SYNTHESIS OF PROCYANIDINS C2 AND C1 USING LEWIS ACID MEDIATED EQUIMOLAR CONDENSATION

Synthesis of procyanidins C2 and C1 was achieved via a stereoselective intermolecular condensation of equimolar amount of dimeric catechin or epicatechin nucleophile and monomeric catechin or epicatechin electrophile using Lewis acid. In the case of synthesis of procyanidin C2, AgBF4 and AgOTf afforded condensed product in excellent yield. As to the synthesis of procyanidin C1, Yb(OTf)(3) was effective for equimolar condensation.ArticleHETEROCYCLES. 85(9):2241-2250 (2012)journal articl

Characteristics of Advanced Colorectal Cancer Detected by Fecal Immunochemical Test Screening in Participants with a Negative Result the Previous Year

Background: There is sufficient evidence to show the mortality reduction effect of colorectal cancer (CRC) screening programs using the fecal occult blood test (FOBT). However, we see cases that are found to be advanced CRC despite yearly FOBT screening. Methods: The aim of this study was to investigate the characteristics of advanced CRC detected by a fecal immunochemical test (FIT) screening program in participants with a negative screening result the previous year, which we call “Negative advanced CRC”. A total of 109,639 participants (10.0% required colonoscopy, of whom 76.9% received one) underwent a CRC screening program using a FIT from fiscal 2009 to 2017. Negative advanced CRC was compared with advanced CRC (First advanced CRC) found at the first visit in a person who had not had a FIT screening history for more than 3 years. In addition, we compared the characteristics of Negative advanced CRC with those of interval cancer: cancer cases detected after a negative screening result and before the date of the next recommended screening. Results: A total of 339 cases of CRC (175 male: 164 female, 173 early stage: 166 advanced stage) were detected in the nine-year CRC screening period. The rate of right-sided CRCs was significantly higher in female (P < 0.01), advanced stage (P < 0.01), negative result previous year (P < 0.01), and symptom-negative (P < 0.01) participants than in each counterpart, respectively. The ratio of female (22/35; 62.9%) patients in Negative advanced CRCs tended to be high compared with that (40/83; 48.2%) in First advanced CRCs (P = 0.145). Overall, 22 (62.9%) of 35 Negative advanced CRCs and 28 (33.7%) of 83 First advanced CRCs were located in the right-sided colon, and the rate was significantly higher in Negative advanced CRCs (P < 0.01). In addition, the frequency of female patients was significantly higher in right-sided Negative advanced CRCs than in right-sided First advanced CRCs (P = 0.03). Conclusion: The characteristics of Negative advanced CRC cases (female and right-sided colon) were similar to those of interval cancer reported so far. In the future, it will be necessary to introduce a screening program that is highly sensitive to right-sided CRC

Genome-wide association study of individual differences of human lymphocyte profiles using large-scale cytometry data

Human immune systems are very complex, and the basis for individual differences in immune phenotypes is largely unclear. One reason is that the phenotype of the immune system is so complex that it is very difficult to describe its features and quantify differences between samples. To identify the genetic factors that cause individual differences in whole lymphocyte profiles and their changes after vaccination without having to rely on biological assumptions, we performed a genome-wide association study (GWAS), using cytometry data. Here, we applied computational analysis to the cytometry data of 301 people before receiving an influenza vaccine, and 1, 7, and 90 days after the vaccination to extract the feature statistics of the lymphocyte profiles in a nonparametric and data-driven manner. We analyzed two types of cytometry data: measurements of six markers for B cell classification and seven markers for T cell classification. The coordinate values calculated by this method can be treated as feature statistics of the lymphocyte profile. Next, we examined the genetic basis of individual differences in human immune phenotypes with a GWAS for the feature statistics, and we newly identified seven significant and 36 suggestive single-nucleotide polymorphisms associated with the individual differences in lymphocyte profiles and their change after vaccination. This study provides a new workflow for performing combined analyses of cytometry data and other types of genomics data

Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation

Total synthesis of prodelphinidin B3 and C2 have been accomplished. The key step is Lewis acid-mediated equimolar condensations between a catechin and/or gallocatechin nucleophile and a gallocatechin electrophile. The antitumor effects of synthetic prodelphidin B3 and C2 against PC-3 prostate cancer cell lines have been investigated. Both compounds showed significant antitumor effects. Their activity was almost the same as that of EGCG, a known antitumor agent.ArticleTETRAHEDRON. 69(17):3543-3550 (2013)journal articl

Synthesis of Arecatannin A1 from Dimeric Epicatechin Electrophile

Synthesis of arrecatarmin A1 (1) was accomplished from dimeric epicatechin electrophile, which was prepared by Zn(OTf)(2) mediated self-condensation, and monomeric catechin nucleophile. The condensation was successfully worked using Yb(OTf)(3) as a Lewis acid in good yield.ArticleNATURAL PRODUCT COMMUNICATIONS. 10(6):959-962 (2015)journal articl

Syntheses of prodelphinidin B1, B2, and B4 and their antitumor activities against human PC-3 prostate cancer cell lines

Total synthesis of prodelphinidin B1, B2, and B4 has been accomplished. The key step is Lewis acid-mediated equimolar condensations between an epigallocatechin and/or a gallocatechin nucleophile and an epigallocatechin and/or a gallocatechin electrophile. The antitumor effects of synthetic prodelphinidin B1-B4 against human PC-3 prostate cancer cell lines have been investigated. These compounds showed significant antitumor effects. Their activity seemed to be little bit stronger than EGCG and prodelphinidin B3, known antitumor agent.ArticleTETRAHEDRON LETTERS. 54(52):7188-7192 (2013)journal articl

Polymer-Coated Carbon Nanotubes as a Molecular Heater Platform for Hyperthermic Therapy

福岡歯科大学2017年

Salvage Photodynamic Therapy Using Talaporfin Sodium for Local Failure of Esophageal Squamous Cell Carcinoma

[Background] Talaporfin sodium photodynamic therapy (TS-PDT) for local failure after chemoradiotherapy (CRT) in patients with esophageal squamous cell carcinoma has recently been reported to be highly effective and less invasive, compared to other treatment modalities. TS-PDT was recently introduced at the Tottori University Hospital, Japan. The aim of this study is to clarify the efficacy and safety of PDT in our hospital. [Methods] This was a single-center observational study. We examined eight cases of TS-PDT performed between January 2016 and December 2019. The main endpoints were local complete remission (L-CR) rate and the adverse events. In addition, age, gender, histology, tumor location, TNM stage, tumor depth, irradiation dose, and overall survival (OS) were examined. [Results] The patients included 7 men and a woman, with an average age of 72.1 years (range 63–82 years). The baseline clinical stages before CRT or radiotherapy were stage I in 1, stage II in 3, stage III in 3, and stage IVA in 1 patient. The T stage on endoscopic assessment before TS-PDT was T1 in 6 patients and T2 in 2 patients. Treatment outcomes and adverse events were evaluated. There were no treatment-related deaths, and no significant adverse events occurred intraoperatively or postoperatively. The L-CR rate was 7/8 (87.5%); T1 cases had 100% (6/6) L-CR, while T2 cases had 50% (1/2). The 2-year OS rates were 87%. [Conclusion] TS-PDT was observed to be safe and effective in the first eight cases of its application following its introduction in our hospital

Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)(3) and their antitumor activities

Synthesis of procyanidin B2 and B3 gallate derivatives, 3-O-gallate, 3 ''-O-gallate, and 3,3 ''-di-O-gallate, were synthesized using equimolar condensation mediated by Yb(OTf)(3). Synthesized compounds showed significant antitumor effects against human prostate PC-3 cell lines. Their activities were weaker than well-known EGCG and prodelphinidin B3.ArticleBIOORGANIC & MEDICINAL CHEMISTRY LETTERS. 23(17):4935-4939 (2013)journal articl