoma MCF7 cell line. The molecular docking study, obtained for ten different conformations of the new compound, showed its inhibitory nature against CDKS protein. Lower inhibition constant, relative to one of 4-OH-coumarine, proved stronger and more numerous interactions with CDKS protein. These interactions were carefully examined for both parent molecule and derivative and explained from a structural point of view. PB - Hindawi Ltd, London T2 - Oxidative Medicine and Cellular Longevity T1 - Synthesis and Characterization of 3-(1-((3,4-Dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione as a Potential Antitumor Agent VL - 2019 DO - 10.1155/2019/2069250 ER -
@article{ author = "Dimić, Dusan S. and Marković, Zoran S. and Saso, Luciano and Avdović, Edina H. and Dorović, Jelena R. and Petrović, Isidora and Stanisavljević Ninković, Danijela and Stevanović, Milena and Potocnak, Ivan and Samol'ova, Erika and Trifunović, Srecko R. and Marković, Jasmina M. Dimitric", year = "2019", abstract = "The newly synthesized coumarin derivative with dopamine, 3-(1-((3,4-dihydroxyphenethyDamino)ethylidene)-chroman-2,4-dione, was completely structurally characterized by X-ray crystallography. It was shown that several types of hydrogen bonds are present, which additionally stabilize the structure. The compound was tested in vitro against different cell lines, healthy human keratinocyte HaCaT, cervical squamous cell carcinoma SiHa, breast carcinoma MCF7, and hepatocellular carcinoma HepG2. Compared to control, the new derivate showed a stronger effect on both healthy and carcinoma cell lines, with the most prominent effect on the breast carcinoma MCF7 cell line. The molecular docking study, obtained for ten different conformations of the new compound, showed its inhibitory nature against CDKS protein. Lower inhibition constant, relative to one of 4-OH-coumarine, proved stronger and more numerous interactions with CDKS protein. These interactions were carefully examined for both parent molecule and derivative and explained from a structural point of view.", publisher = "Hindawi Ltd, London", journal = "Oxidative Medicine and Cellular Longevity", title = "Synthesis and Characterization of 3-(1-((3,4-Dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione as a Potential Antitumor Agent", volume = "2019", doi = "10.1155/2019/2069250" }
Dimić, D. S., Marković, Z. S., Saso, L., Avdović, E. H., Dorović, J. R., Petrović, I., Stanisavljević Ninković, D., Stevanović, M., Potocnak, I., Samol'ova, E., Trifunović, S. R.,& Marković, J. M. D.. (2019). Synthesis and Characterization of 3-(1-((3,4-Dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione as a Potential Antitumor Agent. in Oxidative Medicine and Cellular Longevity Hindawi Ltd, London., 2019. https://doi.org/10.1155/2019/2069250
Dimić DS, Marković ZS, Saso L, Avdović EH, Dorović JR, Petrović I, Stanisavljević Ninković D, Stevanović M, Potocnak I, Samol'ova E, Trifunović SR, Marković JMD. Synthesis and Characterization of 3-(1-((3,4-Dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione as a Potential Antitumor Agent. in Oxidative Medicine and Cellular Longevity. 2019;2019. doi:10.1155/2019/2069250 .
Dimić, Dusan S., Marković, Zoran S., Saso, Luciano, Avdović, Edina H., Dorović, Jelena R., Petrović, Isidora, Stanisavljević Ninković, Danijela, Stevanović, Milena, Potocnak, Ivan, Samol'ova, Erika, Trifunović, Srecko R., Marković, Jasmina M. Dimitric, "Synthesis and Characterization of 3-(1-((3,4-Dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione as a Potential Antitumor Agent" in Oxidative Medicine and Cellular Longevity, 2019 (2019), https://doi.org/10.1155/2019/2069250 . .