Cytotoxicity and DNA binding property of phenanthrene imidazole with polyglycol side chains

Shuxiang Wang; Hongdong Li; Chao Chen; Jinchao Zhang; Shenghui Li; Xinying Qin; Xiaoliu Li; Kerang Wang

doi:10.1016/j.bmcl.2012.08.079

Cytotoxicity and DNA binding property of phenanthrene imidazole with polyglycol side chains

Shuxiang Wang
, Hongdong Li
, Chao Chen
, Jinchao Zhang^*
, Shenghui Li
, Xinying Qin
, Xiaoliu Li
, Kerang Wang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

A series of phenanthrene imidazole with polyglycol side chain (2a-2c and 3a-3c) were synthesized and characterized by IR, NMR and MS. The cytotoxicity of 2a-2c and 3a-3c against cancer cell lines (HL-60, BGC-823, Bel-7402 and KB) in vitro were measured using MTT method. The DNA binding properties of 3a-3c were investigated by UV, fluorescence, CD spectroscopies and thermal denaturation. The results indicate that 2a exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines, 3b and 3c exhibit higher cytotoxicity than 2b and 2c against BGC-823, Bel-7402 and KB cell lines. The cytotoxic effect of 2a-2c decrease with the increase of side chains length, the cytotoxic effect of 3a-3c increased with the increasing length of side chains against BGC-823, Bel-7402 and KB cell lines. Compounds 3a-3c intercalated DNA with a vertical orientation in the intercalation pocket. The binding constants of 3a-3c with Ct-DNA are 1.68 × 10⁶, 1.51 × 10⁶ and 0.709 × 10⁶ M^-1, respectively. The binding affinity of 3a-3c with Ct-DNA trended to decrease with the increasing length of polyglycol side chains.

Original language	English
Pages (from-to)	6347-6351
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	20
DOIs	https://doi.org/10.1016/j.bmcl.2012.08.079
Publication status	Published - 15 Oct 2012
Externally published	Yes

Access to Document

10.1016/j.bmcl.2012.08.079

Cite this

@article{9db6344944e54735b9ff5d23f0cbd98a,

title = "Cytotoxicity and DNA binding property of phenanthrene imidazole with polyglycol side chains",

abstract = "A series of phenanthrene imidazole with polyglycol side chain (2a-2c and 3a-3c) were synthesized and characterized by IR, NMR and MS. The cytotoxicity of 2a-2c and 3a-3c against cancer cell lines (HL-60, BGC-823, Bel-7402 and KB) in vitro were measured using MTT method. The DNA binding properties of 3a-3c were investigated by UV, fluorescence, CD spectroscopies and thermal denaturation. The results indicate that 2a exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines, 3b and 3c exhibit higher cytotoxicity than 2b and 2c against BGC-823, Bel-7402 and KB cell lines. The cytotoxic effect of 2a-2c decrease with the increase of side chains length, the cytotoxic effect of 3a-3c increased with the increasing length of side chains against BGC-823, Bel-7402 and KB cell lines. Compounds 3a-3c intercalated DNA with a vertical orientation in the intercalation pocket. The binding constants of 3a-3c with Ct-DNA are 1.68 × 106, 1.51 × 106 and 0.709 × 106 M-1, respectively. The binding affinity of 3a-3c with Ct-DNA trended to decrease with the increasing length of polyglycol side chains.",

keywords = "Binding property, Cytotoxicity, Phenanthrene imidazole derivatives, Polyglycol side chain",

author = "Shuxiang Wang and Hongdong Li and Chao Chen and Jinchao Zhang and Shenghui Li and Xinying Qin and Xiaoliu Li and Kerang Wang",

year = "2012",

month = oct,

day = "15",

doi = "10.1016/j.bmcl.2012.08.079",

language = "English",

volume = "22",

pages = "6347--6351",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd.",

number = "20",

}

TY - JOUR

T1 - Cytotoxicity and DNA binding property of phenanthrene imidazole with polyglycol side chains

AU - Wang, Shuxiang

AU - Li, Hongdong

AU - Chen, Chao

AU - Zhang, Jinchao

AU - Li, Shenghui

AU - Qin, Xinying

AU - Li, Xiaoliu

AU - Wang, Kerang

PY - 2012/10/15

Y1 - 2012/10/15

N2 - A series of phenanthrene imidazole with polyglycol side chain (2a-2c and 3a-3c) were synthesized and characterized by IR, NMR and MS. The cytotoxicity of 2a-2c and 3a-3c against cancer cell lines (HL-60, BGC-823, Bel-7402 and KB) in vitro were measured using MTT method. The DNA binding properties of 3a-3c were investigated by UV, fluorescence, CD spectroscopies and thermal denaturation. The results indicate that 2a exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines, 3b and 3c exhibit higher cytotoxicity than 2b and 2c against BGC-823, Bel-7402 and KB cell lines. The cytotoxic effect of 2a-2c decrease with the increase of side chains length, the cytotoxic effect of 3a-3c increased with the increasing length of side chains against BGC-823, Bel-7402 and KB cell lines. Compounds 3a-3c intercalated DNA with a vertical orientation in the intercalation pocket. The binding constants of 3a-3c with Ct-DNA are 1.68 × 106, 1.51 × 106 and 0.709 × 106 M-1, respectively. The binding affinity of 3a-3c with Ct-DNA trended to decrease with the increasing length of polyglycol side chains.

AB - A series of phenanthrene imidazole with polyglycol side chain (2a-2c and 3a-3c) were synthesized and characterized by IR, NMR and MS. The cytotoxicity of 2a-2c and 3a-3c against cancer cell lines (HL-60, BGC-823, Bel-7402 and KB) in vitro were measured using MTT method. The DNA binding properties of 3a-3c were investigated by UV, fluorescence, CD spectroscopies and thermal denaturation. The results indicate that 2a exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines, 3b and 3c exhibit higher cytotoxicity than 2b and 2c against BGC-823, Bel-7402 and KB cell lines. The cytotoxic effect of 2a-2c decrease with the increase of side chains length, the cytotoxic effect of 3a-3c increased with the increasing length of side chains against BGC-823, Bel-7402 and KB cell lines. Compounds 3a-3c intercalated DNA with a vertical orientation in the intercalation pocket. The binding constants of 3a-3c with Ct-DNA are 1.68 × 106, 1.51 × 106 and 0.709 × 106 M-1, respectively. The binding affinity of 3a-3c with Ct-DNA trended to decrease with the increasing length of polyglycol side chains.

KW - Binding property

KW - Cytotoxicity

KW - Phenanthrene imidazole derivatives

KW - Polyglycol side chain

UR - https://www.scopus.com/pages/publications/84866743325

U2 - 10.1016/j.bmcl.2012.08.079

DO - 10.1016/j.bmcl.2012.08.079

M3 - Article

SN - 0960-894X

VL - 22

SP - 6347

EP - 6351

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 20

ER -

Cytotoxicity and DNA binding property of phenanthrene imidazole with polyglycol side chains

Abstract

Access to Document

Other files and links

Fingerprint

Cite this