DOI: 10.1002/anie.199503521. Electron Transfer through DNA: Site‐Specific Modification of Duplex DNA with Ruthenium Donors and Acceptors

Electron Transfer through DNA: Site‐Specific Modification of Duplex DNA with Ruthenium Donors and Acceptors

10.1002/anie.199503521

Crossref journal-article

Wiley

Angewandte Chemie International Edition in English (311)

Abstract

The rate of the electron transfer between two ruthenium centersat the ends of an octanucleotide duplex (metal‐to‐metal distance = 21 Å) was determined to be 1.6(4) × 106s−1. By using automated DNA synthesis techniques, modified oligonucleotides were prepared with a protected phosphoroamidite of 2′‐amino‐2′‐deoxyuridine. The NH2‐modified oligonucleotides were hybridized with complementary DNA sequences to protect nucleotide bases, and then treated with ruthenium complexes. In this way the ruthenium complex was bound only to the free NH2group.

Bibliography

Meade, T. J., & Kayyem, J. F. (1995). Electron Transfer through DNA: SiteâSpecific Modification of Duplex DNA with Ruthenium Donors and Acceptors. Angewandte Chemie International Edition in English, 34(3), 352â354. Portico.

Authors 2

Thomas J. Meade (first)
Jon F. Kayyem (additional)

References 25 Referenced 249

10.1002/9780470166390.ch5
Met. Ions Biol. Syst. 1991 27
10.1021/cr00011a001
10.1021/ja00059a057
10.1002/ange.19931050506
10.1002/anie.199306661
10.1093/nar/22.6.920
10.1002/ange.19911030604
10.1002/anie.199106133
10.1021/ja00200a049
10.1021/bc00003a001
10.1021/ja00021a047
10.1126/science.7802858
10.1021/jo01326a037
10.1080/07328319308018549
10.1093/nar/22.1.20
Unprotected oligonucleotides react with the ruthenium complexes very efficiently. Isolated products from these reactions show that several sites are labeled.
10.1093/oso/9780199632800.001.0001 / Oligonucleotides and Analogues: A Practical Approach by Eckstein F. (1991)
The yield of ruthenium‐modified aminoribose duplex is typically 25–50% (see Fig. 2 peak C).
Temperatures at which 50% of the DNA strands are dissociated (Tm) were determined by thermal denaturation and annealing in 0.9 M NaCl and 0.1MNa phosphate buffer (pH 7) by means of a Hewlett Packard 8452A diode‐array spectrophotometer with HP 89090A Peltier temperature‐control accessory. Unmodified octamers as controls revealed a single helix‐to‐coil transition point and aTmof 45 °C. The aminoribose oligomers showed a lowerTmof 40 °C. The ruthenium‐modified oligomers when hybridized to their unmodified complements showed broad helix‐to‐coil transitions between 36 °C and 42 °C. All kinetic measurements were performed in the presence of 1 M Na+to insure that the modified oligonucleotides were annealed at ambient temperature (22 °C).
J. F.Kayyem Y.Hi S. L.Mayo T. J.Meade unpublished.
10.1021/ja00018a064
The metal–metal distance was estimated from molecular graphics calculations.
10.1021/ja00498a016
10.1021/j100152a007

Dates

Type	When
Created	21 years, 7 months ago (Jan. 16, 2004, 9:21 a.m.)
Deposited	1 year, 7 months ago (Jan. 11, 2024, 6:23 p.m.)
Indexed	2 months ago (July 2, 2025, 1:12 p.m.)
Issued	30 years, 6 months ago (Feb. 21, 1995)
Published	30 years, 6 months ago (Feb. 21, 1995)
Published Online	21 years, 8 months ago (Dec. 22, 2003)
Published Print	30 years, 6 months ago (Feb. 21, 1995)

Funders 0

None

BibTeX

@article{Meade_1995, title={Electron Transfer through DNA: Site‐Specific Modification of Duplex DNA with Ruthenium Donors and Acceptors}, volume={34}, ISSN={0570-0833}, url={http://dx.doi.org/10.1002/anie.199503521}, DOI={10.1002/anie.199503521}, number={3}, journal={Angewandte Chemie International Edition in English}, publisher={Wiley}, author={Meade, Thomas J. and Kayyem, Jon F.}, year={1995}, month=feb, pages={352–354} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        2
      ]
    ],
    "date-time": "2025-07-02T17:12:04Z",
    "timestamp": 1751476324266
  },
  "reference-count": 25,
  "publisher": "Wiley",
  "issue": "3",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2003,
            12,
            22
          ]
        ],
        "date-time": "2003-12-22T00:00:00Z",
        "timestamp": 1072051200000
      },
      "content-version": "vor",
      "delay-in-days": 3226,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1995,
        2,
        21
      ]
    ]
  },
  "abstract": "<jats:p><jats:bold>The rate of the electron transfer between two ruthenium centers</jats:bold>at the ends of an octanucleotide duplex (metal\u2010to\u2010metal distance = 21 \u00c5) was determined to be 1.6(4) \u00d7 10<jats:sup>6</jats:sup>s<jats:sup>\u22121</jats:sup>. By using automated DNA synthesis techniques, modified oligonucleotides were prepared with a protected phosphoroamidite of 2\u2032\u2010amino\u20102\u2032\u2010deoxyuridine. The NH<jats:sub>2</jats:sub>\u2010modified oligonucleotides were hybridized with complementary DNA sequences to protect nucleotide bases, and then treated with ruthenium complexes. In this way the ruthenium complex was bound only to the free NH<jats:sub>2</jats:sub>group.</jats:p>",
  "DOI": "10.1002/anie.199503521",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2004,
        1,
        16
      ]
    ],
    "date-time": "2004-01-16T14:21:29Z",
    "timestamp": 1074262889000
  },
  "page": "352-354",
  "source": "Crossref",
  "is-referenced-by-count": 249,
  "title": "Electron Transfer through DNA: Site\u2010Specific Modification of Duplex DNA with Ruthenium Donors and Acceptors",
  "prefix": "10.1002",
  "volume": "34",
  "author": [
    {
      "given": "Thomas J.",
      "family": "Meade",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Jon F.",
      "family": "Kayyem",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2003,
        12,
        22
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_1_1_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/9780470166390.ch5"
    },
    {
      "key": "e_1_2_1_2_2",
      "unstructured": "Met. Ions Biol. Syst. 1991 27"
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr00011a001"
    },
    {
      "key": "e_1_2_1_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00059a057"
    },
    {
      "key": "e_1_2_1_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19931050506"
    },
    {
      "key": "e_1_2_1_5_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.199306661"
    },
    {
      "key": "e_1_2_1_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1093/nar/22.6.920"
    },
    {
      "key": "e_1_2_1_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19911030604"
    },
    {
      "key": "e_1_2_1_7_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.199106133"
    },
    {
      "key": "e_1_2_1_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00200a049"
    },
    {
      "key": "e_1_2_1_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/bc00003a001"
    },
    {
      "key": "e_1_2_1_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00021a047"
    },
    {
      "key": "e_1_2_1_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1126/science.7802858"
    },
    {
      "key": "e_1_2_1_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01326a037"
    },
    {
      "key": "e_1_2_1_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1080/07328319308018549"
    },
    {
      "key": "e_1_2_1_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1093/nar/22.1.20"
    },
    {
      "key": "e_1_2_1_15_2",
      "unstructured": "Unprotected oligonucleotides react with the ruthenium complexes very efficiently. Isolated products from these reactions show that several sites are labeled."
    },
    {
      "key": "e_1_2_1_16_2",
      "doi-asserted-by": "crossref",
      "DOI": "10.1093/oso/9780199632800.001.0001",
      "volume-title": "Oligonucleotides and Analogues: A Practical Approach",
      "author": "Eckstein F.",
      "year": "1991"
    },
    {
      "key": "e_1_2_1_17_2",
      "unstructured": "The yield of ruthenium\u2010modified aminoribose duplex is typically 25\u201350% (see Fig. 2 peak C)."
    },
    {
      "key": "e_1_2_1_18_2",
      "unstructured": "Temperatures at which 50% of the DNA strands are dissociated (Tm) were determined by thermal denaturation and annealing in 0.9 M NaCl and 0.1MNa phosphate buffer (pH 7) by means of a Hewlett Packard 8452A diode\u2010array spectrophotometer with HP 89090A Peltier temperature\u2010control accessory. Unmodified octamers as controls revealed a single helix\u2010to\u2010coil transition point and aTmof 45 \u00b0C. The aminoribose oligomers showed a lowerTmof 40 \u00b0C. The ruthenium\u2010modified oligomers when hybridized to their unmodified complements showed broad helix\u2010to\u2010coil transitions between 36 \u00b0C and 42 \u00b0C. All kinetic measurements were performed in the presence of 1 M Na+to insure that the modified oligonucleotides were annealed at ambient temperature (22 \u00b0C)."
    },
    {
      "key": "e_1_2_1_19_2",
      "unstructured": "J. F.Kayyem Y.Hi S. L.Mayo T. J.Meade unpublished."
    },
    {
      "key": "e_1_2_1_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00018a064"
    },
    {
      "key": "e_1_2_1_21_2",
      "unstructured": "The metal\u2013metal distance was estimated from molecular graphics calculations."
    },
    {
      "key": "e_1_2_1_22_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00498a016"
    },
    {
      "key": "e_1_2_1_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/j100152a007"
    }
  ],
  "container-title": "Angewandte Chemie International Edition in English",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.199503521",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.199503521",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2024,
        1,
        11
      ]
    ],
    "date-time": "2024-01-11T23:23:44Z",
    "timestamp": 1705015424000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/anie.199503521"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1995,
        2,
        21
      ]
    ]
  },
  "references-count": 25,
  "journal-issue": {
    "issue": "3",
    "published-print": {
      "date-parts": [
        [
          1995,
          2,
          21
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/anie.199503521"
  ],
  "URL": "http://dx.doi.org/10.1002/anie.199503521",
  "relation": {},
  "ISSN": [
    "0570-0833"
  ],
  "subject": [],
  "container-title-short": "Angew. Chem. Int. Ed. Engl.",
  "published": {
    "date-parts": [
      [
        1995,
        2,
        21
      ]
    ]
  }
}