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Cyclodextrin-modified MEKC for enantioseparation of hexaconazole, penconazole, and myclobutanil

Wan Ibrahim WA, Hermawan D, Sanagi MM, Aboul-Enein HY

J Sep Sci, 2009 Feb;32(3):466-71.
PMID: 19142910 DOI: 10.1002/jssc.200800512

A CD-modified micellar EKC (CD-MEKC) method with 2-hydroxypropyl-gamma-CD (HP-gamma-CD) as chiral selector for the enantioseparation of three chiral triazole fungicides, namely hexaconazole, penconazole, and myclobutanil, is reported for the first time. Simultaneous enantioseparation of the three triazole fungicides was successfully achieved using a CD-MEKC system containing 40 mM HP-gamma-CD and 50 mM SDS in 25 mM phosphate buffer (pH 3.0) solution with resolutions (R(s)) greater than 1.60, peak efficiencies (N) greater than 200,000 for all enantiomers and an analysis time within 15 min compared to 36 min as previously reported using sulfated-beta-CD.

Matched MeSH terms: Triazoles/isolation & purification*; Triazoles/chemistry
Determination of hexaconazole in field samples of an oil palm plantation

Muhamad H, Zainol M, Sahid I, Abu Seman I

Drug Test Anal, 2012 Aug;4 Suppl 1:112-7.
PMID: 22851367 DOI: 10.1002/dta.1351

In oil palm plantations, the fungicide hexaconazole is used to control Ganoderma infection that threatens to destroy or compromisethe palm. The application of hexaconazole is usually through soil drenching, trunk injection, or a combination of these two methods. It is therefore important to have a method to determine the residual amount of hexaconazole in the field such as in samples of water, soil, and leaf to monitor the use and fate of the fungicide in oil palm plantations. This study on the behaviour of hexaconazole in oil palm agro-environment was carried out at the UKM-MPOB Research Station, Bangi Lama, Selangor. Three experimental plots in this estate with 7-year-old Dura x Pisifera (DxP) palms were selected for the field trial. One plot was sprayed with hexaconazole at the manufacturer's recommended dosage, one at double the recommended dosage, and the third plot was untreated control. Hexaconazole residues in the soil, leaf, and water were determined before and after fungicide treatment. Soil samples were randomly collected from three locations at different depths (0-50 cm) and soil collected fromthe same depth were bulked together. Soil, water, and palm leaf were collected at -1 (day before treatment), 0 (day of treatment), 1, 3, 7, 14, 21, 70, 90, and 120 days after treatment. Hexaconazole was detected in soil and oil palm leaf, but was not detected in water from the nearby stream.

Matched MeSH terms: Triazoles/analysis*; Triazoles/isolation & purification
Fulltext Triazoloquinazolines as a new class of potent α-glucosidase inhibitors: in vitro evaluation and docking study

Abuelizz HA, Anouar EH, Ahmad R, Azman NIIN, Marzouk M, Al-Salahi R

PLoS One, 2019;14(8):e0220379.
PMID: 31412050 DOI: 10.1371/journal.pone.0220379

Previously, we synthesized triazoloquinazolines 1-14 and characterized their structure. In this study, we aimed to evaluate the in vitro activity of the targets 1-14 as α-glucosidase inhibitors using α-glucosidase enzyme from Saccharomyces cerevisiae type 1. Among the tested compounds, triazoloquinazolines 14, 8, 4, 5, and 3 showed the highest inhibitory activity (IC50 = 12.70 ± 1.87, 28.54 ± 1.22, 45.65 ± 4.28, 72.28 ± 4.67, and 83.87 ± 5.12 μM, respectively) in relation to that of acarbose (IC50 = 143.54 ± 2.08 μM) as a reference drug. Triazoloquinazolines were identified herein as a new class of potent α-glucosidase inhibitors. Molecular docking results envisaged the plausible binding interaction between the target triazoloquinazolines and α-glucosidase enzyme and indicated considerable interaction with the active site residues.

Matched MeSH terms: Triazoles
Antibacterial, antifungal and anticonvulsant evaluation of novel newly synthesized 1-[2-(1H-tetrazol-5-yl)ethyl]-1H-benzo[d][1, 2,3]triazoles

Rajasekaran A, Murugesan S, AnandaRajagopal K

Arch Pharm Res, 2006 Jul;29(7):535-40.
PMID: 16903071

Several novel 1-[2-(1H-tetrazol-5-yl) ethyl]-1H-benzo[d][1,2,3]triazoles (3a-h) have been synthesized by the condensation of 1-[2-(1H-tetrazol-5-yl)-ethyl]-1H-benzotriazole (2) and appropriate acid chlorides. 1-[2-(1H-tetrazol-5-yl)-ethyl]-1H-benzotriazole (2) was synthesized by reacting 3-(1H-benzo[d][1,2,3]triazol-1-yl)propanenitrile with sodium azide and ammonium chloride in the presence of dimethylformamide. The synthesized compounds were characterized by IR and PMR analysis. The titled compounds were evaluated for their in-vitro antibacterial and antifungal activity by the cup plate method and anticonvulsant activity evaluated by the maximal electroshock induced convulsion method in mice. All synthesized compounds exhibited moderate antibacterial activity against Bacillus subtilis and moderate antifungal activity against Candida albicans. Compounds 5-(2-(1H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(4-aminophenyl)methanone 3d and 5-(2-(1 H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(2-aminophenyl)methanone 3e elicited excellent anticonvulsant activity.

Matched MeSH terms: Triazoles/chemical synthesis; Triazoles/pharmacology*
Fulltext New thiosemicarbazides and 1,2,4-triazolethiones derived from 2-(ethylsulfanyl) benzohydrazide as potent antioxidants

Nazarbahjat N, Nordin N, Abdullah Z, Abdulla MA, Yehye WA, Halim SN, et al.

Molecules, 2014;19(8):11520-37.
PMID: 25093989 DOI: 10.3390/molecules190811520

New thiosemicarbazide derivatives 2-6 were synthesised by reacting 2-(ethylsulfanyl)benzohydrazide with various aryl isothiocyanates. The cyclisation of compounds 2-6 under reflux conditions in a basic medium (aqueous NaOH, 4 N) yielded compounds 7-11 that contain a 1,2,4-triazole ring. All of the synthesised compounds were screened for their antioxidant activities. Compounds 2, 3, and 7 showed better radical scavenging in a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, with IC50 values of 1.08, 0.22, and 0.74 µg/mL, respectively, compared to gallic acid (IC50, 1.2 µg/mL). Compound 3 also showed superior results in a ferric reducing antioxidant power (FRAP) assay (3054 µM/100 g) compared to those of ascorbic acid (1207 µM/100 g).

Matched MeSH terms: Triazoles/chemical synthesis*; Triazoles/pharmacology*
Fulltext Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study

Kareem HS, Nordin N, Heidelberg T, Abdul-Aziz A, Ariffin A

Molecules, 2016 Feb 17;21(2).
PMID: 26901175 DOI: 10.3390/molecules21020224

A series of heterocyclic compounds bearing the well-known free radical scavenging 3,4,5-trimethoxybenzyloxy group, was synthesized. The key compound 4-(3,4,5-trimethoxybenzyl-oxy)benzohydrazide was converted into thiosemicarbazide derivatives, which were subsequently cyclized with NaOH to provide 1,2,4-triazole derivatives. Alternative treatment of the acid hydrazide with carbon disulfide in the presence of KOH led to the corresponding 1,3,4-oxadiazole and various alkylated derivatives. The newly synthesized compounds were purified and the structures of the products were elucidated and confirmed on the basis of their analytical and spectral data. Their antioxidant activities were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH(•)) and Ferric Reducing Antioxidant Power (FRAP) assays. The thiosemicarbazide derivatives were highly active in both antioxidant assays with the lowest IC50 value for DPPH radical scavenging. Theoretical calculations based on density functional theory (DFT) were performed to understand the relative importance of NH, SH and CH hydrogens on the radical scavenging activities of these compounds.

Matched MeSH terms: Triazoles/chemical synthesis*; Triazoles/pharmacology; Triazoles/chemistry
Fulltext Effect of Tilt Angle and Pin Depth on Dissimilar Friction Stir Lap Welded Joints of Aluminum and Steel Alloys

Chitturi V, Pedapati SR, Awang M

Materials (Basel), 2019 Nov 26;12(23).
PMID: 31779107 DOI: 10.3390/ma12233901

Automobile, aerospace, and shipbuilding industries are looking for lightweight materials for cost effective manufacturing which demands the welding of dissimilar alloy materials. In this study, the effect of tool rotational speed, welding speed, tilt angle, and pin depth on the weld joint were investigated. Aluminum 5052 and 304 stainless-steel alloys were joined by friction stir welding in a lap configuration. The design of the experiments was based on Taguchi's orthogonal array for conducting the experiments with four factors and three levels for each factor. The microstructural analysis showed tunnel defects, micro voids, and cracks which formed with 0° and 1.5° tilt angles. The defects were eliminated when the tilt angle increased to 2.5° and a mixed stir zone was formed with intermetallic compounds. The presence of the intermetallic compounds increased with the increase in tilt angle and pin depth which further resulted in obtaining a defect-free weld. Hooks were formed on either side of the weld zone creating a mechanical link for the joint. A Vickers hardness value of HV 635.46 was achieved in the mixed stir zone with 1000 rpm, 20 mm/min, and 4.2 mm pin depth with a tilt angle of 2.5°, which increased by three times compared to the hardness of SS 304 steel. The maximum shear strength achieved with 800 rpm, 40 mm/min, and a 4.3 mm pin depth with a tilt angle of 2.5° was 3.18 kN.

Matched MeSH terms: Triazoles
Copper Catalysis in Living Systems and In Situ Drug Synthesis

Clavadetscher J, Hoffmann S, Lilienkampf A, Mackay L, Yusop RM, Rider SA, et al.

Angew Chem Int Ed Engl, 2016 12 12;55(50):15662-15666.
PMID: 27860120 DOI: 10.1002/anie.201609837

The copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction has proven to be a pivotal advance in chemical ligation strategies with applications ranging from polymer fabrication to bioconjugation. However, application in vivo has been limited by the inherent toxicity of the copper catalyst. Herein, we report the application of heterogeneous copper catalysts in azide-alkyne cycloaddition processes in biological systems ranging from cells to zebrafish, with reactions spanning from fluorophore activation to the first reported in situ generation of a triazole-containing anticancer agent from two benign components, opening up many new avenues of exploration for CuAAC chemistry.

Matched MeSH terms: Triazoles
Fulltext A 23 bp cyp51A Promoter Deletion Associated With Voriconazole Resistance in Clinical and Environmental Isolates of Neocosmospora keratoplastica

James JE, Lamping E, Santhanam J, Milne TJ, Abd Razak MF, Zakaria L, et al.

Front Microbiol, 2020;11:272.
PMID: 32296397 DOI: 10.3389/fmicb.2020.00272

In the fungal pathogen Aspergillus fumigatus, resistance to azole antifungals is often linked to mutations in CYP51A, a gene that encodes the azole antifungal drug target lanosterol 14α-demethylase. The aim of this study was to investigate whether similar changes could be associated with azole resistance in a Malaysian Fusarium solani species complex (FSSC) isolate collection. Most (11 of 15) clinical FSSC isolates were Neocosmospora keratoplastica and the majority (6 of 10) of environmental isolates were Neocosmospora suttoniana strains. All 25 FSSC isolates had high minimum inhibitory concentrations (MICs) for itraconazole and posaconazole, low MICs for amphotericin B, and various (1 to >32 mg/l) voriconazole susceptibilities. There was a tight association between a 23 bp CYP51A promoter deletion and high (>32 mg/l) voriconazole MICs; of 19 FSSC strains sequenced, nine isolates had voriconazole MICs > 32 mg/l, and they all contained the 23 bp CYP51A promoter deletion, although it was absent in the ten remaining isolates with low (≤12 mg/l) voriconazole MICs. Surprisingly, this association between voriconazole resistance and the 23 bp CYP51A promoter deletion held true across species boundaries. It was randomly distributed within and across species boundaries and both types of FSSC isolates were found among environmental and clinical isolates. Three randomly selected N. keratoplastica isolates with low (≤8 mg/l) voriconazole MICs had significantly lower (1.3-7.5 times) CYP51A mRNA expression levels than three randomly selected N. keratoplastica isolates with high (>32 mg/l) voriconazole MICs. CYP51A expression levels, however, were equally strongly induced (~6,500-fold) by voriconazole in two representative strains reaching levels, after 80 min of induction, that were comparable to those of CYP51B. Our results suggest that FSSC isolates with high voriconazole MICs have a 23 bp CYP51A promoter deletion that provides a potentially useful marker for voriconazole resistance in FSSC isolates. Early detection of possible voriconazole resistance is critical for choosing the correct treatment option for patients with invasive fusariosis.

Matched MeSH terms: Triazoles
Utility of labile plasma iron and transferrin saturation in addition to serum ferritin as iron overload markers in different underlying anemias before and after deferasirox treatment

Porter JB, El-Alfy M, Viprakasit V, Giraudier S, Chan LL, Lai Y, et al.

Eur. J. Haematol., 2016 Jan;96(1):19-26.
PMID: 25691036 DOI: 10.1111/ejh.12540

Plasma markers in addition to serum ferritin (SF) may be useful for the assessment of iron overload; however, predictive utility may differ depending on underlying, transfusion-dependent, anemias.

Matched MeSH terms: Triazoles/administration & dosage*
Fulltext Economic burden in the management of transfusion-dependent thalassaemia patients in Malaysia from a societal perspective

Shafie AA, Wong JHY, Ibrahim HM, Mohammed NS, Chhabra IK

Orphanet J Rare Dis, 2021 04 07;16(1):157.
PMID: 33827621 DOI: 10.1186/s13023-021-01791-8

BACKGROUND: Transfusion-dependent thalassaemia (TDT) is a hereditary blood disorder in which blood transfusion is the mainstay treatment to prolong survival and improve quality of life. Patients with this disease require blood transfusion at more than 100 ml/kg annually and iron-chelating therapy (ICT) to prevent iron overload (IOL) complications. There are substantial numbers of TDT patients in Malaysia, but limited data are available regarding the economic burden associated with this disease. The purpose of this study was to determine the lifetime cost of TDT from a societal perspective and identify potential factors increasing patient and family expenditures among thalassaemia populations.
METHODS: The total lifetime cost per TDT patient (TC1) is the sum of lifetime healthcare cost (TC2) and lifetime patient and family healthcare expenditure (TC3). TC2 was simulated using the Markov model, taking into account all costs subsidized by the government, and TC3 was estimated through a cross-sectional health survey approach. A survey was performed using a two-stage sampling method in 13 thalassaemia centres covering all regions in Malaysia.
RESULTS: A TDT patient is expected to incur TC2 of USD 561,208. ICT was the main driver of cost and accounted for 56.9% of the total cost followed by blood transfusion cost at 13.1%. TC3 was estimated to be USD 45,458. Therefore, the estimated TC1 of a TDT patient was USD 606,665. Sensitivity analyses showed that if all patients were prescribed oral ICT deferasirox for their lifetime, the total healthcare cost would increase by approximately 65%. Frequency of visits to health facilities for blood transfusion/routine monitoring and patients who were prescribed desferrioxamine were observed to be factors affecting patient and family monthly expenses.
CONCLUSION: The lifetime cost per TDT patient was USD 606,665, and this result may be useful for national health allocation planning. An estimation of the economic burden will provide additional information to decision makers on implementing prevention interventions to reduce the number of new births and medical service reimbursement.

Matched MeSH terms: Triazoles
Fulltext The α6 subunit-containing GABAA receptor: A novel drug target for inhibition of trigeminal activation

Fan PC, Lai TH, Hor CC, Lee MT, Huang P, Sieghart W, et al.

Neuropharmacology, 2018 09 15;140:1-13.
PMID: 30016665 DOI: 10.1016/j.neuropharm.2018.07.017

Novel treatments against migraine are an urgent medical requirement. The α6 subunit-containing GABAA receptors (α6GABAARs) are expressed in trigeminal ganglia (TG), the hub of the trigeminal vascular system (TGVS) that is involved in the pathogenesis of migraine. Here we reveal an unprecedented role of α6GABAARs in ameliorating TGVS activation using several pharmacological approaches in an animal model mimicking pathological changes in migraine. TGVS activation was induced by intra-cisternal (i.c.) instillation of capsaicin in Wistar rats. Centrally, i.c. capsaicin activated the trigeminal cervical complex (TCC) measured by the increased number of c-Fos-immunoreactive (c-Fos-ir) TCC neurons. Peripherally, it elevated calcitonin gene-related peptide immunoreactivity (CGRP-ir) in TG and depleted CGRP-ir in the dura mater. Pharmacological approaches included a recently identified α6GABAAR-selective positive allosteric modulator (PAM), the pyrazoloquinolinone Compound 6, two α6GABAAR-active PAMs (Ro15-4513 and loreclezole), an α6GABAAR-inactive benzodiazepine (diazepam), an α6GABAAR-selective antagonist (furosemide), and a clinically effective antimigraine agent (topiramate). We examined effects of these compounds on both central and peripheral TGVS responses induced by i.c. capsaicin. Compound 6 (3-10 mg/kg, i.p.) significantly attenuated the TCC neuronal activation and TG CGRP-ir elevation, and dural CGRP depletion induced by capsaicin. All these effects of Compound 6 were mimicked by topiramate, Ro15-4513 and loreclezole, but not by diazepam. The brain-impermeable furosemide antagonized the peripheral, but not central, effects of Compound 6. These results suggest that the α6GABAAR in TG is a novel drug target for TGVS activation and that α6GABAAR-selective PAMs have the potential to be developed as a novel pharmacotherapy for migraine.

Matched MeSH terms: Triazoles/pharmacology
Fulltext Residual analysis of chitosan-based agronanofungicides as a sustainable alternative in oil palm disease management

Maluin FN, Hussein MZ, Yusof NA, Fakurazi S, Maznah Z, Idris AS, et al.

Sci Rep, 2020 12 18;10(1):22323.
PMID: 33339951 DOI: 10.1038/s41598-020-79335-6

The nanoformulations of pesticides have shown great interest from many parties due to their slow release capability and site-specific delivery. Hence, in this work, a new nanoformulation of a fungicide, namely chitosan-hexaconazole nanoparticles with a mean diameter size of 18 nm was subjected to the residual analysis on oil palm tissue, leaf and palm oil (crude palm oil and crude palm kernel oil) using a quick, easy, cheap, effective, rugged and safe (QuEChERS) method coupled with the gas chromatography-micro electron capture detector (GC-µECD). The chitosan-hexaconazole nanoparticles were applied using the trunk injection method at 4.5 g a.i./palm (standard single dose) and 9.0 g a.i./palm (double dose). The fungicide residue was analyzed at 0 (6 h after application), 1, 3, 7, 14, 30, 60, 90, and 120 days after treatment. The palm oil matrices; the crude palm oil (CPO) and crude palm kernel oil (CPKO) were found to be residue-free. However, it was observed that high accumulation of the fungicide in the stem tissue and leaf after the treatment using the chitosan-hexaconazole nanoparticles, which is good for better bioavailability for the treatment of the fungi, Ganoderma boninense. The dissipation kinetic at double dose treatment in the tissue and leaf was found to govern by the second-order kinetic with half-lives (t1/2) of 383 and 515 days, respectively.

Matched MeSH terms: Triazoles/pharmacology; Triazoles/chemistry
Fulltext Phytotoxicity of chitosan-based agronanofungicides in the vegetative growth of oil palm seedling

Maluin FN, Hussein MZ, Yusof NA, Fakurazi S, Idris AS, Hilmi NHZ, et al.

PLoS One, 2020;15(4):e0231315.
PMID: 32315346 DOI: 10.1371/journal.pone.0231315

Although fungicides could be the best solution in combating fungal infections in crops, however, the phytotoxic level of fungicides to the crops should be tested first to ensure that it is safe for the crops. Moreover, nanocarrier systems of fungicides could play a significant role in the advancement of crop protection. For this reason, chitosan was chosen in the present study as a nanocarrier for fungicides of hexaconazole and/or dazomet in the development of a new generation of agronanofungicides with a high antifungal potent agent and no phytotoxic effect. Hence, the encapsulation of fungicides into the non-toxic biopolymer, chitosan was aims to reduce the phytotoxic level of fungicides. In the present study, the in vivo phytotoxicity of chitosan-fungicides nanoparticles on the physiological and vegetative growth of oil palm seedlings was evaluated in comparison to its pure fungicides as well as the conventional fungicides. The results revealed the formation of chitosan-fungicides nanoparticles could reduce the phytotoxic effect on oil palm seedlings compared to their counterparts, pure fungicides. The chitosan-fungicides nanoparticles were seen to greatly reduce the phytotoxic effect compared to the conventional fungicides with the same active ingredient.

Matched MeSH terms: Triazoles/toxicity; Triazoles/chemistry
Antifungal susceptibility profile and biofilm-producing capability of Candida tropicalis isolates in a tertiary medical centre

Navarathinam SD, Neoh HM, Tan TL, Wahab AA, Mohd Nizam Tzar MN, Ding CH

Malays J Pathol, 2023 Dec;45(3):417-424.
PMID: 38155383

BACKGROUND: Candida tropicalis is a globally distributed yeast that has been popping up in the medical literature lately, albeit for unenviable reasons. C. tropicalis is associated with substantial morbidity, mortality as well as drug resistance. The aims of this study were to ascertain the antifungal susceptibility profile and the biofilm-producing capability of this notorious yeast in our centre.
METHODS: C. tropicalis isolates from sterile specimens were collected over a 12-month period. Conclusive identification was achieved biochemically with the ID 32 C kit. Susceptibility to nine antifungal agents was carried out using the colourimetric broth microdilution kit Sensititre YeastOne YO10. Biofilm-producing capability was evaluated by quantifying biomass formation spectrophotometrically following staining with crystal violet.
RESULTS: Twenty-four non-repetitive isolates of C. tropicalis were collected. The resistance rates to the triazole agents were 29.2% for fluconazole, 16.7% for itraconazole, 20.8% for voriconazole and 8.3% for posaconazole-the pan-azole resistance rate was identical to that of posaconazole. No resistance was recorded for amphotericin B, flucysosine or any of the echinocandins tested. A total of 16/24 (66.7%) isolates were categorized as high biomass producers and 8/24 (33.3%) were moderate biomass producers. None of our isolates were low biomass producers.
CONCLUSION: The C. tropicalis isolates from our centre were resistant only to triazole agents, with the highest resistance rate being recorded for fluconazole and the lowest for posaconazole. While this is not by itself alarming, the fact that our isolates were prolific biofilm producers means that even azole-susceptible isolates can be paradoxically refractory to antifungal therapy.

Matched MeSH terms: Triazoles
Fulltext Hexaconazole-Micelle Nanodelivery System Prepared Using Different Surfactants for Ganoderma Antifungal Application

Mustafa IF, Hussein MZ, Idris AS, Hilmi NHZ, Fakurazi S

Molecules, 2021 Sep 26;26(19).
PMID: 34641379 DOI: 10.3390/molecules26195837

Reports on fungicide-based agronanochemicals in combating disastrous basal stem rot disease in the oil palm industry are scant. Herein, we describe the potential of fungicide nanodelivery agents based on hexaconazole-micelle systems produced using three different surfactants; sodium dodecylbenze sulfonate (SDBS), sodium dodecyl sulfate (SDS) and Tween 80 (T80). The resulting nanodelivery systems were characterized and the results supported the encapsulation of the fungicide into the micelles of the surfactants. We have investigated in detail the size-dependent effects of the as-synthesized micelles towards the inhibition growth of Ganoderma Boninense fungi. All the nanodelivery systems indicate that their size decreased as the surfactant concentration was increased, and it directly affects the fungal inhibition. It was also found that Tween 80, a non-ionic surfactant gave the lowest effective concentration, the EC50 value of 2, on the pathogenic fungus Ganoderma boninense compared to the other anionic surfactants; SDBS and SDS. This study opens up a new generation of agronanofungicide of better efficacy for Ganoderma disease treatment.

Matched MeSH terms: Triazoles/pharmacology*; Triazoles/chemistry
Synthesis of triazole-linked oligonucleotides with high affinity to DNA complements and an analysis of their compatibility with biosystems

Varizhuk AM, Kaluzhny DN, Novikov RA, Chizhov AO, Smirnov IP, Chuvilin AN, et al.

J Org Chem, 2013 Jun 21;78(12):5964-9.
PMID: 23724994 DOI: 10.1021/jo400651k

New oligonucleotide analogues with triazole internucleotide linkages were synthesized, and their hybridization properties were studied. The analogues demonstrated DNA binding affinities similar to those of unmodified oligonucleotides. The modification was shown to protect the oligonucleotides from nuclease hydrolysis. The modified oligonucleotides were tested as PCR primers. Modifications remote from the 3'-terminus were tolerated by polymerases. Our results suggest that these new oligonucleotide analogues are among the most promising triazole DNA mimics characterized to date.

Matched MeSH terms: Triazoles/chemistry*
Fulltext Crystal structure of 3-(adamantan-1-yl)-4-(4-chloro-phen-yl)-1H-1,2,4-triazole-5(4H)-thione

Al-Wabli RI, El-Emam AA, Alroqi OS, Chidan Kumar CS, Fun HK

Acta Crystallogr E Crystallogr Commun, 2015 Feb 1;71(Pt 2):o115-6.
PMID: 25878859 DOI: 10.1107/S2056989015000596

The title compound, C18H20ClN3S, is a functionalized triazoline-3-thione derivative. The benzene ring is almost perpendic-ular to the planar 1,2,4-triazole ring [maximum deviation = 0.007 (1) Å] with a dihedral angle of 89.61 (5)° between them and there is an adamantane substituent at the 3-position of the triazole-thione ring. In the crystal, N-H⋯S hydrogen-bonding inter-actions link the mol-ecules into chains extending along the c-axis direction. The crystal packing is further stabilized by weak C-H⋯π inter-actions that link adjacent chains into a two-dimensional structure in the bc plane. The crystal studied was an inversion twin with a 0.50 (3):0.50 (3) domain ratio.

Matched MeSH terms: Triazoles
Fulltext Crystal structure of tetra-aqua-bis(3,5-di-amino-4H-1,2,4-triazol-1-ium)cobalt(II) bis-[bis-(pyridine-2,6-di-carboxyl-ato)cobaltate(II)] dihydrate

Johnson A, Mbonu J, Hussain Z, Loh WS, Fun HK

Acta Crystallogr E Crystallogr Commun, 2015 Jun 1;71(Pt 6):m139-40.
PMID: 26090171 DOI: 10.1107/S2056989015010014

The asymmetric unit of the title compound, [Co(C2H6N5)2(H2O)4][Co(C7H3NO4)2]2·2H2O, features 1.5 Co(II) ions (one anionic complex and one half cationic complex) and one water mol-ecule. In the cationic complex, the Co(II) atom is located on an inversion centre and is coordinated by two triazolium cations and four water mol-ecules, adopting an octa-hedral geometry where the N atoms of the two triazolium cations occupy the axial positions and the O atoms of the four water mol-ecules the equatorial positions. The two triazole ligands are parallel offset (with a distance of 1.38 Å between their planes). In the anionic complex, the Co(II) ion is six-coordinated by two N and four O atoms of the two pyridine-2,6-di-carboxyl-ate anions, exhibiting a slightly distorted octa-hedral coordination geometry in which the mean plane of the two pyridine-2,6-di-carboxyl-ate anions are almost perpendicular to each other, making a dihedral angle of 85.87 (2)°. In the crystal, mol-ecules are linked into a three-dimensional network via C-H⋯O, C-H⋯N, O-H⋯O and N-H⋯O hydrogen bonds.

Matched MeSH terms: Triazoles
The influence of genetic polymorphisms on the efficacy and side effects of anastrozole in postmenopausal breast cancer patients

Abubakar MB, Wei K, Gan SH

Pharmacogenet Genomics, 2014 Dec;24(12):575-81.
PMID: 25203739 DOI: 10.1097/FPC.0000000000000092

Breast cancer is a common cause of cancer mortality among women. Several genetic factors have been implicated in its development. Current treatment guidelines for estrogen receptor-positive breast cancer recommend that anastrozole [or any of the other two aromatase inhibitors (letrozole and exemestane)] is used as an alternative to tamoxifen or following several years of tamoxifen treatment. Nevertheless, this approach is still associated with many challenges, ranging from the recurrence of breast cancer to considerable interindividual variability in the tolerability of anastrozole, which may cause adverse effects, such as musculoskeletal symptoms, and lead to the withdrawal of many patients from treatment. Variabilities in the genes encoding the drug target (aromatase) or its metabolizing enzymes (CYP3A and UGT1A) contribute toward the interindividual variability in anastrozole's pharmacokinetics and/or pharmacodynamics. This paper reviews the role of genetic polymorphisms of CYP19A1, CYP3A4, and UGT1A4 in the responses of female hormone receptor-positive postmenopausal breast cancer patients to anastrozole. Many reviews in the literature have suggested that the study of functional polymorphisms and investigation of relevant genetic markers may provide valuable information in predicting responses to anastrozole in terms of its therapeutic and adverse effects. Nevertheless, more studies are required before the knowledge of its pharmacogenomics can be applied to the individualization of treatment to ensure that patients receive the maximum benefits. Therefore, future analyses, including but not limited to genome-wide association studies, are encouraged to address some of the gray areas in the pharmacogenomics of anastrozole therapy in postmenopausal breast cancer cases; this will help in providing guidance for future pharmacogenomics protocols when anastrozole is utilized in patients' management.

Matched MeSH terms: Triazoles/adverse effects; Triazoles/pharmacokinetics*

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