The Journey of 1-Keto-1,2,3,4-Tetrahydrocarbazole Based Fluorophores: From Inception to Implementation

Overview

Journal J Fluoresc

Specialties Biophysics
Chemistry

Date 2022 Jul 13

PMID 35829843

Authors

Amrit Krishna Mitra

Affiliations

Soon will be listed here.

Abstract

Carbazole is a unique template associated with several biological activities. It is due to the diverse and versatile biological properties of carbazole derivatives that they are of immense interest to the research community. 1-keto-1,2,3,4-tetrahydrocarbazoles are important synthetic intermediates to obtain carbazole derivatives. Several members of this family emit fluorescence on photoexcitation. In the context of biochemical and biophysical research, designing and characterising small molecule environment sensitive fluorophores is extremely significant. This article aims to be a state of the art review with synthetic and photophysical details of a variety of fluorophores based on 1-keto-1,2,3,4-tetrahydrocarbazole skeleton.

Citing Articles

Synthetic, biological and optoelectronic properties of phenoxazine and its derivatives: a state of the art review.

Sadhu C, Mitra A Mol Divers. 2023; 28(2):965-1007.

PMID: 36757655 PMC: 9909160. DOI: 10.1007/s11030-023-10619-5.

References

Loving G, Sainlos M, Imperiali B . Monitoring protein interactions and dynamics with solvatochromic fluorophores. Trends Biotechnol. 2009; 28(2):73-83. PMC: 2818466. DOI: 10.1016/j.tibtech.2009.11.002. View

Venkatraman P, Nguyen T, Sainlos M, Bilsel O, Chitta S, Imperiali B . Fluorogenic probes for monitoring peptide binding to class II MHC proteins in living cells. Nat Chem Biol. 2007; 3(4):222-8. PMC: 3444530. DOI: 10.1038/nchembio868. View

Dong S, Li Z, Qin J . New carbazole-based fluorophores: synthesis, characterization, and aggregation-induced emission enhancement. J Phys Chem B. 2008; 113(2):434-41. DOI: 10.1021/jp807510a. View

Knolker H, Reddy K . Isolation and synthesis of biologically active carbazole alkaloids. Chem Rev. 2002; 102(11):4303-427. DOI: 10.1021/cr020059j. View

Schmidt A, Reddy K, Knolker H . Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids. Chem Rev. 2012; 112(6):3193-328. DOI: 10.1021/cr200447s. View

Katritzky A, Zhang G, Xie L, Ghiviriga I . Efficient Syntheses of Substituted Carbazoles and Cyclopent[b]indoles from 1-Methyl-3-(benzotriazol-1-ylmethyl)indole. J Org Chem. 1996; 61(21):7558-7563. DOI: 10.1021/jo9604954. View

Sohrab M, Mazid M, Rahman E, Hasan C, Rashid M . Antibacterial activity of Clausena heptaphylla. Fitoterapia. 2001; 72(5):547-9. DOI: 10.1016/s0367-326x(00)00320-8. View

Chakraborty A, Chowdhury B, Bhattacharyya P . Clausenol and clausenine--two carbazole alkaloids from Clausena anisata. Phytochemistry. 1995; 40(1):295-8. DOI: 10.1016/0031-9422(95)00047-b. View

Chakraborty A, Saha C, Podder G, Chowdhury B, Bhattacharyya P . Carbazole alkaloid with antimicrobial activity from Clausena heptaphylla. Phytochemistry. 1995; 38(3):787-9. DOI: 10.1016/0031-9422(94)00666-h. View

10.

Zhao G, Han K . Effects of hydrogen bonding on tuning photochemistry: concerted hydrogen-bond strengthening and weakening. Chemphyschem. 2008; 9(13):1842-6. DOI: 10.1002/cphc.200800371. View

11.

Zhao G, Han K . Early time hydrogen-bonding dynamics of photoexcited coumarin 102 in hydrogen-donating solvents: theoretical study. J Phys Chem A. 2007; 111(13):2469-74. DOI: 10.1021/jp068420j. View

12.

Zhao G, Han K . Ultrafast hydrogen bond strengthening of the photoexcited fluorenone in alcohols for facilitating the fluorescence quenching. J Phys Chem A. 2007; 111(38):9218-23. DOI: 10.1021/jp0719659. View

13.

Zhao G, Han K . Role of intramolecular and intermolecular hydrogen bonding in both singlet and triplet excited states of aminofluorenones on internal conversion, intersystem crossing, and twisted intramolecular charge transfer. J Phys Chem A. 2009; 113(52):14329-35. DOI: 10.1021/jp903200x. View

14.

Ghosh S, Mitra A, Saha C, Basu S . Tuning the solution phase photophysics of two de novo designed hydrogen bond sensitive 9-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one derivatives. J Fluoresc. 2013; 23(6):1179-95. DOI: 10.1007/s10895-013-1249-z. View

15.

Mitra A, Sau A, Bera S, Chakraborty S, Saha C, Basu S . Monitoring the Competence of a New Keto-tetrahydrocarbazole Based Fluorosensor Under Homogeneous, Micro-Heterogeneous and Serum Albumin Environments. J Fluoresc. 2015; 25(6):1931-49. DOI: 10.1007/s10895-015-1685-z. View

16.

Gupta S, Rather S, Kundu M, Sen P . Origin of strong synergism in weakly perturbed binary solvent system: a case study of primary alcohols and chlorinated methanes. J Phys Chem B. 2011; 116(4):1345-55. DOI: 10.1021/jp207741h. View

17.

Cavalli V, da Silva D, Machado C, Machado V, Soldi V . The fluorosolvatochromism of Brooker's merocyanine in pure and in mixed solvents. J Fluoresc. 2006; 16(1):77-86. DOI: 10.1007/s10895-005-0053-9. View

18.

Dixit S, Crain J, Poon W, Finney J, Soper A . Molecular segregation observed in a concentrated alcohol-water solution. Nature. 2002; 416(6883):829-32. DOI: 10.1038/416829a. View

19.

Roy S, Banerjee S, Biyani N, Jana B, Bagchi B . Theoretical and computational analysis of static and dynamic anomalies in water-DMSO binary mixture at low DMSO concentrations. J Phys Chem B. 2010; 115(4):685-92. DOI: 10.1021/jp109622h. View

20.

Wong D, Sokolowsky K, El-Barghouthi M, Fenn E, Giammanco C, Sturlaugson A . Water dynamics in water/DMSO binary mixtures. J Phys Chem B. 2012; 116(18):5479-90. DOI: 10.1021/jp301967e. View