Synthesis of water-soluble novel bioactive pyridine-based azo coumarin derivative and competitive cytotoxicity, DNA binding, BSA binding study, and in silico analysis with coumarin
Copyright © 2023 Elsevier Inc. All rights reserved..
The diazo coupliling reaction of 3- amino pyridine with coumarin in water medium produces water soluble 6-[3-pyridyl]azocoumarin. The synthesised compound has been fully charecterised by IR, NMR, and Mass spectroscopy. The frontier molecular orbital calculations reveal that 6-[3-pyridyl]azocoumarin is more biologically and chemically active in comparison to coumarin. The cytotoxicity evaluation confirms that 6-[3-pyridyl]azocoumarin is more active than coumarin against human brain glioblastoma cell lines, LN-229 with IC50 value 9.09 μM (IC50 value for coumarin is 9.9 μM). The compound (I) has been synthesized by coupling of diazotized solution of 3-aminopyridine with coumarin in an aqueous medium at ∼ pH 10. The structure of the compound (I) has been characterized using UV-vis, IR, NMR, and Mass spectral studies. Frontier molecular orbital calculations reveal that 6-[3-pyridyl]azocoumarin (I) is more active chemically and biologically in comparison to coumarin. IC50 value 9.09 and 9.9 μM of 6-[3-pyridyl]azocoumarin and coumarin respectively obtained in cytotoxicity evaluation confirms the enhanced activity of the synthesized compound against human brain glioblastoma cell lines, LN-229. The synthesized compound also shows strong binding interactions with DNA and BSA in comparison with coumarin. The DNA binding study shows groove binding interaction of the synthesized compound with CT-DNA. The nature of interaction, binding parameters and structural variations of BSA in the presence of the synthesized compound and coumarin have been evaluated using several usefull spectroscopy approaches such as UV -Vis, time resolved and stady state flurescence. The molecular docking interaction has been carried out to justify the experimental binding interaction with DNA and BSA.
Medienart: |
E-Artikel |
---|
Erscheinungsjahr: |
2023 |
---|---|
Erschienen: |
2023 |
Enthalten in: |
Zur Gesamtaufnahme - volume:138 |
---|---|
Enthalten in: |
Bioorganic chemistry - 138(2023) vom: 01. Sept., Seite 106532 |
Sprache: |
Englisch |
---|
Beteiligte Personen: |
Karan, Putul [VerfasserIn] |
---|
Links: |
---|
Anmerkungen: |
Date Completed 10.07.2023 Date Revised 21.11.2023 published: Print-Electronic Citation Status MEDLINE |
---|
doi: |
10.1016/j.bioorg.2023.106532 |
---|
funding: |
|
---|---|
Förderinstitution / Projekttitel: |
|
PPN (Katalog-ID): |
NLM356752887 |
---|
LEADER | 01000naa a22002652 4500 | ||
---|---|---|---|
001 | NLM356752887 | ||
003 | DE-627 | ||
005 | 20231226071132.0 | ||
007 | cr uuu---uuuuu | ||
008 | 231226s2023 xx |||||o 00| ||eng c | ||
024 | 7 | |a 10.1016/j.bioorg.2023.106532 |2 doi | |
028 | 5 | 2 | |a pubmed24n1189.xml |
035 | |a (DE-627)NLM356752887 | ||
035 | |a (NLM)37172438 | ||
035 | |a (PII)S0045-2068(23)00192-X | ||
040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
041 | |a eng | ||
100 | 1 | |a Karan, Putul |e verfasserin |4 aut | |
245 | 1 | 0 | |a Synthesis of water-soluble novel bioactive pyridine-based azo coumarin derivative and competitive cytotoxicity, DNA binding, BSA binding study, and in silico analysis with coumarin |
264 | 1 | |c 2023 | |
336 | |a Text |b txt |2 rdacontent | ||
337 | |a ƒaComputermedien |b c |2 rdamedia | ||
338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
500 | |a Date Completed 10.07.2023 | ||
500 | |a Date Revised 21.11.2023 | ||
500 | |a published: Print-Electronic | ||
500 | |a Citation Status MEDLINE | ||
520 | |a Copyright © 2023 Elsevier Inc. All rights reserved. | ||
520 | |a The diazo coupliling reaction of 3- amino pyridine with coumarin in water medium produces water soluble 6-[3-pyridyl]azocoumarin. The synthesised compound has been fully charecterised by IR, NMR, and Mass spectroscopy. The frontier molecular orbital calculations reveal that 6-[3-pyridyl]azocoumarin is more biologically and chemically active in comparison to coumarin. The cytotoxicity evaluation confirms that 6-[3-pyridyl]azocoumarin is more active than coumarin against human brain glioblastoma cell lines, LN-229 with IC50 value 9.09 μM (IC50 value for coumarin is 9.9 μM). The compound (I) has been synthesized by coupling of diazotized solution of 3-aminopyridine with coumarin in an aqueous medium at ∼ pH 10. The structure of the compound (I) has been characterized using UV-vis, IR, NMR, and Mass spectral studies. Frontier molecular orbital calculations reveal that 6-[3-pyridyl]azocoumarin (I) is more active chemically and biologically in comparison to coumarin. IC50 value 9.09 and 9.9 μM of 6-[3-pyridyl]azocoumarin and coumarin respectively obtained in cytotoxicity evaluation confirms the enhanced activity of the synthesized compound against human brain glioblastoma cell lines, LN-229. The synthesized compound also shows strong binding interactions with DNA and BSA in comparison with coumarin. The DNA binding study shows groove binding interaction of the synthesized compound with CT-DNA. The nature of interaction, binding parameters and structural variations of BSA in the presence of the synthesized compound and coumarin have been evaluated using several usefull spectroscopy approaches such as UV -Vis, time resolved and stady state flurescence. The molecular docking interaction has been carried out to justify the experimental binding interaction with DNA and BSA | ||
650 | 4 | |a Journal Article | |
650 | 4 | |a Research Support, Non-U.S. Gov't | |
650 | 4 | |a Aqueous medium | |
650 | 4 | |a Azo derivative | |
650 | 4 | |a BSA binding | |
650 | 4 | |a Coumarin | |
650 | 4 | |a Cytotoxicity | |
650 | 4 | |a DNA binding | |
650 | 4 | |a LN-229 | |
650 | 4 | |a Molecular docking | |
650 | 7 | |a Antineoplastic Agents |2 NLM | |
650 | 7 | |a DNA |2 NLM | |
650 | 7 | |a 9007-49-2 |2 NLM | |
650 | 7 | |a Organic Chemicals |2 NLM | |
650 | 7 | |a Pyridines |2 NLM | |
650 | 7 | |a Coumarins |2 NLM | |
650 | 7 | |a Water |2 NLM | |
650 | 7 | |a 059QF0KO0R |2 NLM | |
650 | 7 | |a Serum Albumin, Bovine |2 NLM | |
650 | 7 | |a 27432CM55Q |2 NLM | |
700 | 1 | |a Shit, Basudev |e verfasserin |4 aut | |
700 | 1 | |a Panja, Poulami |e verfasserin |4 aut | |
700 | 1 | |a Khatun, Amina |e verfasserin |4 aut | |
700 | 1 | |a Pal, Jagannath |e verfasserin |4 aut | |
700 | 1 | |a Chakarabarti, Sudipta |e verfasserin |4 aut | |
700 | 1 | |a Pal, Sutanuka |e verfasserin |4 aut | |
700 | 1 | |a Ghosh, Avishek |e verfasserin |4 aut | |
700 | 1 | |a Hossain, Maidul |e verfasserin |4 aut | |
773 | 0 | 8 | |i Enthalten in |t Bioorganic chemistry |d 1986 |g 138(2023) vom: 01. Sept., Seite 106532 |w (DE-627)NLM012846570 |x 1090-2120 |7 nnns |
773 | 1 | 8 | |g volume:138 |g year:2023 |g day:01 |g month:09 |g pages:106532 |
856 | 4 | 0 | |u http://dx.doi.org/10.1016/j.bioorg.2023.106532 |3 Volltext |
912 | |a GBV_USEFLAG_A | ||
912 | |a GBV_NLM | ||
951 | |a AR | ||
952 | |d 138 |j 2023 |b 01 |c 09 |h 106532 |