Novel metal chelating molecules with anticancer activity. Striking effect of the imidazole substitution of the histidine-pyridine-histidine system

被引：21

作者：

Ali, Taha F. S. ^{[1
]}

Iwamaru, Kana ^{[1
]}

Ciftci, Halil Ibrahim ^{[1
]}

Koga, Ryoko ^{[1
]}

Matsumoto, Masahiro ^{[1
]}

Oba, Yasunori ^{[1
]}

Kurosaki, Hiromasa ^{[2
]}

Fujita, Mikako ^{[3
]}

Okamoto, Yoshinari ^{[1
]}

Umezawa, Kazuo ^{[5
]}

Nakao, Mitsuyoshi ^{[4
]}

Hide, Takuichiro ^{[6
]}

Makino, Keishi ^{[6
]}

Kuratsu, Jun-ichi ^{[6
]}

Abdel-Aziz, Mohamed ^{[7
]}

Abuo-Rahma, Gamal El-Din A. A. ^{[7
]}

Beshr, Eman A. M. ^{[7
,8
]}

Otsuka, Masami ^{[1
]}

机构：

[1] Kumamoto Univ, Fac Life Sci, Dept Bioorgan Med Chem, Chuo Ku, Kumamoto 8620973, Japan

[2] Kinjo Gakuin Univ, Coll Pharm, Moriyama Ku, Nagoya, Aichi 4638521, Japan

[3] Kumamoto Univ, Sch Pharm, Res Inst Drug Discovery, Chuo Ku, Kumamoto 8620973, Japan

[4] Aichi Med Univ, Sch Med, Dept Mol Target Med Screening, Nagakute, Aichi 4801195, Japan

[5] Kumamoto Univ, Inst Mol Embryol & Genet, Dept Med Cell Biol, Kumamoto 8600811, Japan

[6] Kumamoto Univ, Fac Med, Dept Neurosurg, Chuo Ku, Kumamoto 8608556, Japan

[7] Menia Univ, Fac Pharm, Dept Med Chem, Menia 61519, Egypt

[8] Umm Al Qura Univ, Dept Pharmaceut Chem, Coll Pharm, Mecca 21955, Saudi Arabia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2015年 / 23卷 / 17期

基金：

日本学术振兴会;

关键词：

Histidine-pyridine-histidine; AsPC-1; U87; U251; DNA cleavage; DIOXYGEN-ACTIVATING CAPABILITY; BINDING-SITE; SYNTHETIC MODELS; CARCINOMA-CELLS; BLEOMYCIN; APOPTOSIS; LIGANDS; ANALOGS;

D O I：

10.1016/j.bmc.2015.07.044

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Previously we have reported a metal chelating histidine-pyridine-histidine system possessing a trityl group on the histidine imidazole, namely HPH-2Trt, which induces apoptosis in human pancreatic adenocarcinoma AsPC-1 cells. Herein the influence of the imidazole substitution of HPH-2Trt was examined. Five related compounds, HPH-1Trt, HPH-2Bzl, HPH-1Bzl, HPH-2Me, and HPH-1Me were newly synthesized and screened for their activity against AsPC-1 and brain tumor cells U87 and U251. HPH-1Trt and HPH-2Trt were highly active among the tested HPH compounds. In vitro DNA cleavage assay showed both HPH-1Trt and HPH-2Trt completely disintegrate pUC19 DNA. The introduction of trityl group decisively potentiated the activity. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5476 / 5482

页数：7

共 18 条

[1] Synthesis and evaluation of deglycobleomycin A(2) analogues containing a tertiary N-methyl amide and simple ester replacement for the L-histidine secondary amide: Direct functional characterization of the requirement for secondary amide metal complexation [J].

Boger, DL ;

Teramoto, S ;

Cai, H .

BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (02) :179-193

[2] Bleomycins: Towards better therapeutics [J].

Chen, JY ;

Stubbe, J .

NATURE REVIEWS CANCER, 2005, 5 (02) :102-112

[3] PICKET-FENCE PORPHYRINS - SYNTHETIC MODELS FOR OXYGEN BINDING HEMOPROTEINS [J].

COLLMAN, JP ;

GAGNE, RR ;

REED, CA ;

HALBERT, TR ;

LANG, G ;

ROBINSON, WT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1427-1439

[4] Synthesis and biology of new thyrotropin-releasing hormone (TRH) analogues [J].

Jain, R ;

Singh, J ;

Perlman, JH ;

Gershengorn, MC .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (01) :189-194

[5]

KITTAKA A, 1988, TETRAHEDRON, V44, P2811

[6] TRANSITION-METAL BINDING-SITE OF BLEOMYCIN - A REMARKABLY EFFICIENT DIOXYGEN-ACTIVATING MOLECULE BASED ON BLEOMYCIN-FE(II) COMPLEX [J].

KITTAKA, A ;

SUGANO, Y ;

OTSUKA, M ;

OHNO, M ;

SUGIURA, Y ;

UMEZAWA, H .

TETRAHEDRON LETTERS, 1986, 27 (31) :3631-3634

[7] Pinacolborane as the Boron Source in Nitrogen-Directed Borylations of Aromatic N,N-Dimethylhydrazones [J].

Lopez-Rodriguez, Rocio ;

Ros, Abel ;

Fernandez, Rosario ;

Lassaletta, Jose M. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (21) :9915-9920

[8]

Matsumoto M, 2006, HETEROCYCLES, V69, P311

[9] RAPID COLORIMETRIC ASSAY FOR CELLULAR GROWTH AND SURVIVAL - APPLICATION TO PROLIFERATION AND CYTO-TOXICITY ASSAYS [J].

MOSMANN, T .

JOURNAL OF IMMUNOLOGICAL METHODS, 1983, 65 (1-2) :55-63

[10] High-valent iron(IV)-oxo complexes of heme and non-heme ligands in oxygenation reactions [J].

Nam, Wonwoo .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (07) :522-531

← 1 2 →