Intercalation of ethidium and analogues with nucleic acids: A molecular orbital study

Steven Patterson; James M. Coxon; Lucjan Strekowski

doi:10.1016/S0968-0896(96)00242-8

Intercalation of ethidium and analogues with nucleic acids: A molecular orbital study

Steven Patterson, James M. Coxon, Lucjan Strekowski

Center for Drug Design

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

31 Scopus citations

Abstract

Semiempirical calculations suggest that the intercalation complexes of phenanthridinium cations 1-4 with G-C/C-G and 1 with A-U/U-A are stabilized by frontier orbital interactions between the LUMO of the intercalator and the HOMOs of the adjacent purine bases. The charge on the ring nitrogen of 1-4 appears to be necessary for the orbital interactions, lowering the LUMO, facilitating mixing of this orbital with the HOMOs of the adjacent purine bases to give an extended HOMO stabilizing the complex and resulting in the bathochromic shift in the electron absorption spectrum. Noncationic phenanthridine 5 shows no frontier orbital interactions in the forced intercalation complex with G-C/C-G. The results of the calculations parallel experimental T(m) values.

Original language	English (US)
Pages (from-to)	277-281
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	5
Issue number	2
DOIs	https://doi.org/10.1016/S0968-0896(96)00242-8
State	Published - Feb 1997

Bibliographical note

Funding Information:
This work was supported by grant AI-27196 of the National Instituteso f Health, U.S.A. (L.S.), grant of the ResearchC orporation,U .S.A. (L.S.), and the New Zealand Lotteries board and the PGS Fund for Grants (J.M.C.). We thank Farial Tanious and Dr David

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@article{495cf804ca7a4ef58aa64eb948698070,

title = "Intercalation of ethidium and analogues with nucleic acids: A molecular orbital study",

abstract = "Semiempirical calculations suggest that the intercalation complexes of phenanthridinium cations 1-4 with G-C/C-G and 1 with A-U/U-A are stabilized by frontier orbital interactions between the LUMO of the intercalator and the HOMOs of the adjacent purine bases. The charge on the ring nitrogen of 1-4 appears to be necessary for the orbital interactions, lowering the LUMO, facilitating mixing of this orbital with the HOMOs of the adjacent purine bases to give an extended HOMO stabilizing the complex and resulting in the bathochromic shift in the electron absorption spectrum. Noncationic phenanthridine 5 shows no frontier orbital interactions in the forced intercalation complex with G-C/C-G. The results of the calculations parallel experimental T(m) values.",

author = "Steven Patterson and Coxon, {James M.} and Lucjan Strekowski",

note = "Funding Information: This work was supported by grant AI-27196 of the National Instituteso f Health, U.S.A. (L.S.), grant of the ResearchC orporation,U .S.A. (L.S.), and the New Zealand Lotteries board and the PGS Fund for Grants (J.M.C.). We thank Farial Tanious and Dr David",

year = "1997",

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doi = "10.1016/S0968-0896(96)00242-8",

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T1 - Intercalation of ethidium and analogues with nucleic acids

T2 - A molecular orbital study

AU - Patterson, Steven

AU - Coxon, James M.

AU - Strekowski, Lucjan

N1 - Funding Information: This work was supported by grant AI-27196 of the National Instituteso f Health, U.S.A. (L.S.), grant of the ResearchC orporation,U .S.A. (L.S.), and the New Zealand Lotteries board and the PGS Fund for Grants (J.M.C.). We thank Farial Tanious and Dr David

PY - 1997/2

Y1 - 1997/2

N2 - Semiempirical calculations suggest that the intercalation complexes of phenanthridinium cations 1-4 with G-C/C-G and 1 with A-U/U-A are stabilized by frontier orbital interactions between the LUMO of the intercalator and the HOMOs of the adjacent purine bases. The charge on the ring nitrogen of 1-4 appears to be necessary for the orbital interactions, lowering the LUMO, facilitating mixing of this orbital with the HOMOs of the adjacent purine bases to give an extended HOMO stabilizing the complex and resulting in the bathochromic shift in the electron absorption spectrum. Noncationic phenanthridine 5 shows no frontier orbital interactions in the forced intercalation complex with G-C/C-G. The results of the calculations parallel experimental T(m) values.

AB - Semiempirical calculations suggest that the intercalation complexes of phenanthridinium cations 1-4 with G-C/C-G and 1 with A-U/U-A are stabilized by frontier orbital interactions between the LUMO of the intercalator and the HOMOs of the adjacent purine bases. The charge on the ring nitrogen of 1-4 appears to be necessary for the orbital interactions, lowering the LUMO, facilitating mixing of this orbital with the HOMOs of the adjacent purine bases to give an extended HOMO stabilizing the complex and resulting in the bathochromic shift in the electron absorption spectrum. Noncationic phenanthridine 5 shows no frontier orbital interactions in the forced intercalation complex with G-C/C-G. The results of the calculations parallel experimental T(m) values.

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SN - 0968-0896

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EP - 281

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 2

ER -

Intercalation of ethidium and analogues with nucleic acids: A molecular orbital study

Abstract

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