The Therapeutic and Diagnostic Value of Fluorine

  • Isma Attique Department of Chemistry, Lahore Garrison University, Lahore, Pakistan
  • Shabbir Hussain Department of Chemistry,Lahore Garrison University, Lahore, Pakistan
  • Muhammad Amjad Department of Chemistry,Lahore Garrison University, Lahore, Pakistan
  • Khalida Nazir Department of Chemistry, University of Sargodha, Women Campus Faisalabad, Pakistan
  • Muhammad Shahid Nazir Department of Textile Chemistry, National Textile University Faisalabad, Pakistan
Keywords: anticancer, fluorine, medical, positron, radiolabel

Abstract

Abstract Views: 296

Fluorine has a useful positron transmitting isotope and it enjoys broad application in the medical field. It is utilized in fluorinated agents, therapeutic sciences and steroid field. Fluorine incorporation via fluoroalkylation is a useful approach in the development of new functional materials and in drug design. Fluorine also plays its role as an anticancer agent and is a successful chemotherapeutic agent for certain sorts of malignant growth. 5-fluorouracil plays a vital role in the treatment of cancer.18Factsas a radiolabel tracer at o min PET imaging.19F has the second most sensitive and stable NMR-active nucleus.

Copyright(c) The Authors

Downloads

Download data is not yet available.

References

Kirk KL, Yoshida S, Haufe G. Synthesis and biochemical evaluation of fluorinated monoamine oxidase inhibitors. In: Tressaud A, Haufe G, eds. Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals. London: Elsevier; 2008. 661–697.

Gillis EP, Eastman KJ, Hill MD, Donnelly DJ Meanwell NA. Applications of fluorine in medicinal chemistry. J Med Chem. 2015;58(21): 8315–8359.

Swallow S. Fluorine in medicinal chemistry. In: Lawton G, Witty D, eds. Progress in Medicinal Chemistry. London: Elsevier; 2015. 65–133.

Isanbor C, O’Hagan D. Fluorine in medicinal chemistry: a review of anti-cancer agents. J Fluorine Chem. 2006;127(3): 303–319.

Arntson KE, Pomerantz WC. Protein-observed fluorine NMR: a bioorthogonal approach for small molecule discovery: miniperspective. J Med Chem. 2015;59(11): 5158–5171.

O’Hagan D, Harper DB. Fluorine-containing natural products. J Fluorine Chem. 1999;100(1-2): 127–133.

Shah P, Westwell AD. The role of fluorine in medicinal chemistry. J Enzyme Inhib Med Chem. 2007;22(5): 527–540.

Ojima I. Use of fluorine in the medicinal chemistry and chemical biology of bioactive compounds—a case study on fluorinated taxane anticancer agents. Chem Bio Chem. 2004;5(5): 628–635.

Ghorab MM, Alsaid MS, El-Gaby MS, Elaasser MM, Nissan YM. Antimicrobial and anticancer activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties: synthesis, biological evaluation and molecular docking. Chem Central J. 2017;11(1): 32.

Hussain S, Bukhari IH, Ali S, Shahzadi S, Shahid M, Munawar KS. Synthesis and spectroscopic and thermogravimetric characterization of heterobimetallic complexes with Sn(IV) and Pd(II); DNA binding, alkaline phosphatase inhibition and biological activity studies. J Coord Chem. 2015;68(4): 662–677.

Hussain S, Ali S, Shahzadi S, Tahir MN, Shahid M. Synthesis, characterization, biological activities, crystal structure and DNA binding of organotin (IV) 5–chlorosalicylates. J Coord Chem. 2015;68(14): 2369–2387.

Mariam S, Hussain S, Ali S, Shahzadi S, Ramzan S, Shahid M. Homobimetallic (Sn, Sn) Complexes with [2-Dithiocarboxy (methyl) amino] acetic acid: synthesis, characterization and biological studies. Iran J Sci Technol, Trans A: Sci. 2018;42(3): 1277–1284.

Saleem S, Nazli Z-e-h, Saleem N, Bashir MS, Hussain S. Synthesis, spectroscopy and biological studies of chalcone derived pyrimidines. Der Pharma Chemica. 2018;10(10): 110–117.

Dinoiu V. Fluorine chemistry: past, present and future. Rev Roum Chim. 2006;51(12): 1141.

Chua M-S, Shi D-F, Wrigley S, Bradshaw TD, Hutchinson I,… Stevens MF. Antitumor benzothiazoles. 7. Synthesis of 2-(4-acylaminophenyl) benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines. J Med Chem. 1999;42(3): 381–392.

Mortimer CG, Wells G, Crochard J-P, Stone EL, Bradshaw TD,… Westwell AD. Antitumor benzothiazoles. 26. 2-(3, 4-Dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines. J Med Chem. 2006;49(1): 179–185.

Menaa F, Menaa B, Sharts ON. Importance of fluorine and fluorocarbons in medicinal chemistry and oncology. J Mol Pharm Org Process Res. 2013;1(104): 2.

Chambers RD. Fluorine in organic chemistry. Florida, FL: CRC press; 2004.

Bonasera TA, Ortu G, Rozen Y, Krais R, Freedman NM,… Mishani E. Potential 18F-labeled biomarkers for epidermal growth factor receptor tyrosine kinase. Nucl Med Biol. 2001;28(4): 359–374.

Brunet VA, O'Hagan D. Catalytic asymmetric fluorination comes of age. Angew Chem Int Ed. 2008;47(7): 1179–1182.

Hollingworth C, Gouverneur V. Transition metal catalysis and nucleophilic fluorination. Chem Commun. 2012;48(24): 2929–2942.

Yu JX, Cui W, Zhao D, Mason RP. Non‐invasive physiology and pharmacology using 19F magnetic resonance. In: Tressaud A, Haufe G, eds. Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals. London: Elsevier; 2008. 197–276.

Haranahalli K, Honda T, Ojima I. Recent progress in the strategic incorporation of fluorine into medicinally active compounds. J Fluorine Chem. 2019;217: 29–40.

Ni C, Hu J. The unique fluorine effects in organic reactions: recent facts and insights into fluoroalkylations. Chem Soc Rev. 2016;45(20): 5441–5454.

Wechalekar K, Sharma B, Cook G. PET/CT in oncology—a major advance. Clin Radiol. 2005;60(11): 1143–1155.

An Y-S, Kang DK, Jung YS, Han S, Kim TH. Tumor metabolism and perfusion ratio assessed by 18F-FDG PET/CT and DCE-MRI in breast cancer patients: correlation with tumor subtype and histologic prognostic factors. Eur J Radiol. 2015;84(7): 1365–1370.

Kumar R, Chauhan A, Zhuang H, Chandra P, Schnall M, Alavi A. Clinicopathologic factors associated with false negative FDG–PET in primary breast cancer. Breast Cancer Res Treat. 2006;98(3): 267–274.

Park BK, Kitteringham NR, O'Neill PM. Metabolism of fluorine-containing drugs. Annu Rev Pharmacol Toxicol. 2001;41(1): 443–470.

Purser S, Moore PR, Swallow S, Gouverneur V. Fluorine in medicinal chemistry. Chem Soc Rev. 2008;37(2): 320–330.

Kirk KL. Fluorination in medicinal chemistry: methods, strategies, and recent developments. Org Process Res Dev. 2008;12(2): 305–321.

Focaccetti C, Bruno A, Magnani E, Bartolini D, Principi E,…Noonan DM. Effects of 5-fluorouracil on morphology, cell cycle, proliferation, apoptosis, autophagy and ROS production in endothelial cells and cardiomyocytes. PLoS One. 2015;10(2): 1–25.

Sun S, Adejare A. Fluorinated molecules as drugs and imaging agents in the CNS. Curr Top Med Chem. 2006;6(14): 1457–1464.

Nayak N, Ramprasad J, Dalimba U. Synthesis and antitubercular and antibacterial activity of some active fluorine containing quinoline–pyrazole hybrid derivatives. J Fluorine Chem. 2016;183: 59–68.

Strunecká A, Patočka J, Connett P. Fluorine in medicine. J Appl Biomed. 2004;2: 141–150.

Lee HJ, Taraporewala I, Heiman A. Anti-inflammatory steroids: research trends and new compounds. Drugs Today. 1989;25(9): 577–588.

Barradell LB, Faulds D, McTavish D. Lansoprazole. Drugs. 1992;44(2): 225–250.

O’Hagan D. Fluorine in health care: organofluorine containing blockbuster drugs. J Fluorine Chem. 2010;131(11): 1071–1081.

Filler R, Saha R. Fluorine in medicinal chemistry: a century of progress and a 60-year retrospective of selected highlights. Future Med Chem. 2009;1(5): 777–791.

Published
2020-03-27
How to Cite
1.
Isma Attique, Shabbir Hussain, Muhammad Amjad, Khalida Nazir, Muhammad Shahid Nazir. The Therapeutic and Diagnostic Value of Fluorine. Sci Inquiry Rev. [Internet]. 2020Mar.27 [cited 2024Jun.12];4(1):17-9. Available from: https://journals.umt.edu.pk/index.php/SIR/article/view/759
Section
Orignal Article