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Munaza Batool, Batool Fatima, Dilshad Hussain, Rubaida Mahmood, Muhammad Imran, Saeed Akhter, Muhammad Saqib Khan, Saadat Majeed, Muhammad Najam-ul-Haq. Radiotracer labelled thymohydroquinyl gallate capped gold nanoparticles as theranostic radiopharmaceutical for targeted antineoplastic and bioimaging[J]. Journal of Pharmaceutical Analysis. doi: 10.1016/j.jpha.2024.100965
Citation: Munaza Batool, Batool Fatima, Dilshad Hussain, Rubaida Mahmood, Muhammad Imran, Saeed Akhter, Muhammad Saqib Khan, Saadat Majeed, Muhammad Najam-ul-Haq. Radiotracer labelled thymohydroquinyl gallate capped gold nanoparticles as theranostic radiopharmaceutical for targeted antineoplastic and bioimaging[J]. Journal of Pharmaceutical Analysis. doi: 10.1016/j.jpha.2024.100965

Radiotracer labelled thymohydroquinyl gallate capped gold nanoparticles as theranostic radiopharmaceutical for targeted antineoplastic and bioimaging

doi: 10.1016/j.jpha.2024.100965
  • Received Date: Sep. 16, 2023
  • Accepted Date: Mar. 11, 2024
  • Rev Recd Date: Mar. 02, 2024
  • Thymoquinone (Tq) and gallic acid (GA) are known for counter-tumorigenic characteristics. GA inhibits cancer cell proliferation by interfering with many apoptotic signaling pathways, producing more reactive oxygen species (ROS), focusing on the cell cycle, and suppressing the expression of oncogenes and matrix metalloproteinases (MMPs). In this study, thymoquinone (after reducing to thymohydroquinone) and gallic acid are esterified to form thymohydroquinyl gallate (a prodrug). Thymohydroquinyl gallate (THQG) possesses enhanced antineoplastic efficacy and targeted delivery potential. The chemical and spectroscopic analysis confirms ester synthesis. Gold nanoparticles (AuNPs) are employed as nanocarriers due to their physicochemical and optical characteristics, biocompatibility, and low toxicity. As an efficient drug transporter, gold nanoparticles (AuNPs) shield conjugated drugs from enzymatic digestion. The prodrug acts as a reducing agent for Au metal atoms and is loaded onto it after reduction. The nano drug is radiolabeled with 99mTc and 131I to monitor the drug biodistribution in animals using a gamma camera and single-photon emission computerized tomography (SPECT). 131I is an antineoplastic that helps enhance the drug's efficiency. Chromatographic results reveal promising radiolabeling percentages. In vitro, drug release shows sustained release at pH 5.8. In vitro 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) cytotoxicity assay reveals drug potency on CAL 27 and MCF 7 cell lines.
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  • [1]
    S. Darakhshan, A. Bidmeshki Pour, A. Hosseinzadeh Colagar, et al., Thymoquinone and its therapeutic potentials, Pharmacol. Res. 95-96(2015) 138–158.
    [2]
    M. Khader, P.M. Eckl, Thymoquinone: An emerging natural drug with a wide range of medical applications, Iran. J. Basic Med. Sci. 17(2014) 950–957.
    [3]
    L. Reddy, B. Odhav, K.D. Bhoola, Natural products for cancer prevention: A global perspective, Pharmacol. Ther. 99(2003) 1–13.
    [4]
    A.M. Shoieb, M. Elgayyar, P.S. Dudrick, J.L. Bell, P.K. Tithof, In vitro inhibition of growth and induction of apoptosis in cancer cell lines by thymoquinone, Int. J. Oncol. 22(2003) 107–113.
    [5]
    F. Alhmied, Molecular mechanisms of thymoquinone as an anticancer agent, Comb. Chem. High Throughput Screen. 24(2021) 1644–1653.
    [6]
    S. Keyvani-Ghamsari, M. Rahimi, K. Khorsandi, An update on the potential mechanism of Gallic acid as an antibacterial and anticancer agent, Food Sci. Nutr. 11(2023) 5856–5872.
    [7]
    S. Verma, A. Singh, A. Mishra, Gallic acid: Molecular rival of cancer, Environ. Toxicol. Pharmacol. 35(2013) 473–485.
    [8]
    P. Urizzi, M.C. Monje, J.P. Souchard, et al., Antioxidant activity of phenolic acids and esters present in red wine on human Low-Density Lipoproteins, J. Chim. Phys. 96(1999) 110–115.
    [9]
    D. Li, Z. Liu, W. Zhao, et al., A straightforward method to determine the cytocidal and cytopathic effects of the functional groups of Gallic acid, Process. Biochem. 46(2011) 2210–2214.
    [10]
    A. Serrano, C. Palacios, G. Roy, et al., Derivatives of Gallic acid induce apoptosis in tumoral cell lines and inhibit lymphocyte proliferation, Arch. Biochem. Biophys. 350(1998) 49–54.
    [11]
    S. Saba, K. Cagino, C. Bennett, Using NMR spectroscopy to probe the chemo- and diastereoselectivity in the NaBH4 reduction of benzoin acetate and benzoin benzoate, J. Chem. Educ. 92(2015) 543–547.
    [12]
    G. Greber, Vogel’s textbook of practical organic chemistry (5th Ed.), revised by Brian S. Furniss, Antony J. Hannaford, Peter W. G. Smith, and Austin R. Tatchell, John Wiley & Sons, New York, 1514 pp. J. Polym. Sci. A Polym. Chem. 29(1991), 1223.
    [13]
    Shaffer, C. Bionanotechnology Applications. News-Medical. 201926 februuary 12 august 2020]; Available from: https://www.news-medical.net/life-sciences/Bionanotechnology-Applications.aspx.
    [14]
    T. Jung, Biodegradable nanoparticles for oral delivery of peptides: Is there a role for polymers to affect mucosal uptake? Eur. J. Pharm. Biopharm. 50(2000) 147–160.
    [15]
    L. Illum, Nanoparticulate systems for nasal delivery of drugs: A real improvement over simple systems? J. Pharm. Sci. 96(2007) 473–483.
    [16]
    A.K. Khan, R. Rashid, G. Murtaza, et al., Gold nanoparticles: Synthesis and applications in drug delivery, Trop. J. Pharm Res 13(2014), 1169.
    [17]
    A. Basu, S. Kundu, A. Das, et al., Polyphenol capping on a gold nanosurface modulates human serum albumin fibrillation, Mater. Adv. 1(2020) 1142–1150.
    [18]
    S.R. Chavva, S.K. Deshmukh, R. Kanchanapally, et al., Epigallocatechin gallate-gold nanoparticles exhibit superior antitumor activity compared to conventional gold nanoparticles: Potential synergistic interactions, Nanomaterials 9(2019), 396.
    [19]
    S. Tariq, S.A.R. Naqvi, S. Naz, et al., Dose-dependent internalization and externalization integrity study of newly synthesized 99mTc-thymoquinone radiopharmaceutical as cancer theranostic agent, Dose Response 18(2020), 1559325820914189.
    [20]
    W.M.A. Darwish, N.A. Bayoumi, Gold nanorod-loaded (PLGA-PEG) nanocapsules as near-infrared controlled release model of anticancer therapeutics, Lasers Med. Sci. 35(2020) 1729–1740.
    [21]
    C. Maioli, A. Bestetti, F. Milani, et al., Evaluation of different counting methods for use in radiochemical purity testing procedures for 99mTc-labelled radiopharmaceuticals, Appl. Radiat. Isot. 66(2008) 556–559.
    [22]
    S. Reis, M.J. Gomes, S. Martins, et al., Lipid nanoparticles for topical and transdermal application for alopecia treatment: Development, physicochemical characterization, and in vitro release and penetration studies, Int. J. Nanomed. (2014), 1231.
    [23]
    S. Shamaila, N. Zafar, S. Riaz, et al., Gold nanoparticles: An efficient antimicrobial agent against enteric bacterial human pathogen, Nanomaterials 6(2016), 71.
    [24]
    S. Balakrishnan, S. Mukherjee, S. Das, et al., Gold nanoparticles-conjugated quercetin induces apoptosis via inhibition of EGFR/PI3K/Akt-mediated pathway in breast cancer cell lines (MCF-7 and MDA-MB-231), Cell Biochem. Funct. 35(2017) 217–231.
    [25]
    S.R. Guntur, N.S. Kumar, M.M. Hegde, et al., In vitro studies of the antimicrobial and free-radical scavenging potentials of silver nanoparticles biosynthesized from the extract of Desmostachya bipinnata, Anal. Chem. Insights 13(2018), 1177390118782877.
    [26]
    Y. Yamakita, M. Tasumi, Vibrational analyses of p-benzoquinodimethane and p-benzoquinone based on ab initio Hartree-Fock and second-order Moller-Plesset calculations, J. Phys. Chem. 99(1995) 8524– 8534.
    [27]
    D. Arizmendi-Cotero, A. Villanueva-Carvajal, R.M. Gómez-Espinoza, et al., Radical scavenging activity of an inulin-gallic acid graft and its prebiotic effect on Lactobacillus acidophilus in vitro growth, J. Funct. Foods 29(2017) 135–142.
    [28]
    B.C. Smith, The C= O bond, part III: Carboxylic acids, (2018).
    [29]
    B.C. Smith, The C= O bond, part VI: Esters and the rule of three, (2018).
    [30]
    A. Singh, R. Raju, M. Mrad, et al., The reciprocal EC50 value as a convenient measure of the potency of a compound in bioactivity-guided purification of natural products, Fitoterapia 143(2020), 104598. Journal Pre-proof
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