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Journal articles on the topic 'Cycloguanil'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Brown, Jennifer I., Peng Wang, Alan Y. L. Wong, et al. "Cycloguanil and Analogues Potently Target DHFR in Cancer Cells to Elicit Anti-Cancer Activity." Metabolites 13, no. 2 (2023): 151. http://dx.doi.org/10.3390/metabo13020151.

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Dihydrofolate reductase (DHFR) is an established anti-cancer drug target whose inhibition disrupts folate metabolism and STAT3-dependent gene expression. Cycloguanil was proposed as a DHFR inhibitor in the 1950s and is the active metabolite of clinically approved plasmodium DHFR inhibitor Proguanil. The Cycloguanil scaffold was explored to generate potential cancer therapies in the 1970s. Herein, current computational and chemical biology techniques were employed to re-investigate the anti-cancer activity of Cycloguanil and related compounds. In silico modeling was employed to identify promisi

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2

Edstein, M. D., S. Bahr, B. Kotecka, G. D. Shanks, and K. H. Rieckmann. "In vitro activities of the biguanide PS-15 and its metabolite, WR99210, against cycloguanil-resistant Plasmodium falciparum isolates from Thailand." Antimicrobial Agents and Chemotherapy 41, no. 10 (1997): 2300–2301. http://dx.doi.org/10.1128/aac.41.10.2300.

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The in vitro activities of the new biguanide PS-15 and its putative active metabolite, WR99210, were determined against seven different isolates or clones of Plasmodium falciparum. The mean 50% inhibitory concentrations of PS-15 and WR99210 were 1,015 and 0.06 ng/ml, respectively. WR99210 was up to 363 times more potent than cycloguanil, the active metabolite of proguanil, against cycloguanil-resistant parasites. The pronounced activity of WR99210 against multidrug-resistant P. falciparum indicates that further studies are required to determine the value of the prodrug, PS-15, as an antimalari

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3

Zhigulin, Arseniy S., Anastasiya O. Novikova, and Oleg I. Barygin. "Mechanisms of NMDA Receptor Inhibition by Biguanide Compounds." Pharmaceuticals 17, no. 9 (2024): 1234. http://dx.doi.org/10.3390/ph17091234.

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N-methyl-D-aspartate (NMDA) receptors are inhibited by many medicinal drugs. The recent successful repurposing of NMDA receptor antagonists ketamine and dextromethorphan for the treatment of major depressive disorder further enhanced the interest in this field. In this work, we performed a screening for the activity against native NMDA receptors of rat CA1 hippocampal pyramidal neurons among biguanide compounds using the whole-cell patch-clamp method. Antimalarial biguanides proguanil and cycloguanil, as well as hypoglycemic biguanide phenformin, inhibited them in micromolar concentrations, wh

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4

Kurniawan, Isman, Muhammad Salman Fareza, and Ponco Iswanto. "CoMFA, Molecular Docking and Molecular Dynamics Studies on Cycloguanil Analogues as Potent Antimalarial Agents." Indonesian Journal of Chemistry 21, no. 1 (2020): 66. http://dx.doi.org/10.22146/ijc.52388.

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Malaria is a disease that commonly infects humans in many tropical areas. This disease becomes a serious problem because of the high resistance of Plasmodium parasite against the well-established antimalarial agents, such as Artemisinin. Hence, new potent compounds are urgently needed to resolve this resistance problem. In the present study, we investigated cycloguanil analogues as a potent antimalarial agent by utilizing several studies, i.e., comparative of molecular field analysis (CoMFA), molecular docking and molecular dynamics (MD) simulation. A CoMFA model with five partial least square

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5

Schwalbe, C. H., G. J. B. Williams, and T. F. Koetzle. "Structure of cycloguanil hydrochloride by neutron diffraction." Acta Crystallographica Section C Crystal Structure Communications 45, no. 3 (1989): 468–71. http://dx.doi.org/10.1107/s0108270188012193.

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6

Ralaimazava, P., R. Durand, N. Godineau, et al. "Profile and evolution of the chemosusceptibility of falciparum malaria imported into France in 2000." Eurosurveillance 7, no. 7 (2002): 113–18. http://dx.doi.org/10.2807/esm.07.07.00355-en.

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In 2000, the chemosusceptibility of imported malaria was stable in France. All countries of infection considered, the bi-resistance to chloroquine and cycloguanil has not changed from 1996 to 2000. The monotherapy using quinine or mefloquine remains the first-line treatment to falciparum malaria. Resistance to these two antimalarials is rare in Africa and has not evolved over the past 15 years.

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7

Pudney, Mary, Win Gutteridge, Anton Zeman, Maurice Dickins, and Joseph L. Woolley. "Atovaquone and Proguanil Hydrochloride: A Review of Nonclinical Studies." Journal of Travel Medicine 6, S1 (1999): S8—S12. http://dx.doi.org/10.1093/jtm/6.suppl.s8.

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Abstract Background: Safe and effective antimalarial drugs are needed for treatment and prophylaxis of malaria. The combination of atovaquone and proguanil hydrochloride is a new antimalarial drug combination that has recently become available in many countries. Methods: Data were reviewed from nonclinical studies evaluating the microbiology, secondary pharmacology, pharmacokinetics, and toxicology of atovaquone and proguanil hydrochloride. Results: Atovaquone is highly active against asexual erythrocytic stages of Plasmodium falciparum in vitro (IC60 0.7-6 nM) and in animal models. Proguanil

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8

Arnold, Megan S. J., Jessica A. Engel, Ming Jang Chua, Gillian M. Fisher, Tina S. Skinner-Adams, and Katherine T. Andrews. "Adaptation of the [3H]Hypoxanthine Uptake Assay forIn Vitro-Cultured Plasmodium knowlesi Malaria Parasites." Antimicrobial Agents and Chemotherapy 60, no. 7 (2016): 4361–63. http://dx.doi.org/10.1128/aac.02948-15.

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ABSTRACTThe zoonotic malaria parasitePlasmodium knowlesihas recently been established in continuousin vitroculture. Here, thePlasmodium falciparum[3H]hypoxanthine uptake assay was adapted forP. knowlesiand used to determine the sensitivity of this parasite to chloroquine, cycloguanil, and clindamycin. The data demonstrate thatP. knowlesiis sensitive to all drugs, with 50% inhibitory concentrations (IC50s) consistent with those obtained withP. falciparum. This assay provides a platform to useP. knowlesi in vitrofor drug discovery.

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9

Barata, Lídia, Pascal Houzé, Khadija Boutbibe, et al. "In VitroAnalysis of the Interaction between Atovaquone and Proguanil against Liver Stage Malaria Parasites." Antimicrobial Agents and Chemotherapy 60, no. 7 (2016): 4333–35. http://dx.doi.org/10.1128/aac.01685-15.

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ABSTRACTThe interaction between atovaquone and proguanil has never been studied against liver stage malaria, which is the main target of this drug combination when used for chemoprevention. Using human hepatocytes lacking cytochrome P450 activity, and thus avoiding proguanil metabolizing into potent cycloguanil, we showin vitrothat the atovaquone-proguanil combination synergistically inhibits the growth of rodentPlasmodium yoeliiparasites. These results provide a pharmacological basis for the high efficacy of atovaquone-proguanil used as malaria chemoprevention.

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10

Scott, H. V., M. D. Edstein, J. R. Veenendaal, and K. H. Rieckmann. "A sensitive bioassay for serum cycloguanil using Plasmodium falciparumin vitro." International Journal for Parasitology 18, no. 5 (1988): 605–9. http://dx.doi.org/10.1016/0020-7519(88)90094-x.

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11

Bygbjerg, I. C. "Effect of proguanil and cycloguanil on human lymphocytes in vitro." European Journal of Clinical Pharmacology 28, no. 3 (1985): 287–90. http://dx.doi.org/10.1007/bf00543325.

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12

Kulatee, Suriyawut, Pisanu Toochinda, Anotai Suksangpanomrung, and Luckhana Lawtrakul. "Theoretical Investigation of the Enantioselective Complexations between pfDHFR and Cycloguanil Derivatives." Scientia Pharmaceutica 85, no. 4 (2017): 37. http://dx.doi.org/10.3390/scipharm85040037.

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13

Basco, L. K., O. Ramiliarisoa, P. Ringwald, J. C. Doury, and J. Le Bras. "In vitro activity of cycloguanil against African isolates of Plasmodium falciparum." Antimicrobial Agents and Chemotherapy 37, no. 4 (1993): 924–25. http://dx.doi.org/10.1128/aac.37.4.924.

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14

Ramanaiah, T. Venkata, and A. Gajanana. "Superior antimalarial activity of proguanil to cycloguanil after in vitro bioconversion." Transactions of the Royal Society of Tropical Medicine and Hygiene 82, no. 3 (1988): 358–59. http://dx.doi.org/10.1016/0035-9203(88)90115-0.

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15

Beerahee, Misba. "Clinical Pharmacology of Atovaquone and Proguanil Hydrochloride." Journal of Travel Medicine 6, S1 (1999): S13—S20. http://dx.doi.org/10.1093/jtm/6.suppl.s13.

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Abstract Background: Atovaquone and proguanil hydrochloride is a new antimalarial combination that is used for treatment and prophylaxis of malaria. Methods: The clinical pharmacology of atovaquone and proguanil was reviewed. Results: Atovaquone is a highly lipophilic compound with low aqueous solubility, the absorption of which is limited by the rate and extent of dissolution. Dietary fat increases the rate and extent of atovaquone absorption, increasing AUC two- to threefold and C fivefold over fasting. Proguanil is rapidly and extensively absorbed regardless of food intake. Atovaquone is hi

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16

Edstein, M. D., J. R. Veenendaal, H. V. Scott, and K. H. Rieckmann. "Steady-State Kinetics of Proguanil and Its Active Metabolite, Cycloguanil, in Man." Chemotherapy 34, no. 5 (1988): 385–92. http://dx.doi.org/10.1159/000238597.

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17

Thapar, Mita M., Seema Gupta, Carl Spindler, Walther H. Wernsdorfer, and Anders Björkman. "Pharmacodynamic interactions among atovaquone, proguanil and cycloguanil against Plasmodium falciparum in vitro." Transactions of the Royal Society of Tropical Medicine and Hygiene 97, no. 3 (2003): 331–37. http://dx.doi.org/10.1016/s0035-9203(03)90162-3.

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18

Petersen, E., B. Hogh, A. P. Hanson, A. Bjorkman, and H. Flacks. "In vitroandin vivosusceptibility ofPlasmodium falciparumisolates from Liberia to pyrimethamine, cycloguanil and chlorcycloguanil." Annals of Tropical Medicine & Parasitology 84, no. 6 (1990): 563–71. http://dx.doi.org/10.1080/00034983.1990.11812511.

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19

Peterson, D. S., W. K. Milhous, and T. E. Wellems. "Molecular basis of differential resistance to cycloguanil and pyrimethamine in Plasmodium falciparum malaria." Proceedings of the National Academy of Sciences 87, no. 8 (1990): 3018–22. http://dx.doi.org/10.1073/pnas.87.8.3018.

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20

Landi, Giacomo, Pasquale Linciano, Chiara Borsari, et al. "Structural Insights into the Development of Cycloguanil Derivatives asTrypanosoma bruceiPteridine-Reductase-1 Inhibitors." ACS Infectious Diseases 5, no. 7 (2019): 1105–14. http://dx.doi.org/10.1021/acsinfecdis.8b00358.

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21

Yeo, Anthony E. T., and Karl H. Rieckmann. "The activity in vitro of cycloguanil and pyrimethamine in combination against Plasmodium falciparum." Transactions of the Royal Society of Tropical Medicine and Hygiene 86, no. 3 (1992): 234. http://dx.doi.org/10.1016/0035-9203(92)90287-m.

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22

McGready, R., K. Stepniewska, E. Seaton, et al. "Pregnancy and use of oral contraceptives reduces the biotransformation of proguanil to cycloguanil." European Journal of Clinical Pharmacology 59, no. 7 (2003): 553–57. http://dx.doi.org/10.1007/s00228-003-0651-x.

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23

Yeo, A. E. T., and R. I. Christopherson. "Comparative effects of cycloguanil and WR99210 in human leukaemia cells and intra-erythrocyticPlasmodium." Annals of Tropical Medicine & Parasitology 92, no. 3 (1998): 331–33. http://dx.doi.org/10.1080/00034983.1998.11813297.

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24

Basak, S. C., and D. Mills. "Quantitative structure-activity relationships for cycloguanil analogs as PfDHFR inhibitors using mathematical molecular descriptors." SAR and QSAR in Environmental Research 21, no. 3-4 (2010): 215–29. http://dx.doi.org/10.1080/10629361003770951.

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25

Kaneko, Akira, Yngve Bergqvist, Miho Takechi, et al. "Intrinsic Efficacy of Proguanil against Falciparum and Vivax Malaria Independent of the Metabolite Cycloguanil." Journal of Infectious Diseases 179, no. 4 (1999): 974–79. http://dx.doi.org/10.1086/314683.

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26

Sivaprakasam, Prasanna, Perrer N. Tosso, and Robert J. Doerksen. "Structure−Activity Relationship and Comparative Docking Studies for Cycloguanil Analogs as PfDHFR-TS Inhibitors." Journal of Chemical Information and Modeling 49, no. 7 (2009): 1787–96. http://dx.doi.org/10.1021/ci9000663.

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27

Edstein, M. D. "Simultaneous measurement of proguanil and cycloguanil in human plasma by high-performance liquid chromatography." Journal of Chromatography B: Biomedical Sciences and Applications 380 (January 1986): 184–89. http://dx.doi.org/10.1016/s0378-4347(00)83641-5.

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28

Yeo, A. E. T., M. D. Edstein, G. D. Shanks, and K. H. Rieckmann. "A statistical analysis of the antimalarial activity of proguanil and cycloguanil in human volunteers." Annals of Tropical Medicine & Parasitology 88, no. 6 (1994): 587–94. http://dx.doi.org/10.1080/00034983.1994.11812909.

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29

Funck-Brentano, Christian, Olivier Bosco, Evelyne Jacqz-Aigrain, Annick Keundjian, and Patrice Jaillon. "Relation between chloroguanide bioactivation to cycloguanil and the genetically determined metabolism of mephenytoin in humans." Clinical Pharmacology and Therapeutics 51, no. 5 (1992): 507–12. http://dx.doi.org/10.1038/clpt.1992.55.

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30

Edstein, M. D., A. E. T. Yeo, G. D. Shanks, and K. H. Rieckmann. "Ex vivo antimalarial activity of proguanil combined with dapsone against cycloguanil-resistant Plasmodium falciparum isolates." Acta Tropica 66, no. 3 (1997): 127–35. http://dx.doi.org/10.1016/s0001-706x(97)00044-2.

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31

Kelly, J. A., and K. A. Fletcher. "High-performance liquid chromatographic method for the determination of proguanil and cycloguanil in biological fluids." Journal of Chromatography B: Biomedical Sciences and Applications 381 (January 1986): 464–71. http://dx.doi.org/10.1016/s0378-4347(00)83616-6.

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32

Gyang, Frederick N., David S. Peterson, and Thomas E. Wellems. "Plasmodium falciparum: Rapid detection of dihydrofolate reductase mutations that confer resistance to cycloguanil and pyrimethamine." Experimental Parasitology 74, no. 4 (1992): 470–72. http://dx.doi.org/10.1016/0014-4894(92)90209-s.

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33

Watkins, W. M., E. K. Mberu, C. G. Nevill, S. A. Ward, A. M. Breckenridge, and D. K. Koech. "Variability in the metabolism of proguanil to the active metabolite cycloguanil in healthy Kenyan adults." Transactions of the Royal Society of Tropical Medicine and Hygiene 84, no. 4 (1990): 492–95. http://dx.doi.org/10.1016/0035-9203(90)90010-c.

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34

Ward, SA, WM Watkins, E. Mberu, et al. "Inter-subject variability in the metabolism of proguanil to the active metabolite cycloguanil in man." British Journal of Clinical Pharmacology 27, no. 6 (1989): 781–87. http://dx.doi.org/10.1111/j.1365-2125.1989.tb03440.x.

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35

Wanwimolruk, Sompon, and Emma L. Pratt. "A Simple HPLC Assay for Proguanil and Its Active Metabolite Cycloguanil: Application to Oxidation Phenotyping." Journal of Liquid Chromatography 18, no. 20 (1995): 4097–105. http://dx.doi.org/10.1080/10826079508013747.

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36

Maitarad, Phornphimon, Sumalee Kamchonwongpaisan, Jarunee Vanichtanankul, Tirayut Vilaivan, Yongyuth Yuthavong, and Supa Hannongbua. "Interactions between cycloguanil derivatives and wild type and resistance-associated mutant Plasmodium falciparum dihydrofolate reductases." Journal of Computer-Aided Molecular Design 23, no. 4 (2009): 241–52. http://dx.doi.org/10.1007/s10822-008-9254-z.

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37

Parker, Elijah Joshua Ugochi Olivia Njoku Zikora Kizito Anyaegbunam Joseph Chinedum Ndefo Amaechi Lydia Ogara Samuel Cosmas* Olanrewaju Ayodeji Durojaye*. "EVALUATION OF THE INHIBITORY EFFECT OF A CANNABIDIOL DERIVATIVE AGAINST THE PLASMODIUM FALCIPARUM DIHYDROFOLATE REDUCTASE." INDO AMERICAN JOURNAL OF PHARMACEUTICAL SCIENCES o6, no. 07 (2019): 13510–20. https://doi.org/10.5281/zenodo.3344821.

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<strong><em>Introduction:</em></strong><em>The alarming rate of drug failure against malaria necessitates the development and deployment of novel and highly efficacious antimalarial drugs. The use of natural plant remedies in curtailing the malaria catastrophe remains uncertain, as only a small fraction of plants has been evaluated and developed for their medicinal potentials. However, many communities in malaria-affected regions still rely on natural plants and herbs, despite documented concerns about efficacy and adverse effects. One plant of continuous controversy is <em>Cannabis

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38

Hill, J. "The activity of drug combinations against established infections of rodent malaria." Parasitology 95, no. 1 (1987): 17–23. http://dx.doi.org/10.1017/s0031182000057504.

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SUMMARYIn the experiments reported here treatment (with a single dose or daily for 4 days) was delayed until 3 days after inoculation. Various combinations of M&B 35769, 2:4-diamino-5-[3(4–4′-chlorophenylphenoxy)propyl-l-oxy]-6-methylpyrimidine HC1, plus sulphadoxine, and of M&B 35769 plus dapsone, were examined and it was concluded that no universally ideal ratio of constituents in a combination is possible because the optimum ratio depends upon the activity of the constituents on their own and therefore varies from strain to strain. Activity was assessed on the 24th day after infecti

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39

Tassone, Giusy, Giacomo Landi, Pasquale Linciano, et al. "Evidence of Pyrimethamine and Cycloguanil Analogues as Dual Inhibitors of Trypanosoma brucei Pteridine Reductase and Dihydrofolate Reductase." Pharmaceuticals 14, no. 7 (2021): 636. http://dx.doi.org/10.3390/ph14070636.

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Trypanosoma and Leishmania parasites are the etiological agents of various threatening neglected tropical diseases (NTDs), including human African trypanosomiasis (HAT), Chagas disease, and various types of leishmaniasis. Recently, meaningful progresses in the treatment of HAT, due to Trypanosoma brucei (Tb), have been achieved by the introduction of fexinidazole and the combination therapy eflornithine–nifurtimox. Nevertheless, due to drug resistance issues and the exitance of animal reservoirs, the development of new NTD treatments is still required. For this purpose, we explored the combine

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40

Vanichtanankul, Jarunee, Supannee Taweechai, Chayasith Uttamapinant, et al. "Combined Spatial Limitation around Residues 16 and 108 of Plasmodium falciparum Dihydrofolate Reductase Explains Resistance to Cycloguanil." Antimicrobial Agents and Chemotherapy 56, no. 7 (2012): 3928–35. http://dx.doi.org/10.1128/aac.00301-12.

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ABSTRACTNatural mutations ofPlasmodium falciparumdihydrofolate reductase (PfDHFR) at A16V and S108T specifically confer resistance to cycloguanil (CYC) but not to pyrimethamine (PYR). In order to understand the nature of CYC resistance, the effects of various mutations at A16 on substrate and inhibitor binding were examined. Three series of mutations at A16 with or without the S108T/N mutation were generated. Only three mutants with small side chains at residue 16 (G, C, and S) were viable from bacterial complementation assay in the S108 series, whereas these three and an additional four mutan

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41

Inthajak, K., P. Toochinda, and L. Lawtrakul. "Application of molecular docking and PSO–SVR intelligent approaches in antimalarial activity prediction of enantiomeric cycloguanil analogues." SAR and QSAR in Environmental Research 29, no. 12 (2018): 957–74. http://dx.doi.org/10.1080/1062936x.2018.1536678.

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42

Lejeune, Delphine, Isabelle Souletie, Sandrine Houzé, et al. "Simultaneous determination of monodesethylchloroquine, chloroquine, cycloguanil and proguanil on dried blood spots by reverse-phase liquid chromatography." Journal of Pharmaceutical and Biomedical Analysis 43, no. 3 (2007): 1106–15. http://dx.doi.org/10.1016/j.jpba.2006.09.036.

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43

Basco, Leonardo K., Philippe Eldin de Pécoulas, Craig M. Wilson, Jacques Le Bras, and André Mazabraud. "Point mutations in the dihydrofolate reductase-thymidylate synthase gene and pyrimethamine and cycloguanil resistance in Plasmodium falciparum." Molecular and Biochemical Parasitology 69, no. 1 (1995): 135–38. http://dx.doi.org/10.1016/0166-6851(94)00207-4.

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44

Adane, Legesse, and Prasad V. Bharatam. "3D-QSAR analysis of cycloguanil derivatives as inhibitors of A16V+S108T mutant Plasmodium falciparum dihydrofolate reductase enzyme." Journal of Molecular Graphics and Modelling 28, no. 4 (2009): 357–67. http://dx.doi.org/10.1016/j.jmgm.2009.09.001.

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45

Nattee, Cholwich, Nirattaya Khamsemanan, Luckhana Lawtrakul, Pisanu Toochinda, and Supa Hannongbua. "A novel prediction approach for antimalarial activities of Trimethoprim, Pyrimethamine, and Cycloguanil analogues using extremely randomized trees." Journal of Molecular Graphics and Modelling 71 (January 2017): 13–27. http://dx.doi.org/10.1016/j.jmgm.2016.09.010.

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46

Yeo, A. E. T., K. K. Seymour, K. H. Rieckmann, and R. I. Christopherson. "Effects of folic and folinic acids on the activities of cycloguanil and WR99210 againstPlasmodium falciparumin erythrocytic culture." Annals of Tropical Medicine & Parasitology 91, no. 1 (1997): 17–23. http://dx.doi.org/10.1080/00034983.1997.11813107.

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47

Tonelli, Michele, Lieve Naesens, Sabrina Gazzarrini, et al. "Host dihydrofolate reductase (DHFR)-directed cycloguanil analogues endowed with activity against influenza virus and respiratory syncytial virus." European Journal of Medicinal Chemistry 135 (July 2017): 467–78. http://dx.doi.org/10.1016/j.ejmech.2017.04.070.

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48

Arfeen, Minhajul, Dhilon S. Patel, Sheenu Abbat, Nikhil Taxak, and Prasad V. Bharatam. "Importance of cytochromes in cyclization reactions: Quantum chemical study on a model reaction of proguanil to cycloguanil." Journal of Computational Chemistry 35, no. 28 (2014): 2047–55. http://dx.doi.org/10.1002/jcc.23719.

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49

Ang, H. H., K. L. Chan, and J. W. Mak. "Susceptibility Studies of Plasmodium falciparum Isolates and Clones against Cycloguanil and Pyrimethamine Using the Modified In vitro Microtechnique." Journal of Parasitology 82, no. 6 (1996): 1029. http://dx.doi.org/10.2307/3284218.

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50

Basco, L. K., O. Ramiliarisoa, and J. Le Bras. "In Vitro Activity of Pyrimethamine, Cycloguanil, and Other Antimalarial Drugs Against African Isolates and Clones of Plasmodium falciparum." American Journal of Tropical Medicine and Hygiene 50, no. 2 (1994): 193–99. http://dx.doi.org/10.4269/ajtmh.1994.50.193.

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