DOI: 10.1002/anie.199113511. Bis(hydroperoxy)naphthaldiimide as a “Photo‐Fenton Reagent”: Sequence‐Specific Photocleavage of DNA

Bis(hydroperoxy)naphthaldiimide as a “Photo‐Fenton Reagent”: Sequence‐Specific Photocleavage of DNA

10.1002/anie.199113511

Crossref journal-article

Wiley

Angewandte Chemie International Edition in English (311)

Bibliography

Matsugo, S., Kawanishi, S., Yamamoto, K., Sugiyama, H., Matsuura, T., & Saito, I. (1991). Bis(hydroperoxy)naphthaldiimide as a âPhotoâFenton Reagentâ: SequenceâSpecific Photocleavage of DNA. Angewandte Chemie International Edition in English, 30(10), 1351â1353. Portico.

Authors 6

Seiichi Matsugo (first)
Shosuke Kawanishi (additional)
Koji Yamamoto (additional)
Hiroshi Sugiyama (additional)
Teruo Matsuura (additional)
Isao Saito (additional)

References 34 Referenced 71

10.1016/B978-0-12-566503-2.50008-2
10.1016/B978-0-12-566501-8.50008-0
10.1042/bj2190001
10.1016/B978-0-12-642760-8.50008-9
10.1007/978-94-009-0897-0_26
For photolysis or radiolysis of water see [1].
10.1021/ja00158a067
10.1021/bi00263a026
10.1016/S0021-9258(18)48018-0 / J. Biol. Chem. by Davis K. J. A. (1987)
10.1021/bc00005a010
10.1021/bi00312a022
10.1126/science.2996145
{'key': 'e_1_2_1_5_4', 'first-page': '6522', 'volume': '47', 'author': 'Inoue S.', 'year': '1987', 'journal-title': 'Cancer Res.'} / Cancer Res. by Inoue S. (1987)
{'key': 'e_1_2_1_5_5', 'first-page': '221', 'volume-title': 'The Chemical Bases of Radiation Biology', 'author': 'von Sonntag C.', 'year': '1987'} / The Chemical Bases of Radiation Biology by von Sonntag C. (1987)
10.1021/bi00487a003
10.1021/bi00480a003
10.1021/ja00162a077
10.1021/ja00164a075
10.1021/ja00164a076
M.p. 142–145°C (dec.); UV: (CH3CN) λmax[nm] = 340 nm (Ig ε = 4.20). 357 (4.38) 377 (4.45);1H NMR (CDCl3): δ = 3.59 (s 6 H) 4.40 (dd J= 2.8 14 Hz 2H) 4.67 (dd J= 8.2 14 Hz 2H) 4.91 (dd J= 2.8 8.2 Hz 2H). 8.85 (s 4H) 9.56 (s 2H OOH); MS:m/z446 (M⊕) 410.
The quantum yield was determined by using phenylglyoxylic acid (ϕ = 0.72 at 365 nm) as an actinometer.
10.1016/0003-9861(80)90323-9
(a) Intramolecular electron transfer from the methoxy group of the side chain would provide a similar biradical 4;
{'key': 'e_1_2_1_10_3', 'first-page': '421', 'volume': '5', 'author': 'Mazzochi P. H.', 'year': '1981', 'journal-title': 'Org. Photochem.'} / Org. Photochem. by Mazzochi P. H. (1981)
{'key': 'e_1_2_1_10_4', 'first-page': 'S. 61', 'volume-title': 'Photochemistry in Organic Synthesis', 'author': 'Horspool W. M.', 'year': '1986'} / Photochemistry in Organic Synthesis by Horspool W. M. (1986)
Addition of sodium benzoate (1 mM) in the presence of 10 μM of1resulted in a complete inhibition of the formation of form III DNA with a diminished yield of form II DNA.
10.1016/S0021-9258(19)84847-0
10.1093/nar/5.2.615
10.1016/S0021-9258(17)38496-X
{'key': 'e_1_2_1_13_4', 'first-page': '751', 'volume': '1987', 'author': 'Blau W.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'} / J. Chem. Soc. Chem. Commun. by Blau W.
The reactivity of hydroxyl radicals toward the ribose moiety leading to direct DNA cleavage is known to be considerably less than that toward the purine and pyrimidine bases[15].
10.1021/cr00093a003
10.1021/bi00488a035
The binding constant of1to calf thymus DNA as measured by the equilibrium dialysis method was 1.50 × 104.

Dates

Type	When
Created	21 years, 8 months ago (Dec. 30, 2003, 7:10 p.m.)
Deposited	1 year, 10 months ago (Oct. 23, 2023, 3:08 a.m.)
Indexed	2 months ago (July 1, 2025, 6:30 a.m.)
Issued	33 years, 11 months ago (Oct. 1, 1991)
Published	33 years, 11 months ago (Oct. 1, 1991)
Published Online	21 years, 8 months ago (Dec. 22, 2003)
Published Print	33 years, 11 months ago (Oct. 1, 1991)

Funders 0

None

BibTeX

@article{Matsugo_1991, title={Bis(hydroperoxy)naphthaldiimide as a “Photo‐Fenton Reagent”: Sequence‐Specific Photocleavage of DNA}, volume={30}, ISSN={0570-0833}, url={http://dx.doi.org/10.1002/anie.199113511}, DOI={10.1002/anie.199113511}, number={10}, journal={Angewandte Chemie International Edition in English}, publisher={Wiley}, author={Matsugo, Seiichi and Kawanishi, Shosuke and Yamamoto, Koji and Sugiyama, Hiroshi and Matsuura, Teruo and Saito, Isao}, year={1991}, month=oct, pages={1351–1353} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        1
      ]
    ],
    "date-time": "2025-07-01T10:30:07Z",
    "timestamp": 1751365807697
  },
  "reference-count": 34,
  "publisher": "Wiley",
  "issue": "10",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2003,
            12,
            22
          ]
        ],
        "date-time": "2003-12-22T00:00:00Z",
        "timestamp": 1072051200000
      },
      "content-version": "vor",
      "delay-in-days": 4465,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1991,
        10
      ]
    ]
  },
  "DOI": "10.1002/anie.199113511",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2003,
        12,
        31
      ]
    ],
    "date-time": "2003-12-31T00:10:44Z",
    "timestamp": 1072829444000
  },
  "page": "1351-1353",
  "source": "Crossref",
  "is-referenced-by-count": 71,
  "title": "Bis(hydroperoxy)naphthaldiimide as a \u201cPhoto\u2010Fenton Reagent\u201d: Sequence\u2010Specific Photocleavage of DNA",
  "prefix": "10.1002",
  "volume": "30",
  "author": [
    {
      "given": "Seiichi",
      "family": "Matsugo",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Shosuke",
      "family": "Kawanishi",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Koji",
      "family": "Yamamoto",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Hiroshi",
      "family": "Sugiyama",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Teruo",
      "family": "Matsuura",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Isao",
      "family": "Saito",
      "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": "10.1016/B978-0-12-566503-2.50008-2"
    },
    {
      "key": "e_1_2_1_1_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/B978-0-12-566501-8.50008-0"
    },
    {
      "key": "e_1_2_1_1_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1042/bj2190001"
    },
    {
      "key": "e_1_2_1_1_5",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/B978-0-12-642760-8.50008-9"
    },
    {
      "key": "e_1_2_1_1_6",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/978-94-009-0897-0_26"
    },
    {
      "key": "e_1_2_1_2_2",
      "unstructured": "For photolysis or radiolysis of water see [1]."
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00158a067"
    },
    {
      "key": "e_1_2_1_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/bi00263a026"
    },
    {
      "key": "e_1_2_1_4_3",
      "doi-asserted-by": "crossref",
      "first-page": "9895",
      "DOI": "10.1016/S0021-9258(18)48018-0",
      "volume": "26",
      "author": "Davis K. J. A.",
      "year": "1987",
      "journal-title": "J. Biol. Chem."
    },
    {
      "key": "e_1_2_1_4_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/bc00005a010"
    },
    {
      "key": "e_1_2_1_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/bi00312a022"
    },
    {
      "key": "e_1_2_1_5_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1126/science.2996145"
    },
    {
      "key": "e_1_2_1_5_4",
      "first-page": "6522",
      "volume": "47",
      "author": "Inoue S.",
      "year": "1987",
      "journal-title": "Cancer Res."
    },
    {
      "key": "e_1_2_1_5_5",
      "first-page": "221",
      "volume-title": "The Chemical Bases of Radiation Biology",
      "author": "von Sonntag C.",
      "year": "1987"
    },
    {
      "key": "e_1_2_1_5_6",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/bi00487a003"
    },
    {
      "key": "e_1_2_1_5_7",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/bi00480a003"
    },
    {
      "key": "e_1_2_1_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00162a077"
    },
    {
      "key": "e_1_2_1_6_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00164a075"
    },
    {
      "key": "e_1_2_1_6_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00164a076"
    },
    {
      "key": "e_1_2_1_7_2",
      "unstructured": "M.p. 142\u2013145\u00b0C (dec.); UV: (CH3CN) \u03bbmax[nm] = 340 nm (Ig \u03b5 = 4.20). 357 (4.38) 377 (4.45);1H NMR (CDCl3): \u03b4 = 3.59 (s 6 H) 4.40 (dd J= 2.8 14 Hz 2H) 4.67 (dd J= 8.2 14 Hz 2H) 4.91 (dd J= 2.8 8.2 Hz 2H). 8.85 (s 4H) 9.56 (s 2H OOH); MS:m/z446 (M\u2295) 410."
    },
    {
      "key": "e_1_2_1_8_2",
      "unstructured": "The quantum yield was determined by using phenylglyoxylic acid (\u03d5 = 0.72 at 365 nm) as an actinometer."
    },
    {
      "key": "e_1_2_1_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0003-9861(80)90323-9"
    },
    {
      "key": "e_1_2_1_10_2",
      "unstructured": "(a) Intramolecular electron transfer from the methoxy group of the side chain would provide a similar biradical 4;"
    },
    {
      "key": "e_1_2_1_10_3",
      "first-page": "421",
      "volume": "5",
      "author": "Mazzochi P. H.",
      "year": "1981",
      "journal-title": "Org. Photochem."
    },
    {
      "key": "e_1_2_1_10_4",
      "first-page": "S. 61",
      "volume-title": "Photochemistry in Organic Synthesis",
      "author": "Horspool W. M.",
      "year": "1986"
    },
    {
      "key": "e_1_2_1_11_2",
      "unstructured": "Addition of sodium benzoate (1 mM) in the presence of 10 \u03bcM of1resulted in a complete inhibition of the formation of form III DNA with a diminished yield of form II DNA."
    },
    {
      "key": "e_1_2_1_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0021-9258(19)84847-0"
    },
    {
      "key": "e_1_2_1_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1093/nar/5.2.615"
    },
    {
      "key": "e_1_2_1_13_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0021-9258(17)38496-X"
    },
    {
      "key": "e_1_2_1_13_4",
      "first-page": "751",
      "volume": "1987",
      "author": "Blau W.",
      "journal-title": "J. Chem. Soc. Chem. Commun."
    },
    {
      "key": "e_1_2_1_14_2",
      "unstructured": "The reactivity of hydroxyl radicals toward the ribose moiety leading to direct DNA cleavage is known to be considerably less than that toward the purine and pyrimidine bases[15]."
    },
    {
      "key": "e_1_2_1_15_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr00093a003"
    },
    {
      "key": "e_1_2_1_15_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/bi00488a035"
    },
    {
      "key": "e_1_2_1_16_2",
      "unstructured": "The binding constant of1to calf thymus DNA as measured by the equilibrium dialysis method was 1.50 \u00d7 104."
    }
  ],
  "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.199113511",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.199113511",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        23
      ]
    ],
    "date-time": "2023-10-23T07:08:14Z",
    "timestamp": 1698044894000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/anie.199113511"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1991,
        10
      ]
    ]
  },
  "references-count": 34,
  "journal-issue": {
    "issue": "10",
    "published-print": {
      "date-parts": [
        [
          1991,
          10
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/anie.199113511"
  ],
  "URL": "http://dx.doi.org/10.1002/anie.199113511",
  "relation": {},
  "ISSN": [
    "0570-0833"
  ],
  "subject": [],
  "container-title-short": "Angew. Chem. Int. Ed. Engl.",
  "published": {
    "date-parts": [
      [
        1991,
        10
      ]
    ]
  }
}