Improved Synthesis of 5-Nitrohomovanillic Acid and 6-Nitrohomovanillic Acid as Probes for Metabolism Studies of Endothelium-Derived Dopamines: Identification in Human Amniotic Fluid
6-Nitrodopamine is an endogenous catecholamine responsible for numerous biological activities. Here, an improved method for the synthesis of both 6-nitrohomovanillic acid (6-NHVA) and its regioisomer 5-nitrohomovanillic acid (5-NHVA) is reported. The developed one-step synthetic procedures ensured the efficient preparation of the target compounds in good yields. Comprehensive structural characterization was achieved through one- and two-dimensional NMR studies and by high-resolution mass spectrometry (HR-MS/MS). The presence of both substances was identified in human amniotic fluid by LC-MS/MS.
Authors
- Vincenzo Santagada (ORCID: https://orcid.org/0000-0001-8377-8990)
- Ferdinando Fiorino (ORCID: https://orcid.org/0000-0001-7357-5751)
- Beatrice Ulloa Severino (ORCID: https://orcid.org/0000-0002-3887-8869)
- Paolo Luciano
- Carmela Dell’Aversano (ORCID: https://orcid.org/0000-0001-8337-3029)
- Francesco Frecentese (ORCID: https://orcid.org/0000-0001-8821-2937)
- Elisa Perissutti (ORCID: https://orcid.org/0000-0002-1754-1191)
- Antonia Scognamiglio (ORCID: https://orcid.org/0000-0002-4282-2788)
- Elisa Magli (ORCID: https://orcid.org/0000-0002-9930-9467)
- Rosa Sparaco (ORCID: https://orcid.org/0009-0003-4221-5560)
- Angela Corvino (ORCID: https://orcid.org/0000-0002-0617-156X)
- Giuseppe Caliendo (ORCID: https://orcid.org/0000-0002-5098-6045)
- Gilberto De Nucci (ORCID: https://orcid.org/0000-0002-4346-7941)
- Alex Henrique Miller (ORCID: https://orcid.org/0000-0001-8269-850X)
- Pierfrancesco Cinque
- Giorgia Andreozzi
- Stefania Vertuccio
Institutions
- Universidade Estadual de Campinas (UNICAMP) (BR)
- Federico II University Hospital (IT)
- Faculdade São Leopoldo Mandic (BR)
- University of Naples Federico II (IT)
Publication Details
- Journal
- Molecules
- Published
- 2025-10-15
- DOI
- https://doi.org/10.3390/molecules30204096
- Citations
- 1
- Primary Topic
- Nitric Oxide and Endothelin Effects
- Type
- article
- Field-Weighted Citation Impact
- 1.16