SYNTHESIS OF SOME NOVEL PERYLENE DI IMIDES AND EVALUATION OF THEIR ANTI CANCER ACTIVITY

Authors

  • Hemalatha CN Research Scholar, Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Vels Institute of Science, Technology and Advanced Studies, VISTAS, Pallavaram, Chennai, Tamil Nadu, India.
  • Vijey Aanandhi M Department of Pharmaceutical Chemistry and Analysis, School of Pharmaceutical Sciences, Vels Institute of Science, Technology and Advanced Studies, Chennai, Tamil Nadu, India.

DOI:

https://doi.org/10.22159/ajpcr.2018.v11i8.26539

Keywords:

Perylene derivatives, QSAR plus, G-Quadruplex ligand database, Docking, Anti oxidant study, Cell line study

Abstract

Objective: The main objective of the study is to synthesis some novel perylene di imides and to evaluate for anti oxidant activity and anticancer activity.

Methods: Antioxidant assay was carried on to study the reducing activity of the compounds. The cytotoxicity assay was studied to find the best potent compound among the synthesized compound by using the HCT-116, a colon cancer cell line. Synthesized substituted amine derivatives of perylene di imides. From the evaluation study Compound, A shows potent activity when compared with the standard drug 5-Fluorouracil.

Results: The results of the total antioxidant capacity assay of perylene compounds are evaluated by the 1,1-diphenyl-2-picryl hydrazyl (DPPH) method and nitric oxide scavenging method. All the synthesized compounds are evaluated for their antioxidant power. From the results of DPPH and nitric oxide scavenging assay, Compound A, B, C and D showed potent activity when compared with the standard. For further evaluation of cell line studies, based upon the IC50 values, Compound A, B and C were taken for study. The molecular modeling data's are exactly correlated with the in vitro studies. We have used 5-Fluorouracil and PIPER as a standard for in vitro study and molecular modeling study respectively.

Conclusions: From the results, Compound A will be efficient to inhibit telomerase enzyme and the Compound A will be effective for anti-cancer therapy.

Downloads

Download data is not yet available.

References

Schwab M. Encyclopedia of Cancer. 2nd ed. New York: Springer; 2008. p. 310-2.

Antonio MD, Rodriguez R, Balasubramanian S. Experimental approaches to identify cellular G-Quadruplex structures and functions. Methods 2012;57:84-92.

Sen D, Gilbert W. Formation of parallel four-stranded complexes by guanine-rich motifs in DNA and its implications for meiosis. Nature 1988;334:364-6.

Davis JT. G-quartets 40 years later: From 5’-GMP to molecular biology and supramolecular chemistry.Chem. Int Ed Engl 2004;43:668-98.

Brya TM, Baumann P. G-Quadruplexes: From guanine gels to chemotherapeutics. Mol Biotechnol 2011;49:198-208.

Patel DJ, Phan AT, Kuryavyi V. Human telomere, oncogenic promoter and 5’-UTRG-quadruplexes: Diverse higher order DNA and RNA targets for cancer therapeutics. Nucleic Acids Res 2007;35:7429-55.

Grand CL, Han H, Muñoz RM, Weitman S, Von Hoff DD, Hurley LH, et al. The cationic porphyrin tmpyp4 down-regulates c-MYC and human telomerase reverse transcriptase expression and inhibits tumor growth in vivo. Mol Cancer 2002;1:565-73.

Lu YJ, Ou TM, Tan JH, Hou JQ, Shao WY, Peng D, et al. 5-N-methylated quindoline derivatives as telomeric g-quadruplex stabilizing ligands: Effects of 5-N positive charge on quadruplex binding affinity and cell proliferation. J Med Chem 2008;51:6381-92.

Bejugam M, Sewitz S, Shirude PS, Rodriguez R, Shahid R, Balasubramanian S. Trisubstituted isoalloxazines as a new class of g-quadruplex binding ligands: Small molecule regulation of c-kit oncogene expression. J Am Chem Soc 2007;129:12926-7.

Duan W, Rangan A, Vankayalapati H, Kim MY, Zeng Q, Sun D, et al. Design and synthesis of fluoroquinophenoxazines that interact with human telomeric g-quadruplexes and their biological effects. Mol Cancer Ther 2001;1:103-20.

Hemalatha CN, Aanandhi MV. G-Quadruplex ligands as stabilizer targeting telomerase as anti-cancer agents. Asian J Pharm Clin Res 2017;10:50-3.

Hemalatha CN, Aanandhi MV. 3D QSAR and docking study of perylene- di imides analogues as potent apoptosis inducer and efficacious anticancer agent. Indian Drugs 2017;54:15-27.

Hemalatha CN, Aanandhi MV. Application of 3D QSAR and docking studies in optimization of perylene di imides as anti cancer agent. Indian J Pharm Educ Res 2018;52:46-54.

Sissi C, Lucatello L, Krapcho AP, Maloney DJ, Boxer MB, Camarasa MV, et al. Tri-, tetra- and heptacyclic perylene analogues as new potential antineoplastic agents based on DNA telomerase inhibition. Bioorg Med Chem 2007;15:555-62.

Taner K, Belgin SI, Yasemin GI, Funda Y. Evaluation of perylenediimide derivatives for potential therapeutic benefits on cancer chemotherapy. Chem Biol Drug Des 2012;80:675-81.

Von Gadow A, Joubert E, Hansmann CF. Comparison of antioxidant activity of aspalathin with that of other plant phenols of Rooibosed tea (Aspalathon linearis), α-tocopherol, BHT and BHA. J Agric Food Chem 1997;45:632-8.

Yen GC, Duh PD. Scavenging effect of methanolic extracts of peanut hulls on free-radical and active oxygen species. J Agric Food Chem 1994;42:629-32.

Marcocci I, Marguire JJ, Droy-Lefaiz MT, Packer L. The nitric oxide scavenging properties Ginkgo biloba extract. Biochem Biophys Res Commun 1994;201:748-55.

Shahriar M, Hossain I, Sharmin FA, Akhter S, Haque A, Bhuiyan MA. In vitro antioxidant and free radical scavenging activity of Withania somnifera Root. IOSR J Pharm 2013;3:38-47.

Abondanza TS, Oliveria CR, Barbosa CM. Bcl-2 expression and apoptosis induction in human HL-60 leukaemic cells treated with a novel organotellurium compound RT-04. Food Chem Toxicol 2008;46:2540-45.

Mosmann T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55-63.

Lakshmi S, Dhanaya GS, Joy B, Padmaja G, Remani P. Inhibitory effect of an extract of Curcuma zedoaria on human cervical carcinoma cells. Med Chem Res 2008;17:335-44.

Rossetti L, Franceschin M, Schirripa S, Bianco A, Ortaggi G, Savino M. Selective Interactions of Perylene derivatives having different side chains with inter- and intramolecular G-Quadruplex DNA Structures. A correlation with telomerase inhibition. Luigi Rossetti, Marco Franceschin. Bioorg Med Chem Lett 2005;15:413-20.

Sarvesh H, Vimal K. In vitro cytotoxicity effect On MCF-7 cell line of co-encapsulated artesunate and curcumin liposome. Int J Pharm Pharm Sci 2017;9:123-8.

Bashari MH, Hidayat S, Ruswandi YA, Putri T, Qomarilla N, Dwiwina RG. The N-Hexane fraction of Myrmecodia pendans inhibits cell survival and proliferation in colon cancer cell line. Int J Pharm Pharm Sci 2018;10:108-12.

Published

07-08-2018

How to Cite

CN, H., and V. A. M. “SYNTHESIS OF SOME NOVEL PERYLENE DI IMIDES AND EVALUATION OF THEIR ANTI CANCER ACTIVITY”. Asian Journal of Pharmaceutical and Clinical Research, vol. 11, no. 8, Aug. 2018, pp. 425-33, doi:10.22159/ajpcr.2018.v11i8.26539.

Issue

Section

Original Article(s)

Most read articles by the same author(s)

1 2 > >>