Enantioselective synthesis of dictyoceratin-A (smenospondiol) and -C, hypoxia-selective growth inhibitors from marine sponge

Sumii, Yuji; Kotoku, Naoyuki; Fukuda, Akinori; Kawachi, Takashi; Sumii, Yuta; Arai, Masayoshi; Kobayashi, Mariko

doi:10.1016/j.bmc.2015.01.021

Cited by 26 publications

(19 citation statements)

References 18 publications

(19 reference statements)

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“…58 In addition, localization of ZO-1 and ZO-2 has been observed to shift from plasma membrane to cell interior during in vitro hypoxia. 59 These results are in agreement with the data obtained in vivo in hypoxic-treated rats. 60 Recent studies also indicate that tricellulin, a tricellular tightening protein, is very sensitive to redox changes and undergoes rearrangement during hypoxia.…”

Section: Changes In Endothelial Monolayer Permeability and Tj Proteinsupporting

confidence: 90%

Stroke and Drug Delivery— In Vitro Models of the Ischemic Blood-Brain Barrier

Tornabene

Brodin

2016

Journal of Pharmaceutical Sciences

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Stroke is a major cause of death and disability worldwide. Both cerebral hypoperfusion and focal cerebral infarcts are caused by a reduction of blood flow to the brain, leading to stroke and subsequent brain damage. At present, only few medical treatments of stroke are available, with the Food and Drug Administration-approved tissue plasminogen activator for treatment of acute ischemic stroke being the most prominent example. A large number of potential drug candidates for treatment of ischemic brain tissue have been developed and subsequently failed in clinical trials. A deeper understanding of permeation pathways across the barrier in ischemic and postischemic brain endothelium is important for development of new medical treatments. The blood-brain barrier, that is, the endothelial monolayer lining the brain capillaries, changes properties during an ischemic event. In vitro models of the blood-brain barrier are useful tools to investigate the effects of induced ischemia under controlled conditions. In the present mini review, we aim to give a brief overview of the in vitro models of ischemia. Special focus is given to the expression of uptake and efflux transport pathways in the ischemic and postischemic endothelium. Finally, we will point toward future challenges within the field of in vitro models of brain ischemia.

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Section: Changes In Endothelial Monolayer Permeability and Tj Proteinsupporting

confidence: 90%

Stroke and Drug Delivery— In Vitro Models of the Ischemic Blood-Brain Barrier

Tornabene

Brodin

2016

Journal of Pharmaceutical Sciences

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“…772 and 773) were synthesised for the rst time. Meroterpenoids that had initial total syntheses are panicein A 2 , 774,775 dictyoceratins A 776 and C, [777][778][779] and neopetrosiquinones A and B. 780,781 The structure of siphondictyal B 782 has been revised to 1112, based upon total synthesis.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2017

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Covering: 2015. Previous review: Nat. Prod. Rep., 2016, 33, 382-431This review covers the literature published in 2015 for marine natural products (MNPs), with 1220 citations (792 for the period January to December 2015) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1340 in 429 papers for 2015), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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“…Enantioselective total synthesis of 1 and 2 yielded hundreds of milligrams of these compounds [ 9 ]. In order to verify the potential of these compounds as promising drug leads for cancer treatment, we examined their in vivo antitumor activity in mice subcutaneously inoculated with sarcoma S180 cells.…”

Section: Resultsmentioning

confidence: 99%

“…To obtain compounds in sufficient yields for further evaluation, we recently reported the enantioselective total synthesis of 1 and 2 , with confirmation of absolute stereochemistry [ 9 ]. Moreover, we found that unnatural enantiomers of 1 and 2 also showed similar hypoxia-selective growth inhibitory activity against DU145 cells.…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, we found that unnatural enantiomers of 1 and 2 also showed similar hypoxia-selective growth inhibitory activity against DU145 cells. It implies that the pharmacophore of these compounds is the para -hydroxybenzoyl ester moiety of the side chain and the chiral decalin moiety might not play a crucial role [ 9 ]. However, more precise structure-activity relationship (SAR) information is needed to develop promising anticancer drug leads based on these compounds.…”

Section: Introductionmentioning

confidence: 99%

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Structure-Activity Relationship and in Vivo Anti-Tumor Evaluations of Dictyoceratin-A and -C, Hypoxia-Selective Growth Inhibitors from Marine Sponge

et al. 2015

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Oral dictyoceratin-C (1) and A (2), hypoxia-selective growth inhibitors, showed potent in vivo antitumor effects in mice subcutaneously inoculated with sarcoma S180 cells. Structurally modified analogs were synthesized to assess the structure–activity relationship of the natural compounds 1 and 2 isolated from a marine sponge. Biological evaluation of these analogs showed that the exo-olefin and hydroxyl and methyl ester moieties were important for the hypoxia-selective growth inhibitory activities of 1 and 2. Thus far, only substitution of the methyl ester with propargyl amide in 1 was found to be effective for the synthesis of probe molecules for target identification.

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Enantioselective synthesis of dictyoceratin-A (smenospondiol) and -C, hypoxia-selective growth inhibitors from marine sponge

Cited by 26 publications

References 18 publications

Stroke and Drug Delivery— In Vitro Models of the Ischemic Blood-Brain Barrier

Stroke and Drug Delivery— In Vitro Models of the Ischemic Blood-Brain Barrier

Marine natural products

Structure-Activity Relationship and in Vivo Anti-Tumor Evaluations of Dictyoceratin-A and -C, Hypoxia-Selective Growth Inhibitors from Marine Sponge

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