Abstract
Increased rate of emergence of cancer cases has led to increased demand of new molecules that have low toxicity profile and high efficiency. Therefore, in pursuit of new molecules scientists came across quinoline, a privileged scaffold that has been associated with multiple biological activities like antiviral, antibacterial, antimalarial, antifungal, antitubercular, antileishmanial, anti-inflammatory, anti-HIV, and anticancer. This multifarious profile helped quinoline to gain attention of researchers to develop new anticancer moieties by sequential modification of the substituents attached to it. This chapter provides brief knowledge about the recent developments of quinoline derivatives as anticancer drugs, which includes structure activity relationship, molecular docking studies and their mechanism. Therefore, this compilation could assist the global researchers to develop novel and potent quinolone-based therapeutics to treat various cancerous conditions.
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References
Almansour AI, Arumugam N, Suresh Kumar R, Mahalingam SM, Sau S, Bianchini G, Menéndez JC, Altaf M, Ghabbour HA (2017) Design, synthesis and antiproliferative activity of decarbonyl luotonin analogues. Eur J Med Chem 138:932–941. https://doi.org/10.1016/J.EJMECH.2017.07.027
Alonso C, Fuertes M, Martín-Encinas E, Selas A, Rubiales G, Tesauro C, Knudssen BK, Palacios F (2018) Novel topoisomerase I inhibitors. Syntheses and biological evaluation of phosphorus substituted quinoline derivates with antiproliferative activity. Eur J Med Chem 149:225–237. https://doi.org/10.1016/J.EJMECH.2018.02.058
Antoni F, Bause M, Scholler M, Bauer S, Stark SA, Jackson SM, Manolaridis I, Locher KP, König B, Buschauer A, Bernhardt G (2020) Tariquidar-related triazoles as potent, selective and stable inhibitors of ABCG2 (BCRP). Eur J Med Chem 191:112133. https://doi.org/10.1016/J.EJMECH.2020.112133
Chen C, Hou X, Wang G, Pan W, Yang X, Zhang Y, Fang H (2017) Design, synthesis and biological evaluation of quinoline derivatives as HDAC class I inhibitors. Eur J Med Chem 133:11–23. https://doi.org/10.1016/J.EJMECH.2017.03.064
Cheung WY, Le LW, Zimmermann C (2009) Symptom clusters in patients with advanced cancers. Support Care Cancer 17:1223–1230. https://doi.org/10.1007/s00520-009-0577-7
Crespo I, Giménez-Dejoz J, Porté S, Cousido-Siah A, Mitschler A, Podjarny A, Pratsinis H, Kletsas D, Parés X, Ruiz FX, Metwally K, Farrés J (2018) Design, synthesis, structure-activity relationships and X-ray structural studies of novel 1-oxopyrimido[4,5-c]quinoline-2-acetic acid derivatives as selective and potent inhibitors of human aldose reductase. Eur J Med Chem 152:160–174. https://doi.org/10.1016/J.EJMECH.2018.04.015
Ge R, Zhao Q, Xie Z, Lu L, Guo Q, Li Z, Zhao L (2016) Synthesis and biological evaluation of 6-fluoro-3-phenyl-7-piperazinyl quinolone derivatives as potential topoisomerase I inhibitors. Eur J Med Chem 122:465–474. https://doi.org/10.1016/J.EJMECH.2016.06.054
Hauguel C, Ducellier S, Provot O, Ibrahim N, Lamaa D, Balcerowiak C, Letribot B, Nascimento M, Blanchard V, Askenatzis L, Levaique H, Bignon J, Baschieri F, Bauvais C, Bollot G, Renko D, Deroussent A, Prost B, Laisne MC, Michallet S, Lafanechère L, Papot S, Montagnac G, Tran C, Alami M, Apcher S, Hamze A (2022) Design, synthesis and biological evaluation of quinoline-2-carbonitrile-based hydroxamic acids as dual tubulin polymerization and histone deacetylases inhibitors. Eur J Med Chem 240:114573. https://doi.org/10.1016/J.EJMECH.2022.114573
He R, Xu B, Ping L, Lv X (2021) Structural optimization towards promising β-methyl-4-acrylamido quinoline derivatives as PI3K/mTOR dual inhibitors for anti-cancer therapy: the in vitro and in vivo biological evaluation. Eur J Med Chem 214:113249. https://doi.org/10.1016/J.EJMECH.2021.113249
Jitender Dev G, Poornachandra Y, Ratnakar Reddy K, Naresh Kumar R, Ravikumar N, Krishna Swaroop D, Ranjithreddy P, Shravan Kumar G, Nanubolu JB, Ganesh Kumar C, Narsaiah B (2017) Synthesis of novel pyrazolo[3,4-b]quinolinyl acetamide analogs, their evaluation for antimicrobial and anticancer activities, validation by molecular modeling and CoMFA analysis. Eur J Med Chem 130:223–239. https://doi.org/10.1016/J.EJMECH.2017.02.052
John SKP, George S, Primrose JN, Fozard JBJ (2011) Symptoms and signs in patients with colorectal cancer. Color Dis 13:17–25. https://doi.org/10.1111/j.1463-1318.2010.02221.x
Joshi PV, Sayed AA, RaviKumar A, Puranik VG, Zinjarde SS (2017) 4-phenyl quinoline derivatives as potential serotonin receptor ligands with antiproliferative activity. Eur J Med Chem 136:246–258. https://doi.org/10.1016/J.EJMECH.2017.05.002
Khelifi I, Naret T, Renko D, Hamze A, Bernadat G, Bignon J, Lenoir C, Dubois J, Brion JD, Provot O, Alami M (2017) Design, synthesis and anticancer properties of IsoCombretaQuinolines as potent tubulin assembly inhibitors. Eur J Med Chem 127:1025–1034. https://doi.org/10.1016/J.EJMECH.2016.11.012
Khelifi I, Naret T, Hamze A, Bignon J, Levaique H, Garcia Alvarez MC, Dubois J, Provot O, Alami M (2019) N,N-bis-heteroaryl methylamines: potent anti-mitotic and highly cytotoxic agents. Eur J Med Chem 168:176–188. https://doi.org/10.1016/J.EJMECH.2019.02.038
Krstulović L, Stolić I, Jukić M, Opačak-Bernardi T, Starčević K, Bajić M, Glavaš-Obrovac L (2017) New quinoline-arylamidine hybrids: synthesis, DNA/RNA binding and antitumor activity. Eur J Med Chem 137:196–210. https://doi.org/10.1016/J.EJMECH.2017.05.054
Kwak SH, Shin S, Lee JH, Shim JK, Kim M, Lee SD, Lee A, Bae J, Park JH, Abdelrahman A, Müller CE, Cho SK, Kang SG, Bae MA, Yang JY, Ko H, Goddard WA, Kim YC (2018) Synthesis and structure-activity relationships of quinolinone and quinoline-based P2X7 receptor antagonists and their anti-sphere formation activities in glioblastoma cells. Eur J Med Chem 151:462–481. https://doi.org/10.1016/J.EJMECH.2018.03.023
Kwon S, Lee Y, Jung Y, Kim JH, Baek B, Lim B, Lee J, Kim I, Lee J (2018) Mitochondria-targeting indolizino[3,2-c]quinolines as novel class of photosensitizers for photodynamic anticancer activity. Eur J Med Chem 148:116–127. https://doi.org/10.1016/J.EJMECH.2018.02.016
Lee HY, Chang CY, Su CJ, Huang HL, Mehndiratta S, Chao YH, Hsu CM, Kumar S, Sung TY, Huang YZ, Li YH, Yang CR, Liou JP (2016) 2-(Phenylsulfonyl)quinoline N-hydroxyacrylamides as potent anticancer agents inhibiting histone deacetylase. Eur J Med Chem 122:92–101. https://doi.org/10.1016/J.EJMECH.2016.06.023
Li W, Shuai W, Sun H, Xu F, Bi Y, Xu J, Ma C, Yao H, Zhu Z, Xu S (2019) Design, synthesis and biological evaluation of quinoline-indole derivatives as anti-tubulin agents targeting the colchicine binding site. Eur J Med Chem 163:428–442. https://doi.org/10.1016/J.EJMECH.2018.11.070
Liu M, Hou Y, Yin W, Zhou S, Qian P, Guo Z, Xu L, Zhao Y (2016a) Discovery of a novel 6,7-disubstituted-4-(2-fluorophenoxy)quinolines bearing 1,2,3-triazole-4-carboxamide moiety as potent c-Met kinase inhibitors. Eur J Med Chem 119:96–108. https://doi.org/10.1016/J.EJMECH.2016.04.035
Liu J, Nie M, Wang Y, Hu J, Zhang F, Gao Y, Liu Y, Gong P (2016b) Design, synthesis and structure-activity relationships of novel 4-phenoxyquinoline derivatives containing 1,2,4-triazolone moiety as c-Met kinase inhibitors. Eur J Med Chem 123:431–446. https://doi.org/10.1016/J.EJMECH.2016.07.059
Ma CC, Zhang CM, Tang LQ, Liu ZP (2018) Discovery of novel quinazolinone derivatives as high potent and selective PI3Kδ and PI3Kδ/γ inhibitors. Eur J Med Chem 151:9–17. https://doi.org/10.1016/J.EJMECH.2018.03.068
Nippu BN, Sandeep Kumar Jain R, Rahman A, Kumaraswamy HM, Satyanarayan ND (2022) Design and synthesis of novel tetrazolo quinoline bridged isatin derivatives as potential anticancer leads against MIA PaCa-2 human pancreatic cancer cell line. J Mol Struct 1263:133103. https://doi.org/10.1016/J.MOLSTRUC.2022.133103
Omidkhah N, Hadizadeh F, Abnous K, Ghodsi R (2022) Synthesis, structure activity relationship and biological evaluation of a novel series of quinoline–based benzamide derivatives as anticancer agents and histone deacetylase (HDAC) inhibitors. J Mol Struct 1267:133599. https://doi.org/10.1016/J.MOLSTRUC.2022.133599
Palluotto F, Sosic A, Pinato O, Zoidis G, Catto M, Sissi C, Gatto B, Carotti A (2016) Quinolino[3,4-b]quinoxalines and pyridazino[4,3-c]quinoline derivatives: synthesis, inhibition of topoisomerase IIα, G-quadruplex binding and cytotoxic properties. Eur J Med Chem 123:704–717. https://doi.org/10.1016/J.EJMECH.2016.07.063
Perin N, Nhili R, Cindrić M, Bertoša B, Vušak D, Martin-Kleiner I, Laine W, Karminski-Zamola G, Kralj M, David-Cordonnier MH, Hranjec M (2016) Amino substituted benzimidazo[1,2-a]quinolines: Antiproliferative potency, 3D QSAR study and DNA binding properties. Eur J Med Chem 122:530–545. https://doi.org/10.1016/J.EJMECH.2016.07.007
Qin QP, Wang ZF, Huang XL, Tan MX, Zou BQ, Liang H (2019) Strong in vitro and vivo cytotoxicity of novel organoplatinum(II) complexes with quinoline-coumarin derivatives. Eur J Med Chem 184:111751. https://doi.org/10.1016/J.EJMECH.2019.111751
Shaikh SKJ, Kamble RR, Somagond SM, Devarajegowda HC, Dixit SR, Joshi SD (2017) Tetrazolylmethyl quinolines: design, docking studies, synthesis, anticancer and antifungal analyses. Eur J Med Chem 128:258–273. https://doi.org/10.1016/J.EJMECH.2017.01.043
Shen WY, Jia CP, Mo AN, Liang H, Chen ZF (2021) Chemodynamic therapy agents cu(II) complexes of quinoline derivatives induced ER stress and mitochondria-mediated apoptosis in SK-OV-3 cells. Eur J Med Chem 223:113636. https://doi.org/10.1016/J.EJMECH.2021.113636
Shobeiri N, Rashedi M, Mosaffa F, Zarghi A, Ghandadi M, Ghasemi A, Ghodsi R (2016) Synthesis and biological evaluation of quinoline analogues of flavones as potential anticancer agents and tubulin polymerization inhibitors. Eur J Med Chem 114:14–23. https://doi.org/10.1016/J.EJMECH.2016.02.069
Soliman MHA, Ali IAI, El-Sakka SSA, Mohamed OESAB (2022) Novel quinoline derivatives as antitumor agents against HepG2 cells: synthesis, characterization, in silico, in vitro and docking studies. J Mol Struct 1254:132325. https://doi.org/10.1016/J.MOLSTRUC.2021.132325
Teng Y, Li X, Ren S, Cheng Y, Xi K, Shen H, Ma W, Luo G, Xiang H (2020) Discovery of novel quinazoline derivatives as potent PI3Kδ inhibitors with high selectivity. Eur J Med Chem 208:112865. https://doi.org/10.1016/J.EJMECH.2020.112865
Zaraei SO, Al-Ach NN, Anbar HS, El-Gamal R, Tarazi H, Tokatly RT, Kalla RR, Munther MA, Wahba MM, Alshihabi AM, Shehata MK, Sbenati RM, Shahin AI, El-Awady R, Al-Tel TH, El-Gamal MI (2022) Design and synthesis of new quinoline derivatives as selective C-RAF kinase inhibitors with potent anticancer activity. Eur J Med Chem 238:114434. https://doi.org/10.1016/J.EJMECH.2022.114434
Zhang J, Lv X, Ma X, Hu Y (2017) Discovery of a series of N-(5-(quinolin-6-yl)pyridin-3-yl)benzenesulfonamides as PI3K/mTOR dual inhibitors. Eur J Med Chem 127:509–520. https://doi.org/10.1016/J.EJMECH.2017.01.016
Zhang L, Zhao J, Zhang B, Lu T, Chen Y (2018) Discovery of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives as novel, potent and selective c-met kinase inhibitors: synthesis, SAR study, and biological activity. Eur J Med Chem 150:809–816. https://doi.org/10.1016/J.EJMECH.2018.03.049
Zhou Y, Yan W, Cao D, Shao M, Li D, Wang F, Yang Z, Chen Y, He L, Wang T, Shen M, Chen L (2017) Design, synthesis and biological evaluation of 4-anilinoquinoline derivatives as novel potent tubulin depolymerization agents. Eur J Med Chem 138:1114–1125. https://doi.org/10.1016/J.EJMECH.2017.07.040
Acknowledgments
This work was supported by the research funds under Indian Council of Medical Research (ICMR: BMI/11(04)/2022 and, Council of Scientific and Industrial Research (CSIR: 02(0319)17/EMRII). The contents of this article are solely the responsibility of the authors. The authors are very thankful to Guru Nanak Dev University, Amritsar, India for providing various basic facilities to complete the work.
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All authors declare that they have no conflict of interest. No writing assistance was utilized in the production of this manuscript.
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Kaur, K., Kumar, N., Singh, J.V., Bedi, P.M.S., Singh, H. (2023). Recent Development of Quinoline Derivatives as Anticancer Agents: 2015–2022. In: Rezaei, N. (eds) Cancer Treatment: An Interdisciplinary Approach. Interdisciplinary Cancer Research, vol 2. Springer, Cham. https://doi.org/10.1007/16833_2023_125
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DOI: https://doi.org/10.1007/16833_2023_125
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