10476-41-2Relevant articles and documents
Total syntheses of tambjamines C, E, F, G, H, i and J, BE-18591, and a related alkaloid from the marine bacterium pseudoalteromonas tunicata
Pinkerton, David M.,Banwell, Martin G.,Willis, Anthony C.
, p. 5127 - 5130 (2007)
The acetate salts of tambjamines C, E, and F (2-4, respectively), as well as those of the related alkaloids BE-18591 (5) and 6, have been prepared by treatment of bipyrrole aldehyde 16 with the relevant amine in the presence of acetic acid. The 5′-bromc-a
DNA binding by 4-methoxypyrrolic natural products. Preference for intercalation at AT sites by tambjamine E and prodigiosin
Melvin, Matt S.,Ferguson, David C.,Lindquist, Neils,Manderville, Richard A.
, p. 6861 - 6869 (1999)
The 4-methoxypyrrolic natural products contain a common 4-methoxy-2,2'- bipyrrole chromophore and exhibit promising anticancer, antimicrobial, and immunosuppressive activities. Herein, the ability of two representative members, tambjamine E (1) and prodigiosin (2), to bind calf thymus DNA (CT- DNA), polyd[G-C]2, and polyd[A-T]2 has been characterized using absorption and fluorescence spectroscopy. Scatchard plots showed that 1 occupies a site size (n) of ca. three base pairs and possesses affinity constants (K) ranging from 1 to 0.1 x 105 M-1. Prodigiosin (2) binds DNA by mixed modes, as isobestic points were not evident in titration experiments. The neutral aldehyde precursor 4 was found to possess no measurable DNA binding affinity, indicating that the enamine structure of 1 and the pyrromethene of 2 are essential elements for DNA binding affinity. The enamine of 1 was found to undergo hydrolysis to 4 with a half-life (t( 1/2 )) of 14.5 h at pH 7.4 and 37.5 °C. For the B-ring nitrogen atom of 1, a pK(a) value of 10.06 was also established. From fluorescence spectroscopy it was found that 1, 2, and 4 possess weak emission spectra in water that is increased in nonaqueous solvents. For 1 and 2, DNA binding also increased the emission yield. Energy- transfer measurements suggested an intercalative binding mode, with preference for AT sites. The ability of distamycin to displace 1 and 2 from the helix also suggested that they intercalate from the minor-groove. This specificity differs from other unfused aromatic cations that bind by a minor- groove mode at AT sequences and intercalate at GC sites. Reasons for the specificity displayed by 1 and 2, as well as the implications of our findings to their biological properties are discussed.
Defensive Metabolites from Three Nembrothid Nudibranchs
Carte, Brad,Faulkner, D. John
, p. 2314 - 2318 (1983)
The nembrothid nudibranchs Tambje abdere, T. eliora, and Roboastra tigris all contain Tambjamines A-D (4-7).The aldehydes 1-3, produced during extraction with methanol, were key compounds in the structural elucidation.The tambjamines were traced to a food source, the bryozoan Sessibugula translucens, and were implicated in the chemical defense mechanism of the Tambje species.
Total Synthesis and Antimalarial Activity of 2-(p-Hydroxybenzyl)-prodigiosins, Isoheptylprodigiosin, and Geometric Isomers of Tambjamine MYP1 Isolated from Marine Bacteria
Kancharla, Papireddy,Li, Yuexin,Yeluguri, Monish,Dodean, Rozalia A.,Reynolds, Kevin A.,Kelly, Jane X.
, p. 8739 - 8754 (2021)
Highly efficient and straightforward synthetic routes toward the first total synthesis of 2-(p-hydroxybenzyl)-prodigiosins (2-5), isoheptylprodigiosin (6), and geometric isomers of tambjamine MYP1 ((E/Z)-7) have been developed. The crucial steps involved in these synthetic routes are the construction of methoxy-bipyrrole-carboxaldehydes (MBCs) and a 20-membered macrocyclic core and a regioselective demethylation of MBC analogues. These new synthetic routes enabled us to generate several natural prodiginines24-27in larger quantity. All of the synthesized natural products exhibited potent asexual blood-stage antiplasmodial activity at low nanomolar concentrations against a panel ofPlasmodium falciparumparasites, with a great therapeutic index. Notably, prodiginines6and24-27provided curative in vivo efficacy against erythrocyticPlasmodium yoeliiat 25 mg/kg × 4 days via oral route in a murine model. No overt clinical toxicity or behavioral change was observed in any mice treated with prodiginines and tambjamines.
Novel imidazopyridine suppresses STAT3 activation by targeting SHP-1
Su, Jung-Chen,Wu, Szu-Hsien,Shiau, Chung-Wai,Chang, Chuan-Hsun
, p. 1248 - 1255 (2018/10/31)
The unregulated activation of STAT3 has been demonstrated to occur in many cancers and enhances tumour growth, migration, and invasion. Stimulation by cytokines, growth factors, and hormones triggers this activation by phosphorylating STAT3 at tyrosine 705. Novel imidazopyridine compounds were synthesized to evaluate the inhibition of STAT3 at Y705. Among the tested compounds, 16 reduced the level of phospho-STAT3, inhibited the downstream signalling cascade and subsequently attenuated the survival of hepatocellular carcinoma (HCC) cells. Further assays showed that the reduction effects of compound 16 on tyrosine 705 of STAT3 were attributed to up-regulation of protein tyrosine phosphatase SHP-1.
