Abstract:
:Many aminodihydroquinoline compounds have been studied to determine their cytotoxicity to cancer cells. However, anti-cancer stem cells (CSCs) activity of aminodihydroquinoline has not been tested in spite that CSC is believed to do an important roles in chemotherapy resistance and recurrence. The CSC selective targeting activities of 10 recently synthesized 2-aminodihydroquinoline analogs were examined on CSCs and bulk culture of a glioblastoma cell line. A diethylaminopropyl substituted aminodihydroquinoline, 5h, showed a strong anti-CSC effect and general cytotoxicity. However, a benzyl substituted aminodihydroquinoline, 5i, displayed the most effective anti-CSC effect, with no or small significant cytotoxic effect in bulk culture conditions. While 5h temporarily enhanced CSC marker-positive cells and eventually suppressed the CSC population, which is similar to other cytotoxic anticancer reagents reported, 5i selectively eliminated CSC marker-positive cells based on fluorescence activated cell sorter (FACS) analysis. 5h also temporarily activated some genes associated with signaling required for CSC, while 5i selectively suppressed these genes supporting that the differential effects are resulted from different molecular responses. In addition, the selective CSC effect is also found against a colon cancer cell line. Collectively, we suggest that these two novel aminodihydroquinoline compounds possess novel anti-CSC effects in colon and brain tumor derived cell lines probably through independent pathways.
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Park H,Yu Y,Kim H,Lee E,Lee H,Jeon R,Kim WYdoi
10.1248/cpb.c16-00726subject
Has Abstractpub_date
2017-04-01 00:00:00pages
349-355issue
4eissn
0009-2363issn
1347-5223journal_volume
65pub_type
杂志文章abstract::Different crystal packing of hydrates from anhydrate crystals leads to different physical properties, such as solubility and stability. Investigation of the potential of varied hydrate formation, and understanding the stability in an anhydrous/hydrate system, are crucial to prevent an undesired transition during the m...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c15-00262
更新日期:2015-01-01 00:00:00
abstract::We have identified a novel cardiac steroid, 11,19-epoxy-19-methoxytelocinobufagin, named marinosin (1), in the skin of the toad, Bufo marinus (L.) Schneider. The treatment of compound 1 with 50% CH3CN containing 0.1% trifluoroacetic acid yielded a 11 alpha-hydroxyhellebrigenin (2), which has not previously been isolat...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.45.249
更新日期:1997-02-01 00:00:00
abstract::This study demonstrates the structure-activity relationship of Col-003, a potent collagen-heat-shock protein 47 (Hsp47) interaction inhibitor. Col-003 analogues were successfully synthesized by Pd(0)-catalyzed cross-coupling reactions of 5-bromosalicylaldehyde derivatives with alkyl-metal species, and the inhibitory a...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c19-00634
更新日期:2020-03-01 00:00:00
abstract::Cornusiin A (1), cornusiin B (2) and cornusiin C (3), new dimeric, monomeric and trimeric hydrolyzable tannins, were isolated from the fruits of Cornus officinalis (Cornaceae). Their structures, including the orientation of the valoneoyl group in 1 and 3, were established on the basis of chemical and spectroscopic dat...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.2083
更新日期:1989-08-01 00:00:00
abstract::A new neolignan, (7R,8R)-5-O-demethylbilagrewin (1), together with four known lignans (2-5), were isolated from the heartwood of Santalum album (Santalaceae). The structure of 1 was determined by analysis of extensive spectroscopic data. The isolated compounds and derivatives were evaluated for their cytotoxic activit...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.58.587
更新日期:2010-04-01 00:00:00
abstract::To investigate the possible mechanism of the stimulatory effect of a hot water extract from Artemisia leaf (Artemisia princeps PANPANINI) (AFE) on the proliferation of endothelial cells, cells from bovine aorta were cultured for 72 h in RPMI1640 medium supplemented with 10% fetal calf serum in the presence of 5 microg...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.38.2494
更新日期:1990-09-01 00:00:00
abstract::Oiling-out is a unique phenomenon that the liquid phase is separated into two parts during crystallization. The emergence of new liquid phase changes the environment where crystals nucleate and grow, we call "mother phase," because target material and impurities become distributed to each phase according to their own ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c19-01015
更新日期:2020-01-01 00:00:00
abstract::Effect of the basic property of reactants (tertiary amine catalysts, a substrate amine, and acid neutralizers) on catalytic dehydrocondensation between a carboxylic acid and an amine by using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) was studied. The reaction yield was affected by the acid-base equilibrium among re...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c13-00368
更新日期:2013-01-01 00:00:00
abstract::Chemical investigation of the seeds of Adonis aestivalis has led to the isolation of a new cardenolide (3β,5α,14β,17β-tetrahydroxycard-20,22-enolide) (1), two new glycosides (2, 3) of 1, and a new strophanthidin hexaglycoside (4), together with a known compound, strophanthidin 3-O-β-D-glucopyranoside (5). The structur...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c12-00489
更新日期:2012-01-01 00:00:00
abstract::This paper introduces a new delivery system for rapid and controlled drug release. Mixture of hydrophilic, (poly vinyl alcohol, PVA, and randomly methylated beta-cyclodextrin, RM beta-CD), and hydrophobic (poly D,L-lactide, PLA, and poly D,L-lactide-co-glycoside, PLGA) polymers were electrospun to make a multi-layered...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.58.143
更新日期:2010-02-01 00:00:00
abstract::The metabolism of 2,4-dinitrotoluene (2,4-DNT), 2,4-dinitrobenzyl alcohol (2,4-DNB), 2,4-dinitrobenzaldehyde (2,4-DNBAl), 2,6-DNT, 2,6-DNB and 2,6-DNBAl in the microsomal and cytosol fractions prepared from unfortified male Wistar and male Sprague-Dawley (S.D.) rat livers was investigated. Data obtained by high-perfor...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.1904
更新日期:1989-07-01 00:00:00
abstract::Conjugates of 2-aminooxyethyliminodiacetic acid with estrone, testosterone, epiandrosterone, 17-alpha-hydroxy-progesterone and progesterone were synthesized and their complexes with Tc-99m were successfully prepared in good yields, which indicated the agent to be promising for metal-labeling of biomolecules and relate...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.47.413
更新日期:1999-03-01 00:00:00
abstract::Allylamine (ALAM) film was plasma-polymerized on a flat glass (referred to as ALAM(GLA): GLA refers to a flat glass plate) for use as a solid phase in two-site immunoradiometric assay (two-site IRMA). Adsorption of F(ab')2 anti-human immunoglobulin G [formula: see text] to ALAM(GLA) was larger than adsorption on a pol...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.40.501
更新日期:1992-02-01 00:00:00
abstract::A series of joro spider toxins, novel polyamines sharing a common moiety of 2,4-dihydroxyphenylacetyl cadaverine, have been identified using various bioassays, such as inhibition of a glutamatergic transmission and insecticidal activity. In this paper, we tried to chemically find still unknown polyamine toxins in the ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.42.1864
更新日期:1994-09-01 00:00:00
abstract::Analytical studies were carried out, for the first time, to evaluate the use of N-bromosuccinimide (NBS) as an analytical reagent for the spectrophotometric determination of eleven therapeutically important fluoroquinolone antibiotics (FQA). The procedures involved the reaction of the FQA with NBS and subsequent measu...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.55.1551
更新日期:2007-11-01 00:00:00
abstract::Four new compounds 1-4 were obtained from an oxidative coupling reaction of (E)-isorhapontigenin using FeCl(3) as oxidant. Their structures and stereochemistry were determined on the basis of spectroscopic evidence [UV, IR, MS, (1)H-, (13)C-NMR, NOE and 2D NMR], and their possible formation mechanisms were also discus...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.238
更新日期:2004-02-01 00:00:00
abstract::Treatment composed of a gastric mucoadhesive antibiotic with slow release drug delivery is expected to be effective for the eradication of Helicobacter pylori (H. pylori). In this study, we evaluated the slow release property of the tetracycline-sucralfate acidic complex. Tetracycline was the antibiotic selected becau...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.1412
更新日期:2008-10-01 00:00:00
abstract::We used near infrared (NIR) spectroscopy to evaluate the degree of mixing of blended dry syrup (DS) products whose particle sizes are not specified in the Revised 16th Edition of the Japanese Pharmacopoeia, and also evaluated the degree of mixing when powder products or fine granule products were added to DS products....
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.60.624
更新日期:2012-01-01 00:00:00
abstract::Intramolecular [2+2] cycloaddition of γ,δ-unsaturated ketenes derived from hex-5-enoyl chloride derivatives gave bicyclo[2.1.1]hexan-5-ones with complete regioselectivity. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.60.548
更新日期:2012-01-01 00:00:00
abstract::Anti-tauro 1 beta-hydroxycholic acid antisera were prepared by immunizing rabbits with N-(1 beta,3 alpha, 7 alpha, 12 alpha-tetrahydroxy-5 beta-cholan-24-oyl)-2- aminopropionic acid-bovine serum albumin (BSA) conjugate. The antisera raised had high affinity (1.25-1.46 x 10(9) M-1) and specificity for conjugated 1 beta...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.40.1835
更新日期:1992-07-01 00:00:00
abstract::Three new cardiac glycosides named cheiranthoside VIII (1), cheiranthoside IX (2) and cheiranthoside X (3) were isolated from the seeds of Erysimum cheiranthoides. Based on spectroscopic data, the structures of 1-3 were characterized as strophanthidin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-antiaropyranoside, cheiran...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.50.861
更新日期:2002-06-01 00:00:00
abstract::Investigation of an acetone extract of the leaves and twigs of Taxus sumatrana has resulted in the isolation of two new bicyclic taxoids, tasumatrols M (1), and N (2) and a new baccatin III derivative, tasumatrol O (3) together with the previous known 7-deacetylcanadensene (4) and 2alpha,7beta,13alpha-triacetoxy-5alph...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.53.808
更新日期:2005-07-01 00:00:00
abstract::A series of [2-(omega-phenylalkyl)phenoxy]alkylamines was synthesized and their 5-hydroxytryptamine2 (5-HT2) and/or dopamine2 (D2) receptor antagonistic activities were examined in vitro. [2-(4-Phenylbutyl)phenoxy]alkylamines showed strong inhibition of both 5-HT2 and D2 receptors. In particular, [2-(4-Phenylbutyl)phe...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.46.639
更新日期:1998-04-01 00:00:00
abstract::The structural conversion of the prion protein (PrP) from the normal cellular isoform (PrP(C)) to the posttranslationally modified form (PrP(Sc)) is thought to relate to Cu²⁺ binding to histidine (H) residues. Traditionally, the binding of metals to PrP has been investigated by monitoring the conformational conversion...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.59.965
更新日期:2011-01-01 00:00:00
abstract::Novel nucleoside analogues of structure 3-5 were synthesized starting from (+/-)-cis-2-amino-3-cyclopentenylmethanol (1). The chlorine derivative 3 inhibited both HIV-1 and HIV-2 replication in MT-4 cells with IC(50) values of 10.67 microM and of 13.79 microM, respectively. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.54.1418
更新日期:2006-10-01 00:00:00
abstract::Chemical and pharmacological studies of Panax vietnamensis (Vietnamese ginseng; VG) have been reported since its discovery in 1973. However, the content of each saponin in different parts of VG has not been reported. In this study, 17 ginsenosides in the different underground parts of P. vietnamensis were analyzed by ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c15-00369
更新日期:2015-01-01 00:00:00
abstract::From the water-soluble portion of the methanolic extract of the fruit of anise (Pimpinella anisum L.), which has been used as a spice and medicine since antiquity, twelve new and five known glucosides of phenylpropanoids, including four stereoisomers of anethole glycol 2'-O-beta-D-glucopyranoside and four stereoisomer...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.50.1460
更新日期:2002-11-01 00:00:00
abstract::The synthesis and biological evaluation of [2-Valine-A] insulin ([Val2-A]insulin) is reported. In this insulin, the isoleucine residue in position A2, invariant in the majority of mammalian insulins, is substituted by valine. The same substitution, along with four others, occurs naturally in the insulin produced by th...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.670
更新日期:1989-03-01 00:00:00
abstract::Total synthetic studies on natural products with promising biological profiles, coupled with their intriguing structural features, are described. The target molecules dealt with in this article are five helianane-type sesquiterpenes (heliannuols A, D and K and heliespirones A and C) and three meroterpenes (breviones A...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章,评审
doi:10.1248/cpb.c13-00417
更新日期:2013-01-01 00:00:00
abstract::Bis[2-[(E)-2-octenoylamino]ethyl] disulfide (compd. I-3) inhibited collagen- and arachidonic acid-induced rat platelet aggregation, although not adenosine 5'-diphosphate (ADP)-induced rat platelet aggregation. Based on these results, we then investigated the inhibitory effect of compd. I-3 on thromboxane B2 formation ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.778
更新日期:1989-03-01 00:00:00