13877-76-4Relevant articles and documents
Identification and Characterization of Enzymes Catalyzing Pyrazolopyrimidine Formation in the Biosynthesis of Formycin A
Ko, Yeonjin,Wang, Shao-An,Ogasawara, Yasushi,Ruszczycky, Mark W.,Liu, Hung-Wen
, p. 1426 - 1429 (2017)
Genome scanning of Streptomyces kaniharaensis, the producer of formycin A, reveals two sets of purA, purB, purC, and purH genes. The Pur enzymes catalyze pyrimidine assembly of purine nucleobases. To test whether enzymes encoded by the second set of pur genes catalyze analogous transformations in formycin biosynthesis, formycin B 5′-phosphate was synthesized and shown to be converted by ForA and ForB to formycin A 5′-phosphate. These results support that For enzymes are responsible for formycin formation.
Nucleolipids of the Nucleoside Antibiotics Formycins A and B: Synthesis and Biomedical Characterization Particularly Using Glioblastoma Cells
Rosemeyer, Helmut,Knies, Christine,Hammerbacher, Katharina,Bender, Eugenia,Bonaterra, Gabriel A.,Hannen, Ricarda,Bartsch, J?rg W.,Nimsky, Christopher,Kinscherf, Ralf
, (2019/04/08)
Two lipophilic derivatives of formycin A (1) and formycin B (5) carrying an O-2′,3′-(ethyl levulinate) ketal group have been prepared. These were base-alkylated at N(1) (for 1) and N(1) and N(6) (for 5) with both isopentenyl and all-trans-farnesyl residues. Upon the prenylation, side reactions were observed, resulting in the formation of nucleolipids with a novel tricyclic nucleobase (→4a, 4b). In the case of formycin B, O-2′,3′-(ethyl levulinate) (6) farnesylation gave the double prenylated nucleolipid 7. All new compounds were characterized by 1H-, 13C-, UV/VIS and fluorescence spectroscopy, by ESI-MS spectrometry and/or by elemental analysis. Log P determinations between water and octanol as well as water and cyclohexane of a selection of compounds allowed qualitative conclusions concerning their potential blood-brain barrier passage efficiency. All compounds were investigated in vitro with respect to their cytotoxic activity toward rat malignant neuroectodermal BT4Ca as well as against a series of human glioblastoma cell lines (GOS 3, U-87 MG and GBM 2014/42). In order to differentiate between anticancer and side effects of the novel nucleolipids, we also studied their activity on PMA-differentiated human THP-1 macrophages. Here, we show that particularly the formycin A derivative 3b possesses promising antitumor properties in several cancer cell lines with profound cytotoxic effects partly on human glioblastoma cells, with a higher efficacy than the chemotherapeutic drug 5-fluorouridine.
Pyrazolopyrimidine Nucleosides. 9. Studies of the Isomeric N-Methylformycins
Lewis, Arthur F.,Townsend, Leroy B.
, p. 2817 - 2822 (2007/10/02)
The syntheses of 4-methylformycin (7) and 6-methylformycin (8) are described.Structural assignements if 7 and 8 were based on UV, 1H NMR, and 13C NMR data.N-7-Methylformycin (9) was resynthesized by an alternative route and comparisons of the physicochemical properties of all five of the mono-N-methylformycins are presented. 6-Methylformycin (8) was found to be unstable in aqueous solution yielding three products, formycin B (2), N-7-methylformycin (9), and 6-methylformycin B (10). 6-Methylformycin B (10), 4-methylformycin B (11), and 1-methylformycin B (12) were prepared by a reaction of nitrosyl chloride with 8, 7, and 1-methylformycin (3), respectively.
