81-86-7Relevant articles and documents
Naphthalimide-Based DNA-Coupled Hybrid Assembly for Sensing Dipicolinic Acid: A Biomarker for Bacillus anthracis Spores
Verma, Meenakshi,Kaur, Navneet,Singh, Narinder
, p. 6591 - 6600 (2018)
We have designed and synthesized a novel, water-soluble naphthalimide-histidine receptor (1) with excellent fluorescent properties. Functioning of the synthesized receptor was performed through developing their DNA-receptor hybrid assembly (DRHA), which has shown significant changes in the emission profile upon interactions with dipicolinic acid (DPA), a biomarker for Bacillus anthracis spores. DRHA showed fluorescence enhancement upon binding with DPA with the characteristic of internal charge transfer. It is notable that this assembly exhibited a significant limit of detection (12 nM) toward DPA. The mechanism of sensing was fully defined using ethidium bromide (EtBr) interaction studies as well as Fourier transform infrared spectroscopic analysis, which describes the binding mode of DRHA with DPA. This assembly selectively interacts with DPA over other anions, common cellular cations, and aromatic acids in aqueous media.
An indolium ion functionalized naphtha imide chemodosimeter for detection of cyanide in aqueous medium
Maji, Siddhartha,Chowdhury, Bijit,Pal, Sanchari,Ghosh, Pradyut
, p. 321 - 328 (2018)
A naphthalimide platform based indolium ion functionalized colorimetric as well as fluorometric chemodosimeter (L) has been synthesized and characterized. This can selectively sense cyanide (CN?) in aqueous medium with a low limit of detection (approximately 0.5 μM), which is around four times lower than the value of 1.9 μM set by WHO. The UV–vis and PL studies have been carried out in 40% aqueous-acetonitrile medium which shows a significant change in the visible region allowing naked eye colorimetric detection of CNˉ. The mass spectrometry and 1H NMR spectroscopy are used to characterize the corresponding cyanide adduct which has also been corroborated by time-dependent density functional theory (TD-DFT) during the establishment of the sensing mechanism.
Naphthalimide-gold-based nanocomposite for the ratiometric detection of okadaic acid in shellfish
Chaudhary, Monika,Kaur, Navneet,Singh, Amanpreet,Singh, Narinder,Verma, Meenakshi
, p. 8405 - 8413 (2020)
Okadaic acid (OA) is one of the known marine biotoxins produced by various dinoflagellates and exists in seafood such as shellfish. The consumption of contaminated shellfish with OA leads to diarrheic shellfish poisoning (DSP), which results in the inhibition of protein phosphatase enzymes in humans. This poisoning can cause immunotoxicity and tumor promotion due to the accumulation of okadaic acid in more than the allowed limit in bivalve molluscs. The reported methods for the detection of okadaic acid include mouse bioassays, immunoassays, chromatography coupled with spectroscopic techniques, electrochemical sensors and immunosensors. We have developed a naphthalimide-gold-based nanocomposite for the detection of okadaic acid. Individually, the organic nanoparticles (ONPs) of synthesized naphthalimide-based receptors and gold-coated ONPs are less sensitive for detection. However, fabrication of the composite of Au?ONPs and ONPs enhance the sensing properties and selectivity. The composite shows a ratiometric response in the UV-Vis absorption spectrum and quenching in the fluorescence profile with a detection limit of 20 nM for OA in aqueous medium. In cyclic voltammetry, a shift was observed in the cathodic peak (-0.532 V to -0.618 V) as well as in the anodic peak (-0.815 V to -0.847 V) with the addition of okadaic acid. To study the quick binding of the composite with OA, a time response experiment was performed. Also, the developed sensor retains its sensing ability in the pH range of 5-9 and in high salt conditions. Our developed composite can be used for the detection of OA in real applications.
Synthesis and fluorescence quenching mechanism of novel naphthalimide derivative by nanographene oxide
Rouhani, Shohre,Seraj, Sanaz
, (2021/07/30)
Novel naphthalimide derivative with amine functional group was prepared, and its FTIR and 1H and 13C NMR spectral characteristics were reported. The fluorescence quenching of synthesized dye by nanographene oxide was studied using absorption and fluorescence measurements. From the stern-Volmer analysis, we observed that the quenching was mainly due to the dynamic mechanism. The CV plots indicate that the quenching also went through an electron transfer process. The binding constant (K) and the number of binding sites (n) were calculated based on the fluorescence quenching data. In addition, the free energy change (ΔG) for the electron transfer process was calculated.
Synthesis of Triphenylethylene-Naphthalimide Conjugates as topoisomerase-IIα inhibitor and HSA binder
Rani, Sudesh,Luxami, Vijay,Paul, Kamaldeep
, p. 1821 - 1831 (2021/03/31)
A series of triphenylethylene-naphthalimide (TPE-naph) conjugates was synthesized by a molecular hybridization technique, and their anticancer activity was evaluated in vitro on 60 human cancer cell lines through their cytotoxicity. The ratios of E and Z isomers were determined on the basis of HPLC methodology and NMR spectroscopy. The structure-activity relationship for anticancer activity was deduced on the basis of the nature and bulkiness of the amine attached to the C-4 position of the naphthalene ring. Experimental and molecular modeling studies of the most active TPE-naph conjugate bearing a morpholinyl group showed that it was able to inhibit topoisomerase-II (TOPO-II) as a possible intracellular target. Moreover, the transportation behavior of TPE-naph conjugate towards human serum albumin (HSA) indicated efficient binding affinity. The steady-state and time-dependent fluorescent results suggested that this conjugate quenched HSA significantly through static as well as dynamic quenching. Thus, this report discloses the scope of triphenylethylene-naphthalimide (TPE-naph) conjugates as efficient anticancer agents.
Synthesis of naphthalimide-phenanthro[9,10-d]imidazole derivatives: In vitro evaluation, binding interaction with DNA and topoisomerase inhibition
Luxami, Vijay,Paul, Kamaldeep,Singh, Iqubal
, (2020/02/11)
The synthesis and characterization of a series of naphthalimide and phenanthro[9,10-d]imidazole conjugate is described. These compounds are evaluated in vitro for their cytotoxicity towards 60 human cancer cell lines. Derivative 16 shows excellent cytotoxic activity against these cancer cell lines with the range of growth inhibition from ?55.78 to 94.53. The most potent derivative (ethylpiperazine, 16) is further studied to evaluate the interaction with ct-DNA using absorption and emission spectroscopy as well as DNA viscosity measurement. The DNA binding studies indicate that compound 16 is significantly interacted with DNA through groove binding having binding constant value of 7.81 × 104 M?1 alongwith partial intercalation between the base pairs of DNA strands. Further, topoisomerase inhibition study suggests that compound 16 is induced apoptosis and inhibits human topoisomerase (Topo-IIα) as a possible intracellular target. Molecular docking study of compound 16 with ct-DNA shows good docking score.
Study on synthesis and fluorescence property of rhodamine–naphthalene conjugate
Qin, Jing-can,Fu, Zhen-hai,Tian, Li-mei,Yang, Zheng-yin
supporting information, (2019/12/24)
In this study, a novel ligand (HL) consisting of 2-methyl quinoline-4-carboxylic acid, rhodamine and naphthalene moiety, was designed and synthesized, it could be developed a ratiometric fluorescent sensor for selective detection of Al3+ via fluorescence resonance energy transfer (FRET) from naphthalimide moiety to rhodamine moiety. The addition of Al3+ trigger the significant fluorescence enhancement of HL at 550 nm at the expense of the fluorescent emission of HL centered at 524 nm.
Naphthalimide-based optical turn-on sensor for monosaccharide recognition using boronic acid receptor
Seraj, Sanaz,Rouhani, Shohre,Faridbod, Farnoush
, p. 17933 - 17940 (2019/06/24)
A highly selective and sensitive fluorescent sensor for the determination of fructose is developed. The fluorescent sensor was prepared by incorporating a new naphthalimide dye with a planar structure as a selectophore and graphene oxide (GO) nanoplatelets as a quencher for rapid optical detection of fructose. The designed probe, made with the high fusion loop-containing dye, along with the GO nanoplatelets, detected fructose over the other monosaccharides very well. The proposed sensor displays a linear response range of 7 × 10-5 to 3 × 10-2 M with a low limit of detection of 23 × 10-6 M in solution at pH 7.4. This sensor shows a good selectivity towards fructose with respect to other saccharides. The proposed sensor was then applied to the determination of fructose in human plasma with satisfactory results.
Anticancer activity and topoisomerase II inhibition of naphthalimides with Ω-hydroxylalkylamine side-chains of different lengths
Kasprzycki, Przemys?aw,Strama, Klaudia,Tomczyk, Mateusz D.,Walczak, Krzysztof Z.,Wawszków, Martyna,Wyrostek, Anna Byczek
, p. 550 - 560 (2019/07/12)
Background: The substituted 1,8-Naphthalimides (1H-benzo[de]isoquinoline-1,3(2H)- diones) are known as DNA intercalators stabilizing DNA-Topoisomerase II complexes. This interaction disrupts the cleavage-relegation equilibrium of Topo II, resulting in formation of broken strands of DNA. Objective: To investigate the influence of type of substituents and substitution positions in 1,8- naphthalimde skeleton on the inhibition of Topoisomerase II activity. Method: The starting 1,8-naphthalimide were prepared from acenaphthene by introduction of appropriate substituents followed by condensation with ω-hydroxylakylamines of different chain length. The substituents were introduced to 1,8-naphthalimide molecule by nucleophilic substitution of leaving groups like nitro or bromo present in 4 or 4,5- positions using the ω- hydroxylalkylamines. The bioactivity of obtained compounds was examined in model cell lines. Results: Antiproliferative activity of selected compounds against HCT 116 human colon cancer cells, human non-small cell lung cells A549 and non-tumorigenic BEAS-2B human bronchial epithelium cells was examined. Several of investigated compounds exhibit a significant activity (IC50 μM to 7 μM) against model cancer cell lines. It was demonstrated that upon treatment with concentration of 200 μM, all derivatives display Topo II inhibitory activity, which may be compared with activity of Amonafide. Conclusion: The replacement of the nitro groups in the chromophore slightly reduces its anticancer activities, whereas the presence of both nitro group and ω-hydroxylalkylamine chain resulted in seriously increased anticancer activity. Obtained compounds showed Topo II inhibitory activity, moreover, influence of the substitution pattern on the ability to inhibit Topo II activity and cancer cells proliferation was observed.
Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug
Krasnovskaya, Olga O.,Malinnikov, Vladislav M.,Dashkova, Natalia S.,Gerasimov, Vasily M.,Grishina, Irina V.,Kireev, Igor I.,Lavrushkina, Svetlana V.,Panchenko, Pavel A.,Zakharko, Marina A.,Ignatov, Pavel A.,Fedorova, Olga A.,Jonusauskas, Gediminas,Skvortsov, Dmitry A.,Kovalev, Sergey S.,Beloglazkina, Elena K.,Zyk, Nikolay V.,Majouga, Alexander G.
, p. 741 - 750 (2019/03/02)
A novel approach to the synthesis of pH-sensitive prodrugs has been proposed: thiourea drug modification. Resulting prodrugs can release the cytotoxic agent and the biologically active 2-thiohydantoin in the acidic environment of tumor cells. The concept of acid-catalyzed cyclization of thioureas to 2-thiohydantoins has been proven using a FRET model. Dual prodrugs of model azidothymidine, cytotoxic doxorubicin, and 2-thiohydantoin albutoin were obtained, which release the corresponding drugs in the acidic environment. The resulting doxorubicin prodrug was tested on prostate cancer cells and showed that the thiourea-modified prodrug is less cytotoxic (average IC50 ranging from 0.5584 to 0.9885 μM) than doxorubicin (IC50 ranging from 0.01258 to 0.02559 μM) in neutral pH 7.6 and has similar toxicity (average IC50 ranging from 0.4970 to 0.7994 μM) to doxorubicin (IC50 ranging from 0.2303 to 0.8110 μM) under mildly acidic conditions of cancer cells. Cellular and nuclear accumulation in PC3 tumor cells of Dox prodrug is much higher than accumulation of free doxorubicin.
