Synthesis of Bodipy-Tagged Galactoconjugates and Evaluation of Their Antibacterial Properties.

Chiara Maria Antonietta Gangemi, Maura Monforte, Antonino Arrigo, Paola Maria Bonaccorsi, Sabrina Conoci, Antonella Iaconis, Fausto Puntoriero, Domenico Franco, Anna Barattucci
Author Information
  1. Chiara Maria Antonietta Gangemi: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F. Stagno D'Alcontres 31, 98166 Messina, Italy. ORCID
  2. Maura Monforte: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F. Stagno D'Alcontres 31, 98166 Messina, Italy.
  3. Antonino Arrigo: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F. Stagno D'Alcontres 31, 98166 Messina, Italy. ORCID
  4. Paola Maria Bonaccorsi: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F. Stagno D'Alcontres 31, 98166 Messina, Italy. ORCID
  5. Sabrina Conoci: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F. Stagno D'Alcontres 31, 98166 Messina, Italy.
  6. Antonella Iaconis: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F. Stagno D'Alcontres 31, 98166 Messina, Italy. ORCID
  7. Fausto Puntoriero: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F. Stagno D'Alcontres 31, 98166 Messina, Italy. ORCID
  8. Domenico Franco: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F. Stagno D'Alcontres 31, 98166 Messina, Italy. ORCID
  9. Anna Barattucci: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, V.le F. Stagno D'Alcontres 31, 98166 Messina, Italy. ORCID

Abstract

As a development of our research on biocompatible glycoconjugate probes and specifically multi-chromophoric systems, herein, we report the synthesis and early bactericidal tests of two luminescent glycoconjugates whose basic structure is characterized by two boron dipyrromethene difluoride (BODIPY) moieties and three galactoside rings mounted on an oligophenylene ethynylene (OPE) skeleton. BODIPY fluorophores have found widespread application in many branches of biology in the last few decades. In particular, molecular platforms showing two different BODIPY groups have unique photophysical behavior useful in fluorescence imaging. Construction of the complex architecture of the new probes is accomplished through a convergent route that exploits a series of copper-free Heck-Cassar-Sonogashira cross-couplings. The great emergency due to the proliferation of bacterial infections, in conjunction with growing antibiotic resistance, requires the production of new multifunctional drugs and efficient methods for their targeted delivery to control bacteria-associated diseases. Preliminary studies of the glycoconjugate properties as antibacterial agents against representatives of Gram-negative () and Gram-positive () pathogens, which are associated with chronic infections, indicated significant bactericidal activity ascribable to their structural features.

Keywords

References

  1. RSC Adv. 2020 Sep 11;10(56):33642-33650 [PMID: 35519035]
  2. J Am Chem Soc. 2013 Jul 31;135(30):11330-44 [PMID: 23863135]
  3. Nat Commun. 2020 Sep 14;11(1):4608 [PMID: 32929085]
  4. Expert Rev Anti Infect Ther. 2015 May;13(5):605-13 [PMID: 25746414]
  5. Curr Opin Chem Biol. 2023 Aug;75:102314 [PMID: 37156204]
  6. Sci Rep. 2022 May 30;12(1):9027 [PMID: 35637237]
  7. Org Biomol Chem. 2016 Mar 7;14(9):2665-70 [PMID: 26831779]
  8. Chem Commun (Camb). 2008 Dec 28;(48):6567-9 [PMID: 19057781]
  9. J Pharm Sci. 1969 Jul;58(7):836-9 [PMID: 4980332]
  10. ACS Appl Bio Mater. 2023 Aug 21;6(8):2995-3018 [PMID: 37462316]
  11. Chem Asian J. 2006 Jul 17;1(1-2):176-87 [PMID: 17441053]
  12. Mater Sci Eng C Mater Biol Appl. 2021 Jan;118:111394 [PMID: 33254999]
  13. Chem Asian J. 2023 Jun 1;18(11):e202300178 [PMID: 37088718]
  14. Eur J Med Chem. 2016 Mar 23;111:58-71 [PMID: 26854378]
  15. Sci China Technol Sci. 2022;65(5):1000-1010 [PMID: 35018171]
  16. Chemistry. 2018 Aug 1;24(43):11119-11130 [PMID: 29771471]
  17. Chem Rev. 2007 Nov;107(11):4891-932 [PMID: 17924696]
  18. Adv Mater. 2023 May;35(18):e2207546 [PMID: 36398522]
  19. Probiotics Antimicrob Proteins. 2020 Mar;12(1):82-90 [PMID: 30737650]
  20. Nat Commun. 2022 Jan 14;13(1):314 [PMID: 35031604]
  21. J Mol Liq. 2020 Dec 1;319:114164 [PMID: 32904480]
  22. Bioconjug Chem. 2006 May-Jun;17(3):575-8 [PMID: 16704193]
  23. Chem Commun (Camb). 2012 Nov 4;48(85):10550-2 [PMID: 22992695]
  24. Molecules. 2021 Feb 19;26(4): [PMID: 33669712]
  25. J Org Chem. 2015 Aug 21;80(16):8102-12 [PMID: 26218823]
  26. Int J Mycobacteriol. 2018 Apr-Jun;7(2):134-136 [PMID: 29900888]
  27. J Med Chem. 2022 Jul 14;65(13):8525-8549 [PMID: 35777073]
  28. Chem Rev. 2007 Mar;107(3):874-922 [PMID: 17305399]
  29. Chem Soc Rev. 2020 Jan 21;49(2):593-641 [PMID: 31915764]
  30. Chem Rev. 2021 Nov 10;121(21):13086-13131 [PMID: 34558282]
  31. Angew Chem Int Ed Engl. 2001 Jan 19;40(2):385-387 [PMID: 29712397]
  32. Chem Commun (Camb). 2003 Jan 7;(1):130-1 [PMID: 12611000]
  33. Thromb Haemost. 2019 Apr;119(4):517-533 [PMID: 30620995]
  34. Am J Respir Crit Care Med. 2021 Feb 1;203(3):328-338 [PMID: 32750253]
  35. Int J Mol Sci. 2021 Jun 24;22(13): [PMID: 34202677]
  36. Chem Commun (Camb). 2013 Apr 7;49(27):2747-9 [PMID: 23338477]
  37. ACS Cent Sci. 2021 Feb 24;7(2):327-334 [PMID: 33655070]
  38. Adv Sci (Weinh). 2021 Oct;8(19):e2100368 [PMID: 34351704]
  39. Chem Soc Rev. 2023 Oct 16;52(20):7036-7070 [PMID: 37671645]

MeSH Term

Boron Compounds
Anti-Bacterial Agents
Microbial Sensitivity Tests
Pseudomonas aeruginosa
Staphylococcus aureus
Glycoconjugates
Molecular Structure
Fluorescent Dyes

Chemicals

Boron Compounds
Anti-Bacterial Agents
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Glycoconjugates
Fluorescent Dyes

Word Cloud

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