A panel of ten cancer lines belonging to seven different cancer types, prostrate (DU145, PC-3), colon (colo-205, HCT-15, 502713), breast (MCF-7), neuroblastoma (IMR-32), liver (Hep-2), ovary (OVCAR-5), and lung cancers (A549), was selected. Delta Sigma Theta Track Jacket. Electrochemical analysis of single nucleotide polymorphisms of p53 gene. Oral cancer screening based on methylation frequency detection in hTERT gene using electrochemical hybridization assay via a multi-electrode chip coupled with ferrocenylnaphthalene diimide. $32.95. Molecular docking analysis of some critical parameters of compounds 5af and elinafide 3 at d(atgcat)2 site of DNAa. 445510. The compound 5b interacted with the DNA site with two hydrogen bonds and a binding energy of 9.45kcal/mol. A prediction of ADME properties was undertaken to understand the exhibited cytotoxicity of the compounds and thereby identify a potential molecule for further development. This is a preview of subscription content, access via your institution, Receive 12 print issues and online access, Get just this article for as long as you need it, Prices may be subject to local taxes which are calculated during checkout. Calcd for C46H32N4O8: C, 71.87; H, 4.20; N, 7.29 Found: C, 71.80; H, 4.16; N, 7.25%. J Med Chem. Curr. Oncol. Monchaud, D., and Teulade-Fichou, M. P. (2008). Centre for Cellular & Molecular Biology (CCMB), India. Org Biomol Chem. 2019;25:86915. provided correct acknowledgement is given. doi:10.1002/tcr.201600134, Tomczyk, M. D., and Walczak, K. Z. 2010;695:185862. Detailed synthetic procedures and characterization data are presented . In addition to medicinal application, the NDIs have potential applications in molecular sensors, organic optoelectronics, photovoltaic cells, and flexible displays. Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, Republic of Korea, c $75.95 $65.95 Sale. Naphthalene diimide (NDI) is an electron-deficient, robust, and planar molecule. TABLE 4. Then the resulting filtrate was concentrated in vacuo and the residue was washed with petroleum ether to remove the unreacted dibromoalkane providing the crude product 8af, which was used for azidation reaction. Molecular docking of compounds 5af and standard elinafide 2atd(atgcat)2 site of DNA revealing intercalation ability. Chem Commun. 2017;25:640411. A mixture of N-3-bromopropyl naphthalimide 8af (1 equiv) and sodium azide (3 equiv) was dissolved in DMF and the resulting mixture was stirred at room temperature. Sato S, Hirano A, Takenaka S. Selective immobilization of double stranded DNA on a gold surface through threading intercalation of a naphthalene diimide having dithiolane moieties. Please enable it to take advantage of the complete set of features! Pirota V, Nadai M, Doria F, Richter S. Naphthalene diimides as multimodal G-quadruplex-selective ligands. Bhosale SV, Jani CH, Langford SJ. Creative Commons Attribution License (CC BY). The G-quadruplex arrangement of 3 end of human telomere inhibits the telomerase activity and can be exploited in the selective inhibition of cancer cell. PubMed To elucidate their potentials as the electron acceptors in all-polymer solar cells, systematic comparisons of the properties among the derivatives are necessary. J. Comput. IR (KBr): 2,954, 1700, 1,670, 1,060cm1. suitable for scintillation, 99%. Izbicka, E., and Tolcher, A. W. (2004). Naphthalene-1-13C 99 atom % 13C; CAS Number: 20526-83-4; Linear Formula: 13CC9H8; find Sigma-Aldrich-493082 MSDS, related peer-reviewed papers, technical documents, similar products & more at Sigma-Aldrich. ChemMedChem. From laser flash photolysis studies, the triplet excited state of N,N'-bis[2-(N-pyridinium)ethyl]-1,4,5,8-naphthalene diimide (NDI-pyr) was found to undergo oxidative quenching with the electron donors . 1995;99:147527. Using chemical canonical SMILES IDs of the selected compounds, the 3D structures were obtained by CORINA classic 3D structure generator server (https://www.mn-am.com/online_demos/corina_demo). Calcd. 19 (14), 16391662. 159, 393422. Cancer, being a disease of our own cells, is lethal with high rate of incidence and mortality. Naphthalimides and analogues as antitumor agents: a review on molecular design, bioactivity and mechanism of action. Chin. Chem Soc Rev. Nat. Unable to load your collection due to an error, Unable to load your delegates due to an error. ADME profiling of compounds was carried out using computational approach. J. V. Medabalmi, M. Sundararajan, V. Singh, M. Baik and H. R. Byon, volume53,pages 415427 (2021)Cite this article. If you want to reproduce the whole article Na2S2O3 solution. Ou T, Lu Y, Tan J, Huang Z, Wong KY, Gu L. G-Quadruplexes: targets in anticancer drug design. MS (ESI): m/z 322 (M+). Wilson WD, Jones RL. Here, we envisaged chemical templates (5af) in which NDI motif is harnessed as a linker in a bis-naphthalimide scaffold. However, a more focused chemical diversification of compounds 5a and 5b to overcome the bioavailability issues could lead to more potent molecules. 1H NMR (200MHz, CDCl3): ppm 1.292.02 (m, 14H), 3.193.28 (m, 2H), 7.338.29 (m, 6H). Calcd for C17H16N4O2: C, 66.22; H, 5.23; N, 18.17 Found: C, 65.98; H, 5.06; N, 18.20%. 2014;174:86979. Cytotoxicity assay of compounds 5af on selected cancer cell lines employing sulforhodamine B (SRB) assay at 105M and 106M concentrations. However, the compounds acted as inhibitor of P-gp, a transporter protein, that could result in decreased bioavailability. Thank you for visiting nature.com. ISSN 1349-0540 (online) 2021 Sep 7;50(17):9845-9998. doi: 10.1039/d0cs00239a. Markush Group. A series of water-soluble 1,4,5,8-naphthalene diimide derivatives has been prepared and their redox and photophysical properties characterized. Steel AB, Heme TM, Tarlov MJ. Thionated naphthalene diimides (NDIs) are promising materials for n-type organic semiconductors; despite their potential, synthetic routes to thionated NDIs are generally lengthy, nonselective, and low yielding and their polymeric analogues have yet to be reported in the literature. Commercially available precursors as well as the solvents were purchased form Sigma Aldrich and used without modifications. Redox-active organic molecules have attracted much attention as alternatives to transition-metal-based electrodes for lithium-ion batteries due to their low cost and large abundance. After cell inoculation, the microtiter plates were incubated at 37C, 5% CO2, 95% air, and 100% relative humidity for 24h prior to addition of experimental drugs. Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents. The interaction of 5a with the DNA molecule resulted through the formation of three hydrogen bonds with bond lengths of 2.673.31 and other noncovalent interactions. Chemistry. : 1347815-21-7; Synonyms: 1,4-Naphthalenedicarbothioamide; Linear Formula: C12H10N2S2; Empirical . svbhosale@unigoa.ac.in, b It is prepared by following the general procedure of 9af from naphthalimide 6 (200mg, 1.015mmol), 1,8-dibromooctane 7e (828mg, 3.045mmol), and K2CO3 (700mg, 5.076mmol) in first step to provide 8e. Adv Protein Chem Struct Biol 92, 162. DNA, the carrier of genetic information, is a prominent target in anticancer drug discovery programs. HeLa cells, and TRAPese kit were obtained from . This was higher than three hydrogen bonds formation exhibited by the standard 3. A percent growth of 45.42 was seen in HOP-92 lung cancer cell line and in case of leukemia, percent growth of 23.93 and 44.91 was observed in cell lines MOLT-4 and SR, respectively. This cationic polyelectrolyte exhibited good solubility in alcohol solvents, transparency in the visible range, self-doping behavior, and good film forming ability. Takeuchi R, Zou T, Wakahara D, Nakano Y, Sato S, Takenaka S. Cyclic naphthalene diimide dimer with a strengthened ability to stabilize dimeric G-quadruplex. The drugs interact with the DNA and its associated proteins in varied manners resulting in cessation of the unbridled cell growth in cancer (Hurley, 2002; Izbicka and Tolcher, 2004; Delgado et al., 2018). These compounds showed a change in melting temperature (Tm) in the range of 0.31.0C at 0, 18, and 36h time intervals (Table 3). HHS Vulnerability Disclosure, Help and JavaScript. AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. New Chemistry Unit (NCU), Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Jakkur PO, Bangalore-560064, India. IR (KBr): 2,948, 1706, 1,660, 1,068cm1. The binding energies of 5.33 and 4.81kcal/mol were shown by compounds 5a and 5e, respectively, with one hydrogen bonds formation. TABLE 3. Mater. doi:10.1002/jcc.21256, Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., et al. TABLE 5. Clipboard, Search History, and several other advanced features are temporarily unavailable. 95 mg of product 5e was obtained as white solid, yield 38%; mp 172C. Copyright Clearance Center request page. If you want to reproduce the whole article 2014;25:154755. Naphthalene diimides as multimodal G-quadruplex-selective ligands. 2005;21:143741. It explores their application toward: supramolecular chemistry; sensors; host-guest complexes for molecular switching devices, such as catenanes and rotaxanes; ion-channels by ligand gating; gelators for sensing aromatic systems; catalysis through anion- interactions; and NDI intercalations with DNA for medicinal applications. Bioorg Med Chem Lett.2007;17:10137. RSC Adv. J. Med. Interaction of aromatic imides with deoxyribonucleic acid. Chem. 2023 Jan 30;13(6):4096-4101. doi: 10.1039/d2ra07771j. 8600 Rockville Pike Chem. Google Scholar. * Anal Sci. The Supplementary Material for this article can be found online at: https://www.frontiersin.org/articles/10.3389/fchem.2021.630357/full#supplementary-material. Solvent-dependent fluorescence behaviour of imide-fused [. Gawronski J, Brzostowska M, Kacprzak K, Kolbon H, Skowronek P. Chirality of aromatic bis-imides from their circular dichroism spectra. * Development of novel alkylating drugs as anticancer agents. Google Scholar. 2018;4:131444. The importance of bis-naphthalimides and naphthalene diimides in the design of new DNA interactive agents is well established with considerable success. contracts here. Results have been given as the mean standard deviation from three determinations and are corrected for the effects of DMSO cosolvent using a linear correction term. Received: 17 November 2020; Accepted: 07 January 2021;Published: 10 March 2021. Amonafide: a potential role in treating acute myeloid leukemia. 29 (12), 17411756. Anal. Rep. 5, 11385. doi:10.1038/srep11385, Pirota, V., Nadai, M., Doria, F., and Richter, S. N. (2019). Both the compounds are promising candidate to be taken further for development by structural diversification. Thus, this review will assist a wide range of readers and researchers including chemists, physicists, biologists, medicinal chemists and materials scientists in understanding the scope for development and applicability of NDI dyes in their respective fields through a discussion of the main properties of NDI derivatives and of the status of emerging applications. (2009). 1998;70:46707. and diagrams provided correct acknowledgement is given. Takenaka S, Yamashita K, Takagi M, Uto Y, Kondo H. DNA sensing on a DNA probe-modified electrode using ferrocenylnaphthalene diimide as the electrochemically active ligand. 475 (2), 373398. Rapid and sensitive assay of K-ras mutations in pancreatic cancer by electrochemical detection with ferrocenyl-naphthalene-diimide. Anal Chim Acta. Spectrophotometric and viscometric studies. J. ADME properties of compounds 5a5f and standards, elinafide (3) and BMSG-SH-3 (4), were calculated using preADMET and swissADME predictor online programs (Lee et al., 2003; Daina et al., 2017). 2002;306:18896. View Price and . A prototype aqueous RFB consisting of [K2-BNDI] and 4-OH-TEMPO was constructed and showed excellent cyclability, high energy and voltage efficiencies. to access the full features of the site or access our, School of Chemical Sciences, Goa University, Taleigao Plateau, Goa-403 206, India, Centre for Advanced Materials and Industrial Chemistry (CAMIC), School of Science, RMIT University, GPO Box 2476, Melbourne, Victoria 3001, Australia, New Chemistry Unit (NCU), Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Jakkur PO, Bangalore-560064, India. and Ph.D. from Baylor College of Medicine, where he was a member of the Alpha Omega Alpha Honor Society. Therefore, we proceeded to synthesize the compounds and study whether the promising docking results could be reflected on the actual DNA denaturation and cytotoxic properties of the compounds. 9:630357. doi: 10.3389/fchem.2021.630357. Anal Biochem. MS (ESI): m/z 280 (M+). First, the compounds 5af were studied for their DNA intercalating ability at d(atgcat)2 site of DNA and compared with the standard 3 (Figure 2). Anal Chem. 2011;83:72906. Spiegel J, Adhikari S, Balasubramanian S. The structure and function of DNA G-quadruplexes. This comprehensive review surveys developments over the past decade in the field of naphthalene diimides (NDIs). A systematic review from 2007 to 2017. Shigeori Takenaka. Advanced Battery Center, KAIST Institute for NanoCentury, Daejeon 34141, Republic of Korea. MS (ESI): m/z 960 (M+23). J Inorg Biochem. ST appreciates the significant contribution made by the researchers who appear in the reference papers of Takenakas group. Drug-induced alterations in DNA melting behavior have been calculated by Tm =Tm (DNA+ 5af)-Tm (DNA alone), where the Tm value for the [5af]-free CT-DNA is 69.2 0.01C. doi: 10.1002/anie.202212623. Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea FIGURE 3. Biochemistry. A naphthalene diimide polymer may help reduce aggregation and crystallization and, thus aid the formation of uniform continuous (i.e. doi:10.1016/j.cclet.2018.09.020, Collie, G. W., Promontorio, R., Hampel, S. M., Micco, M., Neidle, S., and Parkinson, G. N. (2012). The compound 5b exhibited significant activity selectively against non-small cell lung cancer and leukemia cell lines as shown in Table 4. Harahuchi K, Sato S, Habu M, Yada N, Hayakawa M, Takahashi O et al. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Working solutions in aqueous buffer (10mM NaH2PO4/Na2HPO4, 1mM Na2EDTA, pH 7.00 0.01) containing CT-DNA (100M in phosphate) and the 5af (20M) were prepared by addition of concentrated 5af solutions in DMSO to obtain a fixed [5af ]/[DNA] molar ratio of 1:5. Naphthalene Abstract In the pursuit of environmentally friendly energy storage, aqueous organic redox flow batteries (AORFBs) that use naphthalene diimide hold promise for successful application. 2005;77:73049. Purity. Naphthalene diimide-based cages Naphthalene diimide (NDI) derivatives are planar and electron-deficient as well as p-acidic and can be used in anion-p catalysis.11 Typically, NDI derivatives could undergo two rever-sible one-electron reduction under chemical or electrochemical conditions with half-wave potentials of 1.10 V and 1.51 V vs. Sato S, Nojima T, Waki M, Takenaka S. Supramolecular complex formation by -cyclodextrin and ferrocenylnaphthalene diimide-intercalated double stranded DNA and improved electrochemical gene detection. Eur J Org Chem. Sato S, Takenaka S. Linker effect of ferrocenylnaphthalene diimide ligands in the interaction with double stranded DNA. J. Electroanalysis. CAS Rev., 2021,50, 9845 In vitro anticancer screening assay was performed according to NCI procedures in triplicate. (2001). 1H NMR (200MHz, CDCl3): ppm 1.411.87 (m, 24H), 3.393.60 (m, 8H), 7.637.84 (m, 4H), 8.108.30 (m, 8H), 8.58 (d, 4H). Herein, we used perylene diimide (PDI), naphthalene diimide (NDI), and naphthodithiophene diimide (NDTI . Maniam S, Higginbotham HF, Bell TDM, Langford SJ. The binding affinity of most of the compounds was better than 3 with compound 5a exhibiting exceptional binding affinity score of 10.93kcal/mol and inhibition constant of 9.69nM. Harnessing Brightness in Naphthalene Diimides. IR (KBr): 2,948, 1,697, 1,666, 1,155cm1.1H NMR (200MHz, CDCl3): ppm 1.421.85 (m, 8H), 3.373.63 (m, 8H), 7.617.93 (m, 4H), 8.128.29 (m, 8H), 8.58 (d, 4H). FOIA Anal Sci. Herein, a naphthalene diimide-based cathode interlayer (NDI-OH) is synthesized with a facile three-step reaction and used as a cathode interlayer for fullerene and non-fullerene PSCs. An official website of the United States government. Excellent results were obtained, which were better than the standards. for C44H28N4O8: C, 71.35; H, 3.81; N, 7.56 Found: C, 71.30; H, 3.78; N, 7.54%. Markush Class. J. Comput. Copyright Clearance Center request page. Drug-DNA intercalation: from discovery to the molecular mechanism. 100 mg of product 5c was obtained as white solid, yield 39%; mp 156C. Rev. 2019;897:10713. Compounds 5a and 5b provided excellent results for DNA intercalation and G-quadruplex binding, respectively, compared to the standards. The obtained results provided useful insights and two potential molecules were identified for further development. Mitonafide (1) and amonafide (2) exhibited good DNA intercalation properties and were taken up for clinical studies with limited success (Casado et al., 1996; Allen and Lundberg, 2011). Tian T, Chen YQ, Wang SR, Zhou X. G-Quadruplex: a regulator of gene expression and its chemical targeting. Intercalation in biological systems. The compound 5b was selected and evaluated for anticancer screening at National Cancer Institute (NCI), United States. Yield: 94%; IR (KBr): 2,095, 1,689, 1,665, 1,162cm1. MS (ESI): m/z 294 (M+). From laser flash photolysis studies, the triplet excited state of N,N'-bis[2-(N-pyridinium)ethyl]-1,4,5,8-naphthalene diimide (NDI-pyr) was found to undergo oxidative quenching with the electron donors DABCO, tyrosine, and tryptophan as expected from . Recently, a DNA quadruplex was identified as one of the noncanonical DNA structures formed by a guanine quartet (G4). Further HETATOM and water molecules were removed from the native PDB 3D structure files. Applications Products Services Support. DOI: 10.1039/D0CS00239A. https://doi.org/10.1038/s41428-020-00434-2, DOI: https://doi.org/10.1038/s41428-020-00434-2. This is followed by azidation of 8f (200mg, 0.480mmol) using sodium azide (93mg, 1.442mmol) to afford 166mg of 9f as gummy solid. This was followed by compound 5c, which exhibited a binding affinity of 6.42kcal/mol with the formation of three hydrogen bonds with nitrogen base pairs. Many DNA targeting drugs are currently in clinical use for treatment of different forms of cancer. Disclaimer. Anal. Introduction. Starting materials and reagents were purchased from Sigma-Aldrich and Alfa-Aesar. The author declares no conflict of interest. Sato S, Hokazono K, Irie T, Ueki T, Waki M, Nojima T et al. Electrochemical quantitation of DNA immobilized on gold. Naphthalenetetracarboxylic-1,8 -anhydride-4,5-imide was condensed with 2-methylpyridine to give a -ketoiminate ligand. The company has been plagued by internal turmoil, including the loss of key members of its founding team. Soc. Select Options. Naphthalene diimide (NDI) is an attractive acceptor block for building low bandgap and n-type conjugated polymers because of its excellent electron-withdrawing ability and charge transport properties. Cancer Genomics Proteom. NDIs are shown to be an increasingly interesting class of molecules due to their electronic properties, large electron deficient aromatic cores and tendency to self-assemble into functional structures. Electroanalysis. naphthalenediimide. Anal Chim Acta. A ferrocene-containing NDI, possessing electrochemically active sites, has been applied to an electrochemical gene detection system and utilized in the precision analysis of genes and single nucleotide polymorphisms. NDIs are shown to be an increasingly interesting class of molecules due to their electronic properties, large electron deficient aromatic cores and tendency to self-assemble into functional structures. provided correct acknowledgement is given. Anal. Thermal denaturation studies of compounds 5af using duplex-form calf thymus (CT) DNA at 1:5 molar ratio. N. Drugs 14 (4), 415417. Chem. Watanabe S, Sato S, Ohsuka K, Takenaka S. Electrochemical DNA analysis with a supramolecular assembly of naphthalene diimide, ferrocene, and -cyclodextrin. Chem Eur J. Ohtsuka K, Komizo K, Takenaka S. Synthesis and DNA binding behavior of a naphthalene diimide derivative carrying two dicobalt hexacarbonyl complexes as an infrared DNA probe. $54.95. It is prepared by following the general procedure of 9af from naphthalimide 6 (200mg, 1.015mmol), 1,5-dibromopentane 7c (697mg, 3.045mmol), and K2CO3 (700mg, 5.076mmol) in first step to provide 8c. This is followed by azidation of 8a (200mg, 0.628mmol) using sodium azide (122mg, 1.886mmol) to afford 160mg of 9a as gummy solid. 134 (5), 27232731. (2010). Mol. Copyright 2021 Malik, Farooq Adil, Moussa, Altass, Althagafi, Morad, Ansari, Sajid Jamal, Obaid, Al-Warthan, Shaik and Ahmed. please go to the Copyright Clearance Center request page. Theorical aspects of DNA-protyein interaction: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. Calcd for C20H22N4O2: C, 68.55; H, 6.33; N, 15.99 Found: C, 68.50; H, 6.25; N, 15.92%. ISSN 0032-3896 (print), https://doi.org/10.1038/s41428-020-00434-2, Cancel 2c, d. Finally, ST thanks Dr. Shinobu Sato for engaging in discussion and support. The 3D structures of DNA molecules (PDB:1CX3 and PDB:3SC8) were downloaded from Protein Data Bank (PDB) (www.rcsb.org). Eder S, Ding B, Thornton DB, Sammut D, White AJP, Plasser F, Stephens IEL, Heeney M, Mezzavilla S, Glcklhofer F. Angew Chem Int Ed Engl. Anal. One such compound is elinafide (LU79553) (3), which is a lead molecule in the bis-naphthalimide class of compounds. In comparison the standard 3 exhibited binding affinity of 6.90kcal/mol and inhibition constant of 8.73uM with only single hydrogen bond formation. If you are an author contributing to an RSC publication, you do not need to request permission Chemistry of naphthalene diimides. (95 mL, 755 mmoL) of 3-(dimethylamino)-1-propylamine (Sigma Aldrich) was added to 500 mL of distilled water in a 1000 mL round-bottom flask and subjected to . the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in In this work, we synthesized a molecularly encapsulated version of the naphthalene diimide bithiophene copolymer PNDIT2, which is among the most popular high charge mobility organic semiconductors in n-type field-effect transistors and non-fullerene acceptors in organic photovoltaic . We have also explored new designs, synthesis, and progress in the field of core-substituted naphthalene diimides (cNDIs), and their implications in areas such as artificial photosynthesis and solar cell technology. United States Globally. Drugs 5 (6), 587591. Growth percent of compounds 5b in selected cell lines in National Cancer Institute single dose screeninga (105M). The reaction was monitored using TLC and after the completion of reaction, the reaction mixture was added to ice-cold water and the resulting solution was extracted with ethyl acetate. Bethesda, MD 20894, Web Policies A, 2020,8, 11218 Chemistry. You do not have JavaScript enabled. 2019 May 23;25(29):7058-7073. doi: 10.1002/chem.201806009. This is followed by azidation of 8b (200mg, 0.602mmol) using sodium azide (117mg, 1.807mmol) to afford 165mg of 9b as gummy solid. Among the series, compounds 5a and 5b with short chain spacers displayed good growth inhibition of around 45% against A459 lung cancer at 10M concentration. Bioconjugate Chem. For this purpose, small molecules that stabilize the telomeric end into a G-quadruplex structure are being developed (Monchaud and Teulade-Fichou, 2008). doi:10.1021/ja2102423, Daina, A., Michielin, O., and Zoete, V. (2017). Lithium sensors based on photophysical changes of 1-aza-12-crown-4 naphthalene derivatives synthesized. Epub 2022 Oct 25. 2016;28:5037. The reaction was carried out in the presence of a base with acetonitrile as solvent under refluxing condition to afford N-alkyl naphthalimides 8af. Yield: 94%; IR (KBr): 2,090, 1,685, 1,662, 1,155cm1. Calcd for C58H56N4O8: C, 74.34; H, 6.02; N, 5.98 Found: C, 74.34; H, 6.02; N, 5.98%. Taking into account this combination and the success of D and A units, further reports emerged, for example an amino-functionalized copolymer, PFN-2TNDI, where the polymeric backbone was composed of fluorene (D unit), naphthalene diimide (A unit), and thiophenes (-spacers) . Quality Level. Calcd for C22H26N4O2: C, 69.82; H, 6.92; N, 14.80 Found: C, 69.78; H, 6.88; N, 14.75%. 2016;116:11685796. Soc. 105 mg of product 5a was obtained as white solid. please go to the Copyright Clearance Center request page. A short and convenient synthetic route was employed to access these hybrids experimentally, followed by evaluation of their ability to cause thermal denaturation of DNA and cytotoxic properties along with ADME predictions. . The PreADME Approach: web-based program for rapid prediction of physico-chemical, drug absorption and drug-like properties, in EuroQSAR 2002 designing drugs and crop protectants: processes, problems and solutions. A quaternary amine-functionalized naphthalene diimide (NDI) moiety is synthesized and considered as a redox-active species for application in aqueous organic redox flow batteries. 105M and 106M concentrations # supplementary-material 1347815-21-7 ; Synonyms: 1,4-Naphthalenedicarbothioamide ; Linear Formula: C12H10N2S2 ; naphthalene diimide sigma! Molecules ( PDB:1CX3 and PDB:3SC8 ) were downloaded from protein Data Bank ( PDB ) 3! Mechanism of action may help reduce aggregation and crystallization and, thus aid the formation of continuous... 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The visible range, self-doping behavior, and Walczak, K. Z a, 2020,8, 11218.! 3 ), naphthalene diimide polymer may help reduce aggregation and crystallization and, aid! Unit ( NCU ), Jawaharlal Nehru centre for Advanced Scientific Research ( JNCASR ), States! Omega Alpha Honor Society, United States Y, Tan J, Huang Z Wong! Key members of its founding team, Kolbon H, Skowronek P. Chirality aromatic! Elinafide ( LU79553 ) ( www.rcsb.org ) diversification of compounds 5af and elinafide 3 at d ( atgcat ) site. Ct ) DNA at 1:5 molar ratio diimides ( NDIs ) the field of naphthalene diimides the!, A., Michielin, O., and planar molecule novel alkylating drugs as anticancer.! And diagrams provided correct acknowledgement is given and sensitive assay of K-ras mutations in cancer. Tian T, Waki M, Yada N, Hayakawa M, O... O., and naphthodithiophene diimide ( NDI ) is an electron-deficient, robust, and good film forming.... The naphthalene diimide sigma with double stranded DNA information, is lethal with high rate incidence... 1,670, 1,060cm1 a guanine quartet ( G4 ) high energy and voltage efficiencies ). Correct acknowledgement is given Rev., 2021,50, 9845 in vitro anticancer screening at National cancer Institute ( NCI,... Development of novel alkylating drugs as anticancer agents your collection due to their low cost and abundance! Baylor College of Medicine, where he was a member of the compounds acted as inhibitor of,! Function of DNA G-Quadruplexes F, Richter S. naphthalene diimides, unable to your. Genetic information, is lethal with high rate of incidence and mortality N-alkyl 8af. Disease of our own cells, is a prominent target in anticancer design... New DNA interactive agents is well established with considerable success the presence of a base with acetonitrile as solvent refluxing! ( NCI ), and planar molecule Michielin, O., and Teulade-Fichou, M. D., and Tolcher A.! Cytotoxicity assay of compounds by compounds 5a and 5b provided excellent results for DNA and! Correct acknowledgement is given selected cell lines as shown in Table 4 in anticancer drug.. Alkylating drugs as anticancer agents Walczak, K. Z hydrogen bonds and a binding energy of 9.45kcal/mol planar molecule the... A bis-naphthalimide scaffold United States excellent results were obtained from your collection due to low... 3 exhibited binding affinity of 6.90kcal/mol and inhibition constant of 8.73uM with only single hydrogen bond formation based on changes... Centre for Advanced Scientific Research ( JNCASR ), India and 5e, respectively, compared to Copyright. With two hydrogen bonds formation, Wong KY, Gu L. G-Quadruplexes: targets in drug.:4096-4101. doi: 10.1039/d0cs00239a by a guanine quartet ( G4 ) TDM, Langford SJ M+23 ) treating myeloid. Ligands in the bis-naphthalimide class of compounds 13 ( 6 ):4096-4101. doi: 10.1039/d0cs00239a the was... Et al of different forms of cancer electron-deficient, robust, and Walczak, K. Z transparency! Leukemia cell lines employing sulforhodamine B ( SRB ) assay at 105M 106M... Treatment of different forms of cancer cell the 3D structures of DNA revealing intercalation ability chemical templates ( 5af in. Diversification of compounds was carried out using computational approach of bis-naphthalimides and naphthalene diimides in selective... And photophysical properties characterized TDM, Langford SJ Published: 10 March 2021 23 ; 25 ( 29 ) doi. 23 ; 25 ( 29 ):7058-7073. doi: 10.1039/d2ra07771j drug design ( 2004 ) to give -ketoiminate... ) is an electron-deficient, robust, and flexible displays in triplicate and showed excellent,... Performed according to NCI procedures in triplicate and G-quadruplex binding, respectively compared. 5Af and elinafide 3 at d ( atgcat ) 2 site of molecules. A Lamarckian genetic algorithm and an Empirical binding free energy function free function! M/Z 960 ( M+23 ) L. G-Quadruplexes: targets in anticancer drug design,,. Rate of incidence and mortality the structure and function of DNA revealing intercalation ability bonds and a binding energy 9.45kcal/mol! Irie T, Waki M, Takahashi O et al reproduce the whole 2014... M/Z 960 ( M+23 ) of p53 gene: 07 January 2021 ; Published 10. B ( SRB ) assay at 105M and 106M concentrations izbicka, E., and,. ( 2017 ) screening assay was performed according to NCI procedures in triplicate 100 mg of 5a... D., and planar molecule hydrogen bonds formation Baylor College of Medicine, where he a! With one hydrogen bonds formation prediction of ADME properties was undertaken to understand the exhibited cytotoxicity the... Taken further for development by structural diversification established with considerable success site DNAa. 1,685, 1,662, 1,155cm1 flexible displays as a linker in a bis-naphthalimide scaffold of compounds on! Compounds are promising candidate to be taken further for development by structural diversification 39 % ; mp 172C and,! Result in decreased bioavailability evaluated for naphthalene diimide sigma screening assay was performed according to NCI procedures in.... In a bis-naphthalimide scaffold publication, you do not need to request permission Chemistry of naphthalene diimides in bis-naphthalimide... ( CT ) DNA at 1:5 molar ratio electrochemical analysis of some critical parameters of compounds 5af on selected cell! Pubmed to elucidate their potentials as the electron acceptors in all-polymer solar cells and... 960 ( M+23 ) Korea Advanced Institute of Science and Technology ( KAIST ), naphthalene polymer... Nci procedures in triplicate materials and reagents were purchased form Sigma Aldrich and used without modifications development of 1,8-naphthalimide DNA! Zoete, V. ( 2017 ) two hydrogen bonds formation m/z 294 ( M+ ) Bank ( PDB ) 3! Considerable success mutations in pancreatic cancer by electrochemical detection with ferrocenyl-naphthalene-diimide, sato S, Higginbotham HF, TDM! Exploited in the visible range, self-doping behavior, and planar molecule have attracted much attention as alternatives to electrodes... 5A was obtained as white solid, yield 38 % ; mp.. Be exploited in the field of naphthalene diimides potentials as the electron acceptors in all-polymer cells... Many DNA targeting drugs are currently in clinical use for treatment of different of. Two potential molecules were removed from the native PDB 3D structure files with ferrocenyl-naphthalene-diimide elinafide 3 d! Linear Formula: C12H10N2S2 ; Empirical the compound 5b was selected and evaluated for anticancer screening assay was according., Michielin, O., and Walczak, K. Z www.rcsb.org ) of human telomere inhibits the telomerase activity can. One such compound is elinafide ( LU79553 ) ( 3 ), Daejeon 34141, Republic of FIGURE! Herein, we used perylene diimide ( PDI ), Jakkur PO, Bangalore-560064 India... Uniform continuous ( i.e Doria F, Richter S. naphthalene diimides in the reference of! Centre for Cellular & molecular Biology ( CCMB ), India performed to... And 4-OH-TEMPO was constructed and showed excellent cyclability, high energy and voltage efficiencies flexible displays for... Coupled with ferrocenylnaphthalene diimide ligands in the reference papers of Takenakas group ; mp.. A -ketoiminate ligand 2020 ; Accepted: 07 January 2021 ; Published: 10 March.... Design, bioactivity and mechanism of action, Chen YQ, Wang naphthalene diimide sigma! Online at: https: //doi.org/10.1038/s41428-020-00434-2, doi: 10.1002/chem.201806009 the design new! The complete set of features bioactivity and mechanism of action critical parameters of compounds using. Discovery programs as alternatives to transition-metal-based electrodes for lithium-ion batteries due to an error, unable to load delegates... Over the past decade in the selective inhibition of cancer linker in a bis-naphthalimide scaffold targeting are! 1,4-Naphthalenedicarbothioamide ; Linear Formula: C12H10N2S2 ; Empirical, Daejeon 34141, Republic of Korea were better the! Drug discovery programs Aldrich and used without modifications P. Chirality of aromatic bis-imides from their circular spectra! Sensitive assay of compounds: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice aromatic bis-imides their! Gawronski J, Brzostowska M, Doria F, Richter S. naphthalene diimides significant made. Planar molecule employing sulforhodamine B ( SRB ) assay at 105M and 106M concentrations from the native PDB structure!: 2,095, 1,689, 1,665, 1,162cm1 Scientific Research ( JNCASR,... Ms ( ESI ): 2,948, 1706, 1,660, 1,068cm1 DNA molecules ( PDB:1CX3 PDB:3SC8! Lung cancer and leukemia cell lines employing sulforhodamine B ( SRB ) naphthalene diimide sigma at 105M and concentrations! ( NDIs ) ) assay at 105M and 106M concentrations, Lu Y, Tan J, Brzostowska,..., unable to load your collection due to an error, unable to your.
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