Skip to main content
SpringerLink
Log in

Syntheses, structures, and biological activities of two supramolecules consisting of resorcinolcalix[4]arene and amino-pyridine moieties

  • Short Communication
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

Self-assembly of C-iso-butyl-resorcinolcalix[4]arene (CBCR) with 4-aminopyridine (4-AP) or 3-dimethylaminopyridine (3-DMAP) in ethanol afforded two host-guest complexes CBCR⋅4-AP (1) and CBCR⋅2(3-DMAP) (2), respectively. Supramolecules 1 and 2 were characterized by FT-IR, 1H NMR, 13C NMR spectroscopies and single crystal X-ray diffraction analysis. The antioxidant and antibacterial experiments were conducted on complexes 1, 2 and the starting materials. The 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl and 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) free radical scavenging rate could reach 91.73% and 98.55% when the concentration of complex 2 was 500 and 31.25 mg/mL, respectively. The antibacterial test of complex 1 showed that the antibacterial circle diameter against Escherichia coli was 10.25 mm, with a MIC value of 12.5 mg/mL, and the antibacterial circle diameter against Staphylococcus aureus was 14.33 mm with a MIC value of 3.12 mg/mL.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Data availability

No datasets were generated or analysed during the current study.

References

  1. Pedersen, C.J.: The discovery of crown ethers (Noble lecture). Angew Chem. Int. Ed. Engl. 27, 1021–1027 (1988)

    Article  Google Scholar 

  2. Gangemi, C.M., Pappalardo, A., Sfrazzetto, G.T.: Applications of supramolecular capsules derived from resorcin[4]arenes, calix[n]arenes and metallo-ligands: From biology to catalysis. RSC Adv. 5, 51919–51933 (2015)

    Article  CAS  Google Scholar 

  3. Wiegmann, S., Fukuhara, G., Neumann, B., Stammler, H.G., Inoue, Y., Mattay, J.: Inherently chiral resorcin[4]arenes with urea and amide side arms: synthesis, structure and chiral recognition. Eur. J. Inorg. Chem. 2013, 1240–1245 (2013)

  4. Gaeta, C., Talotta, C., De Rosa, M., La Manna, P., Soriente, A., Neri, P.: The hexameric resorcinarene capsule at work: Supramolecular catalysis in confined spaces. Chem. Eur. J. 25, 4899–4913 (2019)

    Article  CAS  PubMed  Google Scholar 

  5. Li, N., Harrison, R.G., Lamb, J.D.: Application of resorcinarene derivatives in chemical separations. J. Incl. Phenom. Macro Chem. 78, 39–60 (2014)

    Article  CAS  Google Scholar 

  6. Kane, C.M., Ugono, O., Barbour, L.J., Holman, K.T.: Many simple molecular cavitands are intrinsically porous (zero-dimensional pore) materials. Chem. Mater. 27, 7337–7354 (2015)

    Article  CAS  Google Scholar 

  7. Fujisawa, I., Kitamura, Y., Kato, R., et al.: Crystal structures of resorcin[4]arene and pyrogallol [4] arene complexes with DL-pipecolinic acid. Model compounds for the recognition of the pipecolinyl ring, a key fragment of FK506, through C–H⋯ π interaction. J. Mol. Struct. 1056, 292–298 (2014)

    Article  Google Scholar 

  8. MacGillivray, L.R., Atwood, J.L.: A chiral spherical molecular assembly held together by 60 hydrogen bonds. Nature. 389, 469–472 (1997)

    Article  CAS  Google Scholar 

  9. Blaskovich, M.A., Lin, Q., Delarue, F.L., Sun, J., Park, H.S., Coppola, D., Sebti, S.M.: Design of GFB-111, a platelet-derived growth factor binding molecule with antiangiogenic and anticancer activity against human tumors in mice. Nat. Biotechnol. 18, 1065–1070 (2000)

    Article  CAS  PubMed  Google Scholar 

  10. Wang, K., Guo, D.S., Zhang, H.Q., Li, D., Zheng, X.L., Liu, Y.: Highly effective binding of viologens by p-sulfonatocalixarenes for the treatment of viologen poisoning. J. Med. Chem. 52, 6402–6412 (2009)

    Article  CAS  PubMed  Google Scholar 

  11. Nasuhi Pur, F.: Calixdrugs: Calixarene-based clusters of established therapeutic drug agents. Mol. Divers. 20, 781–787 (2016)

    Article  CAS  PubMed  Google Scholar 

  12. Läppchen, T., Dings, R.P., Rossin, R., Simon, J.F., Visser, T.J., Bakker, M., Grüll, H.: Novel analogs of antitumor agent calixarene 0118: Synthesis, cytotoxicity, click labeling with 2-[18F] fluoroethylazide, and in vivo evaluation. Eur. J. Med. Chem. 89, 279–295 (2015)

    Article  PubMed  Google Scholar 

  13. Santos, D., Medeiros-Silva, J., Cegonho, S., Alves, E., Ramilo-Gomes, F., Santos, A.O., Cruz, C.: Cell proliferation effects of calix[4]arene derivatives. Tetrahedron. 71, 7593–7599 (2015)

    Article  CAS  Google Scholar 

  14. Barbera, L., Gattuso, G., Kohnke, F.H., Notti, A., Pappalardo, S., Parisi, M.F., Villari, V.: Self-assembly of amphiphilic anionic calix[4]arenes and encapsulation of poorly soluble naproxen and flurbiprofen. Org. Biomol. Chem. 13, 6468–6473 (2015)

    Article  CAS  PubMed  Google Scholar 

  15. Puckowska, A., Gawel, M., Komorowska, M., Drozdzal, P., Arning, A., Pawelski, D., Brzezinski, K., Plonska-Brzezinska, M.E.: Synthesis and structural characterization of pyridine-2, 6-dicarboxamide and furan-2, 5-dicarboxamide derivatives. Mol. 27, 1819 (2022)

    Article  CAS  Google Scholar 

  16. Hu, Y., Zhang, J., Yu, C., Li, Q., Dong, F., Wang, G., Guo, Z.: Synthesis, characterization, and antioxidant properties of novel inulin derivatives with amino-pyridine group. Int. J. Bio Macromol. 70, 44–49 (2014)

    Article  CAS  Google Scholar 

  17. Milošević, M.D., Marinković, A.D., Petrović, P., Klaus, A., Nikolić, M.G., Prlainović, N., Cvijetić, I.N.: Synthesis, characterization and SAR studies of bis(imino)pyridines as antioxidants, acetylcholinesterase inhibitors and antimicrobial agents. Bioorg. Chem. 102, 104073 (2020)

    Article  PubMed  Google Scholar 

  18. Khan, E.: Pyridine derivatives as biologically active precursors; organics and selected coordination complexes. ChemistrySelect. 6, 3041–3064 (2021)

    Article  CAS  Google Scholar 

  19. Mohammad Abu-Taweel, G., Ibrahim, M.M., Khan, S., Al-Saidi, H.M., Alshamrani, M., Alhumaydhi, F.A., Alharthi, S.S.: Medicinal importance and chemosensing applications of pyridine derivatives: A review. Crit. Rev. Anal. Chem. 1–18 (2022)

  20. Abu Farha, R., Bustanji, Y., Al-Hiari, Y., Al-Qirim, T., Abu Shiekha, G., Albashiti, R.: Lipid lowering activity of novel N-(benzoylphenyl) pyridine-3-carboxamide derivatives in Triton WR-1339-induced hyperlipidemic rats. J. Enzyme Inhib. Med. Ch. 31, 138–144 (2016)

    Article  CAS  Google Scholar 

  21. Castellan, P., Marchioni, M., Castellucci, R., De Francesco, P., Iantorno, R., Schips, L., Cindolo, L.: Abiraterone acetate for early stage metastatic prostate cancer: Patient selection and special considerations. Ther. Clin. Risk Manag. 14, 2341–2347 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Kim, H.S., Jadhav, J.R., Jung, S.J., Kwak, J.H.: Synthesis and antimicrobial activity of imidazole and pyridine appended cholestane-based conjugates. Bioorg. Med. Chem. Lett. 23, 4315–4318 (2013)

    Article  CAS  PubMed  Google Scholar 

  23. Liu, J.L., Liu, X.L., Jia, A.Q., Shi, H.T., Zhang, Q.F.: Supramolecular structures and crystal stability of diisobutylaminomethylated calix[4]resorcinarenes. J. Incl. Phenom. Macro Chem. 98, 49–56 (2020)

    Article  CAS  Google Scholar 

  24. Liu, X.L., Liu, J.L., Wang, N.N., Jia, A.Q., Zhang, Q.F.: Syntheses and structures of thiophosphorylatocavitands and their reactivity towards first-row transition metal halides. Inorg. Nano-Met Chem. 50, 1315–1321 (2020)

    Article  CAS  Google Scholar 

  25. Liu, X.L., Liu, J.L., Yang, H.M., Jia, A.Q., Zhang, Q.F.: Two hydrogen-bonded supramolecular structures based on C-alkylcalix[4]resorcinarene and 4,4′-bipyridine. J. Chem. Crystallogr. 51, 139–144 (2021)

    Article  CAS  Google Scholar 

  26. Wang, Y.J., Liu, J.L., Yang, H.M., Jia, A.Q., Zhang, Q.F.: Inclusion of ferrocene within the deepened cavities formed from the hydrogen bonding self-assembly of calix[4]resorcinarenes with bis-pyridines. J. Incl. Phenom. Macro Chem. 85, 105–110 (2016)

    Article  CAS  Google Scholar 

  27. Cram, D.J., Karbach, S., Kim, H.E., Knobler, C.B., Maverick, E.F., Ericson, J.L., Helgeson, R.C.: Host-guest complexation. 46. Cavitands as open molecular vessels form solvates. J. Am. Chem. Soc. 110, 2229–2237 (1988)

    Article  CAS  Google Scholar 

  28. Smart and Saint + for, Windows, N.T.: Version 6.02a. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA (1998)

  29. Sheldrick, G.M.: SADABS. University of Göttingen, Germany (1996)

  30. Sheldrick, G.M.: SHELXTL Software Reference Manual. Version 5.1. Bruker AXS Inc., Madison, USA (1997)

    Google Scholar 

  31. Sheldrick, G.M.: A short history of SHELX. Acta Crystallogr. A. 64, 112–122 (2008)

    Article  CAS  PubMed  Google Scholar 

  32. Erdem, E., Yeniceri, M., Aydin, Ç., Mammadov, R., Söyleyici, S.: Antioxidant and DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical scavenging activities of the new calix[4]arene-bodipy derivative. Int. J. Sec Metabolite. 1, 20 (2014)

    Google Scholar 

  33. Ngurah, B.I.G.M.: Synthetic C-methoxyphenyl calix[4]resorcinarene and its antioxidant activity. J. Appl. Chem. Sci. 5, 403–408 (2018)

    Article  CAS  Google Scholar 

  34. Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., Rice-Evans, C.: Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol. Med. 26, 1231–1237 (1999)

    Article  CAS  Google Scholar 

  35. Demirkol, D.O., Yildiz, H.B., Sayın, S., Yilmaz, M.: Enzyme immobilization in biosensor constructions: Self-assembled monolayers of calixarenes containing thiols. RSC Adv. 4, 19900–19907 (2014)

    Article  CAS  Google Scholar 

  36. Hassan, A.U., Sumrra, S.H., Raza, M.A., Zubair, M., Zafar, M.N., Mughal, E.U., Nazar, M.F., Irfan, A., Imran, M., Assiri, M.A.: Design, facile synthesis, spectroscopic characterization, and medicinal probing of metal-based new sulfonamide drugs: A theoretical and spectral study. Appl. Organomet. Chem. 35, 6054 (2021)

    Article  Google Scholar 

  37. Wang, R., Luo, Q., Feng, Y.: Determination of antioxidant energy of kaempferol by DPPH, ABTS and FRAP micrometho. Guangzhou Chem. Ind. 49, 58–63 (2021)

    Google Scholar 

  38. Islam, M.B., Islam, M.I., Nath, N., Emran, T.B., Rahman, M.R., Sharma, R., Matin, M.M.: Recent advances in pyridine scaffold: Focus on chemistry, synthesis, and antibacterial activities. Biomed. Res. Int. 15, 2023 (2023)

    Google Scholar 

  39. Trombetta, D., Castelli, F., Sarpietro, M.G., Venuti, V., Cristani, M., Daniele, C., Saija, A., Mazzanti, G., Bisignano, G.: Mechanisms of antibacterial action of three monoterpenes. Antimicrob. Agents Chem. 49, 2474–2478 (2005)

    Article  CAS  Google Scholar 

  40. Nazzaro, F., Fratianni, F., De Martino, L., Coppola, R., De Feo, V.: Effect of essential oils on pathogenic bacteria. Pharmic. 6, 1451–1474 (2013)

    Google Scholar 

  41. Kibou, Z., Aissaoui, N., Daoud, I., Seijas, J.A., Vázquez-Tato, M.P., Khelil, K., N., Choukchou-Braham, N.: Efficient synthesis of 2-aminopyridine derivatives: Antibacterial activity assessment and molecular docking studies. Mol. 27, 3439 (2022)

    Article  CAS  Google Scholar 

  42. Liu, B.T., Pan, X.H., Nie, D.Y., Hu, X.J., Liu, E.P., Liu, T.F.: Ionic hydrogen-bonded organic frameworks for ion-responsive antimicrobial membranes. Adv. Mater. 32, 2005912 (2020)

    Article  CAS  Google Scholar 

Download references

Funding

This project was supported by National Natural Science Foundation of China (90922008).

Author information

Authors and Affiliations

  1. Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’anshan, 243002, Anhui, P. R. China

    Lu-Si Chen, Xin-Min Zhou, Qing Wang, Ai-Quan Jia & Qian-Feng Zhang

Authors
  1. Lu-Si Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xin-Min Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Qing Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ai-Quan Jia
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Qian-Feng Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Lu-Si Chen and Xin-Min Zhou wrote the main manuscript text and Qing Wang prepared Figs. 1, 2, 3, 4, 5 and 6. All authors reviewed the manuscript.

Corresponding author

Correspondence to Qian-Feng Zhang.

Ethics declarations

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Consent to participate

The authors agreed to participate in this work.

Consent for publication

All authors have given their consent for publication.

Competing interests

The authors declare no competing interests.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary Material 1

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chen, LS., Zhou, XM., Wang, Q. et al. Syntheses, structures, and biological activities of two supramolecules consisting of resorcinolcalix[4]arene and amino-pyridine moieties. J Incl Phenom Macrocycl Chem 104, 171–181 (2024). https://doi.org/10.1007/s10847-024-01231-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-024-01231-7

Keywords

Search

Navigation