Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines
234 derivatives of 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenones were synthesized and tested for antitumor activity in vitro against human cancer cell lines in NCI (National Cancer Institute, USA) bioassay. It was shown high cytostatic and cytotoxic activity for the tested compounds 1-8 (GI...
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Prykhod'ko, A.O. Dubinina, G.G. Khilya, V.P. Yarmoluk, S.M. 2019-06-19T17:56:32Z 2019-06-19T17:56:32Z 2004 Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines / A.O. Prykhod'ko, G.G. Dubinina, V.P. Khilya, S.M. Yarmoluk// Біополімери і клітина. — 2004. — Т. 20, № 1-2. — С. 159-163. — Бібліогр.: 24 назв. — англ. 0233-7657 DOI:http://dx.doi.org/10.7124/bc.0006A3 https://nasplib.isofts.kiev.ua/handle/123456789/157205 547.745:576.385.5 234 derivatives of 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenones were synthesized and tested for antitumor activity in vitro against human cancer cell lines in NCI (National Cancer Institute, USA) bioassay. It was shown high cytostatic and cytotoxic activity for the tested compounds 1-8 (GI50 3.44-41.1 mM and LC50 from 49.6 mM). The relationship between structures of the tested compounds and their antiproliferative activities is discussed. Синтезовано 234 похідних 7-гідрокси-3-арилокси-2-трифторметил-4Н-4-хроменону та досліджено їхню протиракову активність на лініях ракових клітин людини у Національному Інституті Раку (США). Сполуки 1–8 виявили високу цитостатичну та цитотоксичну активність (GI50 3,44–41,1 мкМ та LC50 від 49,6 мкМ). Обговорюється взаємозв'язок між структурою тестованих сполук та їхньою проліферативною активністю. Синтезированы 234 производных 7-гидрокси-З-арилокси-2-mpu-фторметил-4Н-4-хроменона и исследована их противораковая активность на линиях раковых клеток человека в Национальном Институте Рака (США). Соединения 1—8 проявили высокую цитостатическую и цитотоксическую активность (Gl50 3,44—41,1 мкМ и LC50 от 49,6 мкМ). Обсуждается взаимосвязь между структурой тестированных соединений и их пролиферативной активностью. We are grateful to the National Cancer Institute of the USA for generous support of our programs. uk Інститут молекулярної біології і генетики НАН України Біополімери і клітина Ювілеї Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines Антипроліферативна активність деяких похідних 7-гідрокси-З- арилокси-2-трифторметил-4Н-4-хроменону проти 60 ліній клітин раку людини Антипролиферативная активность некоторых производных 7- гидрокси-3-арилокси-2-трифторметил-4Н-4-хроменона против 60 линий раковых клеток человека Article published earlier |
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Digital Library of Periodicals of National Academy of Sciences of Ukraine |
| collection |
DSpace DC |
| title |
Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines |
| spellingShingle |
Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines Prykhod'ko, A.O. Dubinina, G.G. Khilya, V.P. Yarmoluk, S.M. Ювілеї |
| title_short |
Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines |
| title_full |
Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines |
| title_fullStr |
Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines |
| title_full_unstemmed |
Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines |
| title_sort |
antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4h-4-chromenone derivatives against 60 human cancer cell lines |
| author |
Prykhod'ko, A.O. Dubinina, G.G. Khilya, V.P. Yarmoluk, S.M. |
| author_facet |
Prykhod'ko, A.O. Dubinina, G.G. Khilya, V.P. Yarmoluk, S.M. |
| topic |
Ювілеї |
| topic_facet |
Ювілеї |
| publishDate |
2004 |
| language |
Ukrainian |
| container_title |
Біополімери і клітина |
| publisher |
Інститут молекулярної біології і генетики НАН України |
| format |
Article |
| title_alt |
Антипроліферативна активність деяких похідних 7-гідрокси-З- арилокси-2-трифторметил-4Н-4-хроменону проти 60 ліній клітин раку людини Антипролиферативная активность некоторых производных 7- гидрокси-3-арилокси-2-трифторметил-4Н-4-хроменона против 60 линий раковых клеток человека |
| description |
234 derivatives of 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenones were synthesized and tested for antitumor activity in vitro against human cancer cell lines in NCI (National Cancer Institute, USA) bioassay. It was shown high cytostatic and cytotoxic activity for the tested compounds 1-8 (GI50 3.44-41.1 mM and LC50 from 49.6 mM). The relationship between structures of the tested compounds and their antiproliferative activities is discussed.
Синтезовано 234 похідних 7-гідрокси-3-арилокси-2-трифторметил-4Н-4-хроменону та досліджено їхню протиракову активність на лініях ракових клітин людини у Національному Інституті Раку (США). Сполуки 1–8 виявили високу цитостатичну та цитотоксичну активність (GI50 3,44–41,1 мкМ та LC50 від 49,6 мкМ). Обговорюється взаємозв'язок між структурою тестованих сполук та їхньою проліферативною активністю.
Синтезированы 234 производных 7-гидрокси-З-арилокси-2-mpu-фторметил-4Н-4-хроменона и исследована их противораковая активность на линиях раковых клеток человека в Национальном Институте Рака (США). Соединения 1—8 проявили высокую цитостатическую и цитотоксическую активность (Gl50 3,44—41,1 мкМ и LC50 от 49,6 мкМ). Обсуждается взаимосвязь между структурой тестированных соединений и их пролиферативной активностью.
|
| issn |
0233-7657 |
| url |
https://nasplib.isofts.kiev.ua/handle/123456789/157205 |
| citation_txt |
Antiproliferative activities of some 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives against 60 human cancer cell lines / A.O. Prykhod'ko, G.G. Dubinina, V.P. Khilya, S.M. Yarmoluk// Біополімери і клітина. — 2004. — Т. 20, № 1-2. — С. 159-163. — Бібліогр.: 24 назв. — англ. |
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ISSN 0233-7657. Біополімери і клітина. 2004. Т. 20. № 1-2
Antiproliferative activities of some 7-hydroxy-3-
aryloxy-2-trifluoromethyl-4H-4-chromenone
derivatives against 60 human cancer cell lines
A. O. Prykhod'ko, G. G. Dubinina, V. P. Khilya1, S. M. Yarmoluk
Institute of Molecular Biology and Genetics, National Academy of Sciences of Ukraine
150 Acad. Zabolotnoho str., Kyiv, 03143, Ukraine
Kyiv National Taras Shevchenko University
64 Volodymyrska str., Kyiv, 01033, Ukraine
234 derivatives of 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenones were synthesized and tested
for antitumor activity in vitro against human cancer cell lines in NCI (National Cancer Institute, LISA)
bioassay. It was shown high cytostatic and cytotoxic activity for the tested compounds I—8 (GIso
3.44—41.1 fiM and LCso from 49.6 цМ). The relationship between structures of the tested compounds and
their antiproliferative activities is discussed.
Introduction. Isoflavonoids are a large group of na
turally occuring phenolic compounds ubiquitously dis
tributed in the plant kingdom. The biological activity
of isoflavonoids is related to their antioxidative effects
[1—3] and influences tumor cell proliferation, dif
ferentiation and apoptosis [4—8 ]. Antiproliferative
activities of isoflavonoids include inhibition of protein
tyrosine kinase [9—12], DNA topoisomerase I and II
[13, 14], protein kinase С and phosphoinositol kinase
[15—17], casein kinase II [18]. Inhibition of cyclin-
dependent kinases has been also described [19]. The
synthetic flavonoid flavopiridol (phase I clinical and
pharmacokinetic trial) has been shown to be a potent
inhibitor of cdc2 kinase activity (fig. 1) [20, 21 ].
During last years we were interested in the
synthesis of isoflavonoids aimed at finding compounds
with biological activity [22, 23]. The present paper
deals with the synthesis of a combinatorial series of
7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chro-
menone derivatives as potential antitumor agents.
Materials and Methods. Chemical synthesis of
the library of 234 chromenone derivatives was per-
© A. O. P R Y K H O D ' K O , G. G. DUBININA, V. P. KHILYA,
S. M. YARMOLUK, 2 0 0 4
formed by modification of the methods reported
before [22—24]. Structure and purity of synthesized
compounds were confirmed by 'H NMR spectroscopy.
The spectra were obtained with Varian VXR-300
NMR spectrometer at 300 MHz.
The synthesized compounds were tested for cyto
toxic and antitumor activity in vitro in collaboration
with National Cancer Institute of the U.S.A.
(http://dtp.nci.nih.gov/index.html). The calculated
measurement of effect was Percentage Growth (PG).
The effect of the compound on a cell line was
calculated according to the following two expressions:
If (Mean OD t e s l - Mean OD l z e r o) > 0, then
PG - 100- (Mean OD t e s t - Mean O D ^ / M e a n
OD c l r ,-Mean СЮ1гего);
If (Mean OD l e s t - Mean OD l z e r o) < 0, then
PG = 100- (Mean OD t e s, - Mean OD t z e r o)/Mean
where Mean OD t z e r o , Mean OD l e s l and Mean ODctr, are
the averages of optical density measurements of
SRB-derived color just before cells exposure to the
tested compounds, after 48 hours of exposure, and
after 48 hours without any exposure of cells to the
159
http://dtp.nci.nih.gov/index.html
PRYKHOD'KO А. О. ET AL.
ОН о
Fig. 1. Structure of flavopiridol (FLAP or NSC 649890)
stage the pre-screening of all 234 compounds was
carried out against 3 human cancer cell lines, MCF7
(Breast cancer), NCI-H460 (Non-small cancer cell
lung) and SF-268 (CNS), at 10"4 M concentration.
Compounds 1—8 (fig. 2) demonstrated antiproli
ferative activity (PG < 32 %) and were selected for
the advanced testing against 60 human cancer cell
lines at five different concentrations (10 - 8—10 4 M).
Experimental data for compounds 1—8 in repre
sentative cell lines are shown in tables 1, 2. Tested
compounds 1—8 were found to inhibit proliferation of
tumor cells in the range of GI 5 0 3.44—41.1 /иМ, and
exhibited cytotoxic activity against cancer cell lines
(LC 5 0 from 49.6 fiM). A number of cell lines including
RPMI-8226 Leukemia, SK-MEL-5 Melanoma, T-47D
Breast cancer and HCT-116 Colon cancer showed
significant sensitivity to these compounds.
234 tested compounds containes various sub-
stituents at C-3, C-7 and C-8 positions. Active
Fig. 2. Structures of cytotoxic
antitumor 7-hydroxy-3-aryl-
oxy-2-trifluoromethyl-4H-4-
chromenone derivatives 1—8
selected after pre-screening
tested compounds, respectively. The response para- compounds 2-8 containes bulky hydrophobic sub-
meters GI 5 0, TGI, LC 5 0 are interpolated values repre- stituent (2'-naphthyloxy or 4'-phenylphenoxy) at C-3
senting the concentrations at which PG is +50,0 and position and hydrophilic substituents, dialkylami-
-50, respectively. nomethyl at C-8 or O-acyl at C-7 positions. The
Results and Discussion. The combinatorial lib- presence of phenyl residue at C-3 position either
rary of 234 derivatives of 7-hydroxy-3-aryloxy-2- substituted or non-substituted, resulted in the loss of
trifluoromethyl-4H-4-chromenone was synthesized antiproliferative activity. The presence of chlorine
and tested for antitumor activity in vitro against a t o m a t t h e orffto-position in structure 1 is critical for
human cancer cell lines in NCI bioassay. At the first t h e biological activity, as meta- or para-substitution
160
ACTIVITIES OF C H R O M E N O N E D E R I V A T I V E S AGAINST CANCER CELL
Table I
Antiproliferative activities (GI50 and TGI) of 7-hydroxy-3-aryloxy-2-trifluoromethyl-4H-4-chromenone derivatives 1—8 against selected
human cancer cell lines
*ND — not determined.
leads to significant decrease of antiproliferative acti
vity. At the same time, the activity of 2',4'-dichloro
derivative was only slightly lower. Introduction of
some alkylaminomethyl groups into C-8 position of
structure 1 also resulted in the activity decrease.
Activities of compounds 2, containing trifluoromethyl
group, and 3 were close. Analogs of structure 1,
compounds 4—8 without CF3-group at C-2 position
showed decreased activities. Substitution of 2-naph-
thyloxy moiety at C-3 position of compounds 4—8 for
4'-phenylphenoxy group decreased the activity. Com
pound 8 demonstrated significant inhibition of many
161
P R Y K H O D ' K O А. О. E T AL.
Table 2
Cytotoxic activity of 7-hydroxy-3-phenoxy-2-trifluoromethyl-4H-4-chromenone derivatives 1—8 toward selected human cancer cell lines
*ND — not determined.
cell lines. Further studies will be performed on the
optimization of the active structures 1—8 found in the
present data set.
Supporting Information Available: Pre-screening
data for 234 tested compounds and ! H NMR spectra
for compounds 1—8. This material is available free of
charge via the Internet at www.yarmoluk.org.ua.
Acknowledgement. We are grateful to the Na
tional Cancer Institute of the USA for generous
support of our programs.
А. О. Приходько, Г. Г. Дубініна, В. П. Хиля, С. М. Ярмолюк
Антипроліферативна активність деяких похідних 7-гідрокси-З-
арилокси-2-трифторметил-4Н-4-хроменону проти 60 ліній
клітин раку людини
Резюме
Синтезовано 234 похідних 7-гідрокси-3-арилокси-2-трифтор-
метил-4Н-4-хроменону та досліджено їхню протиракову ак
тивність на лініях ракових клітин людини у Національному
Інституті Раку (США). Сполуки 1—4? виявили високу цито-
статичну та цитотоксичну активність (GISQ 3,44—41,1 мкМ
та LCS0 від 49,6 мкМ). Обговорюється взаємозв'язок між
структурою тестованих сполук та їхньою проліферативною
активністю.
А. А. Приходько, Г. Г. Дубинина, В. П. Хиля, С. Н. Ярмолюк
Антипролиферативная активность некоторых производных 7-
гидрокси-3-арилокси-2-трифторметил-4Н-4-хроменона против
60 линий раковых клеток человека
Резюме
Синтезированы 234 производных 7-гидрокси-З-арилокси-2-mpu-
фторметил-4Н-4-хроменона и исследована их противораковая
активность на линиях раковых клеток человека в Националь
ном Институте Рака (США). Соединения 1—8 проявили
высокую цитостатическую и цитотоксическую активность
(Glso 3,44—41,1 мкМ и LC50 от 49,6 мкМ). Обсуждается
взаимосвязь между структурой тестированных соединений и
их пролиферативной активностью.
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