[1]
Ishtapran Sahoo, Department of Biotechnology, Dayananda Sagar College of Engineering, Shavige Malleswara Hills, Bengaluru, Karnataka, India.
[2]
Yashas Devasurmutt, Department of Biotechnology, Dayananda Sagar College of Engineering, Shavige Malleswara Hills, Bengaluru, Karnataka, India.
[3]
Umashankar Thippeswamy, Department of Biotechnology, Dayananda Sagar College of Engineering, Shavige Malleswara Hills, Bengaluru, Karnataka, India.
[4]
Padmalatha Rai Satwadi, School of Life Sciences, Manipal University, Karnataka, India.
[5]
Yarappa Lakshmikanth Ramachandra, Department of Post-Graduation Studies and Research in Biotechnology and Bioinformatics, Kuvempu University, Shankaraghatta, Karnataka, India.
[6]
Kumar Hegde Biliyaru Ananda, Biology Department, Sri Dharmasthala Manjunatheswra College, Ujire, Karnataka, India.
[7]
Govindappa Melappa, Department of Biotechnology, Dayananda Sagar College of Engineering, Shavige Malleswara Hills, Bengaluru, Karnataka, India.
Biological compounds conjugated nanoparticles exhibiting many biological activities. Coumarin and p-coumaric acid have been implicated to alleviate multiple diseases and have isolated from endophytic fungi Alternaria species-1 of Crotalaria pallida. In the present study, the present study interested in assessing the anti-HIV and anticoagulant properties of coumarin and p-coumaric acid by molecular interaction studies. The present study used coumarin, p-coumaric acid, coumarin conjugated fullerene, p-coumaric acid conjugated fullerene, fullerene individually. Two coagulant and nine HIV-1 proteins were selected for molecular docking studies. The results report that p-coumaric acid has greater interaction with coagulant proteins followed by coumarin and fullerene. Among HIV-1 proteins higher interaction was observed with p-coumaric acid especially HIV-1 gp120. However, upon coagulating fullerene to coumarin and p-coumaric acid, coumarin-fullerene showed significantly greater interaction with coagulant proteins and all HIV-1 proteins, compared to p-coumaric acid-fullerene and fullerene. Our in silico study, thus identifies nanoparticles synthesized by fullerene conjugated to naturally occurring coumarin and p-coumaric acid as a potential, safe and cost effective alternative strategy to treating HIV or its use as an anticoagulant.
[1]
Kaur, M., Kohli, S., Sandhu, S., Bansai, Y., Bansal, G. Coumarin: a promising scaffold for anticancer agents. Anticancer Agents Med Chem, 15 (8), 1032-1048, 2015.
[2]
Klenkar, J. and Molnar, M. Natural and synthetic coumarins as potential anticancer agents. J Chem Pharm Res, 7 (7), 1223-1238, 2015.
[3]
Zhou, P., Takaishi, Y., Duan, H., Chen, B., Honda, G., Itoh, M., Takeda, Y., Kodzhimatov, O. K., Lee, K. H. Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. Phytochemistry, 53 (6), 689-697, 2000.
[4]
Kostova. I. Coumarins as inhibitors of HIV reverse transcriptase. Current HIV Research, 4 (3), 347-63, 2006.
[5]
Venugopala, K. N., Rashmi, V., Odhav, B. Review on natural coumarin lead compounds for their pharmacological activity. BioMed Research International, 2013, 14 pages, article ID 963248.
[6]
Kang, S. Y. and Kim, Y. C. Neuroprotective coumarins from the root of Angelica gigas: structure- activity relationships. Arch Pharmacal Res, 30 (11), 1368-1373, 2007.
[7]
Bubols, G. B., Dda, V. R., Medina-Remon, A., von Poser, G., Lamuela-Raventos, R. M., Eigler-Lima, V. L., Garcia, S. C. The antioxidant activity of coumarins and flavonoids. Mini Review on Medicinal Chemistry, 13 (3), 318-334, 2013.
[8]
Kadhum, A. A. H., Al-Amiery, A. A., Musa, A. Y., Mohamad, A. B. The antioxidant activity of new coumarin derivatives. Int J Mol Sci, 12, 5747-5761, 2011.
[9]
Al-Majedy, Y. Antioxidant activity of courmarins. Sys Rev Pharm, 8 (1), 24-30, 2017.
[10]
Arora, R. K. Novel coumarin-benzimidazole derivatives as antioxidants and safer anti-inflammatory agents. Acta Pharmaceutica Sinica A, 4 (5), 368-375, 2014.
[11]
Hadjipavlou-Litina, D. Anti-inflammatory and antioxidant activity of coumarins designed as potential fluorescent zinc sensors. J Enzyme Inhib Med Chem, 22 (3), 287-92, 2007.
[12]
Jain, S. K. and Borthakur, S. K. Ethnobotany of the Mikers of India. Econ Bot, 34, 264-272, 1980.
[13]
Carroll, G. C. The biology of endophytism in plants with particular reference to woody plants. Cambridge University Press, UK 1986.
[14]
Kusari, S. Chemical ecology of endophytic fungi: origins of secondary metabolites. Chem Biol, 19, 792-798, 2012.
[15]
Sachin, N. Do endophytic fungi possess pathway genes for plant secondary metabolites? Curr Sci, 104, 178-182, 2013.
[16]
Heinig, U. Getting to the bottom of Taxol biosynthesis by fungi. Fungal Divers, 60, 161-170, 2013.
[17]
Umashankar, T., Govindappa, M., Ramachandra, Y. L., Channabasava. Isolation and purification of p-coumaric acid from endophytic fungi, Alternaria species of Crotalaria pallida and in vitro cytotoxicity. Inter J Biol Pharm Res, 6 (2), 96-104, 2015a.
[18]
Umashankar, T., Govindappa, M., Ramachandra, Y. L., Chandrappa, C. P., Padmalatha Rai, S., Channabasava, R. Isolation, purification and in vitro cytotoxicity activities of coumarin isolated from endophytic fungi, Alternaria species of Crotalaria pallida. Indo American J Pham Res, 5 (2), 926-936, 2015b.
[19]
Iyer, V. B., Gurupadayya, B. M., Inturi, B., Sairam, V., Pujari, G. V. Synthesis of 1,3,4-oxadiazoles as promising anticoagulant agents. RSC Adv, 6, 24797-24807, 2016.
[20]
Al-Amri, M. S. Q. In silico design of novel anti-coagulant peptides targeting blood coagulation factor VIIa. Sultan Oaboos University Med J, 11 (1), 83-94, 2011.
[21]
Kolyadko, V. N., Lushchekina, S. V., Vuimo, T. A., Surov, S. S., Ovsepyan, R. A., Korneeva, V. A., Vorbiev, I. I., Orlova, N. A., Minakhin, L., Kuznedelov, K., Severinov, K. V., Ataullakhanov, F. I., Panteleev, M. A. New Infestin-4 Mutants with Increased Selectivity against Factor XIIa. PLoS ONE, 10 (12), e0144940, 2015.
[22]
Bashir, T., Patgoankar, M., Kumar, S. C., Pasi, A., Reddy, K. V. R. HbAHP-25, an in silico designed peptide, inhibits HIV-1 entry by blocking gp120 binding to CD4 receptor. PLoS ONE, 10 (4), e0124839, 2015.
[23]
Hamasaki, T., Okamoto, M., Baba, M. Identification of novel inhibitors of human immunodeficiency virus type 1 replication by in silico screening targeting cyclin T1/Tat interaction. Antimicrob Agents Chemother, 57 (2), 1323-1331, 2013.
[24]
Durdagi, S., Okamoto, M., Baba, M. In silico drug screening approach for the design of magic bullets: a successful example with anti-HIV fullerene derivatized amino acids. Journal of Chem Inf Model, 49 (5), 1139-1143, 2009.
[25]
Chander, S., Ashok, P., Singh, A., Murugesan, S. De-novo design, synthesis and evaluation of novel 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as HIV-1 reverse transcriptase inhibitors. Chem Cent J, 9, 33, 2015.
[26]
Wadood, A., Riaz, M., Uddin, R., ul-Haq, Z. In silico identification and evaluation of leads for the simultaneous inhibition of protease and helicase activities of HCV NS3/4A protease using complex based pharmacophore mapping and virtual screening. PLOS one, 9 (2), e89109, 2017.
[27]
Li, Q., Li, X., Li, C., Chen, L., Song, J., Tang, Y., Xu, X. A network-based multi-target computational estimation scheme for anticoagulant activities of compounds. PLoS ONE, 6 (3), e14774, 2011.
[28]
Choi, S. B., Choong, Y. S., Saito, A., Wahab, H. A., Najimudin, N., Watanabe, N., Osada, H., Ong, E. B. B. In silico investigation of a HIV-1 Vpr inhibitor binding site: potential for virtual screening and anti-HIV drug design. Molecular Informatics, 33 (11-12), 742-748, 2014.
[29]
Govindappa, M., Hemmanur, K. C., Nithin, S., Bhat, G. K., Channabasava. In vitro anti-HIV activity of partially purified coumarin(s) isolated from fungal endophyte, Alternaria species of Calophyllum inophyllum. Pharmacology & Pharmacy, 6, 321-328, 2015.
[30]
Shikishima, Y., Takaishi, Y., Honda, G., Ito, M., Takeda, Y., Kodzhimatov, O. K., Ashurmetov, O., Lee, K. H. Chemical constituents of Prangos tschimganica; structure elucidation and absolute configuration of coumarin and furanocoumarin derivatives with anti-HIV activity. Chem Pharm Bul, 49 (7), 877-880, 2001.
[31]
Garro, H. A. and Pungitore, C. R. Coumarins as potential inhibitors of DNA polymerase and reverse transcriptase, searching new antiretroviral and antitumoral drugs. Current Drug Discovery Technologies, 12 (2), 66-79, 2015.
[32]
Jaduan, P., Khopkar, P., Kulkarni, S. Repurposing phytochemicals as anti-HIV agents. Journal of Antivirals and Antiretrovirals, 8, 4, 2016.
[33]
Barron, A. R. [60] fullerene peptides: bio-nano conjugates with structural and chemical diversity. J Enz Inhib Med Chem, 31 (51), 164-176, 2016.
[34]
Ma, X., Wang, D., Wu, Y., Ho, R. J. Y., Jia, L., Guo, P., Hu, L., Xing, L., Xing, G., Zeng, Y., Liang, X. J. AIDS treatment with novel anti-HIV compounds improved by nanotechnology. AAPS J, 12 (3), 272-278, 2010.
[35]
Bakry, E., Vallant, R. M., Najam-ul-Haq, M., Rainer, M., Szabo, Z., Huck, C. W., Bonn, G. K. Medicinal applications of fullerenes. Int J Nanomedicine, 2 (4), 639-649, 2007.
[36]
Nayak, Y., Avadhani, K., Mutalik, S., Nayak, U. Y. Lymphatic delivery of anti-HIV drug nanoparticles. Recent Patents on Nanotechnology, 10 (2), 116-127, 2016.
