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1.
Molecules ; 29(13)2024 Jun 26.
Article in English | MEDLINE | ID: mdl-38998987

ABSTRACT

The inhibition of soluble epoxide hydrolase (sEH) can reduce the level of dihydroxyeicosatrienoic acids (DHETs) effectively maintaining endogenous epoxyeicosatrienoic acids (EETs) levels, resulting in the amelioration of inflammation and pain. Consequently, the development of sEH inhibitors has been a prominent research area for over two decades. In the present study, we synthesized and evaluated sulfonyl urea derivatives for their potential to inhibit sEH. These compounds underwent extensive in vitro investigation, revealing their potency against human and mouse sEH, with 4f showing the most promising sEH inhibitory potential. When subjected to lipopolysaccharide (LPS)-induced acute lung injury (ALI) in studies in mice, compound 4f manifested promising anti-inflammatory efficacy. We investigated the analgesic efficacy of sEH inhibitor 4f in a murine pain model of tail-flick reflex. These results validate the role of sEH inhibition in inflammatory diseases and pave the way for the rational design and optimization of sEH inhibitors based on a sulfonyl urea template.


Subject(s)
Enzyme Inhibitors , Epoxide Hydrolases , Urea , Epoxide Hydrolases/antagonists & inhibitors , Epoxide Hydrolases/metabolism , Animals , Mice , Humans , Urea/pharmacology , Urea/analogs & derivatives , Urea/chemistry , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/chemical synthesis , Acute Lung Injury/drug therapy , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/chemical synthesis , Anti-Inflammatory Agents/therapeutic use , Lipopolysaccharides , Structure-Activity Relationship , Solubility , Disease Models, Animal , Pain/drug therapy
2.
Nanoscale ; 16(20): 9966-9974, 2024 May 23.
Article in English | MEDLINE | ID: mdl-38695085

ABSTRACT

It is well known that the bandgap of 2D transition metal dichalcogenides (TMDs) in the quantum confinement regime increases with a decrease in the number of layers. In this work, we show the effect of lattice strain on the dependence of the gap. We have designed an ideal system in the form of common-cationic alloyed-TMDs, Mo(S1-xSex)2, for such studies. With a large difference between the ionic radii of the two chalcogens, the nanoflakes of the alloys possessed a lattice strain and have been found to yield a lower bandgap than those of both the end-members, MoS2 and MoSe2. More importantly, the dependence of the bandgap on the layer number in the nanoflakes of the alloys turned out to be steeper than in conventional binary TMDs. The experimental results imply that the lattice strain in 2D semiconductors has contributed to the effect of the quantum confinement phenomenon in addition to decreasing the bandgap, the latter being earlier predicted from a theoretical model. We have derived the electronic bandgap and the band-edge energies of the series of alloyed-TMDs in their nanoflake forms and the dependences on the number of layers from the density of states (DOS), as obtained from scanning tunneling spectroscopy (STS) recorded in a scanning tunneling microscope (STM) in an extremely localized manner.

3.
Expert Opin Ther Pat ; 33(10): 651-668, 2023 Oct.
Article in English | MEDLINE | ID: mdl-38037334

ABSTRACT

INTRODUCTION: Physiological and pathophysiological effects arising from detoxification of aldehydes in humans implicate the enzyme aldehyde dehydrogenase (ALDH) gene family comprising of 19 isoforms. The main function of this enzyme family is to metabolize reactive aldehydes to carboxylic acids. Dysregulation of ALDH activity has been associated with various diseases. Extensive research has since gone into studying ALHD isozymes, their structural biology and developing small-molecule inhibitors. Novel chemical strategies to enhance the selectivity of ALDH inhibitors have now appeared. AREAS COVERED: A comprehensive review of patent literature related to aldehyde dehydrogenase inhibitors in the last decade and half (2007-2022) is provided. EXPERT OPINION: Aldehyde dehydrogenase (ALDH) is an important enzyme that metabolizes reactive exogenous and endogenous aldehydes in the body through NAD(P)±dependent oxidation. Hence this family of enzymes possess important physiological as well as toxicological roles in human body. Significant efforts in the field have led to potent inhibitors with approved clinical agents for alcohol use disorder therapy. Further clinical translation of novel compounds targeting ALDH inhibition will validate the promised therapeutic potential in treating many human diseases.The scientific/patent literature has been searched on SciFinder-n, Reaxys, PubMed, Espacenet and Google Patents. The search terms used were 'ALDH inhibitors', 'Aldehyde Dehydrogenase Inhibitors'.


Subject(s)
Aldehyde Dehydrogenase , Patents as Topic , Humans , Aldehyde Dehydrogenase/genetics , Aldehyde Dehydrogenase/metabolism , Aldehydes/pharmacology , Aldehydes/metabolism , Enzyme Inhibitors/pharmacology , Isoenzymes
4.
ACS Omega ; 7(35): 31612-31620, 2022 Sep 06.
Article in English | MEDLINE | ID: mdl-36092569

ABSTRACT

We report the development of a one-pot Bunte's reaction-enabled expeditious platform under aqueous conditions for the scalable conversion of sulfonylureas to synthetically versatile thio-sulfonylureas. The reaction was further propagated in the same pot to yield diverse chiral and achiral isothiosulfonyl analogs. The protocol enabled the synthesis of various drug-like molecules and was applied to an enantiomeric synthesis of a cannabinoid receptor antagonist SLV326.

5.
Adv Sci (Weinh) ; 9(20): e2200637, 2022 Jul.
Article in English | MEDLINE | ID: mdl-35508607

ABSTRACT

Developing high performance, low-cost solid-state light emitters in the telecom wavelength bandwidth is of paramount importance for infrared light-based communications. Colloidal quantum dot (CQD) based light emitting diodes (LEDs) have shown tremendous advances in recent times through improvement in synthesis chemistry, surface property, and device structures. Despite the tremendous advancements of CQD based LEDs in the visible range with efficiency reaching theoretical limits, their short-wave infrared (SWIR) counterparts mainly based on lead chalcogenide CQDs, have shown lower performance (≈8%). Here the authors report on highly efficient SWIR CQD LEDs with a recorded EQE of 11.8% enabled by the use of a binary CQD matrix comprising QD populations of different bandgaps at the emission wavelength of 1550 nm. By further optimizing the optical out-coupling via the use of a hemispherical lens to reduce optical waveguide loss, the EQE of the LED increased to 18.6%. The CQD LED has an electrical bandwidth of 2 MHz, which motivated them to demonstrate its use in the first SWIR free-space optical transmission link based entirely on CQD technology (photodetector and light emitter) opening a new window of applications for CQD optoelectronics.

6.
Expert Opin Ther Pat ; 32(6): 629-647, 2022 Jun.
Article in English | MEDLINE | ID: mdl-35410559

ABSTRACT

INTRODUCTION: Biological effects mediated by the CYP450 arm of arachidonate cascade implicate the enzyme-soluble epoxide hydrolase (sEH) in hydrolyzing anti-inflammatory epoxy fatty acids to pro-inflammatory diols. Hence, inhibiting the sEH offers a therapeutic approach to treating inflammatory diseases. Over three decades of work has shown the role of sEH inhibitors (sEHis) in treating various disorders in rodents and larger veterinary subjects. Novel chemical strategies to enhance the efficacy of sEHi have now appeared. AREAS COVERED: A comprehensive review of patent literature related to soluble epoxide hydrolase inhibitors in the last decade (2010-2021) is provided. EXPERT OPINION: Soluble epoxide hydrolase (sEH) is an important enzyme that metabolizes the bioactive epoxy fatty acids (EFAs) in the arachidonic acid signaling pathway and converts them to vicinal diols, which appear to be pro-inflammatory. Inhibition of sEH hence offers a mechanism to increase in vivo epoxyeicosanoid levels and resolve pro-inflammatory pathways in disease states. Significant efforts in the field have led to potent single target as well as multi-target inhibitors with promising in vitro and widely encompassing in vivo activities. Successful clinical translation of compounds targeting sEH inhibition will further validate the promised therapeutic potential of this pathway in treating human diseases.


Subject(s)
Epoxide Hydrolases , Patents as Topic , Anti-Inflammatory Agents/pharmacology , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/therapeutic use , Fatty Acids , Humans
7.
Eur J Med Chem ; 236: 114304, 2022 Jun 05.
Article in English | MEDLINE | ID: mdl-35413618

ABSTRACT

Topoisomerase IB (Top1), a subcategory of DNA topoisomerase enzymes is expressed much higher in several tumor cells. Therefore, modulating the activity of Top1 in tumor cells to prevent DNA replication and subsequent cell division made it an important drug target for anticancer therapy. FDA-approved camptothecin (CPT) derivatives topotecan and irinotecan exert anticancer activity through stabilization of enzyme-mediated DNA cleavage complex forming a ternary complex between DNA-Top1-drug. However, CPT derivatives suffer from several limitations which prompted interest in the development of 'non-camptothecin' Top1 poisons as anticancer agents. This review aims to provide chronological development of different classes of Top1 poisons from both natural and synthetic sources through strategic structure-activity relationship (SAR) analysis with insight into the important structural features in different chemotypes that imparted Top1 inhibition along with the understanding of the structural basis of inhibition. This review also provides a snapshot of the application of Top1 poisons in various combination therapies in recent times. We believe such a comprehensive review is going to be beneficial for the medicinal chemistry community to design efficient drug development strategies using existing knowledge.


Subject(s)
Antineoplastic Agents , Poisons , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Camptothecin , DNA Topoisomerases, Type I/metabolism , Irinotecan , Topoisomerase I Inhibitors/chemistry , Topoisomerase I Inhibitors/pharmacology
8.
J Med Chem ; 64(13): 9279-9301, 2021 07 08.
Article in English | MEDLINE | ID: mdl-34142551

ABSTRACT

Several toll-like receptors (TLRs) reside inside endosomes of specific immune cells-among them, aberrant activation of TLR7 and TLR9 is implicated in myriad contexts of autoimmune diseases, making them promising therapeutic targets. However, small-molecule TLR7 and TLR9 antagonists are not yet available for clinical use. We illustrate here the importance of C2, C6, and N9 substitutions in the purine scaffold for antagonism to TLR7 and TLR9 through structure-activity relationship studies using cellular reporter assays and functional studies on primary human immune cells. Further in vitro and in vivo pharmacokinetic studies identified an orally bioavailable lead compound 29, with IC50 values of 0.08 and 2.66 µM against TLR9 and TLR7, respectively. Isothermal titration calorimetry excluded direct TLR ligand-antagonist interactions. In vivo antagonism efficacy against mouse TLR9 and therapeutic efficacy in a preclinical murine model of psoriasis highlighted the potential of compound 29 as a therapeutic candidate in relevant autoimmune contexts.


Subject(s)
Purines/pharmacology , Toll-Like Receptor 7/antagonists & inhibitors , Toll-Like Receptor 9/antagonists & inhibitors , Administration, Oral , Animals , Cell Line , Dose-Response Relationship, Drug , Humans , Mice , Mice, Inbred C57BL , Molecular Structure , Purines/administration & dosage , Purines/chemistry , Rats , Structure-Activity Relationship
9.
Eur J Med Chem ; 202: 112551, 2020 Sep 15.
Article in English | MEDLINE | ID: mdl-32682183

ABSTRACT

We have recently reported a new chemotype of a potent topoisomerase I poison with compound 1 as a potential anticancer chemotherapeutic agent. During further optimization, it has been observed that compound 1 suffers from high intrinsic clearance in human liver microsomes. To overcome the metabolic instability of compound 1, we report design and synthesis of metabolically stable Top1 poison 3. Newly identified Top1 poison 3 exhibits t1/2 of 69.1 min in human liver microsomes in comparison to compound 1 with t1/2 of 9.9 min. Molecular dynamic study of the newly optimized Top1 poison 3 was performed to get the insight into the stability of the binding pose in the active site. Compound 3 was able to trap DNA-Top1 cleavage complex and found to be less cytotoxic in non-cancerous cell line as compared to compound 1.


Subject(s)
Antineoplastic Agents/pharmacology , DNA Topoisomerases, Type I/metabolism , Drug Development , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Microsomes, Liver/chemistry , Microsomes, Liver/metabolism , Models, Molecular , Molecular Structure , Recombinant Proteins/metabolism , Structure-Activity Relationship
10.
ACS Nano ; 14(6): 7161-7169, 2020 Jun 23.
Article in English | MEDLINE | ID: mdl-32396326

ABSTRACT

Steady-state access to intraband transitions in colloidal quantum dots (CQDs), via doping, permits exploitation of the electromagnetic spectrum at energies below the band gap. CQD intraband optoelectronics allows envisaging cheap mid- and long-wavelength infrared photodetectors and light-emitting devices, which today employ epitaxial materials. As intraband devices start to emerge, thorough studies of the basic properties of intraband transitions in different CQD materials are needed to guide technological research. In this work, we investigate the size and temperature dependence of the intraband transition in heavily n-doped PbS quantum dot (QD) films. In the studied QD size range (5-8 nm), the intraband energy spans from 209 to 151 meV. We measure the intraband absorption coefficient of heavily doped PbS QD films to be around 2 × 104 cm-1, proving that intraband absorption is as strong as interband absorption. We demonstrate a negative dependence of the intraband energy with temperature, in contrast to the positive dependence of the interband transition. Also opposite to the interband case, the temperature dependence of the intraband energy increases with decreasing size, going from -29 µeV/K to -49 µeV/K in the studied size range.

11.
J Med Chem ; 63(9): 4776-4789, 2020 05 14.
Article in English | MEDLINE | ID: mdl-32302115

ABSTRACT

Toll-like receptor 7 (TLR7) is an established therapeutic target in myriad autoimmune disorders, but no TLR7 antagonist is available for clinical use to date. Herein, we report a purine scaffold TLR7 antagonist, first-of-its-kind to our knowledge, which was developed by rationally dissecting the structural requirements for TLR7-targeted activity for a purine scaffold. Specifically, we identified a singular chemical switch at C-2 that could make a potent purine scaffold TLR7 agonist to lose agonism and acquire antagonist activity, which could further be potentiated by the introduction of an additional basic center at C-6. We ended up developing a clinically relevant TLR7 antagonist with favorable pharmacokinetics and 70.8% oral bioavailability in mice. Moreover, the TLR7 antagonists depicted excellent selectivity against TLR8. To further validate the in vivo applicability of this novel TLR7 antagonist, we demonstrated its excellent efficacy in preventing TLR7-induced pathology in a preclinical murine model of psoriasis.


Subject(s)
Dermatologic Agents/therapeutic use , Purines/therapeutic use , Toll-Like Receptor 7/agonists , Toll-Like Receptor 7/antagonists & inhibitors , Animals , Binding Sites , Caco-2 Cells , Dermatologic Agents/chemical synthesis , Dermatologic Agents/metabolism , Dermatologic Agents/pharmacokinetics , HEK293 Cells , Humans , Male , Mice, Inbred C57BL , Molecular Docking Simulation , Molecular Structure , Psoriasis/drug therapy , Psoriasis/pathology , Purines/chemical synthesis , Purines/metabolism , Purines/pharmacokinetics , Skin/pathology , Structure-Activity Relationship , Toll-Like Receptor 7/metabolism
12.
Comput Struct Biotechnol J ; 17: 291-310, 2019.
Article in English | MEDLINE | ID: mdl-30867893

ABSTRACT

Camptothecin (CPT), a natural product and its synthetic derivatives exert potent anticancer activity by selectively targeting DNA Topoisomerase I (Top1) enzyme. CPT and its clinically approved derivatives are used as Top1 poisons for cancer therapy suffer from many limitations related to stability and toxicity. In order to envisage structurally diverse novel chemical entity as Top1 poison with better efficacy, Ligand-based-pharmacophore model was developed using 3D QSAR pharmacophore generation (HypoGen algorithm) methodology in Discovery studio 4.1 clients. The chemical features of 29 CPT derivatives were taken as the training set. The selected pharmacophore model Hypo1 was further validated by 33 test set molecules and used as a query model for further screening of 1,087,724 drug-like molecules from ZINC databases. These molecules were subjected to several assessments such as Lipinski rule of 5, SMART filtration and activity filtration. The molecule obtained after filtration was further scrutinized by molecular docking analysis on the active site of Top1 crystal structure (PDB ID: 1T8I). Six potential inhibitory molecules have been selected by analyzing the binding interaction and Ligand-Pharmacophore mapping with the validated pharmacophore model. Toxicity assessment TOPKAT program provided three potential inhibitory 'hit molecules' ZINC68997780, ZINC15018994 and ZINC38550809. MD simulation of these three molecules proved that the ligand binding into the protein-DNA cleavage complex is stable and the protein-ligands conformation remains unchanged. These three hit molecules can be utilized for designing future class of potential topoisomerase I inhibitor.

13.
J Med Chem ; 62(7): 3428-3446, 2019 04 11.
Article in English | MEDLINE | ID: mdl-30897325

ABSTRACT

To overcome chemical limitations of camptothecin (CPT), we report design, synthesis, and validation of a quinoline-based novel class of topoisomerase 1 (Top1) inhibitors and establish that compound 28 ( N-(3-(1 H-imidazol-1-yl)propyl)-6-(4-methoxyphenyl)-3-(1,3,4-oxadiazol-2-yl)quinolin-4-amine) exhibits the highest potency in inhibiting human Top1 activity with an IC50 value of 29 ± 0.04 nM. Compound 28 traps Top1-DNA cleavage complexes (Top1ccs) both in the in vitro cleavage assays and in live cells. Point mutation of Top1-N722S fails to trap compound 28-induced Top1cc because of its inability to form a hydrogen bond with compound 28. Unlike CPT, compound 28 shows excellent plasma serum stability and is not a substrate of P-glycoprotein 1 (permeability glycoprotein) advancing its potential anticancer activity. Finally, we provide evidence that compound 28 overcomes the chemical instability of CPT in human breast adenocarcinoma cells through generation of persistent and less reversible Top1cc-induced DNA double-strand breaks as detected by γH2AX foci immunostaining after 5 h of drug removal.


Subject(s)
Antineoplastic Agents/pharmacology , Drug Discovery/methods , Topoisomerase I Inhibitors/pharmacology , Antineoplastic Agents/chemistry , Cell Line, Tumor , DNA Breaks, Double-Stranded/drug effects , DNA Topoisomerases, Type I/genetics , DNA Topoisomerases, Type I/metabolism , Drug Screening Assays, Antitumor , Humans , Point Mutation , Topoisomerase I Inhibitors/chemistry
14.
Med Res Rev ; 39(4): 1338-1371, 2019 07.
Article in English | MEDLINE | ID: mdl-30927319

ABSTRACT

Life on earth depends on the biosynthesis of riboflavin, which plays a vital role in biological electron transport processes. Higher mammals obtain riboflavin from dietary sources; however, various microorganisms, including Gram-negative pathogenic bacteria and yeast, lack an efficient riboflavin-uptake system and are dependent on endogenous riboflavin biosynthesis. Consequently, the inhibition of enzymes in the riboflavin biosynthesis pathway would allow selective toxicity to a pathogen and not the host. Thus, the riboflavin biosynthesis pathway is an attractive target for designing novel antimicrobial drugs, which are urgently needed to address the issue of multidrug resistance seen in various pathogens. The enzymes involved in riboflavin biosynthesis are lumazine synthase (LS) and riboflavin synthase (RS). Understanding the details of the mechanisms of the enzyme-catalyzed reactions and the structural changes that occur in the enzyme active sites during catalysis can facilitate the design and synthesis of suitable analogs that can specifically inhibit the relevant enzymes and stop the generation of riboflavin in pathogenic bacteria. The present review is the first compilation of the work that has been carried out over the last 25 years focusing on the design of inhibitors of the biosynthesis of riboflavin based on an understanding of the mechanisms of LS and RS. This review aimed to address the fundamental advances in our understanding of riboflavin biosynthesis as applied to the rational design of a novel class of inhibitors. These advances have been aided by X-ray structures of ligand-enzyme complexes, rotational-echo, double-resonance nuclear magnetic resonance spectroscopy, high-throughput screening, virtual screenings, and various mechanistic probes.


Subject(s)
Anti-Infective Agents/pharmacology , Riboflavin/biosynthesis , Anti-Infective Agents/chemistry , Crystallography, X-Ray , Molecular Structure
15.
ACS Appl Mater Interfaces ; 10(4): 3750-3760, 2018 Jan 31.
Article in English | MEDLINE | ID: mdl-29345454

ABSTRACT

In this manuscript, the inorganic perovskite CsPbI2Br is investigated as a photovoltaic material that offers higher stability than the organic-inorganic hybrid perovskite materials. It is demonstrated that CsPbI2Br does not irreversibly degrade to its component salts as in the case of methylammonium lead iodide but instead is induced (by water vapor) to transform from its metastable brown cubic (1.92 eV band gap) phase to a yellow phase having a higher band gap (2.85 eV). This is easily reversed by heating to 350 °C in a dry environment. Similarly, exposure of unencapsulated photovoltaic devices to water vapor causes current (JSC) loss as the absorber transforms to its more transparent (yellow) form, but this is also reversible by moderate heating, with over 100% recovery of the original device performance. NMR and thermal analysis show that the high band gap yellow phase does not contain detectable levels of water, implying that water induces the transformation but is not incorporated as a major component. Performances of devices with best efficiencies of 9.08% (VOC = 1.05 V, JSC = 12.7 mA cm-2 and FF = 68.4%) using a device structure comprising glass/ITO/c-TiO2/CsPbI2Br/Spiro-OMeTAD/Au are presented, and further results demonstrating the dependence of the performance on the preparation temperature of the solution processed CsPbI2Br films are shown. We conclude that encapsulation of CsPbI2Br to exclude water vapor should be sufficient to stabilize the cubic brown phase, making the material of interest for use in practical PV devices.

16.
Phys Chem Chem Phys ; 19(41): 28450-28457, 2017 Oct 25.
Article in English | MEDLINE | ID: mdl-29039430

ABSTRACT

We form junctions between a monolayer of a range of metal-phthalocyanines and a monolayer of 2D transition metal dichalcogenides (TMD) through an electrostatic adsorption process. The energy levels of the components, as drawn from scanning tunneling spectroscopy (STS) and the density of states (DOS) thereof, indicated that the hybrid junctions would act as current rectifiers. We have observed that the central metal atom affected the energies of the metalorganics and thereby the rectification ratio of the junctions. In addition, since planar single molecule magnets (SMMs) were used in which magnetization appears due to the 3d-electrons of the metal, we could align the molecules followed by their structural immobilization. We have observed that such an alignment changed their molecular orbitals and hence affected the energy levels at the interface. The rectification ratio of molecule|TMD hybrid junctions depends on the metal in metalorganics and also on their alignment with the substrate electrode. In effect, the rectification ratio in a range of junctions has been correlated to the energy-level diagram at the interface.

17.
Nanotechnology ; 28(9): 095705, 2017 Mar 03.
Article in English | MEDLINE | ID: mdl-28135209

ABSTRACT

Through scanning tunneling spectroscopy, we envisage imaging a heterostructure, namely a junction formed in a single nanorod. While the differential conductance spectrum provides location of conduction and valence band edges, dI/dV images record energy levels of materials. Such dI/dV images at different voltages allowed us to view p- and n-sections of heterojunction nanorods and more importantly the depletion region in such a junction that has a type-II band alignment. Viewing of selective sections in a heterojunction occurred due to band-bending in the junction and is correlated to the density of states spectrum of the individual semiconductors. The dI/dV images recorded at different voltages could be used to generate a band diagram of a pn junction.

18.
Indian J Otolaryngol Head Neck Surg ; 54(3): 184-8, 2002 Jul.
Article in English | MEDLINE | ID: mdl-23119888

ABSTRACT

During a period of 12 years, 874 salivary gland lesions were aspirated of which 740 (86.85%) were from parotid gland. Cystic, inflammatory & neoplastic lesions were 25.25%. 54.45% & 20.30%, respectively. Plcomorphic adenoma was the commonest benign & adenoid cystic carcinoma was the most frequent malignant tumors.On cytohistologic correlation, sensilitvity of cytology for diagnosing cystic, inflammatory, neoplastic lesions proved to be 93.3%. 95.7% & 100% respectively. Overall accuracy for cytodiagnosis of malignant salivary gland lesions in our study was 96.07%.

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