1,310
Views
2
CrossRef citations to date
0
Altmetric
Research Paper

Design, synthesis, molecular modelling and antitumor evaluation of S-glucosylated rhodanines through topo II inhibition and DNA intercalation

ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, & ORCID Icon
Article: 2163996 | Received 15 Nov 2022, Accepted 24 Dec 2022, Published online: 11 Jan 2023

References

  • Ferlay J, Colombet M, Soerjomataram I, Parkin DM, Piñeros M, Znaor A, Bray F. Cancer statistics for the year 2020: an overview. Int J Cancer. 2021;149(4):778–789.
  • Housman G, Byler S, Heerboth S, Lapinska K, Longacre M, Snyder N, Sarkar S. Drug resistance in cancer: an overview. Cancers. 2014; 6(3):1769–1792.
  • Zhuo S-T, Li C-Y, Hu M-H, Chen S-B, Yao P-F, Huang S-L, Ou T-M, Tan J-H, An L-K, Li D, et al. Synthesis and biological evaluation of benzo[a]phenazine derivatives as a dual inhibitor of topoisomerase I and II. Org Biomol Chem. 2013;11(24):3989–4005.
  • Bailly C. Contemporary challenges in the design of topoisomerase II inhibitors for cancer chemotherapy. Chem Rev. 2012;112(7):3611–3640.
  • Pommier Y. Drugging topoisomerases: lessons and challenges. ACS Chem Biol. 2013;8(1):82–95.
  • Pommier Y, Sun Y, Huang SN, Nitis JL. Roles of eukaryotic topoisomerases in transcription, replication and genomic stability. Nat Rev Mol Cell Biol. 2016;17(11):703–721.
  • Capranico G, Marinello J, Chillemi G. Type I DNA Topoisomerases. J Med Chem. 2017;60(6):2169–2192.
  • Nitiss JL. Targeting DNA topoisomerase II in cancer chemotherapy. Nat Rev Cancer. 2009;9(5):338–350.
  • Christodoulou MS, Zarate M, Ricci F, Damia G, Pieraccini S, Dapiaggi F, Sironi M, Lo Presti L, García-Argáez AN, Dalla Via L, et al. 4-(1,2-Diarylbut-1-en-1-yl)isobutyranilide derivatives as inhibitors of topoisomerase II. Eur J Med Chem. 2016; 118:79–89.
  • Christodoulou MS, Calogero F, Baumann M, García-Argáez AN, Pieraccini S, Sironi M, Dapiaggi F, Bucci R, Broggini G, Gazzola S, et al. Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2. Eur J Med Chem. 2015; 92:766–775.
  • Yao BL, Mai YW, Chen SB, Hua HT, Yao PF, Ou TM, Tan JH, Wang HG, Li D, Huang SL, et al. Design, synthesis and biological evaluation of novel 7-alkylamino substituted benzo[a]phenazin derivatives as dual topoisomerase I/II inhibitors. Eur J Med Chem. 2015; 92:540–553.
  • Kucukguzel SG, Oruc EE, Rollas S, Sahin F, Ozbek A. Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem. 2002;37(3):197–206.
  • Gualtieri M, Bastide L, Villain-Guillot P, Michaux-Charachon S, Latouche J, Leonetti J-P. In vitro activity of a new antibacterial rhodanine derivative against Staphylococcus epidermidis biofilms. J Antimicrob Chemother. 2006;58(4):778–783.
  • Sim MM, Ng SB, Buss AD, Crasta SC, Goh KL, Lee SK. Benzylidene Rhodanines as Novel Inhibitors of UDP-N-Acetylmuramate/l-Alanine Ligase. Bioorg Med Chem Lett. 2002;12(4):697–699.
  • Petrikaite V, Tarasevicius E, Pavilonis A. New ethacridine derivatives as the potential antifungal and antibacterial preparations. Medicina (Kaunas)). 2007;43(8):657–663.
  • Capan G, Ulusoy N, Ergenc N, Kiraz M. New 6-phenylimidazo[2,1-b]thiazole derivatives: synthesis and antifungal activity. Monatsh Chem. 1999;130:1399–1407.
  • Sortino M, Delgado P, Juárez S, Quiroga J, Abonía R, Insuasty B, Nogueras M, Rodero L, Garibotto FM, Enriz RD, et al. Synthesis and antifungal activity of (Z)-5-arylidenerhodanines. Bioorg Med Chem. 2007;15(1):484–494.
  • Ergenc N, Capan G. Synthesis and anticonvulsant activity of new 4- thiazolidone and 4-thiazoline derivatives. Farmaco. 1994;49:133–135.
  • Bhatt JJ, Shah BR, Shah HP, Trivedi PB, Undavia NK, Desai NC. Synthesis of anti‐HIV, anticancer and antitubercular 4‐oxo‐ thiazolidines (III), 2‐imino‐4‐oxo‐thiazolidines (VI) and their 5‐ arylidine derivatives. Indian J Chem, Sect B: Org Chem Incl Med Chem. 1994;33(2):189–192.
  • Barreca ML, Chimirri A, Luca LD, Monforte A, Monforte P, Rao A, Zappala M, Balzarini J, De Clercq E, Pannecouque C, et al. Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-hiv-1 agents. Bioorg Med Chem Lett. 2001;11(13):1793–1796.
  • Ozkirimli S, Kazan F, Tunali Y. Synthesis, antibacterial and antifungal activities of 3-(1,2,4-triazol-3-yl)-4-thiazolidinones. J Enzyme Inhib Med Chem. 2009;24(2):447–452.
  • Chandrappa S, Benaka Prasad SB, Vinaya K, Ananda Kumar CS, Thimmegowda NR, Rangappa KS. Synthesis and in vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-diones. Invest New Drugs. 2008;26(5):437–444.
  • Metwally NH, Abdalla MA, Mosselhi MAN, El-Desoky EA. Synthesis and antimicrobial activity of some new N-glycosides of 2-thioxo-4-thiazolidinone derivatives. Carbohydr Res. 2010;345(9):1135–1141.
  • Murugan R, Anbazhagan S, Sriman Narayanan S. Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3 + 2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives. Eur J Med Chem. 2009;44(8):3272–3279.
  • Bukowski L, Janowiec M, Zwolska-Kwiek Z, Andrzejczyk Z. Some reactions of 2-cyanomethylimidazo[4,5-b]pyridine with isothiocyanates. Antituberculotic activity of the obtained compounds. Pharmazie. 1998;53(6):373–376.
  • Chandrappa S, Kavitha CV, Shahabuddin MS, Vinaya K, Ananda Kumar CS, Ranganatha SR, Raghavan SC, Rangappa KS. Synthesis of 2-(5-((5-(4-chlorophenyl)furan-2-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid derivatives and evaluation of their cytotoxicity and induction of apoptosis in human leukemia cells. Bioorg Med Chem. 2009;17(6):2576–2584.
  • Brooke EW, Davies SG, Mulvaney AW, Okada M, Pompeo F, Sim E, Vickers RJ, Westwood IM. Synthesis and in vitro evaluation of novel small molecule inhibitors of bacterial arylamine N-acetyltransferases (NATs). Bioorg Med Chem Lett. 2003;13(15):2527–2530.
  • Rauter AP, Padilha M, Figueiredo JA, Ismael MI, Justino J, Ferreira H, Ferreira MJ, Rajendran C, Wilkins R, Vaz PD, et al. Bioactive Pseudo‐C‐nucleosides Containing Thiazole, Thiazolidinone, and Tetrazole Rings. J. Carbohydr. Chem. 2005;24(3):275–296.
  • Ergenc N, Capan G, Gunay NS, Ozkirimli S, Gungor M, Ozbey S, Kendi E. Synthesis and hypnotic activity of new 4-thiazolidinone and 2-thioxo-4,5-imidazolidinedione derivatives. Arch Pharm Pharm Med Chem. 1999;332(10):343–347.
  • Verma A, Saraf SK. 4-Thiazolidinone – A biologically active scaffold. Eur J Med Chem. 2008;43(5):897–905.
  • Hardy RW, Marcotrigiano J, Blight KJ, Majors JK, Rice CM. Hepatitis C Virus RNA synthesis in a cell-free system isolated from replicon-containing hepatoma cells. J Virol. 2003;77(3):2029–2037.
  • Mallick SK, Martin AR, Lingard RG. Synthesis and antimicrobial evaluation of some 5-(5-nitrofurylidene)rhodanines, 5-(5-nitrofurylidene)thiazolidine-2,4-diones, and their vinylogs. J Med Chem. 1971;14(6):528–532.
  • Kumar R, Lown JW. Synthesis and antitumor cytotoxicity evaluation of novel thiazole-containing glycosylated polyamides. Eur J Org Chem. 2003;2003(24):4842–4851.
  • Foye WO, Tovivich P. N-glucopyranosyl-5-aralkylidenerhodanines: synthesis and antibacterial and antiviral activities. J Pharm Sci. 1977;66(11):1607–1611.
  • El-Barbary AA, Khodair AI, Pedersen EB, Nielsen C. S-glucosylated hydantoins as new antiviral agents. J Med Chem. 1994;37(1):73–77.
  • Khodair AI, el-Subbagh HI, el-Emam AA. Synthesis of certain 5-substituted 2-thiohydantoin derivatives as potential cytotoxic and antiviral agents. Boll Chim Farm. 1997;136(8):561–567.
  • Al-Obaid AM, el-Subbagh HI, Khodair AI, Elmazar MM. 5-Substituted 2-thiohydantoin analogs as a novel class of antitumor agents. Anticancer Drugs. 1996;7(8):873–880.
  • Khodair AI. Glycosylation of 2-thiohydantoin derivatives. synthesis of some novel S-alkylated and S-glucosylatedhydantoins. Carbohydr Res. 2001;331(4):445–453.
  • Khodair AI. Synthesis of 2-thiohydantoins and their S-glucosylated derivatives as potential antiviral and antitumor agents. Nucleosides Nucleotides Nucleic Acids. 2001;20(9):1735–1750.
  • El-Barbary AA, Khodair AI, Pedersen EB, Nielsen C. Synthesis and antiviral evaluation of hydantoin analogues of azt. Arch Pharm. 1994;327(10):653–655.
  • Khodair AI, El-Ashry EH, Al-Masoudi NAL. Thiohydantoin nucleosides. Synthesis approaches, Monatsh Fur Chem. 2004;135:1061–1079.
  • Khodair AI, Attia AM, Gendy EA, Elshaier YAMM, El-Magd MA. Design, synthesis and cytotoxicity evaluation of some novel of S-glycoside of 2-thioxopyridine and N-glycoside of 2-oxopyridine derivatives as antibreast cancer. J Heterocyclic Chem. 2019;56(6):1733–1747.
  • Khodair AI, Alsafi MA, Nafie MS. Synthesis, molecular modeling and anti-cancer evaluation of a series of quinazoline derivatives. Carbohydr Res. 2019; 486:107832.
  • Khodair AI, Elsafi MA, Al‐Issa SA. Simple and efficient synthesis of novel 3-substituded-2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones and their reactions with alkyl halides and α-glycopyranosyl bromides. J Heterocyclic Chem. 2019;56(9):2358–2368.
  • Attia AM, Khodair AI, Gendy EA, El-Magd MA, Elshaier YAMM. New 2-oxopyridine/2-thiopyridine derivatives tethered to a benzotriazole with cytotoxicity on MCF7 cell lines and with antiviral activities. LDDD. 2020;17(2):124–137.
  • Khodair AI, El-Barbary AA, Imam DR, Kheder NA, Elmalki F, Ben Hadda T. Synthesis, DFT, antiviral, and molecular docking studies of some novel 1,2,4-triazine nucleosides as potential bioactive compounds. Carbohydr Res. 2021; 500:108246.
  • Khodair AI, Bakare SB, Awad MK, Al-Issa SA, Nafie MS. Design, synthesis and computational explorations of novel 2-thiohydantoin nucleosides with cytotoxic activities. J Heterocyclic Chem. 2022;59(4):664–685.
  • Nafie MS, Khodair AI, Hassan HAY, Abd El-Fadeal NM, Bogari HA, Elhady SS, Ahmed SA. Evaluation of 2-thioxoimadazolidin-4-one derivatives as potent anti-cancer agents through apoptosis induction and antioxidant activation: in vitro and in vivo approaches. Molecules. 2021;27(1):83.
  • Elsayed GH, Fahim AM, Khodair AI. Synthesis, anti-cancer activity, gene expression and docking stimulation of 2-thioxoimidazolidin-4-one derivatives. J Mol Struct. 2022;1265:133401.
  • El-Barbary AA, Imam DR, El–Tahawy MMT, El-Hallouty SM, Kheder NA, Khodair AI. Unexpected synthesis, characterization and comutaional details of novel triazine-pyrrole hybrid nucleosides. J Mol Struct. 2023;1272:134182.
  • Zsolnai T. Antimicrobial effect of potential isothiocyanate-formers. 5. Arzneimittelforschung. 1969;19(4):558–572.
  • Werbel LM, Headen N, Elslager EF. 3-Phenylrhodanines as potential antimalarial agents. J Med Chem. 1968;11(2):364–365.
  • Brown FC, Bradsher CK, Bond SM, Grantham RJ. Mildew-Preventing Activity of Rhodanine Derivatives. Ind Eng Chem. 1954;46(7):1508–1512.
  • Takematsu T, Furushima M, Hasegawa Y, Morioka M, Tsuchiyama T. Herbicide containing 2-mercapto-4-keto-5-substituted thiazoline derivatives, JP 47013812. 1972. Google Scholar.
  • Mackie A, Stewart GM. In vitro testing of chemical compounds against vinegar eelworm (Turbatrix aceti) attempted correlation of anthelmintic effect and chemical constitution. Arch Int Pharmacodyn Ther. 1955;102(4):476–486.
  • Moers FG, Goossens JWM, Langhout JPM. Rhodanine complexes of copper(I), palladium(II) and platinum(II). J. Inorg. Nucl. Chem. 1973;35(3):855–859.
  • Brockman RW, Sidwell RW, Arnett G, Shaddix S. Heterocyclic thiosemicarbazones: correlation between structure, inhibition of ribonucleotide reductase, and inhibition of DNA VIRUSES. Proc Soc Exp Biol Med. 1970;133(2):609–614.
  • Foye WO, Lange WE, Feldmann EG. Comparative activities and toxicities II.*: sugar and amino acid derivatives of bis-(4-aminophenyl)-sulfone. J Am Pharm Assoc. 1958;47(11):831–833.
  • Houk KN, Liu F. Holy grails for computational organic chemistry and biochemistry. Acc Chem Res. 2017;50(3):539–543.
  • Kabanda MM, Murulana LC, Ozcan M, Karadag F Quantum chemical studies on the corrosion inhibition of mild steel by some triazoles and benzimidazole derivatives in acidic medium. Int. J. Electrochem. Sci. 2012; 7:5035–5056.
  • Udhayakala P, Jayanthi A, Rajendiran TV. Adsorption and quantum chemical studies on the inhibition potentials of some formazan derivatives. Der Pharma Chem. 2011;3:528–539.
  • Awad MK, Masoud MS, Shaker MA, Ali AE, El-Tahawy MMT. MP2 and DFT theoretical studies of the geometry, vibrational and electronic absorption spectra of 2-aminopyrimidine. Res Chem Intermed. 2013;39(6):2741–2761.
  • Atlam FM, Awad MK, El-Bastawissy EA. Computational simulation of the effect of quantum chemical parameters on the molecular docking of HMG-CoA reductase drugs. J Mol Struct. 2014;1075:311–326.
  • Khodair AI, Bakare SB, Awad MK, Nafie MS. Design, synthesis, DFT, molecular modelling studies and biological evaluation of novel 3-substituted (E)-5-(arylidene)-1-methyl-2-thioxoimidazolidin-4-ones with potent cytotoxic activities against breast MCF-7, liver HepG2, and lung A549. J Mol Struct. 2021;1229:129805.
  • Elbadawi MM, Khodair AI, Awad MK, Kassab SE, Elsaady MT, KRA, Abdellatif Design, synthesis and biological evaluation of novel thiohydantoin derivatives as antiproliferative agents: a combined experimental and theoretical assessments. J. Mol. Struct. 2022;1249:131574.
  • Khodair AI, Awad MK, Gesson J-P, Elshaier YAMM. New N-ribosides and N-mannosides of rhodanine derivatives with anticancer activity on leukemia cell line: Design, synthesis, DFT and molecular modelling studies. Carbohydr Res. 2020;487:107894.
  • Awad MK, Abdel-Aal MF, Atlam FM, Hekal HA. Molecular docking, molecular modeling, vibrational and biological studies of some new heterocyclic α-aminophosphonates. Spectrochim Acta A Mol Biomol Spectrosc. 2019;206:78–88.
  • El-Borai MA, Awad MK, Rizk HF, Atlam FM. Design, synthesis and docking study of novel imidazolyl pyrazolopyridine derivatives as antitumor agents targeting MCF7 cell line. COS. 2018;15(2):275–285.
  • Khodair AI, Gesson J-P. A new approach for the N- and S-galactosylation of 5-arylidene-2-thioxo-4-thiazolidinones. Carbohydr. Res. 2011; 346:2831–2337.
  • Khodair AI. Convenient synthesis of 2-arylidene-5H-thiazolo[2,3-b]quinazoline-3,5[2H]-diones and their benzoquinazoline derivatives. J. Heterocycl. Chem. 2002;39(6):1153–1160.
  • Zhou J-F, Zhu F-X, Song Y-Z, Zhu Y-L. Synthesis of 5-arylalkylidenerhodanines catalyzed by tetrabutylammonium bromine in water under microwave irradiation. ARKIVOC. 2007;2006(14):175–180.
  • Chowdhry MM, Mingos DMP, White AJP, Williams DJ. Syntheses and characterization of 5-substituted hydantoins and thiazolines—implications for crystal engineering of hydrogen bonded assemblies. Crystal structures of 5-(2-pyridylmethylene)-hydantoin, 5-(2-pyridylmethylene)-2-thiohydantoin, 5-(2-pyridylmethylene)thiazolidine-2,4-dione, 5-(2-pyridylmethylene)rhodanine and 5-(2-pyridylmethylene)pseudothiohydantoin. J Chem Soc Perkin Trans 1. 2000;(20):3495–3504.
  • Vorbruggen H, Krolikiewicz K, Bennua B. Nucleoside syntheses, XXII1) Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem Ber. 1981;114(4):1234–1255.
  • Walter W, Randau G. Über die oxydationsprodukte von thiocarbonsäureamiden, VIII oxydationsreaktionen an N-acyl-thioamiden. Justus Liebigs Ann Chem. 1965;681(1):55–63.
  • Becke AD. Density-functional thermochemistry II: the effect of the Perdew-Wang generalized-gradient correlation correction. J. Chem. Phys. 1992;97(12):9173–9177.
  • Becke AD. A new mixing of Hartree–Fock and local density-functional theories. J Chem Phys. 1993;98(2):1372–1377.
  • Lee C, Yang W, Parr RG. Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Phys Rev B Condens Matter. 1988;37(2):785–789.
  • Frisch MJ. Gaussian 09, revision B.01, Pittsburgh: Gaussian, Inc.; 2009. https://gaussian.com/g09citation/
  • Senet PL. Chemical harnesses of atoms and molecules from frontier orbitals. Chem Phys Lett. 1997;275(5-6):527–532.
  • Geerlings P, De Proft F, Langenaeker W. De Proft, F. Theory, conceptual density functional. Chem Rev. 2003;103(5):1793–1873.
  • Pu SL. Materials for nonlinear optics-chemical perspectives, chapter 22: observing high second harmonic generation and control of molecular alignment in one dimension. ACS Symp. Ser. 1991;455:331–342.
  • Scrocco E, Tomasi J. Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials. Adv Quant Chem. 1978;11:115–193.
  • Girard ML, Dreux C. Possibilités réactionnelles et structurales de dérivés de la thiazolidine. I.-addition, substitution, Hydrolyse. Bull Soc Chim Fr. 1968;3461(2):34.
  • Nafie MS, Tantawy MA, Elmgeed GA. Screening of different drug design tools to predict the mode of action of steroidal derivatives as anti-cancer agents. Steroids. 2019;152:108485.
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983;65(1-2):55–63.
  • Tantawy ES, Amer AM, Mohamed EK, Abd Alla MM, Nafie MS. Synthesis, characterization of some pyrazine derivatives as anti-cancer agents: In vitro and in Silico approaches. J Mol Struct. 2020;1210:128013.
  • Nafie MS, Amer AM, Mohamed AK, Tantawy ES. Discovery of novel pyrazolo[3,4-b]pyridine scaffold-based derivatives as potential PIM-1 kinase inhibitors in breast cancer MCF-7 cells. Bioorg Med Chem. 2020;28(24):115828.
  • Khalifa MM, Al-Karmalawy AA, Elkaeed EB, Nafie MS, Tantawy MA, Eissa IH, Mahdy HA. Topo II inhibition and DNA intercalation by new phthalazine-based derivatives as potent anticancer agents: design, synthesis, anti-proliferative, docking, and in vivo studies. J Enzyme Inhib Med Chem. 2022;37(1):299–314.
  • Boraei ATA, Eltamany EH, Ali IAI, Gebriel SM, Nafie MS. Synthesis of new substituted pyridine derivatives as potent anti-liver cancer agents through apoptosis induction: In vitro, in vivo, and in silico integrated approaches. Bioorg Chem. 2021;111:104877.
  • Dawood KM, Raslan MA, Abbas AA, Mohamed BE, Abdellattif MH, Nafie MS, Hassan MK. Novel bis-thiazole derivatives: synthesis and potential cytotoxic activity through apoptosis with molecular docking approaches. Front Chem. 2021;9:694870.
  • Gad EM, Nafie MS, Eltamany EH, Hammad MSAG, Barakat A, Boraei ATA. Discovery of new apoptosis-inducing agents for breast cancer based on ethyl 2-amino-4,5,6,7-tetra hydrobenzo[b]thiophene-3-carboxylate: synthesis, in vitro, and in vivo activity evaluation. Molecules. 2020;25(11):2523.
  • Tantawy MA, Shaheen S, Kattan S, Alelwani SW, Barnawi W, Elmgeed IO, Nafie GA, Cytotoxicity MS. In silico predictions and molecular studies for androstane heterocycle compounds revealed potential antitumor agent against lung cancer cells. J. Biomol. Struct. Dyn. 2020;40(10):4352–4365.
  • ElZahabi HSA, Nafie MS, Osman D, Elghazawy NH, Soliman DH, EL-Helby AAH, Arafa RK. Design, synthesis and evaluation of new quinazolin-4-one derivatives as apoptotic enhancers and autophagy inhibitors with potent antitumor activity. Eur J Med Chem. 2021;222:113609.
  • Eltamany EE, Elhady SS, Ahmed HA, Badr JM, Noor AO, Ahmed SA, Nafie MS. Chemical profiling, antioxidant, cytotoxic activities and molecular docking simulation of carrichtera annua DC. (Cruciferae). Antioxidants. 2020;9(12):1286.
  • Kishk SM, Kishk RM, Yassen ASA, Nafie MS, Nemr NA, ElMasry G, Al-Rejaie S, Simons C. Molecular insights into human transmembrane protease serine-2 (tmps2) inhibitors against sars-cov2: homology modelling, molecular dynamics, and docking studies. Molecules. 2020;25(21):5007.
  • Nafie MS, Boraei ATA. Exploration of novel VEGFR2 tyrosine kinase inhibitors via design and synthesis of new alkylated indolyl-triazole Schiff bases for targeting breast cancer. Bioorg Chem. 2022;122:105708.