Investigating the photosensitivity of koneramines for cell imaging and therapeutic applications

Ghosh, Suchismita; Akhir, Abdul; Saxena, D. K.; Singh, Sneha; Sivakumar, Sri; Chopra, Sidharth; Angamuthu, Raja

doi:10.1039/d2dt02834d

Cited by 3 publications

(3 citation statements)

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“…This suggests that the koneramine formation is immune to the size and electronic properties of the N-substitution of ethylenediamine component. This allows one to access the koneramine complex with any groups substituted on the non-coordinating backbone nitrogen (N4) such as lightsensitive anthracenyl, [13] pyrenyl or dansyl groups, redox-active ferrocenyl moiety, proton-sensitive pyridyl or pyrazinyl groups and even small molecule binding 1,3,5-triazinyl group. [12] Even though the koneramine complexes can be assembled in one-pot reactions and they are stable enough to be characterized using multiple analytical techniques, they are fragile in acidic environments and even in protic solvents at times; [12] this is due to the fragile hemiaminal ether linkage that could take part in a dynamic equilibrium with its iminium counterpart, especially in protic and/or nucleophilic solvents (Figure 4).…”

Section: Resultsmentioning

confidence: 99%

“…This suggests that the koneramine formation is immune to the size and electronic properties of the N ‐substitution of ethylenediamine component. This allows one to access the koneramine complex with any groups substituted on the non‐coordinating backbone nitrogen (N4) such as light‐sensitive anthracenyl, [13] pyrenyl or dansyl groups, redox‐active ferrocenyl moiety, proton‐sensitive pyridyl or pyrazinyl groups and even small molecule binding 1,3,5‐triazinyl group [12] …”

Section: Resultsmentioning

confidence: 99%

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Late‐stage Ligand Modification After Coordination Strengthens Stereoselectively Self‐Assembled Hemiaminal Ether Complexes

Raje,

Koner,

Ghosh

et al. 2023

Chemistry An Asian Journal

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Fragile hemiaminal ether linkages present in the backbone of koneramines (LROR’), tridentate ligands, bound to copper(II) in stereoselectively self‑assembled syn‑[Cu(LROR’)X2] complexes were transformed into sturdy methylene linkages to make corresponding rac‑[Cu(LRH)Cl2] complexes by late‐stage ligand modification after metalation with the retention of coordination sphere. The generality of stereoselective self‑assembly of koneramine complexes is shown by utilising a number of metal ions, anions, amines, alcohols and thiols with complete characterisations.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Late‐stage Ligand Modification After Coordination Strengthens Stereoselectively Self‐Assembled Hemiaminal Ether Complexes

Raje,

Koner,

Ghosh

et al. 2023

Chemistry An Asian Journal

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“…This multifaceted approach, harnessing the power of synergistic interactions, enhanced spectrum coverage, and resistance mitigation, epitomizes a judicious and innovative strategy in our ceaseless quest to combat bacterial infections and safeguard the public health. [30,31,32]…”

Section: Combination Assaymentioning

confidence: 99%

Pyridine‐2,6‐Dicarboxamide Proligands and their Cu(II)/Zn(II) Complexes Targeting Staphylococcus Aureus for the Attenuation of In Vivo Dental Biofilm

Chaudhary,

Agrahari,

Biswas

et al. 2024

Adv Healthcare Materials

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In the pursuit to combat stubborn bacterial infections, particularly those stemming from gram‐positive bacteria, our study is an attempt to craft a precision‐driven platform characterized by unparalleled selectivity, specificity, and synergistic antimicrobial mechanisms. Leveraging remarkable potential of metalloantibiotics in antimicrobial applications, herein, we rationally design, synthesize, and characterize a new library of Pyridine‐2,6‐dicarboxamide ligands and their corresponding transition metal Cu(II)/Zn(II) complexes. The lead compound L11 demonstrate robust antibacterial properties against Staphylococcus aureus (MIC = 2‐16 µg/mL), methicillin and vancomycin‐resistant S. aureus (MIC = 2‐4 µg/mL) and exhibit superior antibacterial activity when compared to FDA‐approved vancomycin, the drug of last resort. Additionally, the compound exhibited notable antimicrobial efficacy against resistant enterococcus strains (MIC = 2‐8 µg/mL). To unravel mechanistic profile, advanced imaging techniques including SEM and AFM were harnessed, collectively suggesting a mechanistic pathway involving cell wall disruption. Live/dead fluorescence studies further confirm efficacy of L11 and its complexes against S. aureus membranes. Our translational exploration extends to a rat model, indicating promising In‐vivo therapeutic potential. Thus, our comprehensive research initiative has capabilities to transcends the confines of our laboratory, heralding a pivotal step toward combatting antibiotic‐resistant pathogens and advancing the frontiers of metalloantibiotics based therapy with a profound clinical implication.This article is protected by copyright. All rights reserved

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Metal and solvent dependent formation of imidazolidine or hemiaminal ether complexes

Ghosh,

Butcher,

Angamuthu

2024

Inorganica Chimica Acta

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Investigating the photosensitivity of koneramines for cell imaging and therapeutic applications

Abstract: The photophysical properties of the anthracene appended koneramines (LAn) were analyzed and utilized as a chemosensor for the selective detection of Cd2+ and Zn2+. The complexation-induced inhibition of PET (photo-induced...

Cited by 3 publications

References 69 publications

Late‐stage Ligand Modification After Coordination Strengthens Stereoselectively Self‐Assembled Hemiaminal Ether Complexes

Late‐stage Ligand Modification After Coordination Strengthens Stereoselectively Self‐Assembled Hemiaminal Ether Complexes

Pyridine‐2,6‐Dicarboxamide Proligands and their Cu(II)/Zn(II) Complexes Targeting Staphylococcus Aureus for the Attenuation of In Vivo Dental Biofilm

Metal and solvent dependent formation of imidazolidine or hemiaminal ether complexes

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