Anirban Dolai

University of Calcutta

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Supriya Bhunia

University of Calcutta

Subhas Samanta

University of Calcutta

Satyajit Bera

University of Calcutta

Sk Majid Box

University of Calcutta

Kalipada Manna

Indian Institute of Technology Dhanbad

Subhas Samanta

Indian Institute of Technology Jammu

Ritabrata Saha

College of Medicine & Sagore Dutta Hospital

Subhasish Sarkar

College of Medicine & Sagore Dutta Hospital

Kallol Bhattacharya

University of Calcutta

Arpan Das

R. G. Kar Medical College and Hospital

Cooperative Institutions

University of Calcutta

Indian Institute of Technology Dhanbad

Jadavpur University

College of Medicine & Sagore Dutta Hospital

Saha Institute of Nuclear Physics

Indian Institute of Technology Jammu

University of Jammu

Indian Association for the Cultivation of Science

Indian Institute of Science Education and Research Kolkata

University of Göttingen

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Photoisomerization and Light‐Controlled Antibacterial Activity of Fluoroquinolone‐Azoisoxazole Hybrids

ChemBioChem (2024)

Anirban Dolai Supriya Bhunia Santosh Kumar Jana Satyajit Bera Sukhendu Mandal

Photopharmacology holds a huge untapped potential to locally treat diseases involving photoswitchable drugs via the elimination of drugs' off-target effects. The growth of this field has created a pressing demand to develop such light-active drugs. We explored the potential for creating photoswitchable antibiotic hybrids by attaching pharmacophores norfloxacin/ciprofloxacin and azoisoxazole (photoswitch). All compounds exhibited a moderate to a high degree of bidirectional photoisomerization, long thermal cis half-lives, and impressive photoresistance. Gram-negative pathogens were found to be insensitive to these hybrids, while against Gram-positive pathogens, all hybrids in their trans states exhibited antibacterial activity that is comparable to that of the parent drugs. Notably, the toxicity of the irradiated hybrid 6 was found to be 2-fold lower than the nonirradiated trans isomer, indicating that the pre-inactivated cis-enriched drug can be employed for the site-specific treatment of bacterial infection using light, which could potentially eliminate the unwanted exposure of toxic antibiotics to both beneficial and untargeted harmful microbes in our body. Molecular docking revealed different binding affinity of the cis and trans isomers with the topoisomerase IV enzyme, due to their different shapes.

10.1002/cbic.202300851

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CCDC 2006348: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Supriya Bhunia Anirban Dolai Subhas Samanta

10.5517/ccdc.csd.cc25brx6

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Photoinduced Ultrafast Shape-Changing Self-Assembled Arylazopyrazole-Based Polymeric Micelles

Macromolecules (2024)

Kalipada Manna Anirban Dolai Sanjib Ghosh Subha Samanta Shaon Dey

In recent times, photoinduced shape-changing polymers have demonstrated great potential in various applications. The solvent-dependent/free photochromism and conformation-dependent shear viscosity modulation of the developed materials enhance their relevance from industry to academia. Here, two hydrophobically modified photoresponsive arylazopyrazole-based copolymers have been developed via reversible addition–fragmentation chain-transfer (RAFT) polymerization technique using hydrophilic poly(ethylene glycol) methyl ether methacrylate [PEGMA] moieties. The nonsubstituted arylazopyrazole-based copolymer has a shorter half-life that fosters the development of the difluoro-substituted copolymer with a longer half-life. Both copolymers exhibit self-assembly behavior in water to form micelles, as has been evidenced by photoluminescence spectroscopy and surface morphological analyses. Upon UV light exposure, both copolymeric micelles photoisomerize from trans-state to cis-state. The electron microscopic analyses (both FESEM and TEM) can detect that the shape-changing morphology has been perceived from spherical to deformed spherical only for the difluoro-substituted copolymer. Rheological studies reveal the impact of photoisomerization-induced changes in the hydrophobicity of two arylazopyrazoles on solution aggregation. Two distinct photoinduced glass transition temperatures and phase transition temperatures of both copolymers have been evidenced by differential scanning calorimetry (DSC). The study offers a new finding toward the impact of varying the hydrophobicity of stimuli-responsive end groups on aggregation and viscoelastic behaviors. Nevertheless, it is essential to mention that the extended thermal half-life of the developed material advances its applicability in smart devices for biomedical sciences optics, coating, energy storage, and so on.

Chain transfer

Raft

10.1021/acs.macromol.4c01465

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Robust bi-directional photoswitching of thiomethyl substituted arylazopyrazoles under visible light

Chemical Communications (2020)

Supriya Bhunia Anirban Dolai Subhas Samanta

Mono-ortho- and para-thiomethyl substituted arylazopyrazoles display excellent isomerization in both directions under visible light, and show long cis half-lives. These switches are also resistant to photobleaching and reduction by glutathione.

Visible spectrum

10.1039/d0cc04098c

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Citations (25)

Visible‐Light‐Sensitive Photoliquefiable Arylazoisoxazoles for the Solar Energy Conversion, Storage and Controlled‐Release of Heat at Room Temperature or Lower Temperatures

ChemSusChem (2024)

Anirban Dolai Supriya Bhunia Kalipada Manna Satyajit Bera Sk Majid Box

Abstract The photoswitchable MOlecular Solar Thermal (MOST) energy storage systems that are capable of exhibiting high energy storage densities are found to suffer from the poor cyclability, the use of less abundant UV light of the solar spectrum, or reduced charging/discharging rates and poor photoconversions in solid states. Herein, we have designed and readily synthesized a novel set of para ‐thioalkyl substituted arylazoisoxazoles, that undergo high trans‐cis and cis‐trans photoconversions under visible light, and show fast charging/discharging and impressive cyclability. Remarkably, the presence of C6‐or C10‐thioalkyl chainin photochromes permitted reversible solid‐liquid phase transition with the formation of cis‐enriched charged states by 400 nm light irradiation and trans‐enriched discharged states by 530 nm light at various temperatures (10–35 °C). The solid‐to‐liquid phase transition enabled storage of the latent heat in addition to the isomerization energy, resulting in a high net energy storage density of 189–196 J/g, which are substantially higher than that of many recently reported azobenzene‐based MOST compounds (100–161 J/g). Using a high‐resolution infrared camera, we further demonstrated that a brief irradiation of green light can be employed to readily release the trapped photon energy as heat. Our results suggest that the arylazoisoxazole with C6‐thioalkyl chain at para ‐position can serve as an effective and eco‐friendly photoliquefiable MOST material.

Energy transformation

Solar energy conversion

Light energy

10.1002/cssc.202301700

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Progress of photoantibiotics in overcoming antibiotic resistance

ChemMedChem (2024)

Subhas Samanta Supriya Bhunia Sk Majid Box Satyajit Bera Anirban Dolai

Antibiotic resistance has emerged as a global public health crisis in the 21st century, leading to treatment failures. To address this issue, the medical and pharmaceutical sectors are confronted with two challenges: i) finding potent new antimicrobial agents that would work against resistant–pathogens, and ii) developing conceptually new or unconventional strategies by which a particular antibiotic would remain effective persistently. Photopharmacology with the aid of reversibly controllable light‐active antibiotics that we call “photoantibiotics” shows great promise to meet the second challenge, which has inspired numerous research laboratories worldwide to align their research in inventing or developing such antibiotics. In this review, we have given an overview of the progress made over the last ten years or so towards developing such photoantibiotics. Although making such antibiotics that hold high antimicrobial potency like the native drugs and subsequently maintain a significant activity difference between light irradiated and non‐irradiated states is very challenging, the progress being reported here demonstrates the feasibility of various approaches to engineer photoantibiotics. This review provides a future perspective on the use of such antibiotics in clinical practice with the identification of potential problems and their solutions.

10.1002/cmdc.202400613

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CCDC 2006349: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Supriya Bhunia Anirban Dolai Subhas Samanta

10.5517/ccdc.csd.cc25bry7

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Visible light sensitive photoliquefiable arylazoisoxazoles for the molecular solar thermal energy storage under solvent-free conditions at room temperature and lower temperatures

Anirban Dolai Supriya Bhunia Kalipada Manna Satyajit Bera Majid Box

Solar energy can be transformed into heat energy using molecular solar thermal (MOST) energy storage materials, which can then store the heat energy and release it in response to an external stimulus like light or heat. Arylazoisoxazoles, unlike analogous arylazopyrazoles, fail to draw much attention as MOST materials due to poor photoisomerization yields in both directions and utilization of UV light for trans-cis isomerization. With the para-thioalkyl substitution in the phenyl ring, we have demonstrated that the photoswitching yields in both directions can be drastically improved under visible light irradiations. Additionally, the long thioalkyl chain permitted solid-liquid phase transition followed by very high trans-cis photoisomerization and liquid-solid transition associated with high cis-trans photoconversion at various temperatures (10-35oC). The solid liquefication enabled the storage of the latent heat along with the isomerization energy in the charged state. The compound with a C6 alkyl chain could store ̴ 196 J/g of thermal energy for nearly three weeks at 10 oC and three months at 0 oC; the liquidity of the charged state can be retained at lower temperature down to -15 oC. We further showed that the reverse cis-trans isomerization-related heat release triggered by green light can be monitored by directly recording the sample surface temperature with a high-resolution IR camera. Our results demonstrate that arylazoisoxazoles have the potential to serve as MOST materials.

Thermal energy

10.26434/chemrxiv-2023-xzn0b

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Near-Complete Bidirectional Photoisomerization of para-Dialkylamino-Substituted Arylazopyrazoles under Violet and Green or Red Lights

The Journal of Organic Chemistry (2022)

Supriya Bhunia Anirban Dolai Satyajit Bera Subhas Samanta

para-Dimethylamine- and para-pyrrolidine-substituted arylazopyrazoles display very high to near-quantitative or quantitative bidirectional isomerization under violet and green or red lights in both polar (DMSO and DMSO/aqueous buffer, pH 7.5) and nonpolar solvents. These switches confer a reasonable thermal stability to their cis-states (t1/2 ≈ 4–7 h in DMSO and DMSO/buffer) and also show a high level of resistance to photobleaching and an impressive stability to reduction by glutathione. Using DFT calculations, attempts have been made to decipher the photophysical properties and thermal stabilities of the cis isomers.

Dimethylamine

Pyrrolidine

Thermal Stability

Photobleaching

10.1021/acs.joc.1c02898

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Citations (9)

Photoisomerization of 2-Arylazoimidazoles under Visible Light: Identifying a Predictive Tool to Anticipate and Tune Likely Photoswitching Performance and Cis Half-Life

The Journal of Organic Chemistry (2023)

Anirban Dolai Sk Majid Box Supriya Bhunia Satyajit Bera Arpan Das

Azopyrazoles are an emerging class of photoswitches, whereas analogous azoimidazole-based switches are unable to draw much attention because of their short cis half-lives, poor cis-trans photoreversion yields, and toxic ultraviolet (UV) light-assisted isomerization. A series of 24 various aryl-substituted N-methyl-2-arylazoimidazoles were synthesized, and their photoswitching performances and cis-trans isomerization kinetics were thoroughly investigated experimentally and theoretically. Para-π-donor-substituted azoimidazoles with highly twisted T-shaped cis conformations showed nearly complete bidirectional photoswitching, whereas di-o-substituted switches exhibited very long cis half-lives (days-years) with nearly ideal T-shaped conformations. This study demonstrates how the electron density in the aryl ring affects cis half-life and cis-trans photoreversion via twisting of the NNAr dihedral angle that can be used as a predictive metric for envisaging and tuning the likely switching performance and half-life of any given 2-arylazoimidazole. By applying this tool, two better-performing azoimidazole photoswitches were engineered. All switches permitted irradiation by violet (400-405 nm) and orange (>585 nm) light for forward and reverse isomerization, respectively, and displayed comparatively high quantum yields and impressive resistance to photobleaching.

10.1021/acs.joc.3c00211

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Citations (9)