A Panoptic Review on Improvement in Chemothera-peutic Properties of Cytotoxic Drugs through Calixarene

DOI:

https://doi.org/10.37285/ijpsn.2023.16.3.8

Authors

  • Beena Gidwani Associate Professor, Columbia Institute of Pharmacy, CSVTU
  • Sanjay Kumar Gupta Associate Professor, Shri Rawatpura Sarkar Institute of Pharmacy, CSVTU
  • Jyoti Sahu Assistant Professor, Vishwakarma University, School of Pharmacy

Abstract

Cancer is one of the most fatal and complicated diseases. Chemotherapeutic drugs occupy a crucial position in cancer treatment, although it is still challenging to cure it from the root cause without harming healthy cells. Adjuvant or neoadjuvant and concurrent chemotherapies are usually used along with surgery and radiotherapy, depending on the spreading of tumour cells to its vicinity. However, it cannot wholly kill cancerous cells, which further develop after a while; the reason behind this is poor drug pharmacokinetic and biopharmaceutical parameters. Considering the approach of calixarenes, it has significantly drawn attention that can lodge drug molecules by forming inclusion complexes due to their prominent geometrical shape distinguishing them from other heterocyclic compounds.

Moreover, it can be more beneficial if used with nano carrier-based systems like liposomes, liposomes, nanoparticles, micelles, milliards, and siRNA to deliver anticytotoxic agents. This review highlights the potential of calixarenes properties and nanocarrier calixarene-complexed based molecules, which provide better therapeutic properties without harming healthy cells due to their unique targeted attribution. Thus, it can overcome the problem arising from conventional therapies.

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Keywords:

Calixarenes, inclusion complex, nano carrier-based system, biopharmaceutical parameters, targeting properties

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Published

2023-05-31

How to Cite

1.
Gidwani B, Gupta SK, Sahu J. A Panoptic Review on Improvement in Chemothera-peutic Properties of Cytotoxic Drugs through Calixarene. Scopus Indexed [Internet]. 2023 May 31 [cited 2024 Nov. 19];16(3):6546-55. Available from: https://ijpsnonline.com/index.php/ijpsn/article/view/3855

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References

K. D. Tripathi. Essentials of medical pharma-cology: jaypee brothers medical. 2018; 8th edition: 819

M. Yasir, M. Asif, A. Kumar, and A. Aggarval. Biopharmaceutical classification system an account. International journal of pharmtech research. 2010; 3[2]:1681–1690.

Vyas SP., Khar R.K. Basis of targeted drug delivery. In targeted and controlled drug delivery. C.B.S. publishers and distributors reprint 2008; 74: 42-46.

Stuurman FE., Nuijen B., Beijnenjh et al. Oral anticancer drugs mechanisms of low bioavailability and strategies for improvement. Clinical pharmacokinetics. 2013; 52[6]: 399-414.

Iqbal J., Anwar F., Afridi S. Targeted drug delivery systems and their therapeutic applications in cancer and immune pathological conditions. Infection Disorder. Drug targets. 2017; 17: 149–159.

Unsoy G., Gunduz U. Smart drug delivery systems in cancer therapy. Curr. Drug targets 2018; 19: 202–212.

Ludwig R et al. Calixarene-based molecules for cation recognition sensors. 2002; 22: 397–416.

Chamseddin C. et al. Evaluation of the chromatographic performance of conventional polar-endcapped and calixarene-bonded stationary phases for the separation of water-soluble vitamins. Chromatographia. 2013; 76[9–10]: 449–457.

Schuhle DT. et al. Metal binding calixarenes with potential biomimetic and biomedical applications. Coord chem rev. 2011; 255[23]: 2727–2745.

Patel DP. et al. Application of supramolecules in drug delivery. Journal of current pharmaceutical research. 2012; 9[1]: 1–5.

Mokhtari B. et al. Applications of calixarene nano-baskets in pharmacology. J inclusion phenomena macrocyclon chem. 2012; 73[1–4]: 1-15.

Rodik RV. et al. Calixarenes in bio-medical researches. Curr med chem. 2009; 16[13]:1630–1655.

Trush VV. et al. Calix [4] arene methylenebisphosphonic acids as inhibitors of protein tyrosine phosphatase 1b. Bioorg. med chem lett. 2013; 23[20]: 5619–5623.

Arduini A et al. In macrocycle synthesis Eds. Oxford university press oxford. 1996.

Hart P.D., Armstrong J.A., Brodaty E. Calixarenes with host-mediated potency in experimental tuberculosis further evidence that macrophage lipids are involved in their mechanism of action: Infection and Immunity. 1996; 64: 1491.

Hwang KM., Qi Y.M., Liu S.Y., Choy W., Chen J. Treatment of infection by enveloped virus with calix[n]arene compounds. U.S. Patent; 1995: 5441983.

Hwang K.M., Qi Y.M., Liu S.Y., Choy W., Chen J. Antithrombotic treatment with calix[n]arene compounds. U.S. Patent. 1995: 5409959.

Humesd J.S., Coleman A.W., Aubert-fouchet E. use of calix[n]arenes for treating fibrotic diseases. french patent. 1998: 2782007.

Droogmans G., Maertens C., Prenen J., Nilius B. Sulphonic acid derivatives as probes of pore properties of volume-regulated anion channels in endothelial cells: br. J. Pharmacolology. 1999; 128: 35.

Memmi L., Lazar A., Brioude A., Ball V., Coleman A.W. protein-calixarene interactions complexation of bovine serum albumin by sulfonatocalix[n]arenes. - J. Chem. Soc. Chem. Commun. 2001; 2474.

Lin Q. et al. Design and synthesis of multiple-loop receptors based on a calix [4] arene scaffold for protein surface recognition. - C. R. Chem. 2002; 5: 441-450.

Lin Q et al. Protein surface recognition by synthetic agents designs and structural requirements of a family of artificial receptors that bind to cytochrome c. - biopolym. 1998; 47: 285-297.

Casnati A et al. Peptido- and glycocalixarenes playing with hydrogen bonds around hydrophobic cavities. - acc. Chem. Res. 2003; 36: 246-254.

Kobayashi K. et al. Complexation of hydrophobic sugars and nucleosides in water with tetrasulfonate derivatives of resorcinol cyclic tetramer having a polyhydroxy aromatic cavity importance of guest-host ch-π interaction. - j. Am. Chem. Soc. 1992; 114: 10307-13.

Iwanek W. et al. The complexes of tetramethylresorc [4] arene with amines amino alcohols and pyridine. - tetrahedron 1998; 54: 14031-14040.

Cornforth J.W. et al. Antituberculous effects of certain surface-active polyoxyethylene ethers. Br. J. Pharmacol. Chemother. 1955; 10: 73.

Trushv V. et al. Calix [4] arene methylene bisphosphonic acids as inhibitors of protein tyrosine phosphatase 1b. Bioorg med chem lett. 2013; 23[20]: 5619–5623.

Nasuhipur F. et. al. Calixplatin novel potential anticancer agent based on the platinum complex with functionalized Calixarene. Journal of org. chem. 2014; 67[3]: 440–448.

Hulikova K. et al. Antitumor activity of n-acetyl-d-glucosamine-substituted glycoconjugates and combined therapy with keyhole limpet hemocyanin in b16f10 mouse melanoma model. Folia microbiol. 2010; 55[5]: 528–532.

Cherenok S. et al. Calix [4] arene-α-hydroxyphosphonic acids. Synthesis stereochemistry and inhibition of glutathione s-transferase. 2012; 4: 278–298.

Cherenok S et al. Calix [4] arene α-aminophosphonic acids asymmetric synthesis and enantioselective inhibition of an alkaline phosphatase. Org lett. 2006; 8[4]: 549–552.

Consoli GM. et al. Synthesis of water-soluble nucleotide-calixarene conjugates and preliminary investigation of their in vitro D.N.A. replication inhibitory activity. Tetrahedron. 2007; 63[44]: 10758–10763.

Zhou H et al. Structure-activity studies on a library of potent calix [4] arene-based pdgf antagonists that inhibit PDGF-stimulated P.D.G.F.R. tyrosine phosphorylation. Org biomol chem. 2006; 4[12]: 2376–2386.

Dings RP. et al. Design of nonpeptidic topomimetics of antiangiogenic proteins with antitumor activities. J natl cancer inst. 2006; 98[13]: 932–936.

Dings rp et al. Polycationic calixarene ptx013 a potent cytotoxic agent against tumors and drug resistant cancer. Invest new drugs. 2013; 31[5]: 1142–1150.

Viola S Merlo S Consoli GM Drago F Geraci C Sortino MA. Modulation of C6 glioma cell proliferation by ureido-calix [8] arenes. Pharmacology. 2010; 86[3]: 182–188.

Galindo-Murillo R., Olmedo-Romero A., Cruz-Flores E., Petrar P., Kunsagi-Mate S., Barroso-Flores J. Calix[n]arene-based drug carriers a DFT study of their electronic interactions with a chemotherapeutic agent used against leukemia. Comp Theory Chem. 2014; 103: 584–91.

Piette J Volanti C Vantieghem a Matroule J-Y Habraken Y Agostinis P. Cell death and growth arrest in response to photodynamic therapy with membrane-bound photosensitizers. Biochem Pharmacol. 2003; 66[8]: 1651–1659.

Bhal SK., Kassam K., Peirson IG., Pearl GM. The Rule of Five revisited applying log D in place of log P in drug-likeness filters. Mol Pharm. 2007; 4[4]: 556–560.

Kamada R., Yoshino W., Nomura T., et al. Enhancement of transcriptional activity of mutant p53 tumor suppressor protein through stabilization of tetramer formation by calix [6] arene derivatives. Bioorg Med Chem Lett. 2010; 20[15]: 4412–4415.

Pelizzaro-Rocha KJ., De Jesus., MB Ruela-de-Sousa RR., et. al. Calix [6] arene bypasses human pancreatic cancer aggressiveness downregulation of receptor tyrosine kinases and induction of cell death by reticulum stress and autophagy. B.B.A. Mol Cell Res. 2013; 1833[12]: 2856–2865.

Schrama D., Reisfeld RA., Becker JC. Antibody targeted drugs as cancer therapeutics. Nat Rev Drug Discov. 2006; 5[2]: 147–159.

Geraci C., Consoli GML., Granata G et al. First self-adjuvant multicomponent potential vaccine candidates by tethering of four or eight MUC1 antigenic immunodominant P.D.T.R.P. units on a calixarene platform synthesis and biological evaluation. Bioconjug Chem. 2013; 24[10]: 1710–1720.

Brown SD., Plumb JA., Johnston BF., Wheate NJ. Folding of dinuclear platinum anticancer complexes within the cavity of para-sulphonatocalix [4] arene. Inorg Chim Acta. 2012; 393: 182–186.,

Ostos F.J., Lebron J.A., Moya M.L., Lopez-Lopez M., Sanchez A., Clavero A., Garcia-Calderon C.B., Rosado I.V., Lopez- Cornejo P. P-Sulfocalix[6] arene as nanocarrier for controlled delivery of doxorubicin. Chem. Asian J. 2017; 12: 679–689.

Zhao Z.M., Wang Y., Han J., Zhu H.D. Preparation, and characterization of amphiphilic calixarene nanoparticles as delivery carriers for paclitaxel. Chem. Pharm. Bull. 2015; 63: 180–186.

Eggers Mo J., Yuan P.K., Raston Z.X., Lim C.L. Paclitaxel-loaded phosphonated calixarene nanovesicles as a modular drug delivery platform. Sci. Rep. 2016; 6: 23489.

Gallego-Yerga L., Posadas I., Torre de la., Ruiz-Almansa C. et al. Docetaxel-loaded nanoparticles assembled from beta-cyclodextrin/calixarene giant surfactants Physicochemical properties and cytotoxic effect in prostate cancer and glioblastoma cells. Front. Pharmacol. 2017; 8: 249.

Eggers Mo J. et al. Shear-induced carboplatin binding within the cavity of a phospholipid mimic for increased anticancer efficacy. Sci. Rep. 2015; 5: 10414.

Renziehausen A., Tsiailanis A.D., Perryman R., Stylos E.K., Chatzigiannis C. O’Neill K. Crook T. Tzakos A.G. Syed N. Encapsulation of temozolomide in a calixarene nanocapsule improves its stability and enhances its therapeutic efficacy against glioblastoma. Mol. Cancer Ther. 2019; 18: 1497–1505.

Panchal Jayesh G. et. al. Preparation and physicochemical characterization of carbamazepine [C.B.M.Z.]: Para-sulfonated calix[n]arene inclusion complexes. Journal of Inclusion Phenomena. June 2010; 67 :1-2.

Dmitriy N. Shurpik et. al. Antimicrobial Activity of Calixarenes and Related Macrocycles. Molecules. 2020; 25[21]: 5145.

Gabriel Marc et. al. Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-[acetyl-thiazolidine-2,4-dione] Norfloxacin Analogues as Antimicrobial Agents. Molecules. 2019; 24[21]: 3959.

Wenzhan Yang et. al. Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes. J Pharm Pharmacol. 2004 Jun; 56[6]: 703-8.

Wenzhan Yang et. al. The solubilization of the poorly water-soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes. Eur J Pharm Biopharm. 2004 Nov; 58[3]: 629-36.

Perret F., Shahgaldian P., Mazzorana M., Esposito G., Morel-desrosiers n. coleman a.w. - first steps in the study of the cellular toxicity of the calix-arene. - Book of abstracts international symposium on supramolecular chemistry Japan: 2000.

Gansey M.H.B.G., Dehaan A.S., Bos E.S., Verboow., Reinhoudt D.N. - Conjugation immunoreactivity an immunogenicity of calix [4] arenes model study to potentialcalix[4]arene-based ac3+ chelators. bioconjugate chemistry. 1999;10: 613-623.

Sidorov V., Kotch F.W., Abdrakhmanova G., Mizani R. Fettinger J.C., Davis J.T. - Ion channel formation from a calix [4] arene amide that binds Hcl. - j. Am. Chem. Soc. 2002; 124: 2267-2278.

Tanaka Y., Mayachi M., Kobuke Y. Selective vesicle formation from calixarenes by self-assembly. - angew. Chem. international edition. 1999; 38: 504-506.

Heyse S., Stora T., Schmid E., Lakey J.H., Vogel H. Emerging techniques for investigating molecular interactions at lipid membranes. - biochemistry Biophysics Acta. 1998; 1376: 319-338.

Arimori S., Nagasaki T., Shinkai S. Self-assembly tetracationic amphiphiles bearing a calix [4] arene core. Correlation between the core structure and the aggregation properties. - j. Chem. Soc. perkin trans. 2 phys. Org. Chem. 1995; 4: 679-683.

Mirgorodskaya A. B., Kudryavtseva L. A., Kazakova E., Konovalov A. Reactions of calix [4] resorcinolarene anions with esters of carboxylic acids in h2o-dmf solvent. – russian chem. Bull. 2002; 49[2]: 261-264.

Yongjun Z., Weixiao C. Self-assembly of small molecules an approach combining electrostatic self-assembly technology with host-guest chemistry. - new j. Chem. 2001; 25[3]: 483-486.

Shinkai S., Mori S., Koreish H., Tsubaki T., Manabe O. Hexasulfonated calix [6] arene derivatives a new class of catalysts surfactants and host molecules. - j. Am. Chem. Soc. 1986; 108: 2409-2416.

Thompson N.L., Brian A.A., Mcconnell H.M. Covalent linkage of a synthetic peptide to a fluorescent phospholipid and its incorporation into supported phospholipid monolayers. biochemistry Biophysics Acta. 1984; 772: 10-19.

Britt D.W., Jogikalmath G., Hlady V. Protein interactions with monolayers at the air-water-interface surfactant. Sci. Series. 2003; 10: 415-434.

Shahgaldian P., Coleman A.W. Miscibility studies on amphiphilic calix [4] arene-natural phospholipid mixed films. Langmuir. 2003; 19: 5261-5265.

Muller R.H., Mehnert W., Lucks J.S., Schwarz C., Zur Muehlen A., Weyhers H., Freitas C., Ruehl D. Solid lipid nanoparticles [sln]. An alternative colloidal carrier system for controlled drug delivery. - eur. J. Pharm.biopharm. 1995; 41: 62-69.

Sahagaldian P., Quattrocchi L., Coleman A.W., Goreloff P. A imaging of calix-arene based S.L.N.S. in gel matrices. European Journal of Pham. Biopharm. 2003; 55: 107-113.

Edilma Sanabria Espanol et. al. Calixarenes: Generalities and Their Role in Improving the Solubility, Biocompatibility, Stability, Bioavailability, Detection, and Transport of Biomolecules. Molecules. 2019; 9[3]: 90

Jie Gao et. al. Handbook of Macrocyclic Supramolecular Assembly. Supramolecular Medicine of Diverse Calixarene Derivatives. 23 April 2019; 326: 1-30.

Rossella Basilotta et. al. Role of Calixarene in Chemotherapy Delivery Strategies. Molecules. 2021; 26[13]: 3963.