4116-90-9

Usage

InChI:InChI=1/C13H8BrNO2/c1-15-12(16)8-4-2-3-7-10(14)6-5-9(11(7)8)13(15)17/h2-6H,1H3

Upstream product

• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 74-89-5 methylamine 
• 52559-36-1 4-bromonaphthalene-1,8-dicarboximide 
• 81-84-5 1,8-Naphthalic anhydride 
• 83-32-9 acenaphthene 
• 74-88-4 methyl iodide 

Downstream Products

• 2382-08-3 N-methylnaphthalimide 
• 54229-22-0 4-methylamino-N-methyl-1,8-naphthalic imide 
• 89393-97-5 6-(dimethylamino)-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 5521-31-3 N,N'-Dimethylperylene-3,4,9,10-biscarboximide 
• 634613-10-8 C₄₇H₃₂N₂O₄ 
• 634613-13-1 C₄₁H₂₆N₂O₄ 
• 1040352-96-2 6-({4-[({(2S)-3-[bis(4-methoxyphenyl)(phenyl)methoxy]-2-hydroxypropyl}oxy)methyl]phenyl}ethynyl)-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 1040352-93-9 6-{[4-({[(2R)-2,3-dihydroxypropyl]oxy}methyl)phenyl]ethynyl}-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 1228884-86-3 C₂₉H₁₇NO₂ 
• 1316103-81-7 4-(N'-methyl)benzylamino-N-methyl-1,8-naphthalimide 
• 1206893-89-1 4-(benzylamino)-N-methyl-1,8-naphthalimide 
• 784-03-2 6-hydroxy-2-methyl-1H-benz[d,e]isoquinoline-1,3(2H)-dione 
• 3271-05-4 6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 

Relevant academic research and scientific papers

A naphthalimide fluorescent sensor for Zn2+ based on photo-induced electron transfer

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.

A Ratiometric Fluorescent Probe for Selective Detection of Hypochlorite Anion

A new fluorescent probe based on rhodamine and naphthalimide was synthesized for the discrimination of hypochlorite anion. Upon addition of NaClO, the emission intensities ratio (I576 nm/I528 nm) of the probe 1 increased quickly accompanied with the obvious change of color. The probe 1 also exhibited highly selectivity and fast response to hypochlorite anion. Furthermore, the newly proposed probe has been applied for natural water samples, and a satisfied result was obtained.

Imaging and inhibiting: A dual function molecular flare for cancer cells

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.

Ibuprofen-derived fluorescence inhibitor of COX-2 for breast cancer imaging, prevention and treatment

The integration of precise detection, long-term prevention and effective treatment are beneficial to monitor cancer bioactivity and prevent malignant metastasis for breast cancer patients. Herein, a novel fluorescence probe (IBLN) is designed and synthesized which contains a fluorophore (naphthalimide), a linker and a non-steroidal anti-inflammatory drug (ibuprofen). The specific optical imaging, prevention and treatment effects of breast cancer are relied on the introduction of a powerful cyclooxygenase-2-specific inhibitor, ibuprofen, which makes IBLN possible to successfully differentiate breast cancer cells from normal cells. In addition, fluorescent cellular imaging agent naphthalimide also has anticancer effects via inducing lysosomal membrane permeabilization (LMP). The multi-functional ibuprofen-derived fluorescence inhibitor IBLN realizes the imaging, prevention and treatment for breast cancer, which the selectivity and anticancer effects would be strengthened compared to the single naphthalimide or ibuprofen. Therefore, we envisage that the multi-function strategy in IBLN would be attractive way to explore potential reagent for fluorescence-visible breast cancer therapy in situ.

Antiproliferative and apoptosis-inducing activities of novel naphthalimide-cyclam conjugates through dual topoisomerase (topo) I/II inhibition

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.

Novel metal complexes of naphthalimide-cyclam conjugates as potential multi-target receptor tyrosine kinase (RTK) inhibitors: Synthesis and biological evaluation

A novel series of metal complexes of naphthalimide-cyclam conjugates were synthesized and their in vitro antitumor activities were evaluated. The newly-synthesized compounds showed huge diversity of antiproliferative potency due to variety of metal ions and length of alkyl chains, among which the Zn(II) and Cr(III) complexes exhibited comparable antiproliferative activities with amonafide via multiple tyrosine kinase inhibition. Further research revealed that the representative compound 8a displayed broad-spectrum antiproliferative activity against 15 cancer cell lines with average IC50 value 10.18 ± 3.25 μM, and effective antiangiogenic activity on human microvascular endothelial cells (HMEC-1). In brief, metal complexes of naphthalimide-cyclam conjugates were firstly designed and synthesized as multi-target tyrosine kinase inhibitors and proved of their antitumor capacities.

Naphthalimides exhibit in vitro antiproliferative and antiangiogenic activities by inhibiting both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs)

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 new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide

A new azacrown derived from 1,8-naphthalimide was prepared by a two steps reaction from 4-bromo-1,8-naphthalic anhydride. The spectroscopic properties of this flouroionophore are described both in the absence and in the presence of cations; the compound shows a strong affinity with Ca2+ and Ba2+.

A novel fluorescent sensor for triplex DNA

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.

Smart PET based organic scaffold exhibiting bright “Turn–On” green fluorescence to detect Fe3+ ion: Live cell imaging and logic implication

An efficient and simple photoinduced electron transfer (PET) based fluorescence turn–On probe 7 has been designed and synthesized by bridging naphthalimide and thiophene moieties through a piperazine unit. The photophysical behavior of probe and its affinity toward different metal ions have been investigated in partial aqueous medium, protein medium and live cells. The probe exhibited fluorescence “turn-On” response for Fe3+ ion with high sensitivity (limit of detection 0.373 μM) and selectively along with naked-eye sensitive visible green color in the medium. The significant change in photophysical behavior of the probe, upon a complexation between probe and Fe3+ is attributed to restriction in PET process. The probe 7 showed excellent biocompatibility and has been utilized in cellular imaging experiment to detect Fe3+ in MCF-7 live cells. Also, at molecular level probe 7 mimics the functions of a sequential logic circuit, corresponding to a memory device in which the two inputs (Fe3+ and AcO?) based sequential logic operations mimic the function of a memory element.