Theoretical and experimental investigation of novel quinazoline derivatives: synthesis, photophysical, reactive properties, molecular docking and selective HSA biointeraction

References

• Alhamzani, A. G., Yousef, T. A., Abou-Krisha, M. M., Raghu, M. S., Kumar, K. Y., Prashanth, M. K., & Jeon, B. H. (2022). Design, synthesis, molecular docking and pharmacological evaluation of novel triazine-based triazole derivatives as potential anticonvulsant agents. Bioorganic & Medicinal Chemistry Letters, 77, 129042. https://doi.org/10.1016/j.bmcl.2022.129042
   PubMed Web of Science ®Google Scholar
• Asif, M. (2014). Chemical characteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives. International Journal of Medicinal Chemistry, 2014, 395637. https://doi.org/10.1155/2014/395637
   PubMedGoogle Scholar
• Auti, P. S., George, G., & Paul, A. T. (2020). Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids. RSC Advances, 10(68), 41353–41392. https://doi.org/10.1039/d0ra06642g
   PubMed Web of Science ®Google Scholar
• Bhardwaj, B. K., Venkatesh, T., & Suresh, P. S. (2023). Study on the interaction of the bromodomain inhibitor JQ1 with human serum albumin by spectroscopic and molecular docking studies. Journal of Molecular Structure, 1273, 134374. https://doi.org/10.1016/j.molstruc.2022.134374
   Web of Science ®Google Scholar
• Calvo, M. J., Martínez, M. S., Torres, W., Chavez-Castillo, M., Luzardo, E., Villasmil, N., Salazar, J., Velasco, M., & Bermudez, V. (2017). Omega-3 polyunsaturated fatty acids and cardiovascular health: A molecular view into structure and function. Vessel Plus, 1, 116–128. https://doi.org/10.20517/2574-1209.2017.14
   Google Scholar
• Chamani, J., Moosavi-Movahedi, A. A., & Hakimelahi, G. H. (2005). Structural changes in β-lactoglobulin by conjugation with three different kinds of carboxymethyl cyclodextrins. Thermochimica Acta, 432(1), 106–111. https://doi.org/10.1016/j.tca.2005.04.014
   Web of Science ®Google Scholar
• Chirio Lebrun, M. C., & Prats, M. (1998). Fluorescence resonance energy transfer (FRET): Theory and experiments. Biochemical Education, 26(4), 320–323. https://doi.org/10.1016/S0307-4412(98)80010-1
   Google Scholar
• Darban, R. A., Shareghi, B., Asoodeh, A., & Chamani, J. (2017). Multi-spectroscopic and molecular modeling studies of interaction between two different angiotensin I converting enzyme inhibitory peptides from gluten hydrolysate and human serum albumin. Journal of Biomolecular Structure & Dynamics, 35(16), 3648–3662. https://doi.org/10.1080/07391102.2016.1264892
   PubMed Web of Science ®Google Scholar
• Deepakumari, H. N., Jayanna, B. K., Prashanth, M. K., Revanasiddappa, H. D., & Veeresh, B. (2016). Synthesis and Anticonvulsant Activity of N‐(Substituted)‐1‐methyl‐2,4‐dioxo‐1,2‐dihydroquinazoline‐3(4H)‐carboxamides. Archiv der Pharmazie, 349(7), 566–571. https://doi.org/10.1002/ardp.201600024
   PubMed Web of Science ®Google Scholar
• Domotor, O., Tuccinardi, T., Karcz, D., Walsh, M., Creaven, B. S., & Enyedy, E. A. (2014). Interaction of anticancer reduced Schiff base coumarin derivatives with human serum albumin investigated by fluorescence quenching and molecular modelling. Bioorganic Chemistry, 52, 16–23. https://doi.org/10.1016/j.bioorg.2013.10.003
   PubMed Web of Science ®Google Scholar
• Forster, T., & Sinanoglu, O. (1996). Modern quantum chemistry (p. 93). Academic Press.
   Google Scholar
• Gou, Y., Zhang, Y., Qi, J., Kong, L., Zhou, Z., Liang, S., Yang, F., & Liang, H. (2015). Binding and anticancer properties of plumbagin with human serum albumin. Chemical Biology & Drug Design, 86(3), 362–369. https://doi.org/10.1111/cbdd.12501
   PubMed Web of Science ®Google Scholar
• Guo, Y., Yue, Q., & Gao, B. (2010). Probing the molecular mechanism of CI Acid red 73 binding to human serum albumin. Environmental Toxicology and Pharmacology, 30(1), 45–51. https://doi.org/10.1016/j.etap.2010.03.013
   PubMed Web of Science ®Google Scholar
• Hosseinzadeh, M., Nikjoo, S., Zare, N., Delavar, D., Beigoli, S., & Chamani, J. (2019). Characterization of the structural changes of human serum albumin upon interaction with single-walled and multi-walled carbon nanotubes: Spectroscopic and molecular modeling approaches. Research on Chemical Intermediates, 45(2), 401–423. https://doi.org/10.1007/s11164-018-3608-5
   Web of Science ®Google Scholar
• Jafari, E., Khajouei, M. R., Hassanzadeh, F., Hakimelahi, G. H., & Khodarahmi, G. A. (2016). Quinazolinone and quinazoline derivatives: Recent structures with potent antimicrobial and cytotoxic activities. Research in Pharmaceutical Sciences, 11(1), 1–14.
   PubMedGoogle Scholar
• Lakowicz, J. R. (1988). Principles of frequency-domain fluorescence spectroscopy and applications to cell membranes. Subcellular Biochemistry, 13, 89–126.
   PubMedGoogle Scholar
• Li, W., Chen, S. Y., Hu, W. N., Zhu, M., Liu, J. M., Fu, Y. H., Wang, Z. C., & Ouyang, G. P. (2020). Design, synthesis, and biological evaluation of quinazoline derivatives containing piperazine moieties as antitumor agents. Journal of Chemical Research, 44(9–10), 536–542. https://doi.org/10.1177/1747519820910384
   Web of Science ®Google Scholar
• Liu, C., Li, Y., Jia, B., Qi, Y., & Li, K. (2011). Study on interaction between baicalin and human serum albumin. Journal of Instrumental Analysis, 30, 532–536.
   Google Scholar
• Liu, C., Liu, Z., & Wang, J. (2017). Uncovering the molecular and physiological processes of anticancer leads binding human serum albumin: A physical insight into drug efficacy. PloS One, 12(4), e0176208. https://doi.org/10.1371/journal.pone.0176208
   PubMed Web of Science ®Google Scholar
• Madaiah, M., Prashanth, M. K., & Revanasiddappa, H. D. (2013). Novel synthesis of 4,4-di- fluoro pyrido[4,3- b]indoles via intramolecular Heck reaction. Tetrahedron Letters, 54(11), 1424–1427. https://doi.org/10.1016/j.tetlet.2012.12.115
   Web of Science ®Google Scholar
• Madaiah, M., Prashanth, M. K., Revanasiddappa, H. D., & Veeresh, B. (2016). Synthesis and evaluation of novel imidazo[4,5-c]pyridine derivatives as antimycobacterial agents against Mycobacterium tuberculosis. New Journal of Chemistry, 40(11), 9194–9204. https://doi.org/10.1039/C6NJ02069K
   Web of Science ®Google Scholar
• Madaiah, M., Prashanth, M. K., Revanasiddappa, H. D., & Veeresh, B. (2014). Synthesis and pharmacological evaluation of novel 1′‐[2‐(Difluoromethoxy)benzyl]‐2′ H, 5′ H‐spiro [8‐azabicyclo [3.2. 1] octane‐3, 4′‐imidazolidine]‐2′,5′‐diones and their derivatives. Archiv der Pharmazie, 347(5), 370–380. https://doi.org/10.1002/ardp.201300289
   PubMed Web of Science ®Google Scholar
• Madaiah, M., Prashanth, M. K., Revanasiddappa, H. D., & Veeresh, B. (2013). Synthesis and evaluation of 3-[(2,4-dioxo-1,3,8-triazaspiro[4.6]undec-3-yl)methyl]benzonitrile derivatives as potential anticonvulsants. Archiv der Pharmazie, 346(3), 200–209. https://doi.org/10.1002/ardp.201200400
   PubMed Web of Science ®Google Scholar
• Malasala, S., Gour, J., Ahmad, M. N., Gatadi, S., Shukla, M., Kaul, G., Dasgupta, A., Madhavi, Y. V., Chopra, S., & Nanduri, S. (2020). Copper mediated one-pot synthesis of quinazolinones and exploration of piperazine linked quinazoline derivatives as anti-mycobacterial agents. RSC Advances, 10(71), 43533–43538. https://doi.org/10.1039/d0ra08644d
   PubMed Web of Science ®Google Scholar
• Malek-Esfandiari, Z., Rezvani-Noghani, A., Sohrabi, T., Mokaberi, P., Amiri-Tehranizadeh, Z., & Chamani, J. (2023). Molecular dynamics and multi-spectroscopic of the interaction behaviour between bladder cancer cells and calf thymus DNA with rebeccamycin: Apoptosis through the down regulation of PI3K/AKT signaling pathway. Journal of Fluorescence. https://doi.org/10.1007/s10895-023-03169-4
   Google Scholar
• Marjani, N., Dareini, M., Asadzade-Lotfabad, M., Pejhan, M., Mokaberi, P., Amiri-Tehranizadeh, Z., Saberi, M. R., & Chamani, J. (2022). Evaluation of the binding effect and cytotoxicity assay of 2-Ethyl-5-(4-methylphenyl) pyramido pyrazole ophthalazine trione on calf thymus DNA: Spectroscopic, calorimetric, and molecular dynamics approaches. Luminescence: The Journal of Biological and Chemical Luminescence, 37(2), 310–322. https://doi.org/10.1002/bio.4173
   PubMed Web of Science ®Google Scholar
• Pang, X., Sun, L., Wan, J., Xu, X., Wei, X., Hua, R., Wang, Y., Zhu, M., & Yang, X. (2023). New insights into the binding mechanism of lysozyme by 2-sulfanilamido-4-methylpyrimidine and 3-sulfanilamido-5-methylisoxazole: Density function theory, multispectral techniques and molecular docking. Journal of Luminescence, 255, 119559. https://doi.org/10.1016/j.jlumin.2022.119559
   Web of Science ®Google Scholar
• Patel, R., & Park, S. (2013). An evolving role of piperazine moieties in drug design and discovery. Mini Reviews in Medicinal Chemistry, 13(11), 1579–1601. https://doi.org/10.2174/13895575113139990073
   PubMed Web of Science ®Google Scholar
• Pradeep Kumar, C. B., Prashanth, M. K., Mohana, K. N., Jagadeesha, M. B., Raghu, M. S., Lokanath, N. K., Mahesha, Kumar, K. Y.. (2020). Protection of mild steel corrosion by three new quinazoline derivatives: Experimental and DFT studies. Surfaces and Interfaces, 18, 100446. https://doi.org/10.1016/j.surfin.2020.100446
   Web of Science ®Google Scholar
• Pradeep Kumar, C. B., Prathibha, B. S., Prasad, K. N. N., Raghu, M. S., Prashanth, M. K., Jayanna, B. K., Alharthi, F. A., Chandrasekhar, S., Revanasiddappa, H. D., & Kumar, K. Y. (2021a). Click synthesis of 1,2,3-triazole based imidazoles: Antitubercular evaluation, molecular docking and HSA binding studies. Bioorganic & Medicinal Chemistry Letters, 36, 127810. https://doi.org/10.1016/j.bmcl.2021.127810
   PubMed Web of Science ®Google Scholar
• Pradeep Kumar, C. B., Raghu, M. S., Prasad, K. N. N., Chandrasekhar, S., Jayanna, B. K., Alharthi, F. A., Prashanth, M. K., & Yogesh Kumar, K. (2021b). Investigation of biological activity of 2,3-disubstituted quinazolin-4(1H)-ones against Mycobacterium tuberculosis and DNA via docking, spectroscopy and DFT studies. New Journal of Chemistry, 45(1), 403–414. https://doi.org/10.1039/D0NJ03800H
   Web of Science ®Google Scholar
• Pradeep Kumar, C. B., Raghu, M. S., Prathibha, B. S., Prashanth, M. K., Kanthimathi, G., Kumar, K. Y., Parashuram, L., & Alharthi, F. A. (2021c). Discovery of a novel series of substituted quinolines acting as anticancer agents and selective EGFR blocker: Molecular docking study. Bioorganic & Medicinal Chemistry Letters, 44, 128118. https://doi.org/10.1016/j.bmcl.2021.128118
   PubMed Web of Science ®Google Scholar
• Prashanth, M. K., Madaiah, M., Revanasiddappa, H. D., & Amruthesh, K. N. (2013). Synthesis, characterization, and BSA binding studies of some new benzamides related to schiff base. ISRN Organic Chemistry, 2013, 791591. https://doi.org/10.1155/2013/791591
   PubMedGoogle Scholar
• Prashanth, M. K., & Revanasiddappa, H. D. (2014). Synthesis and antioxidant activity of novel quinazolinones functionalized with urea/thiourea/thiazole derivatives as 5-lipoxygenase inhibitors. Letters in Drug Design & Discovery, 11(6), 712–720. https://doi.org/10.2174/1570180811666131230235157
   Web of Science ®Google Scholar
• Raghu, M. S., Y., Kumar, K., Veena, K., Pradeep Kumar, C. B., Almalki, A. S., Mani, G., Alasmary, F. A., & Prashanth, M. K. (2022). Synthesis, characterization, antimicrobial and interaction studies of pteridines with human serum albumin: A combined multi-spectroscopic and computational study. Journal of Molecular Structure, 1250, 131857. https://doi.org/10.1016/j.molstruc.2021.131857
   Web of Science ®Google Scholar
• Raghu, M. S., Pradeep Kumar, C. B., Yogesh Kumar, K., Prashanth, M. K., & Jayanna, B. K. (2019). Synthesis, characterization, and biological evaluation of novel 3-(4-chlorophenyl)-2-(substituted)quinazolin-4(3H)-one derivatives as multitarget anti-inflammatory agents. Journal of Heterocyclic Chemistry, 56(7), 2046–2051. https://doi.org/10.1002/jhet.3585
   Web of Science ®Google Scholar
• Rathi, A. K., Syed, R., Shin, H. S., & Patel, R. V. (2016). Piperazine derivatives for therapeutic use: A patent review (2010-present). Expert Opinion on Therapeutic Patents, 26(7), 777–797. https://doi.org/10.1080/13543776.2016.1189902
   PubMed Web of Science ®Google Scholar
• Raveesha, R., Yogesh Kumar, K., Raghu, M. S., Benaka Prasad, S. B., Alsalme, A., Krishnaiah, P., & Prashanth, M. K. (2022). Synthesis, in silico ADME, toxicity prediction and molecular docking studies of N-substituted [1,2,4]triazolo[4,3-a]pyrazine derivatives as potential anticonvulsant agents. Journal of Molecular Structure, 1255, 132407. https://doi.org/10.1016/j.molstruc.2022.132407
   Web of Science ®Google Scholar
• Rezaeinasab, R., Jafari, E., & Khodarahmi, G. (2022). Quinazolinone-based hybrids with diverse biological activities: A mini-review. Journal of Research in Medical Sciences: The Official Journal of Isfahan University of Medical Sciences, 27, 68. https://doi.org/10.4103/jrms.jrms_1025_21
   PubMed Web of Science ®Google Scholar
• Sattar, K. M., Sara, E. T., Melika, K. V., Jouyaeian, P., Mokaberi, P., Yazdyani, H., Amiri-Tehranizadeh, Z., Saberi, M. R., & Chamani, J. (2022). Novel perspective into the interaction behavior study of the cyanidin with human serum albumin-holo transferrin complex: Spectroscopic, calorimetric and molecular modeling approaches. Journal of Molecular Liquids, 356, 119042. https://doi.org/10.1016/j.molliq.2022.119042
   Web of Science ®Google Scholar
• Shafaei, P., Rastegari, A. A., Fouladgar, M., Taheri-Kafrani, A., & Moshtaghie, A. A. (2022). Insight into the binding of alpha-linolenic acid (ALA) on human serum albumin using spectroscopic and molecular dynamics (MD) studies. Process Biochemistry, 122, 95–104. https://doi.org/10.1016/j.procbio.2022.09.022
   Web of Science ®Google Scholar
• Sharifi-Rad, A., Mehrzad, J., Darroudi, M., Saberi, M. R., & Chamani, J. (2021). Oil-in-water nanoemulsions comprising Berberine in olive oil: Biological activities, binding mechanisms to human serum albumin or holo-transferrin and QMMD simulations. Journal of Biomolecular Structure & Dynamics, 39(3), 1029–1043. https://doi.org/10.1080/07391102.2020.1724568
   PubMed Web of Science ®Google Scholar
• Sleep, D., Cameron, J., & Evans, L. R. (2013). Albumin as a versatile platform for drug half-life extension. Biochimica et Biophysica Acta, 1830(12), 5526–5534. https://doi.org/10.1016/j.bbagen.2013.04.023
   PubMed Web of Science ®Google Scholar
• Taheri, R., Hamzkanlu, N., Rezvani, Y., Niroumand, S., Samandar, F., Amiri-Tehranizadeh, Z., Saberi, M. R., & Chamani, J. (2022). Exploring the HSA/DNA/lung cancer cells binding behavior of p-Synephrine, a naturally occurring phenyl ethanol amine with anti-adipogenic activity: Multi spectroscopic, molecular dynamic and cellular approaches. Journal of Molecular Liquids, 368, 120826. https://doi.org/10.1016/j.molliq.2022.120826
   Web of Science ®Google Scholar
• Tardioli, S., Lammers, I., Jan-Hein, H., Ariese, F., Van der Zwan, G., & Gooijer, C. (2012). Complementary fluorescence and phosphorescence study of the interaction of brompheniramine with human serum albumin. The Journal of Physical Chemistry. B, 116(24), 7033–7039. https://doi.org/10.1021/jp300055c
   PubMed Web of Science ®Google Scholar
• Veena, K., Raghu, M. S., Yogesh Kumar, K., Dahlous, K. A., Awadh Bahajjaj, A. A., Mani, G., Byong-Hun, J., & Prashanth, M. K. (2022). Development of penipanoid C-inspired 2-benzoyl-1-methyl-2, 3-dihydroquinazolin-4 (1H)-one derivatives as potential EGFR inhibitors: Synthesis, anticancer evaluation and molecular docking study. Journal of Molecular Structure, 1258, 132674. https://doi.org/10.1016/j.molstruc.2022.132674
   Web of Science ®Google Scholar
• Veena, K., Raghu, M. S., Yogesh Kumar, K., Pradeep Kumar, C. B., Alharti, F. A., Prashanth, M. K., & Jeon, B. H. (2022). Design and synthesis of novel benzimidazole linked thiazole derivatives as promising inhibitors of drug-resistant tuberculosis. Journal of Molecular Structure, 1269, 133822. https://doi.org/10.1016/j.molstruc.2022.133822
   Web of Science ®Google Scholar
• Wang, D., & Gao, F. (2013). Quinazoline derivatives: Synthesis and bioactivities. Chemistry Central Journal, 7(1), 95. https://doi.org/10.1186/1752-153X-7-95
   PubMedGoogle Scholar
• Wang, Y., Zhu, M., Shi, T., Ma, X., Wu, X., Li, Q. X., & Hua, R. (2022). Construction of a novel fluorescent nanocarrier with double hollow shells for pH-controlled release of imidacloprid and its distribution and transport in bok choy. Ecotoxicology and Environmental Safety, 246, 114132. https://doi.org/10.1016/j.ecoenv.2022.114132
   PubMed Web of Science ®Google Scholar
• Wu, F., Ji, Z., Wu, Y., & Wan, X. (2006). Interaction of ICT receptor with serum albumins in aqueous buffer. Chemical Physics Letters, 424(4–6), 387–393. https://doi.org/10.1016/j.cplett.2006.05.019
   Web of Science ®Google Scholar
• Xiang, Y., & Wu, F. (2010). Study of the interaction between a new Schiff-base complex and bovine serum albumin by fluorescence spectroscopy. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 77(2), 430–436. https://doi.org/10.1016/j.saa.2010.06.010
   PubMed Web of Science ®Google Scholar
• Yamasaki, K., Chuang, V. T., Maruyama, T., & Otagiri, M. (2013). Albumin-drug interaction and its clinical implication. Biochimica et Biophysica Acta, 1830(12), 5435–5443. https://doi.org/10.1016/j.bbagen.2013.05.005
   PubMed Web of Science ®Google Scholar
• Yogesh Kumar, K., Pradeep Kumar, C. B., Prasad, K. N. N., Jeon, B. H., Alsalme, A., & Prashanth, M. K. (2022). Microwave-assisted N-alkylation of amines with alcohols catalyzed by MnCl2: Anticancer, docking, and DFT studies. Archiv der Pharmazie, 355(5), e2100443. https://doi.org/10.1002/ardp.202100443
   PubMed Web of Science ®Google Scholar
• Yue, Y., Zhang, Y., Zhou, L., Qin, J., & Chen, X. (2008). In vitro study on the binding of herbicide glyphosate to human serum albumin by optical spectroscopy and molecular modelling. Journal of Photochemistry and Photobiology. B, Biology, 90(1), 26–32. https://doi.org/10.1016/j.jphotobiol.2007.10.003
   PubMed Web of Science ®Google Scholar
• Zhu, M., Pang, X., Wan, J., Xu, X., Wei, X., Hua, R., Zhang, X., Wang, Y., & Yang, Y. (2022). Potential toxic effects of sulphonamides antibiotics: Molecular modelling, multiple-spectroscopy techniques and density functional theory calculations. Ecotoxicology and Environmental Safety, 243, 113979. https://doi.org/10.1016/j.ecoenv.2022.113979
   PubMed Web of Science ®Google Scholar
• Zhu, M., Sun, L., Liu, X., Pang, X., Fan, F., Yang, X., Hua, R., & Wang, R. (2023). A reversible CHEF-based NIR fluorescent probe for sensing Hg2+ and its multiple application in environmental media and biological systems. The Science of the Total Environment, 874, 162460. https://doi.org/10.1016/j.scitotenv.2023.162460
   PubMed Web of Science ®Google Scholar
• Zhu, M., Zhao, Z., Huang, Y., Fan, F., Wang, F., Li, W., Wu, X., Hua, R., & Wang, Y. (2021). Hydrazine exposure: A near-infrared ICT-based fluorescent probe and its application in bioimaging and sewage analysis. The Science of the Total Environment, 759, 143102. https://doi.org/10.1016/j.scitotenv.2020.143102
   PubMed Web of Science ®Google Scholar
• Zhu, M., Zhao, Z., Liu, X., Chen, P., Fan, P., Wu, X., Hua, R., & Wang, Y. A. (2021). novel near-infrared fluorometric method for point-of-care monitoring of Fe2+ and its application in bioimaging. Journal of Hazardous Materials, 406, 124767. https://doi.org/10.1016/j.jhazmat.2020.124767
   PubMed Web of Science ®Google Scholar