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  1. Ravindar L, Hasbullah SA, Rakesh KP, Hassan NI
    Eur J Med Chem, 2023 Aug 05;256:115458.
    PMID: 37163950 DOI: 10.1016/j.ejmech.2023.115458
    Malaria is the fifth most lethal parasitic infection in the world. Antimalarial medications have played a crucial role in preventing and eradicating malaria. Numerous heterocyclic moieties have been incorporated into the creation of effective antimalarial drugs. The 4-aminoquinoline moiety is favoured in antimalarial drug discovery due to the diverse biological applications of its derivative. Since the 1960s, 4-aminoquinoline has been an important antimalarial drug due to its low toxicity, high tolerability, and rapid absorption after administration. This review focused on the antimalarial efficacy of the 4-aminoquinoline moiety hybridised with various heterocyclic scaffolds developed by scientists since 2018 against diverse Plasmodium clones. It could aid in the future development of more effective antimalarial agents.
    Matched MeSH terms: Aminoquinolines/pharmacology; Aminoquinolines/therapeutic use
  2. Ravindar L, Hasbullah SA, Rakesh KP, Raheem S, Agustar HK, Ismail N, et al.
    Eur J Med Chem, 2024 Jan 15;264:116043.
    PMID: 38118392 DOI: 10.1016/j.ejmech.2023.116043
    Amongst heterocyclic compounds, quinoline and its derivatives are advantaged scaffolds that appear as a significant assembly motif for developing new drug entities. Aminoquinoline moiety has gained significant attention among researchers in the 21stcentury. Considering the biological and pharmaceutical importance of aminoquinoline derivatives, herein, we review the recent developments (since 2019) in various biological activities of the 4-aminoquinoline scaffold hybridized with diverse heterocyclic moieties such as quinoline, pyridine, pyrimidine, triazine, dioxine, piperazine, pyrazoline, piperidine, imidazole, indole, oxadiazole, carbazole, dioxole, thiazole, benzothiazole, pyrazole, phthalimide, adamantane, benzochromene, and pyridinone. Moreover, by gaining knowledge about SARs, structural insights, and molecular targets, this review may help medicinal chemists design cost-effective, selective, safe, and more potent 4-aminoquinoline hybrids for diverse biological activities.
    Matched MeSH terms: Aminoquinolines/pharmacology; Aminoquinolines/chemistry
  3. Boonyuen U, Jacob BAC, Wongwigkan J, Chamchoy K, Singha-Art N, Pengsuk N, et al.
    Malar J, 2024 Feb 02;23(1):38.
    PMID: 38308253 DOI: 10.1186/s12936-024-04864-8
    BACKGROUND: It was hypothesized that glucose-6-phosphate dehydrogenase (G6PD) deficiency confers a protective effect against malaria infection, however, safety concerns have been raised regarding haemolytic toxicity caused by radical cure with 8-aminoquinolines in G6PD-deficient individuals. Malaria elimination and control are also complicated by the high prevalence of G6PD deficiency in malaria-endemic areas. Hence, accurate identification of G6PD deficiency is required to identify those who are eligible for malaria treatment using 8-aminoquinolines.

    METHODS: The prevalence of G6PD deficiency among 408 Thai participants diagnosed with malaria by microscopy (71), and malaria-negative controls (337), was assessed using a phenotypic test based on water-soluble tetrazolium salts. High-resolution melting (HRM) curve analysis was developed from a previous study to enable the detection of 15 common missense, synonymous and intronic G6PD mutations in Asian populations. The identified mutations were subjected to biochemical and structural characterisation to understand the molecular mechanisms underlying enzyme deficiency.

    RESULTS: Based on phenotypic testing, the prevalence of G6PD deficiency (T) and intronic (c.1365-13T>C and c.486-34delT) mutations was detected with intermediate to normal enzyme activity. The double missense mutations were less catalytically active than their corresponding single missense mutations, resulting in severe enzyme deficiency. While the mutations had a minor effect on binding affinity, structural instability was a key contributor to the enzyme deficiency observed in G6PD-deficient individuals.

    CONCLUSIONS: With varying degrees of enzyme deficiency, G6PD genotyping can be used as a complement to phenotypic screening to identify those who are eligible for 8-aminoquinolines. The information gained from this study could be useful for management and treatment of malaria, as well as for the prevention of unanticipated reactions to certain medications and foods in the studied population.

    Matched MeSH terms: Aminoquinolines/adverse effects
  4. Wani WA, Jameel E, Baig U, Mumtazuddin S, Hun LT
    Eur J Med Chem, 2015 Aug 28;101:534-51.
    PMID: 26188909 DOI: 10.1016/j.ejmech.2015.07.009
    Malaria has been teasing human populations from a long time. Presently, several classes of antimalarial drugs are available in market, but the issues of toxicity, lower efficacy and the resistance by malarial parasites have decreased their overall therapeutic indices. Thus, the search for new promising antimalarials continues, however, the battle against malaria is far from over. Ferroquine is a derivative of chloroquine with antimalarial properties. It is the most successful of the chloroquine derivatives. Not only ferroquine, but also its derivatives have shown promising potential as antimalarials of clinical interest. Presently, much research is dedicated to the development of ferroquine derivatives as safe alternatives to antimalarial chemotherapy. The present article describes the structural, chemical and biological features of ferroquine. Several classes of ferroquine derivatives including hydroxyferroquines, trioxaferroquines, chloroquine-bridged ferrocenophanes, thiosemicarbazone derivatives, ferrocene dual conjugates, 4-N-substituted derivatives, and others have been discussed. Besides, the mechanism of action of ferroquine has been discussed. A careful observation has been made into pharmacologically significant ferroquine derivatives with better or equal therapeutic effects to that of chloroquine and ferroquine. A brief discussion of the toxicities of ferroquine derivatives has been made. Finally, efforts have been made to discuss the current challenges and future perspectives of ferroquine-based antimalarial drug development.
    Matched MeSH terms: Aminoquinolines/chemical synthesis; Aminoquinolines/pharmacology*; Aminoquinolines/chemistry
  5. Azilawati MI, Hashim DM, Jamilah B, Amin I
    Food Chem, 2015 Apr 1;172:368-76.
    PMID: 25442566 DOI: 10.1016/j.foodchem.2014.09.093
    The amino acid compositions of bovine, porcine and fish gelatin were determined by amino acid analysis using 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate as derivatization reagent. Sixteen amino acids were identified with similar spectral chromatograms. Data pre-treatment via centering and transformation of data by normalization were performed to provide data that are more suitable for analysis and easier to be interpreted. Principal component analysis (PCA) transformed the original data matrix into a number of principal components (PCs). Three principal components (PCs) described 96.5% of the total variance, and 2 PCs (91%) explained the highest variances. The PCA model demonstrated the relationships among amino acids in the correlation loadings plot to the group of gelatins in the scores plot. Fish gelatin was correlated to threonine, serine and methionine on the positive side of PC1; bovine gelatin was correlated to the non-polar side chains amino acids that were proline, hydroxyproline, leucine, isoleucine and valine on the negative side of PC1 and porcine gelatin was correlated to the polar side chains amino acids that were aspartate, glutamic acid, lysine and tyrosine on the negative side of PC2. Verification on the database using 12 samples from commercial products gelatin-based had confirmed the grouping patterns and the variables correlations. Therefore, this quantitative method is very useful as a screening method to determine gelatin from various sources.
    Matched MeSH terms: Aminoquinolines/chemistry*
  6. Azilawati MI, Hashim DM, Jamilah B, Amin I
    J Chromatogr A, 2014 Aug 1;1353:49-56.
    PMID: 24797394 DOI: 10.1016/j.chroma.2014.04.050
    In-house method validation was conducted to determine amino acid composition in gelatin by a pre-column derivatization procedure with the 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate reagent. The analytical parameters revealed that the validated method was capable of selectively performing a good chromatographic separation for 18 amino acids in less than 40 min; the overall detection and quantitation limit for amino acids fell into ranges of 5.68-12.48 and 36.0-39.0 pmol/μl, respectively; the matrix effect was not observed, and the linearity range was 37.5-1000 pmol/μl. The accuracy (precision and recovery) analyses of the method were conducted under repeatable conditions on different days in random order. Method precision revealed by HorRat values was significantly less than 2, except for histidine with a precision of 2.19, and the method recoveries had a range of 80-115% except for alanine which was recovered at 79.4%. The findings were reproducible and accurately defined, and the method was found to be suited to routine analysis of amino acid composition in gelatin-based ingredients.
    Matched MeSH terms: Aminoquinolines/chemistry*
  7. Elbashir AA, Saad B, Ali AS, Saleh MI, Aboul-Enein HY
    Biomed Chromatogr, 2009 Mar;23(3):295-301.
    PMID: 18816453 DOI: 10.1002/bmc.1113
    A capillary electrophoretic (CE) method for the baseline separation of the enantiomers of primaquine diphosphate (PQ) and quinocide (QC) (a major contaminant) in pharmaceutical formulations is proposed. Both components were separated under the following conditions: 50 mm tris phosphate buffer (pH 3.0) containing 15 mm hydroxypropyl-gamma-cyclodextrin (HP-gamma-CD) as background electrolyte; applied voltage, 16 kV; capillary temperature, 25 degrees C; detection wavelength, 254 nm; hydrostatic injection, 10 s. The separations were conducted using a 35 cm length and 50 microm i.d. uncoated fused silica capillary column. Under the optimized conditions, the components were successfully separated in about 5 min. Intraday precision of migration time and corrected peak areas when expressed as relative standard deviation ranged from 0.17 to 0.45 and 2.60 to 3.94%, respectively, while the interday precision ranged from 2.59 to 4.20 and 3.15 to 4.21%, respectively. After the validation exercise, the proposed method was applied for the determination of QC impurity in PQ formulations.
    Matched MeSH terms: Aminoquinolines/chemistry*
  8. Rehman K, Aluwi MF, Rullah K, Wai LK, Mohd Amin MC, Zulfakar MH
    Int J Pharm, 2015 Jul 25;490(1-2):131-41.
    PMID: 26003416 DOI: 10.1016/j.ijpharm.2015.05.045
    Imiquimod is a chemotherapeutic agent for many skin-associated diseases, but it has also been associated with inflammatory side effects. The aim of this study was to prevent the inflammatory effect of commercial imiquimod (Aldara(®)) by controlled release of imiquimod through a hydrogel/oleogel colloidal mixture (CA bigel) containing fish oil as an anti-inflammatory agent. Imiquimod permeability from Aldara® cream and bigel through mice skin was evaluated, and the drug content residing in the skin via the tape stripping technique was quantified. The fish oil fatty acid content in skin along with its lipophilic environment was also determined. An inflammation study was conducted using animal models, and Aldara(®) cream was found to potentially cause psoriasis-like inflammation, which could be owing to prolonged application and excessive drug permeation. Controlled release of imiquimod along with fish oil through CA bigel may have caused reduced imiquimod inflammation. NMR studies and computerized molecular modeling were also conducted to observe whether the fish oil and imiquimod formed a complex that was responsible for improving imiquimod transport and reducing its side effects. NMR spectra showed dose-dependent chemical shifts and molecular modeling revealed π-σ interaction between EPA and imiquimod, which could help reduce imiquimod inflammation.
    Matched MeSH terms: Aminoquinolines/pharmacology*
  9. Azilawati MI, Dzulkifly MH, Jamilah B, Shuhaimi M, Amin I
    J Pharm Biomed Anal, 2016 Sep 10;129:389-397.
    PMID: 27454091 DOI: 10.1016/j.jpba.2016.07.012
    A detailed procedure for estimating uncertainty according to the Laboratory of Government Chemists/Valid Analytical Measurement (LGC/VAM) protocol for determination of 18 amino acids in gelatin is proposed. The expanded uncertainty was estimated using mainly the method validation data (precision and trueness). Other sources of uncertainties were contributed by components in standard preparation measurements. The method scope covered a single matrix (gelatin) under a wide range of analyte concentrations. The uncertainty of method precision, μ(P) was 0.0237-0.1128pmolμl(-1) in which hydroxyproline and histidine represented the lowest and highest values of uncertainties, respectively. Proline and phenylalanine represented the lowest and highest uncertainties value for method recovery, μ(R) that was estimated within 0.0064-0.0995pmolμl(-1). The uncertainties from other sources, μ(Std) were 0.0325, 0.0428 and 0.0413pmolμl(-1) that were contributed by hydroxyproline, other amino acids and cystine, respectively. Hydroxyproline and phenylalanine represented the lowest and highest values of expanded uncertainty, U(y) that were determined at 0.0949 and 0.2473pmolμl(-1), respectively. The data were accurately defined and fulfill the technical requirements of ISO 17025:2005.
    Matched MeSH terms: Aminoquinolines/chemistry*
  10. Frances SP, Edstein MD, Debboun M, Shanks GD
    US Army Med Dep J, 2016 Oct-Dec.
    PMID: 27613205
    Australian and US military medical services have collaborated since World War II to minimize vector-borne diseases such as malaria, dengue, and scrub typhus. In this review, collaboration over the last 30 years is discussed. The collaborative projects and exchange scientist programs have resulted in mutually beneficial outcomes in the fields of drug development and personal protection measures against vector-borne diseases.
    Matched MeSH terms: Aminoquinolines/pharmacology
  11. Lai, Jing-Wei, Ng, Chew-Hee, Lim, Yvonne Ai-Lian, Mohd Jamil Maah
    MyJurnal
    Introduction: The spread of multidrug-resistant malaria parasite – Plasmodium sp. to commercially available antimalarial drugs, i.e. artemisinin-based combination therapies (ACTs) and chloroquine (CQ), has become a global treat to eliminate malaria. To limit the impact of antimalarial drug resistance, a new potent and affordable alternative is urgently needed. A number of metal-based compounds (metallodrugs) have been found active against Plasmodium falciparum, the species that causes potentially fatal cerebral malaria, as they are ease in ligand grafting of multi-functional groups. Ferroquine (FQ) is one of the metalloantimalarial drugs that is currently undergoing clinical trials. Methods: In this study, a series of ternary copper(II) and zinc(II) complexes – Cu(phen)(edda) 1, Zn(phen)(edda) 2, [Cu(phen)(cdmg)] NO3 3 and [Zn(phen)(c-dmg)]NO3 4 were synthesized and characterized by the following tests: Fourier transformed infrared (FTIR), CHN elemental analysis, UV-Vis spectroscopy, molar conductivity and magnetic susceptibility measurements. Results: In vitro hemolytic and antimalarial assays using SYBR Green I dye were done to determine the biological properties of these complexes. Preliminary biological evaluation demonstrated that all the complexes 1, 2, 3 and 4 exhibit toxicity against the sensitive blood-stage Plasmodium falciparum 3D7 with IC50 in μM range. Conclusion: Thus, metal complex is a potentially viable candidate as antimalarial drug to overcome the emergence of drug resistance.
    Matched MeSH terms: Aminoquinolines
  12. Elbashir AA, Saad B, Ali AS, Saleh MI, Aboul-Enein HY
    Biomed Chromatogr, 2009 May;23(5):464-71.
    PMID: 19016231 DOI: 10.1002/bmc.1137
    A capillary zone electrophoretic method has been developed and validated for the determination of the impurity quinocide (QC) in the antimalarial drug primaquine (PQ). Different buffer additives such as native cyclodextrins and crown ethers were evaluated. Promising results were obtained when either beta-cyclodextrin (beta-CD) or 18-crown-6 ether (18C6) were used. Their separation conditions such as type of buffer and its pH, buffer additive concentration, applied voltage capillary temperature and injection time were optimized. The use of 18C6 offers slight advantages over beta-CD such as faster elution times and improved resolution. Nevertheless, migration times of less than 5 min and resolution factors (R(s)) in the range of 2-4 were obtained when both additives were used. The method was validated with respect to selectivity, linearity, limits of detection and quantitation, analytical precision (intra- and inter-day variability) and repeatability. Concentrations of 2.12 and 2.71% (w/w) of QC were found in pharmaceutical preparations of PQ from two different manufacturers. A possible mechanism for the successful separation of the isomers is also discussed.
    Matched MeSH terms: Aminoquinolines/analysis*
  13. Mphahlele MJ, Mmonwa MM, Aro A, McGaw LJ, Choong YS
    Int J Mol Sci, 2018 Jul 31;19(8).
    PMID: 30065164 DOI: 10.3390/ijms19082232
    A series of indole-aminoquinazolines was prepared via amination of the 2-aryl-4-chloroquinazolines with the 7-amino-2-aryl-5-bromoindoles. It was then evaluated for cytotoxicity in vitro against human lung cancer (A549), epithelial colorectal adenocarcinoma (Caco-2), hepatocellular carcinoma (C3A), breast adenocarcinoma (MCF-7), and cervical cancer (HeLa) cells. A combination on the quinazoline and indole moieties of a 2-phenyl and 2-(4-fluorophenyl) rings in compound 4b; 2-(4-fluorophenyl) and 3-chlorophenyl rings in compound 4f; or the two 2-(4-fluorophenyl) rings in compound 4g, resulted in significant and moderate activity against the Caco-2 and C3A cell lines. The indole-aminoquinazoline hybrids compounds 4f and 4g induced apoptosis in Caco-2 and C3A cells, and were also found to exhibit moderate (IC50 = 52.5 nM) and significant (IC50 = 40.7 nM) inhibitory activity towards epidermal growth factor receptor (EGFR) against gefitinib (IC50 = 38.9 nM). Molecular docking suggests that 4a⁻h could bind to the ATP region of EGFR like erlotinib.
    Matched MeSH terms: Aminoquinolines/chemistry*
  14. Rehman K, Zulfakar MH
    Pharm Res, 2017 01;34(1):36-48.
    PMID: 27620176 DOI: 10.1007/s11095-016-2036-8
    PURPOSE: To characterize bigel system as a topical drug delivery vehicle and to establish the immunomodulatory role of imiquimod-fish oil combination against skin cancer and inflammation resulting from chemical carcinogenesis.

    METHODS: Imiquimod-loaded fish oil bigel colloidal system was prepared using a blend of carbopol hydrogel and fish oil oleogel. Bigels were first characterized for their mechanical properties and compared to conventional gel systems. Ex vivo permeation studies were performed on murine skin to analyze the ability of the bigels to transport drug across skin and to predict the release mechanism via mathematical modelling. Furthermore, to analyze pharmacological effectiveness in skin cancer and controlling imiquimod-induced inflammatory side effects, imiquimod-fish oil combination was tested in vitro on epidermoid carcinoma cells and in vivo in Swiss albino mice cancer model.

    RESULTS: Imiquimod-loaded fish oil bigels exhibited higher drug availability inside the skin as compared to individual imiquimod hydrogel and oleogel controls through quasi-Fickian diffusion mechanism. Imiquimod-fish oil combination in bigel enhanced the antitumor effects and significantly reduced serum pro-inflammatory cytokine levels such as tumor necrosis factor-alpha and interleukin-6, and reducing tumor progression via inhibition of vascular endothelial growth factor. Imiquimod-fish oil combination also resulted in increased expression of interleukin-10, an anti-inflammatory cytokine, which could also aid anti-tumor activity against skin cancer.

    CONCLUSION: Imiquimod administration through a bigel vehicle along with fish oil could be beneficial for controlling imiquimod-induced inflammatory side effects and in the treatment of skin cancer.

    Matched MeSH terms: Aminoquinolines/administration & dosage*; Aminoquinolines/chemistry
  15. Leung AK, Barankin B, Leong KF, Hon KL
    Drugs Context, 2018;7:212563.
    PMID: 30622585 DOI: 10.7573/dic.212563
    Background: Penile warts are the most common sexually transmitted disease in males. Clinicians should be familiar with the proper evaluation and management of this common condition.

    Objective: To provide an update on the current understanding, evaluation, and management of penile warts.

    Methods: A PubMed search was completed in Clinical Queries using the key terms 'penile warts' and 'genital warts'. The search strategy included meta-analyses, randomized controlled trials, clinical trials, observational studies, and reviews.

    Results: Penile warts are caused by human papillomavirus (HPV), notably HPV-6 and HPV-11. Penile warts typically present as asymptomatic papules or plaques. Lesions may be filiform, exophytic, papillomatous, verrucous, hyperkeratotic, cerebriform, fungating, or cauliflower-like. Approximately one-third of penile warts regress without treatment and the average duration prior to resolution is approximately 9 months. Active treatment is preferable to watchful observation to speed up clearance of the lesions and to assuage fears of transmission and autoinoculation. Patient-administered therapies include podofilox (0.5%) solution or gel, imiquimod 3.75 or 5% cream, and sinecatechins (polypheron E) 15% ointment. Clinician-administered therapies include podophyllin, cryotherapy, bichloroacetic or trichloroacetic acid, oral cimetidine, surgical excision, electrocautery, and carbon dioxide laser therapy. Patients who do not respond to first-line treatments may respond to other therapies or a combination of treatment modalities. Second-line therapies include topical/intralesional/intravenous cidofovir, topical 5-fluorouracil, and topical ingenol mebutate.

    Conclusion: No single treatment has been shown to be consistently superior to other treatment modalities. The choice of the treatment method should depend on the physician's comfort level with the various treatment options, the patient's preference and tolerability of treatment, and the number and severity of lesions. The comparative efficacy, ease of administration, adverse effects, cost, and availability of the treatment modality should also be taken into consideration.

    Matched MeSH terms: Aminoquinolines
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