Cycloguanil (Synonyms: Chlorguanide triazine)

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Cycloguanil (Chlorguanide triazine) is a dihydrofolate reductase (DHFR) inhibitor with an IC₅₀ of 10.8 μM against human DHFR. Cycloguanil blocks the folate metabolic pathway, thereby affecting nucleotide synthesis and interfering with DNA replication. Cycloguanil inhibits DHFR in Plasmodium and is thus used in malaria research. Cycloguanil also potently inhibits DHFR in human cancer cells and blocks the transcriptional activity of STAT3, thereby exhibiting anticancer activity.

At equivalent molar concentrations, both the salt and free forms of a compound exhibit comparable biological activity. Nevertheless, the salt form (Cycloguanil hydrochloride) usually boasts enhanced water solubility and stability.

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Cycloguanil Chemische Struktur

CAS. Nr. : 516-21-2

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Other In-stock Forms of Cycloguanil:

Cycloguanil hydrochloride

Other Forms of Cycloguanil:

3 Publications Citing Use of MCE Cycloguanil

Spezialitätsempfehlungen

•Related Small Molecules:

•Related Proteins:

Alle Parasite Isoform-spezifische Produkte anzeigen:

Alle Isoformen anzeigen

Amebae Coccidia Leishmania Mite Plasmodium Toxoplasma Trypanosoma Schistosome

Alle DNA/RNA Synthesis Isoform-spezifische Produkte anzeigen:

Alle Isoformen anzeigen

RNASE L DNA Polymerases RNA Polymerases Helicases DNA Ligase

Alle STAT Isoform-spezifische Produkte anzeigen:

Alle Isoformen anzeigen

STAT3 STAT5 STAT6 STAT1

Biologische Aktivität
Reinheit & Dokumentation
Verweise
Kundenbewertung

Beschreibung

IC₅₀ & Target

Plasmodium

Cellular Effect

Cell Line	Type	Value	Description	References
BC	IC₅₀	>50 μM Compound: Cycloguanil (C21)	In vitro cytotoxicity against Plasmodium falciparum infected BC cell line. In vitro cytotoxicity against Plasmodium falciparum infected BC cell line.	[PMID: 14736247]
HeLa	EC₅₀	>100 μM Compound: 1	Antiviral activity against coxsackie B4 virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis Antiviral activity against coxsackie B4 virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis	[PMID: 28477572]
HeLa	EC₅₀	>100 μM Compound: 1	Antiviral activity against vesicular stomatitis virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis Antiviral activity against vesicular stomatitis virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis	[PMID: 28477572]
HeLa	EC₅₀	0.55 μM Compound: 1	Antiviral activity against Respiratory syncytial virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis Antiviral activity against Respiratory syncytial virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis	[PMID: 28477572]
KB	IC₅₀	41 μM Compound: Cycloguanil (C21)	In vitro cytotoxicity against Plasmodium falciparum infected KB cell line In vitro cytotoxicity against Plasmodium falciparum infected KB cell line	[PMID: 14736247]
MDCK	CC₅₀	52 μM Compound: 1	Cytotoxicity against dog MDCK cells assessed as reduction in cell viability measured after 5 to 6 days by MTS assay Cytotoxicity against dog MDCK cells assessed as reduction in cell viability measured after 5 to 6 days by MTS assay	[PMID: 28477572]
Vero	EC₅₀	>100 μM Compound: 1	Antiviral activity against Coxsackie B4 virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis Antiviral activity against Coxsackie B4 virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis	[PMID: 28477572]
Vero	EC₅₀	>100 μM Compound: 1	Antiviral activity against para influenza 3 virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis Antiviral activity against para influenza 3 virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis	[PMID: 28477572]
Vero	EC₅₀	>100 μM Compound: 1	Antiviral activity against Punta Toro virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis Antiviral activity against Punta Toro virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis	[PMID: 28477572]
Vero	EC₅₀	>100 μM Compound: 1	Antiviral activity against Reovirus 1 infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis Antiviral activity against Reovirus 1 infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis	[PMID: 28477572]
Vero	EC₅₀	>100 μM Compound: 1	Antiviral activity against Sindbis virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis Antiviral activity against Sindbis virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis	[PMID: 28477572]
Vero	EC₅₀	>100 μM Compound: 1	Antiviral activity against Yellow fever virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis Antiviral activity against Yellow fever virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis	[PMID: 28477572]
Vero	IC₅₀	>50 μM Compound: Cycloguanil (C21)	In vitro cytotoxicity against Plasmodium falciparum infected vero cell line. In vitro cytotoxicity against Plasmodium falciparum infected vero cell line.	[PMID: 14736247]

In Vitro

Cycloguanil exhibits anticancer activity against the NCI-60 panel of human tumor cell lines, and shows selective activity toward the MDA-MB-468 and MCF-7 breast cancer cell lines^[2].
Cycloguanil (72 h) induces growth arrest in MDA-MB-468, MDA-MB-231 and MCF-7 breast cancer cells, with cell viability maintained at approximately 50% of that in the vehicle control group at high concentrations, and this effect cannot be reversed by folinic acid treatment^[2].
Cycloguanil (0.001-10 μM; 24 h) binds to DHFR in intact MDA-MB-468 breast cancer cells, resulting in a dose-dependent accumulation of DHFR protein after 24 hours of treatment^[2].
Cycloguanil (10 μM; 24 h) disrupts folate metabolism and nucleotide homeostasis in MDA-MB-231 breast cancer cells, and supplementation with Folinic acid (HY-17556) reverses the metabolite changes induced by it, a result consistent with DHFR inhibition^[2].
Cycloguanil (0.02-20 μM; 6 h) potently inhibits the transcriptional activity of STAT3 in U3A fibrosarcoma cells at concentrations as low as 0.02 μM, which is consistent with the downstream effects of DHFR inhibition^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molekulargewicht

251.72

Formel

C₁₁H₁₄ClN₅

CAS. Nr.

516-21-2

SMILES

NC1=NC(N)=NC(C)(C)N1C2=CC=C(Cl)C=C2

Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Please store the product under the recommended conditions in the Certificate of Analysis.

Reinheit & Dokumentation

Handling Instructions (2659 KB)

Verweise

[1]. Matthaei J, et al. OCT1 Deficiency Affects Hepatocellular Concentrations and Pharmacokinetics of Cycloguanil, the Active Metabolite of the Antimalarial Drug Proguanil. Clin Pharmacol Ther. 2019;105(1):190-200. [Content Brief]

[2]. Brown JI, et al. Cycloguanil and Analogues Potently Target DHFR in Cancer Cells to Elicit Anti-Cancer Activity. Metabolites. 2023;13(2):151. Published 2023 Jan 19. [Content Brief]

Cycloguanil Related Classifications

Molaritätsrechner
Verdünnungsrechner

Die Formel zur Berechnung von Molaritäten

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass		Concentration		Volume		Molecular Weight *
	=		×		×

The dilution calculator equation

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Diese Gleichung wird häufig abgekürzt als: C₁V₁ = C₂V₂

Concentration _(start)	×	Volume _(start)	=	Concentration _(final)	×	Volume _(final)
	×		=		×
C1		V1		C2		V2

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Cycloguanil (Synonyms: Chlorguanide triazine)

Other Forms of Cycloguanil:

Cycloguanil Related Antibodies

3 Publications Citing Use of MCE Cycloguanil

Spezialitätsempfehlungen

•Related Small Molecules:

•Related Proteins:

Alle Parasite Isoform-spezifische Produkte anzeigen:

Alle DNA/RNA Synthesis Isoform-spezifische Produkte anzeigen:

Alle STAT Isoform-spezifische Produkte anzeigen:

Biologische Aktivität

Reinheit & Dokumentation

Verweise

Kundenbewertung

Cycloguanil Related Antibodies

Cycloguanil Related Classifications

Molaritätsrechner

Verdünnungsrechner

Die Formel zur Berechnung von Molaritäten

The dilution calculator equation

Keywords:

Ihre kürzlich angesehenen Produkte:

Kundenbewertung

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