Chemistry of the Nitric Oxide-Releasing Diazeniumdiolate (“Nitrosohydroxylamine”) Functional Group and Its Oxygen-Substituted Derivatives
Abstract
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChemistry of the Nitric Oxide-Releasing Diazeniumdiolate (“Nitrosohydroxylamine”) Functional Group and Its Oxygen-Substituted DerivativesJoseph A. Hrabie and Larry K. KeeferView Author Information Intramural Research Support Program, SAIC Frederick, National Cancer Institute at Frederick, Frederick, Maryland 21702, and Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, Maryland 21702 Cite this: Chem. Rev. 2002, 102, 4, 1135–1154Publication Date (Web):February 9, 2002Publication History Received20 July 2001Published online9 February 2002Published inissue 1 April 2002https://doi.org/10.1021/cr000028tCopyright © 2002 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views5988Altmetric-Citations385LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (274 KB) Get e-AlertsSUBJECTS:Anions,Functional groups,Oxygen,Reaction products,Salts Get e-Alerts
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
NONOates can also release NO through thermal, photochemical, or enzymatic reactions.
“NONOates can also release NO via thermal, photochemical or enzymatically (e.g., esterase) reactions.136,148”
From Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO) (2016) · cites this paper as [136]
NONOate half-lives range from 1.8 s for PROLI/NO to 20 h for DETA/NO.
“For example, half-lives can range from the shortest reported t1/2 of 1.8 s for the diazeniumdiolated amino acid proline (PROLI/NO) to t1/2 of 20 h for diethylenetriamine (DETA/NO).135,136”
From Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO) (2016) · cites this paper as [136]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Cites
Fukuto, J. M., Hobbs, A. J., & Ignarro, L. J. (1993) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.1993.2307 · Cited by 147 · see citing works
Saavedra, J. E., Booth, M. N., Hrabie, J. A., Davies, K. M., & Keefer, L. K. (1999) · The Journal of Organic Chemistry · doi:10.1021/jo9901539 · Cited by 60 · see citing works
Self-citation
Flagged first, then by citations
Cited by
Sorted by citations
Nitric oxide release: Part I. Macromolecular scaffolds
Riccio, D. A., & Schoenfisch, M. H. (2012) · Chemical Society Reviews · doi:10.1039/c2cs15272j · Cited by 475 · see citing works
Biocompatible Materials for Continuous Glucose Monitoring Devices
Nichols, S. P., Koh, A., Storm, W. L., Shin, J. H., & Schoenfisch, M. H. (2013) · Chemical Reviews · doi:10.1021/cr300387j · Cited by 347 · see citing works
Hong, S., Kim, J., Na, Y. S., Park, J., Kim, S., Singha, K., Im, G., Han, D., Kim, W. J., & Lee, H. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201301646 · Cited by 257 · see citing works
Wo, Y., Brisbois, E. J., Bartlett, R. H., & Meyerhoff, M. E. (2016) · Biomaterials Science · doi:10.1039/c6bm00271d · Cited by 251 · see citing works
Nitric oxide–releasing macromolecular scaffolds for antibacterial applications
Yang, L., Feura, E. S., Ahonen, M. J. R., & Schoenfisch, M. H. (2018) · Advanced Healthcare Materials · doi:10.1002/adhm.201800155 · Cited by 218 · see citing works
Polymer‐Based Nitric Oxide Therapies: Recent Insights for Biomedical Applications
Jen, M. C., Serrano, M. C., van Lith, R., & Ameer, G. A. (2012) · Advanced Functional Materials · doi:10.1002/adfm.201101707 · Cited by 194 · see citing works
Nitric Oxide Donors for Cardiovascular Implant Applications
Naghavi, N., de Mel, A., Alavijeh, O. S., Cousins, B. G., & Seifalian, A. M. (2013) · Small · doi:10.1002/smll.201200458 · Cited by 188 · see citing works
Zhang, H., Annich, G. M., Miskulin, J., Stankiewicz, K., Osterholzer, K., Merz, S. I., Bartlett, R. H., & Meyerhoff, M. E. (2003) · Journal of the American Chemical Society · doi:10.1021/ja0291538 · Cited by 176 · see citing works
Dendrimers as a Scaffold for Nitric Oxide Release
Stasko, N. A., & Schoenfisch, M. H. (2006) · Journal of the American Chemical Society · doi:10.1021/ja060875z · Cited by 157 · see citing works
Water-Soluble Nitric Oxide-Releasing Gold Nanoparticles
Polizzi, M. A., Stasko, N. A., & Schoenfisch, M. H. (2007) · Langmuir · doi:10.1021/la0633841 · Cited by 133 · see citing works
Zhou, Z., & Meyerhoff, M. E. (2005) · Biomaterials · doi:10.1016/j.biomaterials.2005.04.046 · Cited by 115 · see citing works
Kang, Y., Kim, J., Park, J., Lee, Y. M., Saravanakumar, G., Park, K. M., Choi, W., Kim, K., Lee, E., Kim, C., et al. (2019) · Biomaterials · doi:10.1016/j.biomaterials.2019.119297 · Cited by 108 · see citing works
Mechanisms of the interaction of nitroxyl with mitochondria
SHIVA, S., CRAWFORD, J. H., RAMACHANDRAN, A., CEASER, E. K., HILLSON, T., BROOKES, P. S., PATEL, R. P., & DARLEY-USMAR, V. M. (2004) · Biochemical Journal · doi:10.1042/bj20031758 · Cited by 78 · see citing works
The effect of nitric oxide surface flux on the foreign body response to subcutaneous implants
Nichols, S. P., Koh, A., Brown, N. L., Rose, M. B., Sun, B., Slomberg, D. L., Riccio, D. A., Klitzman, B., & Schoenfisch, M. H. (2012) · Biomaterials · doi:10.1016/j.biomaterials.2012.05.053 · Cited by 67 · see citing works
Wu, Y., & Meyerhoff, M. E. (2008) · Talanta · doi:10.1016/j.talanta.2007.06.022 · Cited by 65 · see citing works
Privett, B. J., Nutz, S. T., & Schoenfisch, M. H. (2010) · Biofouling · doi:10.1080/08927014.2010.534552 · Cited by 45 · see citing works
Vavra, A. K., Havelka, G. E., Martinez, J., Lee, V. R., Fu, B., Jiang, Q., Keefer, L. K., & Kibbe, M. R. (2011) · Nitric Oxide · doi:10.1016/j.niox.2011.04.013 · Cited by 24 · see citing works
Self-citationPreparation and characterization of diazeniumdiolate releasing ethylcellulose films
Wan, A., Gao, Q., & Li, H. (2009) · Journal of Materials Science: Materials in Medicine · doi:10.1007/s10856-008-3511-5 · Cited by 14 · see citing works
- Authors
- Hrabie, J. A., & Keefer, L. K.
- Affiliations
- National Cancer Institute (US)
- Venue
- Chemical Reviews
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-02-09
- Volume
- 102
- Issue
- 4
- Pages
- 1135-1154
- ISSN
- 0009-2665 (ISSN-L)
- 1520-6890
- OpenAlex
- W1993482433
- Cited by
- 466
- References
- 2
- Citations by year
- 2026: 14 · 2025: 13 · 2024: 15 · 2023: 22 · 2022: 24 · 2021: 21 · 2020: 36 · 2019: 19 · 2018: 20 · 2017: 28 · 2016: 30 · 2015: 16 · 2014: 20 · 2013: 18 · 2012: 20
- FWCI
- 1.74
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemical Reviews (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institutes of Health (n01co12400-79-0-22)
- National Cancer Institute (N01CO12400)
- Topics
- Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
- Physical Sciences › Chemistry › Organic Chemistry › Structural and Chemical Analysis of Organic and Inorganic Compounds
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
- Keywords
- nitric oxide donors, functional group chemistry, nitric oxide release, reaction products, salt
- MeSH terms
- Azo Compounds, Nitric Oxide, Terminology as Topic, Oxygen, Nitric Oxide Donors
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
