Formycin A
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| Category | Antibiotics |
| Catalog number | BBF-01846 |
| CAS | 6742-12-7 |
| Molecular Weight | 267.24 |
| Molecular Formula | C10H13N5O4 |
| Purity | ≥ 97% |
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Description
Formycin A is produced by the strain of Nocardia intriforma M4-C5. It has the activity of resistance to Salicornia, Pyricularia oryzae and Mole disease Phanerochaetehrysosporium of potato.
Specification
| Synonyms | (1S)-1-(7-amino-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-1,4-anhydro-D-ribitol; NSC 102811; BRN 0624229; 7-Amino-3-beta-D-ribofuranosyl-1H-pyrazolo(4,3-d)pyrimidine |
| Storage | Powder: -20°C: 3 years 4°C: 2 years In solvent: -80°C: 6 months -20°C: 1 month |
| IUPAC Name | (2S,3R,4S,5R)-2-(7-amino-2H-pyrazolo[4,3-d]pyrimidin-3-yl)-5-(hydroxymethyl)oxolane-3,4-diol |
| Canonical SMILES | C1=NC2=C(NN=C2C(=N1)N)C3C(C(C(O3)CO)O)O |
| InChI | InChI=1S/C10H13N5O4/c11-10-6-4(12-2-13-10)5(14-15-6)9-8(18)7(17)3(1-16)19-9/h2-3,7-9,16-18H,1H2,(H,14,15)(H2,11,12,13)/t3-,7-,8-,9+/m1/s1 |
| InChI Key | KBHMEHLJSZMEMI-KSYZLYKTSA-N |
Properties
| Appearance | White Crystalline |
| Application | Antineoplastic Agents |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 709.5°C at 760 mmHg |
| Melting Point | 141-142°C |
| Density | 1.771 g/cm3 |
| Solubility | In vitro: 10 mM in DMSO |
Reference Reading
1. Anti-influenza Virus Activity of Methylthio-Formycin Distinct From That of T-705
Naoki Takizawa, Hisashi Takada, Maya Umekita, Masayuki Igarashi, Yoshiaki Takahashi Front Microbiol. 2022 Feb 18;13:802671. doi: 10.3389/fmicb.2022.802671. eCollection 2022.
Seasonal influenza virus epidemics result in severe illness, and occasionally influenza pandemics cause significant morbidity and mortality, although vaccines and anti-influenza virus drugs are available. By screening an in-house library, we identified methylthio-formycin (SMeFM), an adenosine analog, as a potent inhibitor of influenza virus propagation. SMeFM inhibited the propagation of influenza A and B viruses (IC50: 34.1 and 37.9 nM, respectively) and viruses showing reduced susceptibility to baloxavir and neuraminidase inhibitors but not T-705 (Favipiravir). However, the combination of T-705 and SMeFM inhibited the propagation of the influenza virus not in an antagonistic but in a slightly synergistic manner, suggesting that SMeFM has targets distinct from that of T-705. SMeFM induced A-to-C transversion mutations in virus genome RNA, and SMeFM triphosphate did not inhibit in vitro viral RNA synthesis. Our results show that SMeFM inhibits the propagation of the influenza virus by a mechanism different from that of T-705 and is a potential drug candidate to develop for anti-influenza drug.
2. Synthesis and antiviral activity of formycin derivatives with anti-influenza virus activity
Hisashi Takada, Naoki Takizawa, Shouta Shibasaki, Hiroki Asaba, Masayuki Igarashi, Masakatsu Shibasaki, Yoshiaki Takahashi Bioorg Med Chem. 2022 Mar 1;57:116613. doi: 10.1016/j.bmc.2022.116613. Epub 2022 Jan 18.
In a screening using our unique natural product library, the C-nucleoside antibiotic formycin A, which exerts strong anti-influenza virus activity, was rediscovered. Aiming to develop a new type of anti-influenza virus drug, we synthesized new derivatives of formycin and evaluated its anti-influenza virus activity. Structural modifications were focused on the base moiety and sugar portion, respectively, and >40 novel formycin derivatives were synthesized. Modification of the C-7 position of the pyrazolopyrimidine ring strongly contributed to improve the activity. In particular, excellent anti-influenza virus activity was observed in the NHMe (10), SMe (12), and SeMe (15) derivatives, in which heteroatoms were introduced. In addition, in the modification of the sugar moiety, the presence of a hydroxyl group and its stereochemistry greatly affected both the expression and intensity of the activity. Furthermore, the evaluation results of the 7-SEt derivative (29) and the 2'-modified derivative (59) suggested that structural modifications may reduce cytotoxicity.
3. Comparative Investigation into Formycin A and Pyrazofurin A Biosynthesis Reveals Branch Pathways for the Construction of C-Nucleoside Scaffolds
Meng Zhang, Peichao Zhang, Gudan Xu, Wenting Zhou, Yaojie Gao, Rong Gong, You-Sheng Cai, Hengjiang Cong, Zixin Deng, Neil P J Price, Xiangzhao Mao, Wenqing Chen Appl Environ Microbiol. 2020 Jan 7;86(2):e01971-19. doi: 10.1128/AEM.01971-19. Print 2020 Jan 7.
Formycin A (FOR-A) and pyrazofurin A (PRF-A) are purine-related C-nucleoside antibiotics in which ribose and a pyrazole-derived base are linked by a C-glycosidic bond. However, the logic underlying the biosynthesis of these molecules has remained largely unexplored. Here, we report the discovery of the pathways for FOR-A and PRF-A biosynthesis from diverse actinobacteria and propose that their biosynthesis is likely initiated by a lysine N6-monooxygenase. Moreover, we show that forT and prfT (involved in FOR-A and PRF-A biosynthesis, respectively) mutants are correspondingly capable of accumulating the unexpected pyrazole-related intermediates 4-amino-3,5-dicarboxypyrazole and 3,5-dicarboxy-4-oxo-4,5-dihydropyrazole. We also decipher the enzymatic mechanism of ForT/PrfT for C-glycosidic bond formation in FOR-A/PRF-A biosynthesis. To our knowledge, ForT/PrfT represents an example of β-RFA-P (β-ribofuranosyl-aminobenzene 5'-phosphate) synthase-like enzymes governing C-nucleoside scaffold construction in natural product biosynthesis. These data establish a foundation for combinatorial biosynthesis of related purine nucleoside antibiotics and also open the way for target-directed genome mining of PRF-A/FOR-A-related antibiotics.IMPORTANCE FOR-A and PRF-A are C-nucleoside antibiotics known for their unusual chemical structures and remarkable biological activities. Deciphering the enzymatic mechanism for the construction of a C-nucleoside scaffold during FOR-A/PRF-A biosynthesis will not only expand the biochemical repertoire for novel enzymatic reactions but also permit target-oriented genome mining of FOR-A/PRF-A-related C-nucleoside antibiotics. Moreover, the availability of FOR-A/PRF-A biosynthetic gene clusters will pave the way for the rational generation of designer FOR-A/PRF-A derivatives with enhanced/selective bioactivity via synthetic biology strategies.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
