A new class of symmetric bisbenzimidazole-based DNA minor groove-binding agents showing antitumor activity

The synthesis and evaluation of the novel head-to-head bisbenzimidazole compound 2,2-bis[4'-(3 " -dimethylamino- 1 " -propyloxy)phenyl]-5,5-bi-1H-benzimidazole is described. An X-ray crystallographic study of a complex with the DNA dodecanucleotide sequence d(CGCGAATTCGCG) shows the c...

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Vydáno v:	Journal of medicinal chemistry Ročník 44; číslo 2; s. 138 - 144
Hlavní autoři:	Mann, J, Baron, A, Opoku-Boahen, Y, Johansson, E, Parkinson, G, Kelland, LR, Neidle, S
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	WASHINGTON Amer Chemical Soc 18.01.2001
Témata:	Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Benzimidazoles - chemical synthesis Benzimidazoles - chemistry Benzimidazoles - metabolism Benzimidazoles - pharmacology Chemistry, Medicinal Cisplatin - pharmacology Crystallography, X-Ray DNA - metabolism Drug Resistance, Neoplasm Drug Screening Assays, Antitumor Female Humans Life Sciences & Biomedicine Magnetic Resonance Spectroscopy Mass Spectrometry Mice Mice, Nude Models, Molecular Pharmacology & Pharmacy Science & Technology Structure-Activity Relationship Transplantation, Heterologous Tumor Cells, Cultured PROTEIN BINDER RECOGNITION CRYSTAL-STRUCTURE DRUGS TOPOISOMERASE-I D(CGCGAATTCGCG)2 DERIVATIVES HOECHST 33258
ISSN:	0022-2623, 1520-4804
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Abstract	The synthesis and evaluation of the novel head-to-head bisbenzimidazole compound 2,2-bis[4'-(3 " -dimethylamino- 1 " -propyloxy)phenyl]-5,5-bi-1H-benzimidazole is described. An X-ray crystallographic study of a complex with the DNA dodecanucleotide sequence d(CGCGAATTCGCG) shows the compound bound in the A/T minor groove region of a B-DNA duplex and that the head-to-head bisbenzimidazole motif hydrogen-bonds to the edges of all four consecutive A:T base pairs. The compound showed potent growth inhibition with a mean IC50 across an ovarian carcinoma cell line panel of 0.31 muM, with no significant cross-resistance in two acquired cisplatin-resistant cell lines and a low level of cross-resistance in the P-glycoprotein overexpressing acquired doxorubicin-resistant cell line. Studies with the hollow fiber assay and in vivo tumor xenografts showed some evidence of antitumor activity.
AbstractList	The synthesis and evaluation of the novel head-to-head bisbenzimidazole compound 2,2-bis[4'-(3' '-dimethylamino-1' '-propyloxy)phenyl]-5,5-bi-1H-benzimidazole is described. An X-ray crystallographic study of a complex with the DNA dodecanucleotide sequence d(CGCGAATTCGCG) shows the compound bound in the A/T minor groove region of a B-DNA duplex and that the head-to-head bisbenzimidazole motif hydrogen-bonds to the edges of all four consecutive A:T base pairs. The compound showed potent growth inhibition with a mean IC(50) across an ovarian carcinoma cell line panel of 0.31 microM, with no significant cross-resistance in two acquired cisplatin-resistant cell lines and a low level of cross-resistance in the P-glycoprotein overexpressing acquired doxorubicin-resistant cell line. Studies with the hollow fiber assay and in vivo tumor xenografts showed some evidence of antitumor activity. The synthesis and evaluation of the novel head-to-head bisbenzimidazole compound 2,2-bis[4'-(3 " -dimethylamino- 1 " -propyloxy)phenyl]-5,5-bi-1H-benzimidazole is described. An X-ray crystallographic study of a complex with the DNA dodecanucleotide sequence d(CGCGAATTCGCG) shows the compound bound in the A/T minor groove region of a B-DNA duplex and that the head-to-head bisbenzimidazole motif hydrogen-bonds to the edges of all four consecutive A:T base pairs. The compound showed potent growth inhibition with a mean IC50 across an ovarian carcinoma cell line panel of 0.31 muM, with no significant cross-resistance in two acquired cisplatin-resistant cell lines and a low level of cross-resistance in the P-glycoprotein overexpressing acquired doxorubicin-resistant cell line. Studies with the hollow fiber assay and in vivo tumor xenografts showed some evidence of antitumor activity. The synthesis and evaluation of the novel head-to-head bisbenzimidazole compound 2,2-bis[4'-(3' '-dimethylamino-1' '-propyloxy)phenyl]-5,5-bi-1H-benzimidazole is described. An X-ray crystallographic study of a complex with the DNA dodecanucleotide sequence d(CGCGAATTCGCG) shows the compound bound in the A/T minor groove region of a B-DNA duplex and that the head-to-head bisbenzimidazole motif hydrogen-bonds to the edges of all four consecutive A:T base pairs. The compound showed potent growth inhibition with a mean IC(50) across an ovarian carcinoma cell line panel of 0.31 microM, with no significant cross-resistance in two acquired cisplatin-resistant cell lines and a low level of cross-resistance in the P-glycoprotein overexpressing acquired doxorubicin-resistant cell line. Studies with the hollow fiber assay and in vivo tumor xenografts showed some evidence of antitumor activity.The synthesis and evaluation of the novel head-to-head bisbenzimidazole compound 2,2-bis[4'-(3' '-dimethylamino-1' '-propyloxy)phenyl]-5,5-bi-1H-benzimidazole is described. An X-ray crystallographic study of a complex with the DNA dodecanucleotide sequence d(CGCGAATTCGCG) shows the compound bound in the A/T minor groove region of a B-DNA duplex and that the head-to-head bisbenzimidazole motif hydrogen-bonds to the edges of all four consecutive A:T base pairs. The compound showed potent growth inhibition with a mean IC(50) across an ovarian carcinoma cell line panel of 0.31 microM, with no significant cross-resistance in two acquired cisplatin-resistant cell lines and a low level of cross-resistance in the P-glycoprotein overexpressing acquired doxorubicin-resistant cell line. Studies with the hollow fiber assay and in vivo tumor xenografts showed some evidence of antitumor activity.
Author	Johansson, E Mann, J Neidle, S Kelland, LR Baron, A Opoku-Boahen, Y Parkinson, G
Author_xml	– sequence: 1 givenname: J surname: Mann fullname: Mann, J – sequence: 2 givenname: A surname: Baron fullname: Baron, A – sequence: 3 givenname: Y surname: Opoku-Boahen fullname: Opoku-Boahen, Y – sequence: 4 givenname: E surname: Johansson fullname: Johansson, E – sequence: 5 givenname: G surname: Parkinson fullname: Parkinson, G – sequence: 6 givenname: LR surname: Kelland fullname: Kelland, LR – sequence: 7 givenname: S surname: Neidle fullname: Neidle, S email: s.neidle@icr.ac.uk
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Snippet	The synthesis and evaluation of the novel head-to-head bisbenzimidazole compound 2,2-bis[4'-(3 " -dimethylamino- 1 " -propyloxy)phenyl]-5,5-bi-1H-benzimidazole... The synthesis and evaluation of the novel head-to-head bisbenzimidazole compound 2,2-bis[4'-(3' '-dimethylamino-1' '-propyloxy)phenyl]-5,5-bi-1H-benzimidazole...
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SubjectTerms	Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Benzimidazoles - chemical synthesis Benzimidazoles - chemistry Benzimidazoles - metabolism Benzimidazoles - pharmacology Chemistry, Medicinal Cisplatin - pharmacology Crystallography, X-Ray DNA - metabolism Drug Resistance, Neoplasm Drug Screening Assays, Antitumor Female Humans Life Sciences & Biomedicine Magnetic Resonance Spectroscopy Mass Spectrometry Mice Mice, Nude Models, Molecular Pharmacology & Pharmacy Science & Technology Structure-Activity Relationship Transplantation, Heterologous Tumor Cells, Cultured
Title	A new class of symmetric bisbenzimidazole-based DNA minor groove-binding agents showing antitumor activity
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