Art. -Nr.: HY-124210

Formycin B

Formycin B is an orally active PNP and PARP inhibitor. Formycin B inhibits influenza A virus proliferation and the replication of intracellular Trypanosoma cruzi, Leishmania, and pathogenic trypanosomes by competitively inhibiting PNP (K_i = 68-100 μM) and PARP (quail K_i = 68.9-75.0 μM), and by inhibiting DNA, RNA, and protein synthesis and cell proliferation. Formycin B can be used for research on influenza, PNP deficiency, leukemia, Chagas disease, leishmaniasis, and trypanosomiasis.

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CAS. Nr.: 13877-76-4
Formel: C₁₀H₁₂N₄O₅
Molecular Weight:268.23

Speicherung:

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

Data Sheet (297 KB)

Formycin B Chemical Structure

CAS. Nr.: 13877-76-4

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

^[2]^[3]^[4]

PNP

68 μM (Ki, extracts of human T lymphocytes)

PNP

100 μM (Ki, extracts from dialyzed cells)

PARP

68.9 μM (Ki, chromatin-bound)

PARP

75.0 μM (Ki, soluble)

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Cellular Effect

Cell Line	Type	Value	Description	References
L5178Y	ED₅₀	16.0 μM	Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 72 hrs incubation by cell concentration and doubling count. Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 72 hrs incubation by cell concentration and doubling count.	172231
L5178Y	ED₅₀	31 μM	Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 24 hrs incubation by cell concentration and doubling count. Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 24 hrs incubation by cell concentration and doubling count.	172231
L5178Y	ED₅₀	21.6 μM	Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 72 hrs incubation in the presence of 0.75 μM NAD⁺ by cell concentration and doubling count. Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 72 hrs incubation in the presence of 0.75 μM NAD⁺ by cell concentration and doubling count.	172231
L5178Y	ED₅₀	23.8 μM	Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 72 hrs incubation in the presence of 1.51 μM NAD⁺ by cell concentration and doubling count. Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 72 hrs incubation in the presence of 1.51 μM NAD⁺ by cell concentration and doubling count.	172231
L5178Y	ED₅₀	33.1 μM	Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 72 hrs incubation in the presence of 4.52 μM NAD⁺ by cell concentration and doubling count. Antiproliferative activity against mouse L5178Y leukemia cells assessed as cell proliferation inhibition after 72 hrs incubation in the presence of 4.52 μM NAD⁺ by cell concentration and doubling count.	172231

In Vitro

Anti-cancerNucleotide MetabolismProtein/Amino Acid MetabolismParasitic InfectionInnate ImmunityViral InfectionOthers

Anti-cancer

Formycin B (16.0-31 μM; 24-72 h) inhibits the proliferation of L5178Y mouse leukemia cells, with an ED₅₀ value of 16.0 μM at 72 h and 31 μM at 24 h, exhibiting cytostatic effects at the ED₅₀ and cytotoxic effects above 2× ED₅₀^[4].

Anti-cancer

Nucleotide Metabolism

Formycin B (7.2-36 μM; 24 h) inhibits macromolecule synthesis in L5178Y mouse leukemia cells, reducing [³H]thymidine, [³H]uridine, and [³H]phenylalanine incorporation to 40%, 51%, and 25% of control at 36 μM^[4].

Anti-cancer

Nucleotide Metabolism

Protein/Amino Acid Metabolism

Formycin B (20-40 μM; 12 h) inhibits poly (ADP-Rib) synthesis in intact L5178Y mouse leukemia cells, reducing [¹⁴C]ribose incorporation into HCl extracts to 42% of control at 40 μM, and decreases histone H1 ADP-ribosylation^[4].

Nucleotide Metabolism

Formycin B (0.03 mM-1.0 μM; 10 min) inhibits human purine nucleoside phosphorylase (PNP) in dialyzed cell extracts with a K_i of 100 μM^[3].
Formycin B (40-200 μg/mL; 24 hr) does not significantly inhibit DNA or RNA synthesis and shows no obvious cytotoxicity in PRK cells^[8].

Parasitic Infection

Formycin B (0.2-60 μg/mL) inhibits the replication of epimastigotes of T. cruzi Y strain in brain heart infusion medium only at 60 μg/mL^[5].
Formycin B (0.1-10 μg/mL; 3-9 days) significantly inhibits the intracellular replication of T. cruzi Y strain amastigotes in normal mouse peritoneal macrophage monolayers at 0.1 μg/mL^[5].
Formycin B (0.1-10 μg/mL; 48 h) reduces intracellular amastigotes of the T. cruzi Y strain in L929 cells by 91% at 1 and 10 μg/mL^[5].
Formycin B (1-10 μg/mL; 2 h) pre-exposure slightly reduces subsequent intracellular replication of T. cruzi Y strain amastigotes in mouse peritoneal macrophages^[5].
Formycin B (2.5 mM) is phosphorylated to formycin B monophosphate by cell-free extracts of L. mexicana or L. donovani promastigotes at a rate of 0.75 mmol/h/mg protein when p-nitrophenyl phosphate serves as the phosphate donor^[6].
Formycin B (1-10 μM; 72 h) inhibits the proliferation of L. donovani and L. mexicana promastigotes, reducing L. donovani parasite counts to 14% or less of the control and L. mexicana to 16% or less^[6].
Formycin B (100 μM; 24 h) accumulates as formycin B monophosphate in intact L. mexicana promastigotes, reaching 2.76 μmol/mg protein, with no formycin A monophosphate detected^[6].

Parasitic Infection

Innate Immunity

Formycin B (1-10 μM; 72 h) reduces L. mexicana amastigote infection in J774G8 macrophages, decreasing parasite numbers to 0.48 × 10⁶ at 1 μM and to 0.09 × 10⁶ at 10 μM^[6].

Protein/Amino Acid Metabolism

Formycin B (2000 μM; days 6-7) inhibits DNA synthesis in PHA-stimulated human PBL by approximately 90%, but protein synthesis by only approximately 60%^[2].
Formycin B (500 μM; day 6; 24 h; combined with deoxycytidine 500 μM) does not have its inhibition of cell number or protein synthesis in PHA-stimulated human PBL blocked by deoxycytidine^[2].

Viral Infection

Formycin B (0.004-40 μg/mL; administered 24 hours before challenge, immediately after viral adsorption, or both) exhibits no activity against vaccinia, herpes simplex, and vesicular stomatitis viruses in PRK cells, with an MIC of > 40 μg/mL for each virus^[8].

Others

Formycin B (1000 μM or higher) competitively inhibits human T lymphocyte PNP in the extract, with a K_i of 68 μM when deoxyguanosine is used as the substrate^[2].
Formycin B (10-75 μM; day 0) inhibits DNA synthesis in PHA-stimulated human PBL, with 10 μM causing 90% inhibition and 75 μM or higher causing complete inhibition^[2].
Formycin B (10-75 μM; days 0-6) inhibits DNA synthesis in PHA-stimulated human PBL in a time-dependent manner; addition on day 6 shifts the dose-response curve by approximately 1 log unit, and 75 μM causes only 50% inhibition^[2].
Formycin B (500-2000 μM; 6 h on day 6) does not reduce the number of viable cells in PHA-stimulated human PBLs, but significantly inhibits DNA synthesis per viable cell^[2].
Formycin B (100-2000 μM; day 6; combined with deoxyguanosine 10-500 μM) shows no consistent synergistic effect with deoxyguanosine in inhibiting DNA synthesis in PHA-stimulated human PBL^[2].
Formycin B (10 min) competitively inhibits quail oviduct chromatin-bound and soluble poly (ADP-Rib) polymerase, with K_i values of 68.9 and 75.0 μM^[4].

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

Cell Proliferation Assay^[5]

Cell Line:

L929 cell monolayers infected with Trypanosoma cruzi Y strain amastigotes
Concentration:

0.1, 1, 10 μg/mL
Incubation Time:

48 h
Result:

Infected L929 cells treated with 0.1, 1, or 10 μg/mL formycin B had 27, 91, and 91% fewer intracellular amastigotes, respectively, than controls after 48 h of incubation.

In Vivo

Anti-cancerParasitic Infection

Anti-cancer

Formycin B (2.5-80 mg/kg; daily) does not inhibit L-1210 leukemia in mice^[1].

Parasitic Infection

Formycin B (5.9-11.8 mg/kg; intraperitoneal injection; once daily; for 19 days) completely protects mice infected with the Y strain from acute death and significantly reduces parasitemia, but does not achieve parasitological cure^[5].
Formycin B (11.8 mg/kg; intragastric oral administration; once daily; for 19 days) prevents death and reduces parasitemia in mice infected with the Tulahuen strain of T. cruzi^[5].
Formycin B (11.8 mg/kg; intraperitoneal injection; once daily; for 3 weeks) exhibits activity against multiple T. cruzi strains but fails to clear the infection^[5].
Formycin B (5.9-100 mg/kg; intraperitoneal injection; once daily; for 5-10 weeks) inhibits but does not eliminate T. cruzi in mice^[5].

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

Animal Model:

Swiss Webster (female, 18-22 g)^[5]
Dosage:

11.8 mg/kg
Administration:

p.o. by gavage; once daily; for 19 days
Result:

There were 0/7 deaths and 0 mortality.
Only rare organisms were detected on day 7.
Parasitemia was lower than in controls.

Animal Model:

Swiss Webster (female, 18-22 g)^[5]
Dosage:

11.8 mg/kg
Administration:

i.p.; once daily; for 3 weeks
Result:

Mice infected with MR, CL, or Tulahuen strains responded as did Y strain-infected mice.
Survivors were not cured, as hemocultures and subinoculations revealed organisms after administration completion.

Animal Model:

Swiss Webster (female, 18-22 g)^[5]
Dosage:

11.8 or 5.9 mg/kg (10⁵ inoculation; 10 weeks); 50 mg/kg (10³ inoculation; 9 weeks); 100 mg/kg (10³ inoculation; 5 weeks)
Administration:

i.p.; once daily; for 10 weeks, 9 weeks, or 5 weeks
Result:

After 10 weeks of administration with 11.8 or 5.9 mg/kg, serology and hemocultures were positive at completion.
After 10³ inoculum and 50 or 100 mg/kg for 9 or 5 weeks, circulating parasites were still present at completion by subinoculation.
No parasitological cure was achieved.

Related Protocols :

Chemical Information

CAS. Nr. 13877-76-4
Molecular Weight 268.23
Formel C₁₀H₁₂N₄O₅
SMILES

O[C@H]1[C@@H](O)[C@H](C2=NNC3=C2NC=NC3=O)O[C@@H]1CO
Structure Classification
- Antibiotics
Initial Source
- Microorganism
Nocardia interforma
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

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (297 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Ishizuka M, et al. Biological studies on formycin and formycin B. The Journal of Antibiotics. 1968 Jan 25;21(1):5-12.

[2]. Cowan MJ, et al. Effects of formycin B on human lymphocyte deoxyribonucleic acid synthesis: Optimization of cell culture conditions. Biochemical Pharmacology. 1981 Oct 1;30(19):2651-6.

[3]. Chern JW, et al. Nucleosides. 5. Synthesis of guanine and formycin B derivatives as potential inhibitors of purine nucleoside phosphorylase. Journal of medicinal chemistry. 1993 Apr;36(8):1024-31.

[4]. Müller WE, et al. Influence of formycin B on polyadenosine diphosphoribose synthesis in vitro and in vivo. Cancer research. 1975 Dec;35(12):3673-81.

[5]. McCabe RE, et al. In vitro and in vivo activities of formycin B against Trypanosoma cruzi. Antimicrobial agents and chemotherapy. 1985 Apr;27(4):491-4.

[6]. Carson DA, et al. Phosphorylation and anti-leishmanial activity of formycin B. Biochemical and Biophysical Research Communications. 1981 Jun 16;100(3):1377-83.

[7]. Hofflin JM, et al. Difluoromethylornithine and formycin B in toxoplasmosis. Journal of Infectious Diseases. 1985 Nov 1;152(5):1101-.

[8]. Giziewicz J, et al. Antiviral and antimetabolic activities of formycin and its N1-, N2-, 2′-O-and 3′-O-methylated derivatives. Biochemical Pharmacology. 1975 Oct 1;24(19):1813-7.

Calculators

Molaritätsrechner

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

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

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

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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Formycin B

Alle PARP Isoform-spezifische Produkte anzeigen

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