Corrigendum to “Involvement of sphingosine-1-phosphate and S1P1 in angiogenesis: Analyses using a new S1P1 antagonist of non-sphingosine-1-phosphate analog” [Biochem. Pharmacol. 77 (2009) 1011–1020]

Yonesu, Kiyoaki; Kawase, Yumi; Inoue, Tatsuya; Takagi, Nana; Tsuchida, Jun; Takuwa, Yoh; Kumakura, Seiichiro; Nara, Futoshi

doi:10.1016/j.bcp.2009.11.013

Cited by 9 publications

(15 citation statements)

References 55 publications

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“…26 For the receptor-binding assay, [ 33 P]Sph-1-P was enzymatically synthesized from sphingosine and [g-33 P]ATP using a recombinant murine sphingosine kinase. 27 Human S1P 1 -expressing cells 28 were seeded into 12-well plates (1Â10 6 cells per well) and cultured overnight. The next day, the plates were set on ice and the cells were washed thrice with 3 ml of an ice-cold assay buffer (a-Minimum Essential Medium containing 100 U ml À1 penicillin-G sodium, 100 mg ml À1 streptomycin sulfate, 1 mg ml À1 fatty acid-free bovine serum albumin, 15 mM NaF and 2 mM 4-deoxypyridoxine) and kept on ice for 10 min.…”

Section: Camp and Receptor-binding Assaymentioning

confidence: 99%

Ascotricins A and B, novel antagonists of sphingosine-1-phosphate receptor 1 from Ascotricha chartarum Berk. SANK 14186

et al. 2009

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Ascotricins A and B were isolated as novel sphingosine-1-phosphate receptor 1 (S1P 1 ) antagonists from a cultured broth of a fungus identified as Ascotricha chartarum Berk. SANK 14186. The two compounds were purified by solvent extraction, reversedphase (RP) column chromatography and a preparative RP-HPLC. The structures were determined by various NMR experiments and by LC/MS and GC/MS analyses. The S1P 1 antagonist activities were measured by a cyclic AMP assay using S1P 1 -expressing cells and the IC 50 values were 8.2 and 1.8 lM, respectively. In a [ 33 P]sphingosine-1-phosphate/S1P 1 -binding assay, those values were 120 and 39 lM, and in a migration assay using human umbilical vein endothelial cells (HUVECs), they were 94 and 28 lM, respectively. Thus, ascotricins A and B are novel S1P 1 antagonists showing an inhibition activity toward HUVEC migration. Keywords: Ascotricha chartarum; ascotricins A and B; HUVEC; S1P 1 antagonist; sphingosine-1-phosphate INTRODUCTION Sphingosine-1-phosphate (Sph-1-P) is an intermediate in the sphingomyelin degradation pathway 1 and is also a bioactive lipid messenger. Sph-1-P provokes a variety of cellular responses, including proliferation, prolongation of survival, cytoskeleton rearrangement, etc. 2,3 The first breakthrough in Sph-1-P research was finding its receptor, the endothelial differentiation gene-1/Sphingosine-1-phosphate receptor 1 (Edg-1/S1P 1 ) 4 . Sph-1-P promoted proliferation, migration and tube formation of vascular endothelial cells through S1P 1 , 5-7 and the phenotype of S1P 1 homozygous knockout mice strongly indicated that S1P 1 was indispensable for angiogenesis. 8,9 The second expansion of Sph-1-P research was re-finding S1P 1 as a pharmacological target of a new immunosuppressant, FTY720 (Fingolimod). 10,11 The active metabolite of FTY720 stimulated S1P 1 as do other synthetic S1P 1 agonists and caused lymphopenia and the resultant immunosuppression. 10-12 Currently, FTY720 is in an ongoing developmental stage in clinical trials as a novel immunosuppressant for multiple sclerosis.Although the current physiological research for Sph-1-P has shifted to S1P 1 agonists and to lymphopenia, the relationship of S1P 1 and angiogenesis has not yet been sufficiently studied. A few potent S1P 1 antagonists have been discovered, 13,14 but their capacity as angiogenesis inhibitors has not yet been examined. To obtain a functional S1P 1 antagonist, we searched for one in microorganisms because several microorganisms have sphingolipid synthesis systems, and microbial secondary metabolites are thought to be attractive sources of Sph-1-P analogs.

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Section: Camp and Receptor-binding Assaymentioning

confidence: 99%

Ascotricins A and B, novel antagonists of sphingosine-1-phosphate receptor 1 from Ascotricha chartarum Berk. SANK 14186

et al. 2009

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“…We evaluated the analogs using a well-established tube formation assay. 4,28,29) All experiments were performed 2-6 times. Ten days following the incubation of the fibroblasts and additives, HUVECs were stained using the Tubule Staining Kit for CD31.…”

Section: Resultsmentioning

confidence: 99%

“…7, we performed a proliferation assay because angiogenesis is intimately associated with complex cellular processes, including proliferation of endothelial cells, 4,28,29) which showed that compounds 2a-f promoted the proliferation of HUVECs at a higher concentration (e.g., 2a: 200 µM: 1.12±0.07, n=5, p=0.031), whereas 2f at a concentration of 10 µM only inhibited the proliferation of HUVECs (0.72±0.19, n=5, p=0.005).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Novel Carbocyclic Oxetanocin A (COA-Cl) Derivatives as Potential Tube Formation Agents

Sakakibara

Igarashi

Takata

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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Six novel carbocyclic oxetanocin A analogs (2-chloro-C.OXT-A; COA-Cl) with various hydroxymethylated or spiro-conjugated cyclobutane rings at the N 9 -position of the 2-chloropurine moiety were synthesized and evaluated using human umbilical vein endothelial cells. All prepared compounds (2a-f) showed good to moderate activity with angiogenic potency. Among these compounds, 100 µM cistrans-2′,3′-bis(hydroxymethyl)cyclobutyl derivative (2b), trans-3′-hydroxymethylcyclobutyl analog (2d), and 3′,3′-bis(hydroxymethyl)cyclobutyl derivative (2e) had greater angiogenic activity, with relative tube areas of 3.43±0.44, 3.32±0.53, and 3.59±0.83 (mean±standard deviation (S.D.)), respectively, which was comparable to COA-Cl (3.91±0.78). These data may be important for further development of this class of compounds as potential tube formation agents.

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“…[8][9][10][11] We previously reported that a S1P 1 antagonist, designated as chemical lead 2, showed anti-angiogenesis activity in a rabbit cornea model and inhibition of the swelling of mouse feet in an anti-type II collagen antibody-induced arthritis model. 12) Afterwards, we synthesized derivatives of chemical lead 2 to obtain more effective S1P 1 antagonists and determined the representatives, named as compounds 1 to 5. The aim of this study is to elucidate whether the derivatives inhibit the effect of Sph-1-P both in vitro and in vivo.…”

Section: )mentioning

confidence: 99%

“…[12][13][14] HUVEC were maintained with HuMedia-EG2 medium. CHO-S1P 1 cells were cultured with a-Minimum Essential Medium containing 10% (v/v) dialyzed fetal bovine serum (SAFC Biosciences, Lenexa, KS, U.S.A.), 100 units/ ml penicillin G sodium, 100 mg/ml streptomycin sulfate, and 125 nM methotrexate without ribonucleosides and deoxyribonucleosides.…”

Section: General Reagents and Animalsmentioning

confidence: 99%

A Novel Sphingosine-1-Phosphate Receptor 1 Antagonist Prevents the Proliferation and Relaxation of Vascular Endothelial Cells by Sphingosine-1-Phosphate

Yonesu

Nakamura

Mizuno

et al. 2010

Biological & Pharmaceutical Bulletin

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Sphingosine-1-phosphate (Sph-1-P) is a bioactive plasma lipid which affects cell proliferation and migration, etc., through 5 receptors: sphingosine-1-phosphate receptors 1 (S1P 1 ) to 5 (S1P 5 ).1) Among these receptors, S1P 1 is the most studied and attractive pharmacological target because the S1P 1 agonism provokes lymphopeina 2) and immunosuppression in vivo. Meanwhile, S1P 1 antagonism is supposed to inhibit angiogenesis. 3,4) In the case of agonist compounds, the non-selective Sph-1-P receptor agonist FTY720 (fingolimod, Novartis International AG, Basel, Switzerland) is pre-registered as a drug of multiple sclerosis. Additionally, the S1P 1 specific agonist R-3477 (Actelion Pharmaceuticals Ltd., Basel, Switzerland) is being evaluated in Phase II and I studies as an immunosuppressant for autoimmune disease and organ transplantation, respectively. In the case of antagonist compounds, a preclinical report showed that the small interfering RNA for S1P 1 inhibited tumor growth 5) ; nevertheless, there have been no clinical reports on a chemical compound for the treatment of angiogenic diseases, such as diabetic retinopathy and solid tumors. This is presumably because there are few S1P 1 antagonists that are potent and selective in vivo.Both S1P 1 and S1P 3 also play a role in cardiovascular regulation. The intravenous (i.v.) administration of Sph-1-P at high doses of 100-200 mg/kg caused bradycardia in anesthetized rats.6,7) Moreover, the heart rate of S1P 3 homozygous knockout mice was unchanged by Sph-1-P administration. 7)These results indicate that Sph-1-P caused bradycardia via S1P 3 in the heart, at least in the case of mice. On the other hand, i.v. administration of Sph-1-P at a low dose of 10 mg/kg provoked transient hypotension without affecting the heart rate in anesthetized rats.6) In this case, it is expected that Sph-1-P caused vasodilation on the vascular endothelial cells via S1P 1 and S1P 3 , followed by activation of the endothelial isoform of nitric oxide synthase and NO production. [8][9][10][11] We previously reported that a S1P 1 antagonist, designated as chemical lead 2, showed anti-angiogenesis activity in a rabbit cornea model and inhibition of the swelling of mouse feet in an anti-type II collagen antibody-induced arthritis model. 12) Afterwards, we synthesized derivatives of chemical lead 2 to obtain more effective S1P 1 antagonists and determined the representatives, named as compounds 1 to 5. The aim of this study is to elucidate whether the derivatives inhibit the effect of Sph-1-P both in vitro and in vivo. Therefore, here we describe the Sph-1-P antagonistic activity of the representative derivatives, compounds 1 to 5, through several in vitro and in vivo assays focusing on the proliferation, migration, tube formation, and relaxation of vascular endothelial cells. A sphingosine-1-phosphate receptor 1 (S1P 1 ) antagonist is expected to be an anti-angiogenic compound; however, there are few reports that demonstrated that a S1P 1 inhibitor improved the disease state in an angiogeni...

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Corrigendum to “Involvement of sphingosine-1-phosphate and S1P1 in angiogenesis: Analyses using a new S1P1 antagonist of non-sphingosine-1-phosphate analog” [Biochem. Pharmacol. 77 (2009) 1011–1020]

Cited by 9 publications

References 55 publications

Ascotricins A and B, novel antagonists of sphingosine-1-phosphate receptor 1 from Ascotricha chartarum Berk. SANK 14186

Ascotricins A and B, novel antagonists of sphingosine-1-phosphate receptor 1 from Ascotricha chartarum Berk. SANK 14186

Synthesis and Evaluation of Novel Carbocyclic Oxetanocin A (COA-Cl) Derivatives as Potential Tube Formation Agents

A Novel Sphingosine-1-Phosphate Receptor 1 Antagonist Prevents the Proliferation and Relaxation of Vascular Endothelial Cells by Sphingosine-1-Phosphate

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