Design, Synthesis, In Silico Screening, and Antiproliferative Activity of Novel 1,2,3-Triazole Tethered Dibenzosuberane Conjugates
To explore novel and potent compounds with anticancer activity, two series of 1H-1,2,3-triazole tethered dibenzosuberane conjugates ( 5a-i and 5j-n ) were synthesized using a linear and convergent approach. The synthesized novel compounds were screened for their in vitro antiproliferative activity a...
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| Published in | Biotechnology and bioprocess engineering Vol. 28; no. 5; pp. 761 - 773 |
|---|---|
| Main Authors | , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Seoul
The Korean Society for Biotechnology and Bioengineering
01.10.2023
Springer Nature B.V 한국생물공학회 |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1226-8372 1976-3816 |
| DOI | 10.1007/s12257-023-0077-5 |
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| Abstract | To explore novel and potent compounds with anticancer activity, two series of 1H-1,2,3-triazole tethered dibenzosuberane conjugates (
5a-i
and
5j-n
) were synthesized using a linear and convergent approach. The synthesized novel compounds were screened for their
in vitro
antiproliferative activity against HepG2 cell lines using the MTT assay to explore their binding interactions with the 5EQG protein. IC
50
values revealed that the most active combination against HepG2 cell lines was triazole tethered with an
ortho
chloro-substituted aryl ring (
5g
) (IC
50
: 99.64 µg/mL). The other compounds in the series exhibited comparable cytotoxic activities against HepG2 cell lines. The results were substantiated by molecular docking studies. The majority of the compounds demonstrated high binding affinity for the active site of the targeted protein. In addition,
in silico
drug-likeness prediction by the ADMET method has been explored with these compounds. All synthesized novel derivatives were characterized by mass spectrometry, infrared spectroscopy,
1
H-nuclear magnetic resonance (NMR) spectroscopy, and
13
C-NMR spectroscopy. |
|---|---|
| AbstractList | To explore novel and potent compounds with anticancer activity, two series of 1H-1,2,3-triazole tethered dibenzosuberane conjugates (5a-i and 5j-n) were synthesized using a linear and convergent approach. The synthesized novel compounds were screened for their in vitro antiproliferative activity against HepG2 cell lines using the MTT assay to explore their binding interactions with the 5EQG protein. IC50 values revealed that the most active combination against HepG2 cell lines was triazole tethered with an ortho chloro-substituted aryl ring (5g) (IC50: 99.64 µg/mL). The other compounds in the series exhibited comparable cytotoxic activities against HepG2 cell lines. The results were substantiated by molecular docking studies. The majority of the compounds demonstrated high binding affinity for the active site of the targeted protein. In addition, in silico drug-likeness prediction by the ADMET method has been explored with these compounds. All synthesized novel derivatives were characterized by mass spectrometry, infrared spectroscopy, 1H-nuclear magnetic resonance (NMR) spectroscopy, and 13C-NMR spectroscopy. To explore novel and potent compounds with anticancer activity, two series of 1H-1,2,3-triazole tethered dibenzosuberane conjugates ( 5a-i and 5j-n ) were synthesized using a linear and convergent approach. The synthesized novel compounds were screened for their in vitro antiproliferative activity against HepG2 cell lines using the MTT assay to explore their binding interactions with the 5EQG protein. IC 50 values revealed that the most active combination against HepG2 cell lines was triazole tethered with an ortho chloro-substituted aryl ring ( 5g ) (IC 50 : 99.64 µg/mL). The other compounds in the series exhibited comparable cytotoxic activities against HepG2 cell lines. The results were substantiated by molecular docking studies. The majority of the compounds demonstrated high binding affinity for the active site of the targeted protein. In addition, in silico drug-likeness prediction by the ADMET method has been explored with these compounds. All synthesized novel derivatives were characterized by mass spectrometry, infrared spectroscopy, 1 H-nuclear magnetic resonance (NMR) spectroscopy, and 13 C-NMR spectroscopy. To explore novel and potent compounds with anticancer activity, two series of 1H-1,2,3-triazole tethered dibenzosuberane conjugates (5a-i and 5j-n) were synthesized using a linear and convergent approach. The synthesized novel compounds were screened for their in vitro antiproliferative activity against HepG2 cell lines using the MTT assay to explore their binding interactions with the 5EQG protein. IC₅₀ values revealed that the most active combination against HepG2 cell lines was triazole tethered with an ortho chloro-substituted aryl ring (5g) (IC₅₀: 99.64 µg/mL). The other compounds in the series exhibited comparable cytotoxic activities against HepG2 cell lines. The results were substantiated by molecular docking studies. The majority of the compounds demonstrated high binding affinity for the active site of the targeted protein. In addition, in silico drug-likeness prediction by the ADMET method has been explored with these compounds. All synthesized novel derivatives were characterized by mass spectrometry, infrared spectroscopy, ¹H-nuclear magnetic resonance (NMR) spectroscopy, and ¹³C-NMR spectroscopy. To explore novel and potent compounds with anticancer activity, two series of 1H-1,2,3-triazole tethered dibenzosuberane conjugates (5a-i and 5j-n) were synthesized using a linear and convergent approach. The synthesized novel compounds were screened for their in vitro antiproliferative activity against HepG2 cell lines using the MTT assay to explore their binding interactions with the 5EQG protein. IC50 values revealed that the most active combination against HepG2 cell lines was triazole tethered with an ortho chloro-substituted aryl ring (5g) (IC50: 99.64 μg/mL). The other compounds in the series exhibited comparable cytotoxic activities against HepG2 cell lines. The results were substantiated by molecular docking studies. The majority of the compounds demonstrated high binding affinity for the active site of the targeted protein. In addition, in silico drug-likeness prediction by the ADMET method has been explored with these compounds. All synthesized novel derivatives were characterized by mass spectrometry, infrared spectroscopy, 1H-nuclear magnetic resonance (NMR) spectroscopy, and 13C-NMR spectroscopy. KCI Citation Count: 0 |
| Author | Park, Jong Pil Saini, Keshav Kumar Dasegowda, K. R. Kumar, Rakesh Kumar, Lalita S. Singh, Shishu Pal Kant, Ravi Reddy, Y. Veera Manohara Prabhavati, H. Singh, Yogender Kareem, M. Abdul Upadhyay, Ravindra Kumar |
| Author_xml | – sequence: 1 givenname: Ravi surname: Kant fullname: Kant, Ravi organization: Department of Chemistry, School of Sciences, IGNOU, Department of Chemistry, Government Post Graduate College – sequence: 2 givenname: Keshav Kumar surname: Saini fullname: Saini, Keshav Kumar organization: Department of Chemistry, Dyal Singh College, University of Delhi – sequence: 3 givenname: Ravindra Kumar surname: Upadhyay fullname: Upadhyay, Ravindra Kumar organization: Department of Chemistry, University of Delhi, Department of Chemistry, Sri Venkateswara College, University of Delhi – sequence: 4 givenname: Yogender surname: Singh fullname: Singh, Yogender organization: Department of Chemistry, Government Degree College – sequence: 5 givenname: Y. Veera Manohara surname: Reddy fullname: Reddy, Y. Veera Manohara organization: Department of Chemistry, Sri Venkateswara College, University of Delhi – sequence: 6 givenname: Shishu Pal surname: Singh fullname: Singh, Shishu Pal organization: Department of Computer Science, Government Post Graduate College – sequence: 7 givenname: M. Abdul surname: Kareem fullname: Kareem, M. Abdul organization: Department of Biochemistry, School of Sciences, IGNOU – sequence: 8 givenname: K. R. surname: Dasegowda fullname: Dasegowda, K. R. organization: School of Applied Sciences, REVA University – sequence: 9 givenname: H. surname: Prabhavati fullname: Prabhavati, H. organization: Department of Cytogenomics, Dr Lal Pathlabs – sequence: 10 givenname: Rakesh surname: Kumar fullname: Kumar, Rakesh organization: Department of Chemistry, University of Delhi – sequence: 11 givenname: Jong Pil surname: Park fullname: Park, Jong Pil email: jppark@cau.ac.kr organization: Department of Food Science and Technology, Chung-Ang University – sequence: 12 givenname: Lalita S. surname: Kumar fullname: Kumar, Lalita S. email: lalitaskumar@ignou.ac.in organization: Department of Chemistry, School of Sciences, IGNOU |
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| Keywords | dibenzosuberone docking isatin 1,2,3-triazoles antiproliferative activity |
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| References | Singh, Kumar, Singh, Sonawane, Paliwal, Thareja, Pathak, Grishina, Jaremko, Emwas, Yadav, Verma, Khalilullah, Kumar (CR5) 2022; 15 Moger, Satam, Govindaraju, Paniraj, Gopinath, Hindupur, Pati (CR9) 2014; 25 Grewal (CR18) 2014; 6 Moger, Pati (CR22) 2018; 7 Dallakyan, Olson (CR35) 2015; 1263 Kumar, Saha, Gu, Palma, Perumal, Singh-Pillay, Singh, Anand, Kaur, Kumar (CR26) 2018; 3 Roy, Chatterjee, Pramanik, Roy, Bhaumik, Islam (CR25) 2014; 386 Xiong, Huang, Wu, Zhou, Yang, Saimaiti, Zhao, Shang, Zhang, Gan, Li (CR2) 2022; 27 Soliman, Ali, El-Sakka, Mohamed (CR27) 2022; 1254 Erdogan, Horoz (CR10) 2021; 45 Martins Paulo, Romeiro Gilberto, Ribeiro Carlos (CR8) 2010; 7 Roth, Heckel, Colbatzky, Handschuh, Kley, Lehmann-Lintz, Lotz, Tontsch-Grunt, Walter, Hilberg (CR19) 2009; 52 Kaur, Chawla (CR21) 2017; 8 Almahmoud, Wang, Vennerstrom, Zhong (CR28) 2019; 24 Merkaš, Litvić, Cepanec, Vinković (CR13) 2005; 10 Srinivas Reddy, Swamy Thirukovela, Narsimha, Ravinder, Kumar Nukala (CR3) 2022; 1250 Naredla, Klumpp (CR7) 2013; 69 Ferraz de Paiva, Vieira, Rodrigues da Silva, Wegermann, Costa Ferreira (CR15) 2021; 7 Dong, Wang, Taheri, Xiong, Ihira, Kobayashi, Konno, Yue, Watari (CR29) 2022; 12 Jackson, Woo, Trusselle, Chander, Purohit, Reed, Potter (CR24) 2007; 5 Rashdan, Abdelmonsef, Abou-Krisha, Yousef (CR31) 2021; 26 Upadhyay, Saini, Deswal, Singh, Tripathi, Kaushik, Shakil, Bharti, Kumar (CR17) 2022; 12 Chao, Su, Yen, Wu, Chu (CR23) 2020; 85 Ononamadu, Ibrahim (CR33) 2021; 102 Singh, Saha, Perumal, Kaur, Kumar (CR16) 2018; 3 Lipinski, Lombardo, Dominy, Feeney (CR32) 2012; 64 Shalini, Saha, Kaur, Awolade, Ebenezer, Singh, Kumar (CR4) 2022; 1262 Dastan, Kilic, Saracoglu (CR12) 2018; 50 Veber, Johnson, Cheng, Smith, Ward, Kopple (CR34) 2002; 12 Rastogi, Banerjee, Chellappan, Simon (CR30) 2007; 257 Talib, Mahmod, Awajan, Hamed, Al-Yasari (CR1) 2022; 15 Koçak, Daştan (CR11) 2021; 17 Prenen, Cools, Mentens, Folens, Sciot, Schöffski, Van Oosterom, Marynen, Debiec-Rychter (CR20) 2006; 12 Moger, Pradhan, Singh, Govindaraju, Hindupur, Pati (CR14) 2016; 25 Sharma, Dulta, Nagraik, Dua, Singh, Chellappan, Kumar, Shin (CR6) 2022; 308 M Erdogan (77_CR10) 2021; 45 S Dallakyan (77_CR35) 2015; 1263 H Prenen (77_CR20) 2006; 12 S Merkaš (77_CR13) 2005; 10 G J Roth (77_CR19) 2009; 52 M Moger (77_CR9) 2014; 25 A Sharma (77_CR6) 2022; 308 R C Martins Paulo (77_CR8) 2010; 7 S Roy (77_CR25) 2014; 386 R K Upadhyay (77_CR17) 2022; 12 D F Veber (77_CR34) 2002; 12 S Almahmoud (77_CR28) 2019; 24 C A Lipinski (77_CR32) 2012; 64 P Dong (77_CR29) 2022; 12 A Singh (77_CR16) 2018; 3 M Moger (77_CR22) 2018; 7 A K Singh (77_CR5) 2022; 15 A Dastan (77_CR12) 2018; 50 A S Grewal (77_CR18) 2014; 6 S Kumar (77_CR26) 2018; 3 R-G Xiong (77_CR2) 2022; 27 M H A Soliman (77_CR27) 2022; 1254 M Srinivas Reddy (77_CR3) 2022; 1250 S Rastogi (77_CR30) 2007; 257 S L Shalini (77_CR4) 2022; 1262 M Moger (77_CR14) 2016; 25 H R M Rashdan (77_CR31) 2021; 26 R Koçak (77_CR11) 2021; 17 C J Ononamadu (77_CR33) 2021; 102 R E Ferraz de Paiva (77_CR15) 2021; 7 P Kaur (77_CR21) 2017; 8 W H Talib (77_CR1) 2022; 15 T Chao (77_CR23) 2020; 85 T Jackson (77_CR24) 2007; 5 R R Naredla (77_CR7) 2013; 69 |
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| Snippet | To explore novel and potent compounds with anticancer activity, two series of 1H-1,2,3-triazole tethered dibenzosuberane conjugates (
5a-i
and
5j-n
) were... To explore novel and potent compounds with anticancer activity, two series of 1H-1,2,3-triazole tethered dibenzosuberane conjugates (5a-i and 5j-n) were... |
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| Title | Design, Synthesis, In Silico Screening, and Antiproliferative Activity of Novel 1,2,3-Triazole Tethered Dibenzosuberane Conjugates |
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