Standard Article

Heteroatom-substitued Dioxetanes and their Emerging Biomedical Applications

Peroxides (2014)

  1. GREGORY NKEPANG1,2,
  2. YOUNGJAE YOU1,2

Published Online: 28 APR 2014

DOI: 10.1002/9780470682531.pat0869

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

NKEPANG, G. and YOU, Y. 2014. Heteroatom-substitued Dioxetanes and their Emerging Biomedical Applications. Patai's Chemistry of Functional Groups. 1–29.

Author Information

  1. 1

    Department of Pharmaceutical Sciences, University of Oklahoma Health Sciences Center, Oklahoma City, USA

  2. 2

    Department of Chemistry and Biochemistry, University of Oklahoma, Norman, USA

Publication History

  1. Published Online: 28 APR 2014

Chemistry Terms

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Abstract

Heteroatom-substituted dioxetanes are one subclass of dioxetanes that have at least one heteroatom (such as O, S, N) at its two carbons of dioxetane structures. These are readily formed from the [2+2] cycloaddition reaction of heteroatom-substituted alkenes and singlet oxygen (1O2). Due to their unique characteristics, such as chemiluminescence and spontaneous cleavage, heteroatom-substituted dioxetanes have been used for a number of biomedical applications, for example biomedical analyses and light-controlled drug release. A number of review papers and book chapters have been published for the biomedical analyses of chemiluminescence. However, no comprehensive review or book chapter for the applications to light-controlled drug release have yet been published, although there have been very significant and interesting advances in the field in the last couple of years. In this chapter, we focus mainly on a new and exciting application of dioxetanes for light-controlled drug release. In the latter part of this section, we also introduce briefly another new interesting application of dioxetane chemistry for hydrogen peroxide (H2O2) imaging.

Keywords:

  • heteroatom-substitued dioxetanes;
  • visible and near infrared;
  • drug delivery;
  • photodynamic;
  • singlet oxygen;
  • alkenes;
  • biomedical applications;
  • drug release;
  • light-controlled;
  • hydrogen peroxide imaging

Featured Compounds

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  1. 1 - 74
Compound 55
Molecular Weight:718.0395
Molecular Formula:C40H80NO7P
InChIKey:PEWXKAOBUSBJLD-MCBGMKGZSA-N
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Compound 67c
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 51
Molecular Weight:316.3499
Molecular Formula:C21H16O3
InChIKey:ZSELHGRTZWWKTF-FOCLMDBBSA-N
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Compound 65
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 59
Molecular Weight:700.0672
Molecular Formula:C41H82NO5P
InChIKey:IDOCSMARKPJSBB-QAIJNKCPSA-N
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Compound 35
Molecular Weight:244.375
Molecular Formula:C14H12S2
InChIKey:UHGSEDVQATYWGI-VAWYXSNFSA-N
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Compound 76
Molecular Weight:120.147
Molecular Formula:C5H12O3
InChIKey:Not Available
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Compound 58
Molecular Weight:226.3981
Molecular Formula:C15H30O
InChIKey:XGQJZNCFDLXSIJ-UHFFFAOYSA-N
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Compound 18
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 52
Molecular Weight:330.3765
Molecular Formula:C22H18O3
InChIKey:QAQZVQPYALDQEL-FOCLMDBBSA-N
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Compound 19
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 49
Molecular Weight:332.416
Molecular Formula:C21H16O2S
InChIKey:RMJMTLGWFABDHB-FOCLMDBBSA-N
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Compound 69
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 36
Molecular Weight:99.1311
Molecular Formula:C5H9NO
InChIKey:PNLUGRYDUHRLOF-UHFFFAOYSA-N
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Compound 39
Molecular Weight:197.2325
Molecular Formula:C13H11NO
InChIKey:DNYZBFWKVMKMRM-UHFFFAOYSA-N
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Compound 23
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 32
Molecular Weight:254.347
Molecular Formula:C16H14OS
InChIKey:GZVBPNSXCWYLJU-UHFFFAOYSA-N
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Compound 70
Molecular Weight:1005.0702
Molecular Formula:C28H19I4NO8
InChIKey:XFBUMNSHANSEHI-UHFFFAOYSA-N
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Compound 64
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10
Molecular Weight:204.2634
Molecular Formula:C10H20O4
InChIKey:WQNVSQDMXNPYNW-UHFFFAOYSA-N
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Compound 42
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 61
Molecular Weight:256.4241
Molecular Formula:C16H32O2
InChIKey:IPCSVZSSVZVIGE-UHFFFAOYSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 67
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-QXMHVHEDSA-N
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Compound 9
Molecular Weight:160.2108
Molecular Formula:C8H16O3
InChIKey:SKDYTPBHOGOVME-UHFFFAOYSA-N
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Compound 31
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:HIZVCIIORGCREW-UHFFFAOYSA-N
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Compound 41
Molecular Weight:119.1638
Molecular Formula:C8H9N
InChIKey:HXTGGPKOEKKUQO-VQHVLOKHSA-N
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Compound 53
Molecular Weight:247.356
Molecular Formula:C14H17NOS
InChIKey:ZLBJNRQDXZMPNT-FMIVXFBMSA-N
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Compound 60
Molecular Weight:255.2484
Molecular Formula:C9H22NO5P
InChIKey:OEALVPHVACVCMD-UHFFFAOYSA-N
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Compound 30
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:BUDQDWGNQVEFAC-UHFFFAOYSA-N
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Compound 46
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 48
Molecular Weight:307.3862
Molecular Formula:C20H21NO2
InChIKey:XFYAKFAQWBXRGT-DTQAZKPQSA-N
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Compound 67b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 63
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 56
Molecular Weight:495.6301
Molecular Formula:C24H50NO7P
InChIKey:NEGQHKSYEYVFTD-HSZRJFAPSA-N
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Compound 40
Molecular Weight:211.2591
Molecular Formula:C14H13NO
InChIKey:MFZNRFQCOCWADL-UHFFFAOYSA-N
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Compound 6
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:VTGIVYVOVVQLRL-UHFFFAOYSA-N
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Compound 67a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 29
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:XDHOEHJVXXTEDV-HWKANZROSA-N
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Compound 33
Molecular Weight:212.31
Molecular Formula:C14H12S
InChIKey:NCSYOCXYJXZCGQ-VAWYXSNFSA-N
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Compound 67f
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 38
Molecular Weight:176.2151
Molecular Formula:C10H12N2O
InChIKey:BWERGHWJEBQNQV-SOFGYWHQSA-N
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Compound 17
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 47
Molecular Weight:295.3755
Molecular Formula:C19H21NO2
InChIKey:MCULCDSQHHPXCK-CCEZHUSRSA-N
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Compound 37
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:QPWSKIGAQZAJKS-SNAWJCMRSA-N
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Compound 54
Molecular Weight:230.3055
Molecular Formula:C14H18N2O
InChIKey:QKMSYRRAQOSEKN-FMIVXFBMSA-N
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Compound 15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 25
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 70
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 73
Molecular Weight:848.04
Molecular Formula:C53H41N3O4S2
InChIKey:IZMRVKSZHLUAPB-BLQFNPDESA-N
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Compound 50
Molecular Weight:346.442
Molecular Formula:C22H18O2S
InChIKey:XNOHLFTVXLVCRC-FOCLMDBBSA-N
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Compound 7
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:HDUOBOAWDSZFTJ-AATRIKPKSA-N
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Compound 8
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:HDUOBOAWDSZFTJ-WAYWQWQTSA-N
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Compound 5
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:FJKIXWOMBXYWOQ-UHFFFAOYSA-N
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Compound 21
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 22
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 45
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 72
Molecular Weight:1188.41
Molecular Formula:C73H61N3O9S2
InChIKey:UPWIZHCISBYYMV-YSTXLEOHSA-N
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Compound 34
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:BMUKUQUGQLFWDZ-QXMHVHEDSA-N
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Compound 26
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 69
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 68
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 74
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 67e
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 75
Molecular Weight:308.2833
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 67d
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 27
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:Not Available
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  1. 1 - 74