ANTI-PROLIFERATIVE ACTIVITY OF INDOLES AND RELATED COMPOUNDS: A REVIEW

Main Article Content

SUJIT KUMAR BHOWAL

Abstract

Indoles, imidazole, indazole and carbazole are one of the most important biologically active natural compounds in living system which are even can be synthesized in laboratory. They are known to play functional role in cellular metabolism, cell division, cell growth as well as cellular signaling. The aim of this review is to amalgamate various information already available in the area of study of bio-activity of indole derivatives, including their ability to antagonize uncontrolled cellular proliferation in cancerous growth. An array of such compounds having central indole moiety and variation in their side chains have been synthesized and their bio-activities have been studied by various authors. Most of them show anti-cancer and anti-proliferative activities and functions through caspases 3/7/9, procaspase-3, cytochrome c, intracellular and extracellular apoptosis pathways and modulation of transcription pathways. These compounds are reportedly capable of neutralizing flagellar movements in sperms as well as of leishmanial protists. Reports show such compounds having anti-flagellated activities also seem to have anti-proliferative and anti-cancer properties.

Keywords:
Anticancer, anti-proliferative properties, biological activities, caspases, indoles

Article Details

How to Cite
BHOWAL, S. K. (2021). ANTI-PROLIFERATIVE ACTIVITY OF INDOLES AND RELATED COMPOUNDS: A REVIEW. UTTAR PRADESH JOURNAL OF ZOOLOGY, 42(6), 64-80. Retrieved from http://mbimph.com/index.php/UPJOZ/article/view/2018
Section
Review Article

References

Kaushik NK, Kaushik N, Attri P, Kumar N, Kim CH, Verma AK, Choi EH. Biomedical Importance of Indoles. Molecules. 2013;18: 6620-6662.

Bratulescu G. A new and efficient one-pot synthesis of indoles. Tetrahedron Letters. 2008;49(6):984-986.

Sachdeva H, Mathur J, Guleria A. Indole derivatives as potential anticancer agents: A review. J. Chil. Chem. Soc. 2020;65(3):4900-4907.

Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, et al. Antitumor Activity of Bis-Indole Derivatives. J. Med. Chem. 2008;51:4563–4570.

El-Sayed WA, El-Kosy SM, Ali OM, Emselm HM, Abdel-Rahman AAH. Anticancer activity of new (Tetrazol-5-yl) methylindole derivatives and their acyclic c-nucleoside analogs. Acta Poloniae Pharmaceutica - Drug Research. 2012;4(69):669-677.

Patel H, Darji N, Pillai J, Patel B. Recent advance in anti-cancer activity of indole derivatives. Int. J. Drug Res. Tech. 2012;2(3): 225-230.

Xu H, Lv M. Developments of indoles as anti-HIV-1 inhibitors. Curr Pharm Des. 2009; 15(18):2120-2148.

Sundar L, Chang FN. Antimicrobial activity and biosynthesis of indole antibiotics produced by Xenorhabdus nematophilus. J Gen Microbiol. 1993;139(12):3139-3148.

El-Sayed WA, Megeid REA, Abbas HAS. Synthesis and antimicrobial activity of new 1-[(tetrazol-5-yl) methyl] indole derivatives, their 1,2,4-triazole thioglycosides and acyclic analogs. Arch Pharm Res. 2011;34(7):1085-1096.

El-Nakkady SS, Abbas SES, Roaiah HM, Ali IH. Synthesis, antitumor and anti-inflammatory activities of 2-thienyl-3-substitued indole derivatives. Global Journal of Pharmacology. 2012;6(3):166-177.

Nataraj KS, Venkateshwara Rao J, Jayaveera KN, Naresh K, Sruthi K. Antihelminthic and analgesic activity of some novel indole derivatives Pharmacologyonline. 2010; 2:60-67.

Bhat MA, Al-Omar MA, Raish M, Ansari MA, Abuelizz HA, Bakheit AH, et al. Indole Derivatives as Cyclooxygenase Inhibitors: Synthesis, Biological Evaluation and Docking Studies. Molecules. 2018;23(6):12-50.

El Sayed MT, Hamdy NA, Osman DA, Ahmed KM. Indoles as Anti-cancer Agents. Adv Mod Oncol Res. 2015;1(1):20-35.

Karikas GA. Chemoprevention molecular and biochemical mechanisms involved in cancer control and management. Health Science Journal. 2011;2(5):149-156.

Ahmad A, Sakr WA, Rahman KMW. Role of nuclear factor-kappa b signaling in anticancer properties of Indole compounds. Journal of Experimental and Clinical Medicine. 2011; 3(2):55-62.

Gurkan-Alp AS, Mumcuoglu M, Andac CA, Dayanc E, Cetin-Atalay R, Buyukbingol E. Synthesis, anticancer activities and molecular modeling studies of novel indole retinoid derivatives. European Journal of Medicinal Chemistry. 2012;58:346-354.

Patel HM, Darji N, Pillai J, Patel B. Design, Synthesis and anti-cancer activity of 2-Phenyl-1H Indole derivatives. International Journal of Institutional Pharmacy and Life Sciences. 2012;2(4):42-56.

Patil SS, Dandagvhal KR. Indole – an important scaffold in drug discovery. International Journal of Research in Pharmacy and Chemistry. IJRPC. 2016;6(2):301-311.

Del GP, Gudipudi DK, Montemarano N, Restivo AM, Malanowska-Stega J, Arslan AA. Oral diindolylmethane (DIM): Pilot evaluation of a nonsurgical treatment for cervical dysplasia. Gynecologic Oncology. 2010; 116(3):464–467.

Fares F. The anti-carcinogenic effect of Indole-3-Carbinol and 3,3'-Diindolylmethane and their Mechanism of Action. Fares, Med Chem, 2014;1:1-8.

Jeong YM, Oh MH, Kim SY, Li H, Yun HY, Baek KJ, et al. Indole-3-acetic acid/horseradish peroxidaseinduces apoptosis in TCCSUP human urinary bladder carcinoma cells. Pharmazie. 2010;65(2):122-126.

Tilton SC, Hendricks JD, Orner GA, Pereira CB, Bailey GS, Williams DE. Gene expression analysis during tumor enhancement by the dietary phytochemical, 3,3'-diindolylmethane, in rainbow trout. Carcinogenesis. 2007;28(7): 1589-1598.

Abbassi N, Rakib ME, Chicha H, Bouissane L, Hannioui A, Aiello C, et al. Synthesis and antitumor activity of some substituted indazole derivatives. Arch Pharm (Weinheim). 2014; 347(6):423-431.

Elsayed NMY, El Ella DAA, Serya RAT, Tolba MF, Shalabya R, Abouzid KAM. Design, synthesis and biological evaluation of indazole – pyrimidine based derivatives as anticancer agents with anti-angiogenic and antiproliferative activities. Med Chem Comm. 2016;7:881-899.

Finlay MRV, Acton DG, Andrews DM, Barker AJ, Dennis M, Fisher E, et al. Imidazole piperazines: SAR and development of a potent class of cyclin-dependent kinase inhibitors with a novel binding mode. Bioorganic and Medicinal Chemistry Letters. 2008;18:4442–4446.

Jones CD, Andrews DM, Barker AJ, Bladesa K, Daunt P, East S, et al. The discovery of AZD5597, a potent imidazole pyrimidine amide CDK inhibitor suitable for intravenous dosing. Bioorganic and Medicinal Chemistry Letters. 2008;18:6369–6373.

Romero DH, Heredia VET, García-Barradas O, López MEM, Pavón ES. Synthesis of imidazole derivatives and their biological activities. Journal of Chemistry and Biochemistry. 2014;2(2):45-83.

Salahuddin, Shaharyar M, Mazumder A. Benzimidazoles: A biologically active compounds. Arabian Journal of Chemistry. 2012;1-17.

DOI: 10.1016 /j.arabjc.2012.07.017

Sharma V, Kumar P, Pathak D. Biological importance of the Indole nucleus in recent years: A comprehensive review. J. Heterocyclic Chem. 2010;47:491-502.

El-Sawy ER, Bassyouni FA, Abu-Bakr SH, Rady HM, Abdlla MM. Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3- heterocyclic indole derivatives. Acta Pharm. 2010;60:55–71.

El-Sawy ER, Abo-Salem HM, Mahmoud K, Zarie E. El-Metwally AM, Mandour AH. Synthesis, anticancer activity and molecular docking study of novel 1, 3-Diheterocycles Indole derivatives. International Journal of Pharmacy and Pharmaceutical Science. 2015; 6(7):377-385.

Baroniya S, Anwer Z, Sharma PK, Dudhe R, Kumar N. Recent advancement in imidazole as anti cancer agents: A review. Der Pharmacia Sinica. 2010;1(3):172-182.

Shalini K, Sharma PK, Kumar N. Imidazole and its biological activities: A review. Der Chemica Sinica. 2010;1(3):36-47.

Mounika KN, Jyothi AN, Raju GN, Nadendla RR. Carbazole derivatives in cancer treatment-A review. World Journal of Pharmacy and Pharmaceutical Sciences. 2015;12(4):420-428.

Tylińska B, Jasztold-Howorko R, Biaduń, B, Gębarowski T, Gasiorowski K. New pyridocarbazole derivatives. Synthesis and their in vitro anticancer activity. Acta Poloniae Pharmaceutica. 2013;70:823-832.

Kumar N, Sharma GK, Pathak D. Microwave assisted and parallel synthesis of novel substituted carbazole derivatives of biological interest. Int J Pharm Chem Sci. 2013;2:273-282.

Kumar T, Mahadevan K, Kumara MN. Synthesis and cytotoxic studies of 2, 3-dimethylindoles and tetrahydrocarbazoles. International Journal of Pharmacy and Pharmaceutical Sciences. 2014;6:137-140.

Nagarapu L, Gaikwad HK, Sarikonda K, Mateti J, Bantu R, Raghu PS, et al. Synthesis and cytotoxicity evaluation of 1-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-3-aryl-1H-pyrazole-5-carboxylic acid derivatives. Eur J Med Chem. 2010;45 (11):4720-4725.

Shah PB, Darji N, Patel B. Design, synthesis and anticancer evaluation of carbazole comprised with 1,3,4-thiadiazole derivative. International Journal of Institutional Pharmacy and Life Sciences. 2012;4:57-74.

Haider N, Marian B, Nagel T, Tarnai M, Tropper K. Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents. J. Braz. Chem. Soc. 2014;25(11):1965-1974.

Thuy TTT, Nguyen C, Toan QT, T Ngo, Bui T, Xuan NN, et al. Synthesis of novel derivatives of murrayafoline A and their inhibitory effect on LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Archives of Pharmacal Research. 2013;36(7): 823-832.

Dan X, Zhi X. Indole alkaloids with potential anticancer activity. Current topics in medicinal chemistry, 2020;20 (21):1938-1949.

Li AL, Hao Y, Wang WY, Liu QS, Sun Y, Gu W. Design, synthesis, and anticancer evaluation of novel indole derivatives of ursolic acid as potential topoisomerase ii inhibitors. Int. J. Mol. Sci. 2020;21(8):2876.