A Versatile Molecular Probe of Napthalimide-Derivative for Zn(II) Sensor: A Mini-Review

Authors

  • Pragyan Parimita Das Department of Chemistry, Veer Surendra Sai University of Technology, Odisha 768018, India
  • Patitapaban Mohanty Department of Chemistry, Veer Surendra Sai University of Technology, Odisha 768018, India
  • Aruna Kumar Barick Department of Chemistry, Veer Surendra Sai University of Technology, Odisha 768018, India
  • Priyaranjan Mohapatra Department of Chemistry, Veer Surendra Sai University of Technology, Odisha 768018, India
  • Bigyan Ranjan Jali Department of Chemistry, Veer Surendra Sai University of Technology, Odisha 768018, India https://orcid.org/0000-0002-8405-1678

DOI:

https://doi.org/10.48048/tis.2023.5005

Keywords:

1,8-naphthalimide base, Chromo fluorogenic sensor, Zinc(II), Sensing mechanism

Abstract

In recent years, many more chemists have been focused on fluorescent probe research, and significant progresses, which has been made in terms of design and use. This review begins with a brief overview of the most prevalent chemosensor design concepts, followed by a discussion of the photophysical characteristics of the 1,8-naphthalimide structure, such as great photostability, high fluorescence quantum yield and ease of modification which has been used in Zn2+ cation sensing to date. The contributions of the fluorescent probes built on the 1,8-naphthalimide based platform in the field of chemical sensing, biological sensing, pharmaceutical chemistry, environment and food safety in the last 10 years are then systematically introduced by discussing the probe’s fluorescence behavior in the corresponding recognition process. Simultaneously, we intend to build an overall review on fluorescent chemical sensor that will be able to play larger and more interesting role in the future.

HIGHLIGHTS

  • Napthalimide-based fluorescence molecular probes for zinc(II) detections are described
  • Various napthalimide derivatives are described based on their potent applications
  • Fluorescence chemosensors are described


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References

APD Silva, NQN Gunaratne, T Gunnlaugsson, AJM Huxley, CP McCoy, JT Rademacher and TE Rice. Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 1997; 97, 1515-66.

K Rurack. Flipping the light switch ‘ON’ - the design of sensor molecules that show cation-induced fluorescence enhancement with heavy and transition metal ions. Spectrochim. Acta Mol. Biomol. Spectros. 2001; 57, 2161-95.

B Adhikari and S Majumdar. Polymers in sensor applications. Progr. Polym. Sci. 2004; 29, 699-766.

G Chwatko and E Bald. Determination of cysteine in human plasma by high-performance liquid chromatography and ultraviolet detection after pre-column derivatization with 2-chloro-1-methylpyridinium iodide. Talanta 2000; 52, 509-15.

AR Ivanov, IV Nazimov and LA Baratova. Qualitative and quantitative determination of biologically active low-molecular-mass thiols in human blood by reversed-phase high-performance liquid chromatography with photometry and fluorescence detection. J. Chrom. 2000; 870, 433-42.

X Chen, Y Zhou, X Peng and J Yoon. Fluorescent and colorimetric probes for detection of thiols. Chem. Soc. Rev. 2010; 39, 2120-35.

R Behura, PP Dash, P Mohanty, S Behera, M Mohanty, R Dinda, SK Behera, AK Barick and BR Jali. A Schiff base luminescent chemosensor for selective detection of Zn2+ in aqueous medium. J. Mol. Struct. 2022; 1264, 133310.

P Mohanty, R Behura, V Bhardwaj, PP Dash, SK Sahoo and BR Jali. Recent advancement on chromo-fluorogenic sensing of aluminum (III) with Schiff bases. Trends Environ. Anal. Chem. 2022; 34, e00166.

AP Silva. Recent evolution of luminescent photoinduced electron transfer sensors. A review. Analyst 1996; 121, 1759-62.

S Behera, R Behura, P Mohanty, M Sahoo and R Duggirala. Study of interaction between bovine serum albumin and dolutegravir intermediate: Fluorescence and molecular docking analysis. Biointerface Res. Appl. Chem. 2021; 11, 13102-10.

R Behura, S Behera, P Mohanty, PP Dash, R Panigrahi, BS Mallik, SK Sahoo and BR Jali. Fluorescent sensing of water in DMSO by 2,4-dinitrophenyl hydrazine derived Schiff base. J. Mol. Struct. 2022; 1251, 132086.

PMS Sahoo, S Behera, R Behura, A Acharya, D Biswal, SK Suna, R Sahoo, RC Soren and BR Jali. A brief review: Antibacterial activity of Quinone derivatives. Biointerface Res. Appl. Chem, 2022; 12, 3247-58.

P Jiang and Z Guo. Fluorescent detection of zinc in biological systems: Recent development on the design of chemosensors and biosensors. Coord. Chem. Rev. 2004; 248, 205-29.

E Manandhar, JH Broome, J Myrick, W Lagrone, PJ Cragg and KJ Allace. A pyrene-based fluorescent sensor for Zn2+ ions: A molecular ‘butterfly’. Chem. Comm. 2011; 47, 8796-8.

T Gunnlaugsson, TC Lee and R Parkesh. A highly selective and sensitive fluorescent PET (photoinduced electron transfer) chemosensor for Zn (ii) electronic supplementary information (ESI) available: Synthesis, experimental details and 1H and 13C NMR for 1, 2 and 3. UV-Vis Zn (ii) titrations, fluorescence titration for pH, Hg2+ and Cd2+ for 1. Royal Society of Chemistry, London, 2003.

AI Bush, WH Pettingell, G Multhaup, MD Paradis, JP Vonsattel, JF Gusella, K Beyreuther, CL Masters and RE Tanzi. Rapid induction of Alzheimer Aβ amyloid formation by zinc. Science 1994; 265, 1464-7.

BR Jali, AK Barick, P Mohapatra and SK Sahoo. A comprehensive review on quinones based fluoride selective colorimetric and fluorescence chemosensors. J. Fluorine Chem. 2021; 244, 109744.

CJ Frederickson, JY Koh and AI Bush. The neurobiology of zinc in health and disease. Nat. Rev. Neurosci. 2005; 6, 449-62.

AB Chausmer. Zinc, insulin and diabetes. J. Am. Coll. Nutr. 1998; 17, 109-15.

Z Xu, J Yoon and DR Spring. Fluorescent chemosensors for Zn2+. Chem. Soc. Rev. 2010; 39, 1996-2006.

K Komatsu, K Kikuchi, H Kojima, Y Urano and T Nagano. Selective zinc sensor molecules with various affinities for Zn2+, revealing dynamics and regional distribution of synaptically released Zn2+ in hippocampal slices. J. Am. Chem. Soc. 2005; 127, 10197-204.

K Baba, H Kasai, A Masuhara, H Oikawa and H Nakanishi. Organic solvent-free fluorescence confocal imaging of living cells using pure nanocrystal forms of fluorescent dyes. Jpn. J. Appl. Phys. 2009; 48, 117002.

G Jiang, S Wang, W Yuan, L Jiang, Y Song, H Tian and D Zhu. Highly fluorescent contrast for rewritable optical storage based on photochromic bisthienylethene-bridged naphthalimide dimer. Chem. Mater. 2006; 18, 235-7.

MC Wamberg, K Walczak, L Andersen, AA Hassan and EB Pedersen. Intercalating nucleic acids containing insertions of naphthalimide. Helv. Chim. Acta 2006; 89, 1826-40.

I Grabchev, C Petkov and V Bojinov. 1,8‐Naphthalimides as blue emitting fluorophores for polymer materials. Macromol. Mater. Eng. 2002; 287, 904-8.

GJ Ryan, S Quinn and T Gunnlaugsson. Highly effective DNA photocleavage by novel “rigid” Ru (bpy) 3-4-nitro-and-4-amino-1,8-naphthalimide conjugates. Inorg. Chem. 2008; 47, 401-3.

M Tasior, DT Gryko, M Cembor, JS Jaworski, B Ventura and L Flamigni. Photoinduced energy and electron transfer in 1,8-naphthalimide-corrole dyads. New J. Chem. 2007; 31, 247-59.

X Guo, X Qian and L Jia. A highly selective and sensitive fluorescent chemosensor for Hg2+ in neutral buffer aqueous solution. J. Am. Chem. Soc. 2004; 126, 2272-3.

AP de Silva, NHN Gunaratne, JL Habib‐Jiwan, CP McCoy, TE Rice and JP Soumillion. New fluorescent model compounds for the study of photoinduced electron transfer: The influence of a molecular electric field in the excited state. Angew. Chem. 1995; 34, 1728-31.

B Ramachandram, G Saroja, B Sankaran and A Samanta. Unusually high fluorescence enhancement of some 1,8-naphthalimide derivatives induced by transition metal salts. J. Phys. Chem. B 2000; 104, 11824-32.

J Wang, Y Xiao, Z Zhang, X Qian, Y Yang and Q Xu. A pH-resistant Zn (II) sensor derived from 4-aminonaphthalimide: Design, synthesis and intracellular applications. J. Mater. Chem. 2005; 15, 2836-9.

Z Xu, X Qian and J Cui. Colorimetric and ratiometric fluorescent chemosensor with a large red-shift in emission: Cu (II)-only sensing by deprotonation of secondary amines as receptor conjugated to naphthalimide fluorophore. Org. Lett. 2005; 7, 3029-32.

JB Baruah and BR Jali. Investigation on bindings of a binaphthoquinone derivative with serum albumin proteins by fluorescence spectroscopy. Indian J. Chem. 2021; 60A, 824-9.

J Wang, Y Xiao, Z Zhang, X Qian, Y Yang and Q Xu. A pH-resistant Zn (II) sensor derived from 4-aminonaphthalimide: Design, synthesis and intracellular applications. J. Mater. Chem. 2005; 15, 2836-9.

X Poteau, AI Brown, RG Brown, C Holmes and D Matthew. Fluorescence switching in 4-amino-1, 8-naphthalimides: “on-off-on” operation controlled by solvent and cations. Dyes Pigments 2000; 47, 91-105.

LM Daffy, AP de Silva, HN Gunaratne, C Huber, PM Lynch, T Werner and OS Wolfbeis. Arenedicarboximide building blocks for fluorescent photoinduced electron transfer pH sensors applicable with different media and communication wavelengths. Chem. Eur. J. 1998; 4, 1810-5.

F Cosnard and V Wintgens. A new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide. Tetrahedron Lett. 1998; 39, 2751-4.

B Ramachandram, NB Sankaran, R Karmakar, S Saha and A Samanta. Fluorescence signalling of transition metal ions by multi-component systems comprising 4-chloro-1,8-naphthalimide as fluorophore. Tetrahedron 2000; 56, 7041-4.

I Grabchev, X Qian, Y Xiao and R Zhang. Novel heterogeneous PET fluorescent sensors selective for transition metal ions or protons: Polymers regularly labelled with naphthalimide. New J. Chem. 2002; 26, 920-5.

T Gunnlaugsson, CP McCoy, RJ Morrow, C Phelan and F Stomeo. Towards the development of controllable and reversible ‘on-off’ luminescence switching in soft-matter; synthesis and spectroscopic investigation of 1,8-naphthalimide-based PET (photoinduced electron transfer) chemosensors for pH in water-permeable hydrogels. Arkivoc 2003; 7, 216-28.

M Licchelli, AO Biroli, A Poggi, D Sacchi, C Sangermani and M Zema. Excimer emission induced by metal ion coordination in 1,8-naphthalimide-tethered iminopyridine ligands. Dalton Trans. 2003; 2003, 4537-45.

B Liu and H Tian. A selective fluorescent ratiometric chemodosimeter for mercury ion. Chem. Comm. 2005; 2005, 3156-8.

NB Sankaran, S Banthia and A Samanta. Fluorescence signalling of the transition metal ions: Design strategy based on the choice of the fluorophore component. J. Chem. Sci. 2002; 114, 539-45.

JL Bricks, A Kovalchuk, C Trieflinger, M Nofz, M Büschel, AI Tolmachev, J Daub and K Rurack. On the development of sensor molecules that display FeIII-amplified fluorescence. J. Am. Chem. Soc. 2005; 127, 13522-9.

B Liu and H Tian. A ratiometric fluorescent chemosensor for fluoride ions based on a proton transfer signaling mechanism. J. Mater. Chem. 2005; 15, 2681-6.

T Hirano, K Kikuchi, Y Urano, T Higuchi and T Nagano. Highly zinc-selective fluorescent sensor molecules suitable for biological applications. J. Am. Chem. Soc. 2000; 122, 12399-400.

AP de Silva, NQN Gunaratne, T Gunnlaugsson, AJM Huxley, CP McCoy, JT Rademacher and TE Rice. Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 1997; 97, 1515-66.

LY Zhao, QL Mi, GK Wang, JH Chen, JF Zhang, QH Zhao and Y Zhou. 1,8-Naphthalimide-based ‘turn-on’fluorescent sensor for the detection of zinc ion in aqueous media and its applications for bioimaging. Tetrahedron Lett. 2013; 54, 3353-8.

DY Liu, J Qi, XY Liu, HR He, JT Chen and GM Yang. 4-Amino-1,8-naphthalimide-based fluorescent sensor with high selectivity and sensitivity for Zn2+ imaging in living cells. Inorg. Chem. Comm. 2014; 43, 173-8.

D Liu, Y Zhao, J Shi, H Zhu, T Zhang, P Qi, J Chen, G Yang and H He. A highly selective and sensitive 1,8-naphthalimide-based fluorescent sensor for Zn2+ imaging in living cells. Bioorg. Med. Chem. Lett. 2019; 29, 2646-9.

S Sali, S Guittonneau and I Grabchev. A novel blue fluorescent chemosensor for metal cations and protons, based on 1,8‐naphthalimide and its copolymer with styrene. Polymer. Adv. Tech. 2006; 17, 180-5.

JM Chovelon and I Grabchev. A novel fluorescent sensor for metal cations and protons based of bis-1,8-naphthalimide. Spectrochim. Acta Mol. Biomol. Spectros. 2007, 67, 87-91.

K Hanaoka, Y Muramatsu, Y Urano, T Terai and T Nagano. Design and synthesis of a highly sensitive off-on fluorescent chemosensor for zinc ions utilizing internal charge transfer. Chem. Eur. J. 2010; 16, 568-72.

T Moniz, C Queirós, R Ferreira, A Leite, P Gameiro, AM Silva and M Rangel. Design of a water soluble 1,8-naphthalimide/3-hydroxy-4-pyridinone conjugate: Investigation of its spectroscopic properties at variable pH and in the presence of Fe3+, Cu2+ and Zn2+. Dyes Pigments 2013; 98, 201-11.

Z Xu, X Qian, J Cui and R Zhang. Exploiting the deprotonation mechanism for the design of ratiometric and colorimetric Zn2+ fluorescent chemosensor with a large red-shift in emission. Tetrahedron 2006; 62, 10117-22.

S Lee, JH Lee, T Pradhan, CS Lim, BR Cho, S Bhuniya, S Kim and JS Kim. Fluorescent turn-on Zn2+ sensing in aqueous and cellular media. Sensor. Actuator. B Chem. 2011; 160, 1489-93.

D Liu, M Zhang, S Fang, J Shi, J Zhang, L Yin, G Yang, H Zhu and H He. Naphthalimide based fluorescent sensor for Zn2+ with high selectivity and sensitivity and its imaging in living cells. Inorg. Chem. Comm. 2020; 113, 107798.

SY Kim and JI Hong. Naphthalimide-based fluorescent Zn2+ chemosensors showing PET effect according to their linker length in water. Tetrahedron Lett. 2009; 50, 2822-4.

SM Dimov, NI Georgiev, AM Asiri and VB Bojinov. Synthesis and sensor activity of a PET-based 1,8-naphthalimide probe for Zn2+ and pH determination. J. Fluoresc. 2014; 24, 1621-8.

KT Kim, SA Yoon, J Ahn, Y Choi, MH Lee, JH Jung and J Park. Synthesis of fluorescent naphthalimide-functionalized Fe3O4 nanoparticles and their application for the selective detection of Zn2+ present in contaminated soil. Sensor. Actuator. B Chem. 2017; 243, 1034-41.

D Liu, T Zhang, M Zhang, J Shi, L Yin, Z Shang, H Zhu, G Yang and H He. Water-soluble fluorescent sensor for Zn2+ with high selectivity and sensitivity imaging in living cells. Bioorg. Med. Chem. Lett. 2020; 30, 127073.

J Fan, X Peng, Y Wu, E Lu, J Hou, H Zhang, R Zhang and X Fu. A new PET fluorescent sensor for Zn2+. J. Lumin. 2005; 114, 125-30.

D Xiang, S Zhang, Y Wang, K Sun and H Xu. A novel naphthalimide-based “turn-on” fluorescent chemosensor for highly selective detection of Zn2+. Tetrahedron 2022; 106-107, 132648.

VB Bojinov, IP Panova, DB Simeonov and NI Georgiev. Synthesis and sensor activity of photostable blue emitting 1,8-naphthalimides containing s-triazine UV absorber and HALS fragments. J. Photochem. Photobiol. 2010; 210, 89-99.

D Liu, X Deng, X Yin, Y Wang, J Guo, J Chen, G Yang and H He. 1,8-Naphthalimide-based fluorescent sensor with high selectivity and sensitivity for Zn2+ and its imaging in living cells. Inorg. Chem. Comm. 2019; 101, 117-20.

R Parkesh, TC Lee and T Gunnlaugsson. Highly selective 4-amino-1,8-naphthalimide based fluorescent photoinduced electron transfer (PET) chemosensors for Zn (II) under physiological pH conditions. Org. Biomol. Chem. 2007; 5, 310-7.

M Kumar, N Kumar and V Bhalla. Naphthalimide based chemosensor for Zn2+, pyrophosphate and H2O2: Sequential logic operations at the molecular level. Chem. Comm. 2013; 49, 887-79.

C Zhang, Z Liu, Y Li, W He, X Gao and Z Guo. In vitro and in vivo imaging application of a 1,8-naphthalimide-derived Zn2+ fluorescent sensor with nuclear envelope penetrability. Chem. Comm. 2013; 49, 11430-2.

SM Dimov, NI Georgiev, AM Asiri and VB Bojinov. Synthesis and sensor activity of a PET-based 1,8-naphthalimide probe for Zn2+ and pH determination. J. Fluoresc. 2014, 24, 1621-8.

I Grabchev, S Dumas, JM Chovelon and A Nedelcheva. First generation poly (propyleneimine) dendrimers functionalised with 1,8-naphthalimide units as fluorescence sensors for metal cations and protons. Tetrahedron 2008; 64, 2113-9.

PA Panchenko, MA Zakharko, YV Fedorov, OA Fedorova and PA Ignatov. A fluorescent PET chemosensor for Zn2+ cations based on 4-methoxy-1,8-naphthalimide derivative containing salicylideneamino receptor group. Mendeleev Comm. 2020; 30, 55-8.

J Fan, Y Wu and X Peng. A naphthalimide fluorescent sensor for Zn2+ based on photo-induced electron transfer. Chem. Lett. 2004; 33, 1392-3.

B Mohan, P Balakrishnan, D Umadevi and S Shanmugaraju. A simple 4-amino-1,8-naphthalimide hydrazine based “turn-on” fluorescent chemosensor for selective and reversible detection of Zn (II) ion. Inorg. Chim. Acta 2022; 533, 120798.

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Published

2023-03-17

How to Cite

Das, P. P. ., Mohanty, P. ., Barick, A. K. ., Mohapatra, P. ., & Jali, B. R. (2023). A Versatile Molecular Probe of Napthalimide-Derivative for Zn(II) Sensor: A Mini-Review. Trends in Sciences, 20(7), 5005. https://doi.org/10.48048/tis.2023.5005