4116-90-9Relevant articles and documents
A naphthalimide fluorescent sensor for Zn2+ based on photo-induced electron transfer
Fan, Jiangli,Wu, Yunkou,Peng, Xiaojun
, p. 1392 - 1393 (2004)
A new Zn2+ fluorescent sensor NIDPA (1) which takes 1,8-naphthalimide as a reporting group and di-2-picolylamine (DPA) as a recognizing group has been synthesized via simple steps. Based on photo-induced electron transfer (PET) mechanism, NIDPA has a nearly 5-fold fluorescent enhancement under simulated physiological conditions corresponding to the binding of Zn2+. Apparent dissociation constant for Zn2+ (Kd) is in the sub-nM range, and Ca2+, Mg2+, Fe3+, Ni2+, and Cr3+ have little influence on fluorescence enhancement.
Imaging and inhibiting: A dual function molecular flare for cancer cells
Zhang, Shuangzhe,Li, Miao,Xia, Wenxi,Fan, Jiangli,Wang, Jingyun,Li, Yueqing,Li, Yachen,Wang, Haibo,Dong, Chengyong,Ma, Dandan,Guo, Jianli,Peng, Xiaojun
, (2019)
Wnt pathway is dysregulated and activated in many human malignancies. More than 90% of colon cancers have variations in the Wnt pathway. Sulindac targeting protein Dvl of the Wnt/Dvl/β-catenin pathway which regulates cancer gene expression, has been reported to significantly reduce the incidence and the risk of death from the colorectal and other types of cancer. Herein, a dual functional compound (SLN) containing Sulindac and a linked fluorophore has been reported firstly, to combine the functions of lighting up colon cancer cells as a flare and inhibiting colon tumor as a drug. SLN can not only mark the Dvl protein in Wnt pathway to recognize tumors layer by layer, but also achieve the effective inhibition of colon cancer, providing a promising reagent for chemotherapy and a fluorescence indicator for surgery during removing the colon tumor in situ.
Antiproliferative and apoptosis-inducing activities of novel naphthalimide-cyclam conjugates through dual topoisomerase (topo) I/II inhibition
Tan, Shaoying,Sun, Deheng,Lyu, Jiankun,Sun, Xiao,Wu, Fangshu,Li, Qiang,Yang, Yiqi,Liu, Jianxu,Wang, Xin,Chen, Zhuo,Li, Honglin,Qian, Xuhong,Xu, Yufang
, p. 5672 - 5680 (2015)
A novel series of naphthalimide-cyclam conjugates were designed and synthesized. Among them, compounds 4c, 4d, 8c and 8d which bearing long lipophilic alkyl chains, displayed comparable or more potent cytotoxic activities against human tumor cell lines than amonafide. Furthermore, the four compounds were proved to possess strong inhibition against both topoisomerase I and II. The representative compound 8c exhibited moderate DNA intercalation activity. Molecular modeling studies identified the possible interaction of compound 8c with the molecular target by forming topoisomerase/DNA/drug ternary complex. Finally, derivatives with long lipophilic alkyl chains could efficiently induce apoptosis.
Naphthalimides exhibit in vitro antiproliferative and antiangiogenic activities by inhibiting both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs)
Wang, Xin,Chen, Zhuo,Tong, Linjiang,Tan, Shaoying,Zhou, Wei,Peng, Ting,Han, Kun,Ding, Jian,Xie, Hua,Xu, Yufang
, p. 477 - 486 (2013)
Novel naphthalimide derivatives were designed and synthesized to modulate both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs). Most target compounds exhibited effective and selective antiproliferative activities against three cancer cell lines by inhibiting topo II. The IC50 values ranged from 1.5 to 19.1 μM. Moreover, compounds 8d and 12d moderately inhibited various angiogenesis-related RTKs, including FGFR1, VEGFR2 and PDGFRα. The representative compound 8d was then proved to possess antiangiogenic activity, which was evidenced by the inhibition of migration and tube formation activities of HMEC-1 cells. To our knowledge, it is the first time naphthalimides were identified as tyrosine kinases inhibitors (TKIs) besides their conventional cytotoxicity.
A novel fluorescent sensor for triplex DNA
Lu, Erhu,Peng, Xiaojun,Song, Fengling,Fan, Jiangli
, p. 255 - 257 (2005)
A novel triplex DNA fluorescent sensor which takes 4-aminonaphthalimide as a reporting group and a triplex-select intercalator as a recognizing group has been synthesized. The results show that the fluorescence of the sensor increases greatly upon addition of T?AT triplex, but the response to single strand DNA and duplex DNA is weak in PIPES 20 buffer (pH 7.0). A triplex DNA fluorescent sensor based on PET is described. The sensor takes 4-aminonaphthalimide as a reporting group and a triplex-select intercalator as a recognizing group. The results show that it is a selective sensor for T?AT triplex DNA in compared with duplex and ssDNA by fluorescence enhancement in PIPES 20 buffer.
Mechanistic Analysis of Solid-State Colorimetric Switching: Monoalkoxynaphthalene-Naphthalimide Donor-Acceptor Dyads
Wight, Christopher D.,Xiao, Qifan,Wagner, Holden R.,Hernandez, Eduardo A.,Lynch, Vincent M.,Iverson, Brent L.
, p. 17630 - 17643 (2020)
There is growing interest in creating solids that are responsive to various stimuli. Herein we report the first molecular-level mechanistic picture of the thermochromic polymorphic transition in a series of MAN-NI dyad crystals that turn from orange to yellow upon heating with minimal changes to the microscopic morphology following the transition. Detailed structural analyses revealed that the dyads assemble to create an alternating bilayer type structure, with horizontal alternating alkyl and stacked aromatic layers in both the orange and yellow forms. The observed dynamic behavior in the solid state moves as a yellow wavefront through the orange crystal. The overall process is critically dependent on a complex interplay between the layered structure of the starting crystal, the thermodynamics of the two differently colored forms, and similar densities of the two polymorphs. Upon heating, the orange form alkyl chain layers become disordered, allowing for some lateral diffusion of dyads within their own layer. Moving to either adjacent stack in the same layer allows a dyad to exchange a head-to-head stacking geometry (orange) for a head-to-tail stacking geometry (yellow). This transition is unique in that it involves a nucleation and growth mechanism that converts to a faster cooperative wavefront mechanism during the transition. The fastest moving of the wavefronts have an approximately 38° angle with respect to the long axis of the crystal, corresponding to a nonconventional C-H···O hydrogen bond network of dyad molecules in adjacent stacks that enables a transition with cooperative character to proceed within layers of orange crystals. The orange-to-yellow transition is triggered at a temperature that is very close to the temperature at which the orange and yellow forms exchange as the more stable, while being lower than the melting temperature of the original orange, or final yellow, solids.
Piperazine-bridged naphthalimide aminothiazole oxime compound as well as preparation method and application thereof
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Paragraph 0036-0040, (2021/03/13)
The invention relates to piperazine bridged naphthalimide aminothiazole oxime compounds as well as a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The piperazine-bridged naphthalimide aminothiazole oxime compound is shown as a general formula I, has certain inhibitory activity on one or more of gram-positive bacteria, gram-negative bacteria and fungi, and can be used for preparing antibacterial and/or antifungal drugs, so that more efficient and safe candidate drugs are provided for clinical antimicrobial treatment, and the clinical treatment problems of increasingly serious drug resistance, stubborn pathogenic microorganisms, newly appearing harmful microorganisms and the like are favorably solved. The preparation raw materials are simple, cheap and easy to obtain, the synthetic route is short, and the method has important significance in anti-infection application.
Selectivity of a bromoacridine-containing fluorophore for triplex DNA
Fraser, William,Sharma, Sanjeev Kumar
, p. 1013 - 1016 (2021/08/13)
Fluorophore 1,8-naphthilamide was linked to 2-bromoacridine through an ethylenediamine spacer using a succinct synthetic route to give a bromoacridine-linked, bifunctional fluorophore conjugate for the detection of triplex DNA. Acridine is well known to intercalate into duplex DNA whereas introduction of a bulky bromine atom at position C2 redirects specificity for triplex over duplex DNA. In this work, photoelectron transfer assay was used to demonstrate that the synthesised 2-bromoacridine-linked fluorophore conjugate had good selectivity for the representative triplex DNA target sequence d(T*A.T)20 compared with double-stranded d(T.A)20, single-stranded dT20 or d(G/A)19 DNA sequences. Graphic abstract: [Figure not available: see fulltext.].
