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Article ; Online: Diversity-Oriented Synthesis of Thiazolidine-2-imines via Microwave-Assisted One-Pot, Telescopic Approach and Its Interaction with Biomacromolecules.

Saikia, Ananya Anubhav / Rao, Ramdas Nishanth / Maiti, Barnali / Balamurali, Musuvathi Motilal / Chanda, Kaushik

ACS combinatorial science

2020 Volume 22, Issue 11, Page(s) 630–640

Abstract: In this work, a one-pot, telescopic approach is described for the combinatorial library of thiazolidine-2-imines. The synthetic manipulation proceeds smoothly via the reaction of 2-aminopyridine/pyrazine/pyrimidine with substituted isothiocyanates ... ...

Abstract	In this work, a one-pot, telescopic approach is described for the combinatorial library of thiazolidine-2-imines. The synthetic manipulation proceeds smoothly via the reaction of 2-aminopyridine/pyrazine/pyrimidine with substituted isothiocyanates followed by base catalyzed ring closure with 1,2-dibromoethane to obtain thiazolidine-2-imines with broad substrate scope and high functional group tolerance. The synthetic strategy merges well with the thiourea formation followed by base catalyzed ring closure reaction for the thiazolidine-2-imine synthesis in a more modular and straightforward approach. The synthetic procedure reported herein represents a cleaner route toward thiazolidine-2-imines as compared to traditional methodologies. Moreover, the biological significance of combinatorially synthesized thiazolidin-2-imines has been investigated for their use as possible inhibitors for acetyl cholinesterase through molecular docking studies.
MeSH term(s)	Acetylcholinesterase/metabolism ; Aminopyridines/chemistry ; Anticonvulsants/chemical synthesis ; Antineoplastic Agents/chemical synthesis ; Antitubercular Agents/chemical synthesis ; Catalysis ; Cholinesterase Inhibitors/chemical synthesis ; Cholinesterase Inhibitors/metabolism ; Ethylene Dibromide/chemistry ; Humans ; Imines/chemical synthesis ; Imines/metabolism ; Isothiocyanates/chemistry ; Microwaves ; Pyrazines/chemistry ; Pyrimidines/chemistry ; Small Molecule Libraries/chemical synthesis ; Small Molecule Libraries/metabolism ; Structure-Activity Relationship ; Thiazolidines/chemistry ; Thiourea/chemistry
Chemical Substances	Aminopyridines ; Anticonvulsants ; Antineoplastic Agents ; Antitubercular Agents ; Cholinesterase Inhibitors ; Imines ; Isothiocyanates ; Pyrazines ; Pyrimidines ; Small Molecule Libraries ; Thiazolidines ; Ethylene Dibromide (1N41638RNO) ; isothiocyanic acid (3129-90-6) ; Acetylcholinesterase (EC 3.1.1.7) ; Thiourea (GYV9AM2QAG) ; pyrimidine (K8CXK5Q32L) ; alpha-aminopyridine (WSX981HEWU)
Language	English
Publishing date	2020-09-08
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	2156-8944
ISSN (online)	2156-8944
DOI	10.1021/acscombsci.0c00083
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Article ; Online: Polymorphic Nucleic Acid Binding of Bioactive Isoquinoline Alkaloids and Their Role in Cancer

Gopinatha Suresh Kumar / Motilal Maiti

Journal of Nucleic Acids, Vol

2010 Volume 2010

Keywords	Genetics ; QH426-470 ; Biology (General) ; QH301-705.5 ; Science ; Q ; DOAJ:Genetics ; DOAJ:Biology ; DOAJ:Biology and Life Sciences ; Biochemistry ; QD415-436 ; Organic chemistry ; QD241-441 ; Chemistry ; QD1-999 ; DOAJ:Biochemistry ; DOAJ:Life Sciences
Language	English
Publishing date	2010-01-01T00:00:00Z
Publisher	Hindawi Publishing Corporation
Document type	Article ; Online
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Article: Biophysical aspects and biological implications of the interaction of benzophenanthridine alkaloids with DNA.

Maiti, Motilal / Kumar, Gopinatha Suresh

Biophysical reviews

2009 Volume 1, Issue 3, Page(s) 119–129

Abstract: Benzophenanthridine alkaloids represent a very interesting and significant group of natural products that exhibit a broad range of biological and pharmacological properties. Among this group of alkaloids, sanguinarine, nitidine, fagaronine, and ... ...

Abstract	Benzophenanthridine alkaloids represent a very interesting and significant group of natural products that exhibit a broad range of biological and pharmacological properties. Among this group of alkaloids, sanguinarine, nitidine, fagaronine, and chelerythrine have the potential to form molecular complexes with DNA structures and have attracted recent attention for their possible clinical and pharmacological utility. This review focuses on the interaction of these alkaloids with polymorphic DNA structures (B-form, Z-form, H
Language	English
Publishing date	2009-08-25
Publishing country	Germany
Document type	Journal Article ; Review
ZDB-ID	2486483-3
ISSN	1867-2469 ; 1867-2450
ISSN (online)	1867-2469
ISSN	1867-2450
DOI	10.1007/s12551-009-0014-7
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Article ; Online: Polymorphic nucleic Acid binding of bioactive isoquinoline alkaloids and their role in cancer.

Maiti, Motilal / Kumar, Gopinatha Suresh

Journal of nucleic acids

2009 Volume 2010

Abstract: Bioactive alkaloids occupy an important position in applied chemistry and play an indispensable role in medicinal chemistry. Amongst them, isoquinoline alkaloids like berberine, palmatine and coralyne of protoberberine group, sanguinarine of the ... ...

Abstract	Bioactive alkaloids occupy an important position in applied chemistry and play an indispensable role in medicinal chemistry. Amongst them, isoquinoline alkaloids like berberine, palmatine and coralyne of protoberberine group, sanguinarine of the benzophenanthridine group, and their derivatives represent an important class of molecules for their broad range of clinical and pharmacological utility. In view of their extensive occurrence in various plant species and significantly low toxicities, prospective development and use of these alkaloids as effective anticancer agents are matters of great current interest. This review has focused on the interaction of these alkaloids with polymorphic nucleic acid structures (B-form, A-form, Z-form, H(L)-form, triple helical form, quadruplex form) and their topoisomerase inhibitory activity reported by several research groups using various biophysical techniques like spectrophotometry, spectrofluorimetry, thermal melting, circular dichroism, NMR spectroscopy, electrospray ionization mass spectroscopy, viscosity, isothermal titration calorimetry, differential scanning calorimetry, molecular modeling studies, and so forth, to elucidate their mode and mechanism of action for structure-activity relationships. The DNA binding of the planar sanguinarine and coralyne are found to be stronger and thermodynamically more favoured compared to the buckled structure of berberine and palmatine and correlate well with the intercalative mechanism of sanguinarine and coralyne and the partial intercalation by berberine and palmatine. Nucleic acid binding properties are also interpreted in relation to their anticancer activity.
Language	English
Publishing date	2009-12-15
Publishing country	United States
Document type	Journal Article
ZDB-ID	2549000-X
ISSN	2090-021X ; 2090-021X
ISSN (online)	2090-021X
ISSN	2090-021X
DOI	10.4061/2010/593408
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Article: Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives.

Maiti, Motilal / Kumar, Gopinatha Suresh

Medicinal research reviews

2007 Volume 27, Issue 5, Page(s) 649–695

Abstract: Alkaloids occupy an important position in chemistry and pharmacology. Among the various alkaloids, berberine and coralyne of the protoberberine group, sanguinarine of the benzophenanthridine group, and aristololactam-beta-d-glucoside of the aristolochia ... ...

Abstract	Alkaloids occupy an important position in chemistry and pharmacology. Among the various alkaloids, berberine and coralyne of the protoberberine group, sanguinarine of the benzophenanthridine group, and aristololactam-beta-d-glucoside of the aristolochia group have potential to form molecular complexes with nucleic acid structures and have attracted recent attention for their prospective clinical and pharmacological utility. This review highlights (i) the physicochemical properties of these alkaloids under various environmental conditions, (ii) the structure and functional aspects of various forms of deoxyribonucleic acid (DNA) (B-form, Z-form, H(L)-form, protonated form, and triple helical form) and ribonucleic acid (RNA) (A-form, protonated form, and triple helical form), and (iii) the interaction of these alkaloids with various polymorphic DNA and RNA structures reported by several research groups employing various analytical techniques like absorbance, fluorescence, circular dichroism, and NMR spectroscopy; electrospray ionization mass spectrometry, thermal melting, viscosity, and DNase footprinting as well as molecular modeling and thermodynamic studies to provide detailed binding mechanism at the molecular level for structure-activity relationship. Nucleic acids binding properties of these alkaloids are interpreted in relation to their biological activity.
MeSH term(s)	Alkaloids/chemistry ; Aristolochic Acids/chemistry ; Base Pairing ; Benzophenanthridines/chemistry ; Berberine/chemistry ; Berberine Alkaloids/chemistry ; Binding Sites ; DNA/chemistry ; DNA/metabolism ; Glucosides/chemistry ; Isoquinolines/chemistry ; Nucleic Acid Conformation ; RNA/chemistry ; RNA/metabolism ; Structure-Activity Relationship
Chemical Substances	Alkaloids ; Aristolochic Acids ; Benzophenanthridines ; Berberine Alkaloids ; Glucosides ; Isoquinolines ; Berberine (0I8Y3P32UF) ; aristololactam-glucoside (17413-41-1) ; protoberberine (19716-69-9) ; RNA (63231-63-0) ; coralyne (6872-73-7) ; DNA (9007-49-2) ; sanguinarine (AV9VK043SS)
Language	English
Publishing date	2007-09
Publishing country	United States
Document type	Journal Article ; Review
ZDB-ID	603210-2
ISSN	0198-6325
ISSN	0198-6325
DOI	10.1002/med.20087
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Article ; Online: A Privacy-Preserving Desk Sensor for Monitoring Healthy Movement Breaks in Smart Office Environments with the Internet of Things.

Maiti, Ananda / Ye, Anjia / Schmidt, Matthew / Pedersen, Scott

Sensors (Basel, Switzerland)

2023 Volume 23, Issue 4

Abstract: ... movement breaks for seated workers. The proposed sensor and its privacy-preserving characteristics ...

Abstract	Smart workplace Internet of Things (IoT) solutions rely on several sensors deployed efficiently in the workplace environment to collect accurate data to meet system goals. A vital issue for these sensor-based IoT solutions is privacy. Ideally, the occupants must be monitored discreetly, and the strategies for maintaining privacy are dependent on the nature of the data required. This paper proposes a new sensor design approach for IoT solutions in the workplace that protects occupants' privacy. We focus on a novel sensor that autonomously detects and captures human movements in the office to monitor a person's sedentary behavior. The sensor guides an eHealth solution that uses continuous feedback about desk behaviors to prompt healthy movement breaks for seated workers. The proposed sensor and its privacy-preserving characteristics can enhance the eHealth solution system's performance. Compared to self-reporting, intrusive, and other data collection techniques, this sensor can collect the information reliably and timely. We also present the data analysis specific to this new sensor that measures two physical distance parameters in real-time and uses their difference to determine human actions. This architecture aims to collect precise data at the sensor design level rather than to protect privacy during the data analysis phase.
MeSH term(s)	Humans ; Internet of Things ; Privacy ; Working Conditions ; Workplace ; Data Analysis
Language	English
Publishing date	2023-02-16
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2052857-7
ISSN	1424-8220 ; 1424-8220
ISSN (online)	1424-8220
ISSN	1424-8220
DOI	10.3390/s23042229
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Article ; Online: In situ enzymatic control of colloidal phoresis and catalysis through hydrolysis of ATP.

Shandilya, Ekta / Rallabandi, Bhargav / Maiti, Subhabrata

Nature communications

2024 Volume 15, Issue 1, Page(s) 3603

Abstract: The ability to sense chemical gradients and respond with directional motility and chemical activity ...

Abstract	The ability to sense chemical gradients and respond with directional motility and chemical activity is a defining feature of complex living systems. There is a strong interest among scientists to design synthetic systems that emulate these properties. Here, we realize and control such behaviors in a synthetic system by tailoring multivalent interactions of adenosine nucleotides with catalytic microbeads. We first show that multivalent interactions of the bead with gradients of adenosine mono-, di- and trinucleotides (AM/D/TP) control both the phoretic motion and a proton-transfer catalytic reaction, and find that both effects are diminished greatly with increasing valence of phosphates. We exploit this behavior by using enzymatic hydrolysis of ATP to AMP, which downregulates multivalent interactivity in situ. This produces a sudden increase in transport of the catalytic microbeads (a phoretic jump), which is accompanied by increased catalytic activity. Finally, we show how this enzymatic activity can be systematically tuned, leading to simultaneous in situ spatial and temporal control of the location of the microbeads, as well as the products of the reaction that they catalyze. These findings open up new avenues for utilizing multivalent interaction-mediated programming of complex chemo-mechanical behaviors into active systems.
MeSH term(s)	Adenosine Triphosphate/metabolism ; Adenosine Triphosphate/chemistry ; Hydrolysis ; Catalysis ; Colloids/chemistry ; Microspheres ; Adenosine Monophosphate/metabolism ; Adenosine Monophosphate/chemistry ; Adenosine/metabolism ; Adenosine/chemistry
Chemical Substances	Adenosine Triphosphate (8L70Q75FXE) ; Colloids ; Adenosine Monophosphate (415SHH325A) ; Adenosine (K72T3FS567)
Language	English
Publishing date	2024-04-29
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	2553671-0
ISSN	2041-1723 ; 2041-1723
ISSN (online)	2041-1723
ISSN	2041-1723
DOI	10.1038/s41467-024-47912-2
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Article ; Online: Interaction of isoquinoline alkaloids with polymorphic DNA structures.

Bhadra, Kakali / Maiti, Motilal / Kumar, Gopinatha Suresh

Chemistry & biodiversity

2009 Volume 6, Issue 9, Page(s) 1323–1342

Abstract: The interaction of berberine, palmatine, and coralyne with the B, Z, and H(L) form of poly[d(G-C)] was studied. Berberine and palmatine showed moderate binding to the B form, while coralyne showed higher binding, as revealed from spectroscopic and ... ...

Abstract	The interaction of berberine, palmatine, and coralyne with the B, Z, and H(L) form of poly[d(G-C)] was studied. Berberine and palmatine showed moderate binding to the B form, while coralyne showed higher binding, as revealed from spectroscopic and thermodynamic data. Berberine and coralyne binding to the B form was exothermic and enthalpy-driven, while palmatine showed exothermic binding which was favored by both negative enthalpy and negative entropy changes. Berberine and palmatine neither bind nor converted the Z-form structure to B form. Coralyne, on the other hand, exhibited a strong binding affinity to Z DNA structure that was enthalpy-driven. Berberine binding to the H(L) form was cooperative, exothermic, and favored by both negative enthalpy and negative entropy changes with the formation of an induced CD band. Palmatine showed weak binding, while coralyne showed a strong binding with the H(L) form. The structural differences in the isoquinoline alkaloids appear to influence the affinity and mode of interactions with these polymorphic DNA structures.
MeSH term(s)	Alkaloids/chemistry ; Berberine Alkaloids/chemistry ; Circular Dichroism ; DNA/chemistry ; Isoquinolines/chemistry ; Kinesics ; Polydeoxyribonucleotides/chemistry ; Thermodynamics
Chemical Substances	Alkaloids ; Berberine Alkaloids ; Isoquinolines ; Polydeoxyribonucleotides ; poly(dC-dG) (29855-95-6) ; coralyne (6872-73-7) ; DNA (9007-49-2) ; palmatine (G50C034217) ; isoquinoline (JGX76Y85M6)
Language	English
Publishing date	2009-09
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2139001-0
ISSN	1612-1880 ; 1612-1872
ISSN (online)	1612-1880
ISSN	1612-1872
DOI	10.1002/cbdv.200900017
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Article: Berberine-DNA complexation: new insights into the cooperative binding and energetic aspects.

Bhadra, Kakali / Maiti, Motilal / Kumar, Gopinatha Suresh

Biochimica et biophysica acta

2008 Volume 1780, Issue 9, Page(s) 1054–1061

Abstract: The equilibrium binding of the cytotoxic plant alkaloid berberine to various DNAs and energetics of the interaction have been studied. At low ratios of bound alkaloid to base pair, the binding exhibited cooperativity to natural DNAs having almost equal ... ...

Abstract	The equilibrium binding of the cytotoxic plant alkaloid berberine to various DNAs and energetics of the interaction have been studied. At low ratios of bound alkaloid to base pair, the binding exhibited cooperativity to natural DNAs having almost equal proportions of AT and GC sequences. In contrast, the binding was non-cooperative to DNAs with predominantly high AT or GC sequences. Among the synthetic DNAs, cooperative binding was observed with poly(dA).poly(dT) and poly(dG).poly(dC) while non-cooperative binding was seen with poly(dA-dT).poly(dA-dT) and poly(dG-dC).poly(dG-dC). Both cooperative and non-cooperative bindings were remarkably dependent on the salt concentration of the media. Linear plots of ln K(a) versus [Na(+)] for poly(dA).poly(dT) and poly(dA-dT).poly(dA-dT) showed the release of 0.56 and 0.75 sodium ions respectively per bound alkaloid. Isothermal titration calorimetry results revealed the binding to be exothermic and favoured by both enthalpy and entropy changes in all DNAs except the two AT polymers and AT rich DNA, where the same was predominantly entropy driven. Heat capacity values (DeltaCp(o)) of berberine binding to poly(dA).poly(dT), poly(dA-dT).poly(dA-dT), Clostridium perfringens and calf thymus DNA were -98, -140, -120 and -110 cal/mol K respectively. This study presents new insights into the binding dependent base pair heterogeneity in DNA conformation and the first complete thermodynamic profile of berberine binding to DNAs.
MeSH term(s)	Animals ; Berberine/chemistry ; Berberine/metabolism ; Calorimetry ; Cattle ; DNA/metabolism ; Kinetics ; Osmolar Concentration ; Sodium/pharmacology ; Spectrophotometry ; Temperature ; Thermodynamics ; Titrimetry
Chemical Substances	Berberine (0I8Y3P32UF) ; DNA (9007-49-2) ; calf thymus DNA (91080-16-9) ; Sodium (9NEZ333N27)
Language	English
Publishing date	2008-09
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	60-7
ISSN	1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2642 ; 1879-2618 ; 1879-2650 ; 0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
ISSN (online)	1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2642 ; 1879-2618 ; 1879-2650
ISSN	0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
DOI	10.1016/j.bbagen.2008.05.005
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Article ; Online: Interaction of isoquinoline alkaloid palmatine with deoxyribonucleic acids: binding heterogeneity, and conformational and thermodynamic aspects.

Bhadra, Kakali / Maiti, Motilal / Kumar, Gopinatha Suresh

Chemistry & biodiversity

2008 Volume 5, Issue 4, Page(s) 575–590

Abstract: The binding heterogeneity, conformational aspects, and energetics of the interaction of the cytotoxic plant alkaloid palmatine have been studied with various natural and synthetic DNAs. The alkaloid binds to calf thymus and Escherichia coli DNA that have ...

Abstract	The binding heterogeneity, conformational aspects, and energetics of the interaction of the cytotoxic plant alkaloid palmatine have been studied with various natural and synthetic DNAs. The alkaloid binds to calf thymus and Escherichia coli DNA that have mixed AT and GC sequences in almost equal proportions with positive cooperativity, while, with Clostridium perfringens and Micrococcus lysodeikticus DNA with predominantly high AT and GC sequences, respectively, noncooperative binding was observed. On further investigation with synthetic DNAs, the binding was observed to be cooperative with polymers like poly(dA).poly(dT) and poly(dG).poly(dC) having poly(purine)poly(pyrimidine) sequences, while with polymers poly(dA-dT).poly(dA-dT), poly(dA-dC).poly(dG-dT) and poly(dG-dC).poly(dG-dC), which have alternating purine-pyrimidine sequences, a non-cooperative binding phenomenon was observed. This suggests the binding heterogeneity of palmatine to the two types of sequences of base pairs. Circular dichroism (CD) studies revealed that the binding induced conformational changes in all the DNAs, but more importantly, the bound alkaloid molecules acquired induced optical activity, and the extent was dependent on the AT content and showed AT base-pair specificity. Energetics of the interaction of the alkaloid studied by highly sensitive isothermal titration calorimetry revealed that the binding was in most cases exothermic and favored by both enthalpy and entropy changes, while, in the case of the homo and hetero AT polymers, the same was predominantly entropy-driven. This study defines base-pair-dependent heterogeneity, conformational aspects, and energetics of palmatine binding to DNA.
MeSH term(s)	Berberine Alkaloids/chemistry ; Circular Dichroism ; Clostridium perfringens ; DNA/chemistry ; Nucleic Acid Conformation ; Osmolar Concentration ; Thermodynamics
Chemical Substances	Berberine Alkaloids ; DNA (9007-49-2) ; calf thymus DNA (91080-16-9) ; palmatine (G50C034217)
Language	English
Publishing date	2008-04
Publishing country	Switzerland
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2139001-0
ISSN	1612-1880 ; 1612-1872
ISSN (online)	1612-1880
ISSN	1612-1872
DOI	10.1002/cbdv.200890054
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