Efficient Total Synthesis of Bastadin 6, an anti‐Angiogenic Brominated Tyrosine‐Derived Metabolite from Marine Sponge.

Kotoku, Naoyuki; Tsujita, Hiroaki; Hiramatsu, Atsushi; Mori, Chinatsu; Koizumi, Noriko; Kobayashi, Mariko

doi:10.1002/chin.200546208

Cited by 5 publications

(8 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthesis of the simplified purpurealidin analogs was based on the amide coupling of purpurealidin E 4 or tyramine derivative 11 with aromatic carboxylic acids. Purpurealidin E 4 and 11 were synthesized in four steps from tyramine in an overall yield of 80% and 82%, respectively, improving the literature yields ( Fig 2 ) [ 4 , 13 , 14 ]. The synthetic route started with the bromination of tyramine.…”

Section: Resultsmentioning

confidence: 88%

Synthesis of novel purpurealidin analogs and evaluation of their effect on the cancer-relevant potassium channel KV10.1

et al. 2017

View full text Add to dashboard Cite

In the search for novel anticancer drugs, the potassium channel KV10.1 has emerged as an interesting cancer target. Here, we report a new group of KV10.1 inhibitors, namely the purpurealidin analogs. These alkaloids are produced by the Verongida sponges and are known for their wide variety of bioactivities. In this study, we describe the synthesis and characterization of 27 purpurealidin analogs. Structurally, bromine substituents at the central phenyl ring and a methoxy group at the distal phenyl ring seem to enhance the activity on KV10.1. The mechanism of action of the most potent analog 5 was investigated. A shift of the activation curve to more negative potentials and an apparent inactivation was observed. Since KV10.1 inhibitors can be interesting anticancer drug lead compounds, the effect of 5 was evaluated on cancerous and non-cancerous cell lines. Compound 5 showed to be cytotoxic and appeared to induce apoptosis in all the evaluated cell lines.

show abstract

Section: Resultsmentioning

confidence: 88%

Synthesis of novel purpurealidin analogs and evaluation of their effect on the cancer-relevant potassium channel KV10.1

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Guided by the fact that several naturally occurring bastadins are reported to exhibit anti-angiogenic effects [18,19,20,21], we evaluated if DBHB ( 8 ) also exhibits anti-angiogenic effects. Treatment of two human umbilical vein endothelial cell (HUVEC) lines, i.e.…”

Section: Resultsmentioning

confidence: 99%

“…Several reports have described the cytotoxic activity of various bastadins towards cancer cells [16,17], as well as their anti-angiogenic activity [18,19,20]. While their pro-apoptotic effects have been demonstrated in endothelial cells with respect to their cytotoxic activity [21], the mechanisms of action through which bastadins delay cancer cell growth have not yet been elucidated, to the best of our knowledge.…”

Section: Introductionmentioning

confidence: 99%

Cyclic versus Hemi-Bastadins. Pleiotropic Anti-Cancer Effects: from Apoptosis to Anti-Angiogenic and Anti-Migratory Effects

et al. 2013

View full text Add to dashboard Cite

Bastadins-6, -9 and -16 isolated from the marine sponge Ianthella basta displayed in vitro cytostatic and/or cytotoxic effects in six human and mouse cancer cell lines. The in vitro growth inhibitory effects of these bastadins were similar in cancer cell lines sensitive to pro-apoptotic stimuli versus cancer cell lines displaying various levels of resistance to pro-apoptotic stimuli. While about ten times less toxic than the natural cyclic bastadins, the synthetically derived 5,5'-dibromohemibastadin-1 (DBHB) displayed not only in vitro growth inhibitory activity in cancer cells but also anti-angiogenic properties. At a concentration of one tenth of its in vitro growth inhibitory concentration, DBHB displayed actual antimigratory effects in mouse B16F10 melanoma cells without any sign of cytotoxicity and/or growth inhibition. The serum concentration used in the cell culture media markedly influenced the DBHB-induced antimigratory effects in the B16F10 melanoma cell population. We are currently developing a specific inhalation formulation OPEN ACCESSMolecules 2013, 18 3544 for DBHB enabling this compound to avoid plasmatic albumin binding through its direct delivery to the lungs to combat primary as well as secondary (metastases) tumors.

show abstract

“…The convergent synthesis between oximic amide 2 and oxalamic amide 3 which is shown in Scheme 3 was achieved based on very simple and mild conditions. The obtained unsymmetrical disulfide 14 was then hydrolyzed by potassium hydroxide in THF-water mixture to give psammaplin F ( 1 ) [ 16 ]. By comparison of 1 H-NMR and 13 C-NMR data of synthetic and natural compounds as displayed in Table 1 , we were able to prove that the synthetically material was identical to natural psammaplin F ( 1 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue

et al. 2010

View full text Add to dashboard Cite

Psammaplin F, an unsymmetrical disulfide bromotyrosine, was isolated from the sponge Pseudoceratina purpurea in 2003. We reported here the first total synthesis of psammaplin F in 12% overall yield by employing Cleland’s reagent reduction as key step. The longest linear synthetic sequence starting from 3-bromo-4-hydroxybenzaldehyde and hydantoin was seven steps. In addition, a detailed X-ray crystal structure analysis of psammaplin A analogue 8b is given for the first time.

show abstract

Efficient Total Synthesis of Bastadin 6, an anti‐Angiogenic Brominated Tyrosine‐Derived Metabolite from Marine Sponge.

Cited by 5 publications

References 1 publication

Synthesis of novel purpurealidin analogs and evaluation of their effect on the cancer-relevant potassium channel KV10.1

Synthesis of novel purpurealidin analogs and evaluation of their effect on the cancer-relevant potassium channel KV10.1

Cyclic versus Hemi-Bastadins. Pleiotropic Anti-Cancer Effects: from Apoptosis to Anti-Angiogenic and Anti-Migratory Effects

Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue

Contact Info

Product

Resources

About