Abstract
The present invention reports two novel functional compounds, 2-hydroxy-3-naphthaldehyde thiosemicarbazone (2H3NTS) and 2-hydroxy-3-naphthaldehyde semicarbazone (2H3NS), as plausible fluorescent probes possessing excited state intramolecular proton transfer property, and they are not yet reported to be synthesized by any research group. The DFT study reveals significantly higher Stokes shift (31,476 cm−1) for 2H3NS indicating swift relaxation from initial to the emissive state and reduces self-quenching from self-molecular absorption which favours its practical application. Consequently, successive in vitro activity of 2H3NTS and 2H3NS is studied in silico using molecular docking towards the inhibition capacity of target kinase protein like CDK, primarily responsible for cell growth. As expected, 2H3NS is capable of binding with both competitive ATP binding SITE I and non-competitive SITE II which lies below the T-loop, thereby inhibiting the cell growth and differentiation. However, 2H3NTS with polarizable sulphur is incapable of binding at SITE I with selective inhibition posing the ATP site to be well conserved.
Graphical Abstract
2-Hydroxy-3-naphthaldehyde thiosemicarbazone (2H3NTS) and 2-hydroxy-3-naphthaldehyde semicarbazone (2H3NS) are theoretically established to be fluorescent possessing excited state intramolecular proton transfer (ESIPT) property. The DFT study reveals significantly higher Stokes shift (31,746 cm−1) for 2H3NS indicating swift relaxation which favours its practical application. 2H3NS is capable of binding both competitive ATP binding SITE I and non-competitive SITE II, thereby inhibiting the cell growth and differentiation. However, 2H3NTS with polarizable sulphur is incapable of binding at SITE I with selective inhibition posing the ATP site to be well conserved.
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References
Abo El-Fetoh SH, Eid AE, Abd El-Kareem AI, Wassel MA (2008) Synth React Inorg M 30(3):513–532. https://doi.org/10.1080/00945710009351778
Al-Asbahi BA (2023) Phys Scr 98:095908. https://doi.org/10.1088/1402-4896/ace99a
Anasuya Devi VS, Krishna Reddy V (2013). J Chem. https://doi.org/10.1155/2013/697379
Bose D, Chattopadhyay N (2014) Ind J Chem A 53A:17–26
Bose D, Jana B, Datta S, Chattopadhyay N (2011) J Photochem Photobiol a: Chem 222:220–227. https://doi.org/10.1016/j.jphotochem.2011.06.001
Carrasco F, Hernandez W, Chupayo O, Alvarez CM, Oramas-Royo S, Spodine E, Tamariz-Angeles C, Olivera-Gonzales P, D´avalos JZ (2020). J Chem 7157281(1–9).
Chakraborty T, Dasgupta S, Bhattacharyya A, Zangrando E, Escudero D, Das D (2019) N J Chem 43:13152–13161. https://doi.org/10.1039/C9NJ03481A
Chou PT, Chiou C-H, Yu W-S, Wu G-R, Wei T-H (2003) Chem Phys Lett 370:747–755. https://doi.org/10.1016/S0009-2614(03)00165-9
Dadashi-Silab S, Doran S, Yagsi Y (2016) Chem Rev 116(17):10212–10275. https://doi.org/10.1021/acs.chemrev.5b00586
Dasgupta S, Zangrando E, Majumder I (2017) Chem Select 2:1. https://doi.org/10.1002/slct.201701741
Dilovic I, Rubcic M, Vrdojak V, Pavelic SK, Kralj M, Piantanida I, Cindric M (2008) Bioorg Med Chem 16(9):5189–5198. https://doi.org/10.1016/j.bmc.2008.03.006
Ding Y, Jiang W, Tang X (2022) Bull Mater Sci 45:253. https://doi.org/10.1007/s12034-022-02839-6
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr., Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick, DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford, Cioslowski SJ, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, and Pople JA, Gaussian, Inc., Wallingford CT (2004) Gaussian 03, Revision C.01
Ganorkar K, Mukherjee S, Wankar S, Joshi R, Das C, Ghosh SK (2019) J Photochem Photobiol a: Chem 371:81–90. https://doi.org/10.1016/j.jphotochem.2018.11.002
Hariri E, Mahboubi A, Fathi M, Rahmani P, Tehrani KHME, Babaeian M, Mashayekhi V, Kobarfard F (2016) Iranian J Pharm Res 15:29–35
Hettich CP, Zhang X, Kemper D, Zhao R, Zhou S, Lu Y, Gao J, Zhang J, Liu M (2023) J Am Chem Soc AU 3(7):1800–1819. https://doi.org/10.1021/jacsau.3c00186
Irshad R, Asim S, Mansha A, Arooj Y (2023) J Fluoresc 33:1273–1303. https://doi.org/10.1007/s10895-023-03153-y
Jadhao M, Meitei OR, Joshi R, Kumar H, Das C, Ghosh SK (2016) J Photochem Photobiol a: Chem 326:41–49. https://doi.org/10.1016/j.jphotochem.2016.04.020
Jankowska J, Sobolewski AL (2021) Molecules 26(17):5140. https://doi.org/10.3390/molecules26175140
Javid MT, Rahim F, Taha M, Rehman HU, Nawaz M, Wadood A, Imran S, Uddin I, Mosaddik A, Khan KM (2018) Bioorg Chem 78:201–209. https://doi.org/10.1016/j.bioorg.2018.03.022
Kasha M (1986) J Chem Soc Faraday Trans II 82(12):2379. https://doi.org/10.1039/F29868202379
Kundu P, Chattopadhyay N (2023) J Photochem Photobiol a: Chem 435:114296. https://doi.org/10.1016/j.jphotochem.2022.114296
Li Y, Zhang J, Gao W, Zhang L, Pan Y, Zhang S, Wang Y (2015) Int J Mol Sci 6(12):9314–9340. https://doi.org/10.3390/ijms16059314
Mahanta S, Singh RB, Kar S, Guchhait N (2006) Chem Phys 324(2–3):742–752. https://doi.org/10.1016/j.chemphys.2006.01.036
Nagarajan K, Krishnakumar V, Parimala K (2023) Bull Mater Sci 46:12. https://doi.org/10.1007/s12034-022-02841-y
Naimhwaka JH, Daniel L, Hamukwaya EN, Endjala PT, Rahman A, Uahengo V (2022) Chem Afr 13:31541–31543. https://doi.org/10.1007/s42250-021-00299-9
Olayemi VT, Oladipo AC, Adimula VO, Tella AC (2024) Chem Afr 7:175–183. https://doi.org/10.1007/s42250-023-00746-9
Ovung A, Mavani A, Ghosh A, Chatterjee S, Das A, Kumar GS, Ray D, Aswal VK, Bhattacharyya J (2022) ACS Omega 7(15):13067–13074. https://doi.org/10.1021/acsomega.2c00447
Pavletich NP (1999) J Mol Biol 287(5):821–828. https://doi.org/10.1006/jmbi.1999.2640
Peng C, Shen J, Chen Y, Wu P, Hung W, Hu W, Chou P (2015) J Am Chem Soc 137(45):14349–14357. https://doi.org/10.1021/jacs.5b08562
Pereira TM, Vitorio F, Amaral RC, Zanoni KPS, Iha NYM, Kummerele AE (2016) New J Chem 40:8846–8852. https://doi.org/10.1039/C6NJ01532H
Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE (2004) J Comput Chem 25(13):1605–1612. https://doi.org/10.1002/jcc.20084
Sahadev, Sharma R K, Sindhwani S K (1992). Monatsch Chem. 123(12), 1099–1105. https://doi.org/10.1007/BF00808272
Sahadev, Sharma RK, Sindhwani SK (1993). Proc Ind Acad Sci (Chem Sci). 105(2), 103–110. https://doi.org/10.1007/BF02867144
Sen Chowdhury M, Sarkar A, Rai SR, Dasgupta S, Majumder I, Bhattacharya A, Das D, Bose D, Mukhopadhyay J, Mukhopadhyay M (2021). Appl Orgmet Chem. https://doi.org/10.1002/aoc.6164
Sen Chowdhury M, Gumus S, Dasgupta S, Majumder I, Bhattacharya A, Das D, Mukhopadhyay J, Bose D, Dasgupta S, Akinay Y, Mukhopadhyay M (2022) Chemistry Open 11(6):202200033. https://doi.org/10.1002/open.202200033
Sil A, Mukhopadhyay M, Bose D (2023) Macromol Symp 407:2100375. https://doi.org/10.1002/masy.202100375
Stasyuk A, Chen Y, Chen C, Wu P, Chou P (2016) Phys Chem Chem Phys 18(35):24428–24436. https://doi.org/10.1039/C6CP05236C
Worster SB, Feighan O, Manby FR (2023) Biophysics and Computational. Biology 120(5):e2210811120. https://doi.org/10.1073/pnas.2210811120
Young D (2001) Computational Chemistry: A practical guide for applying techniques to real world problems. Wiley Chapter 3:19–22
Yuan Z, Zhang Y, Xu G, Bi D, Qu H, Zou X, Gao X, Yang H, He H, Wang X, Bao J, Zuo S, Pan X, Zhou B, Wang G-L, Qu S (2018) J Plant Biol 61(3):143–158. https://doi.org/10.1007/s12374-017-0209-6
Zhang J, Xiang Q, Qiu Q, Zhu Y, Zhang C (2021) J Solid State Chem A 298:122123. https://doi.org/10.1016/j.jssc.2021.122123
Zhang J, Gan Y, Li H, Yin J, He X, Lin L, Xu S, Fang Z, Kim B-W, Gao L, Ding L, Zhang E, Ma X, Li J, Li L, Xu Y, Horne D, Xu R, Yu H, Gu Y, Huang W (2022) Nat Commun 13:2835. https://doi.org/10.1038/s41467-022-30264-0
Zhao J, Song P, Ma F (2014) Commun Comput Chem 2:117–130. https://doi.org/10.4208/cicc.2014.v2.n3.3
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The authors acknowledge Amity University, Kolkata, Maulana Abul Kalam Azad University of Technology (MAKAUT), WB, and CSIR-CGCRI, India, for infrastructural support and kind permission to present the work.
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Bose, D., Sil, A., Chakraborty, P. et al. DFT Analyses of arsylsemicarbazone group as functional compound for application as excellent fluorescent probes and medicament: study on virtual screening through molecular docking. Chem. Pap. (2024). https://doi.org/10.1007/s11696-024-03526-y
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DOI: https://doi.org/10.1007/s11696-024-03526-y