Nitrosoamphetamine binding to myoglobin and hemoglobin: Crystal structure of the H64A myoglobin-nitrosoamphetamine adduct

Bing Wang, Samantha M. Powell, Ye Guan, Nan Xu, Leonard M. Thomas, George B. Richter-Addo

Research output: Contribution to journalArticle

Abstract

N-hydroxyamphetamine (AmphNHOH) is an oxidative metabolite of amphetamine and methamphetamine. It is known to form inhibitory complexes upon binding to heme proteins. However, its interactions with myoglobin (Mb) and hemoglobin (Hb) have not been reported. We demonstrate that the reactions of AmphNHOH with ferric Mb and Hb generate the respective heme-nitrosoamphetamine derivatives characterized by UV-vis spectroscopy. We have determined the X-ray crystal structure of the H64A Mb-nitrosoamphetamine complex to 1.73 Å resolution. The structure reveals the N-binding of the nitroso-d-amphetamine isomer, with no significant H-bonding interactions between the ligand and the distal pocket amino acid residues.

Original languageEnglish (US)
Pages (from-to)26-29
Number of pages4
JournalNitric Oxide - Biology and Chemistry
Volume67
DOIs
StatePublished - Jul 1 2017

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Myoglobin
Hemoglobins
Crystal structure
Hemeproteins
Dextroamphetamine
Methamphetamine
Amphetamine
Metabolites
Ultraviolet spectroscopy
Heme
Isomers
Spectrum Analysis
X-Rays
Ligands
Derivatives
Amino Acids
X rays

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physiology
  • Clinical Biochemistry
  • Cancer Research

Cite this

Wang, Bing ; Powell, Samantha M. ; Guan, Ye ; Xu, Nan ; Thomas, Leonard M. ; Richter-Addo, George B. / Nitrosoamphetamine binding to myoglobin and hemoglobin : Crystal structure of the H64A myoglobin-nitrosoamphetamine adduct. In: Nitric Oxide - Biology and Chemistry. 2017 ; Vol. 67. pp. 26-29.
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abstract = "N-hydroxyamphetamine (AmphNHOH) is an oxidative metabolite of amphetamine and methamphetamine. It is known to form inhibitory complexes upon binding to heme proteins. However, its interactions with myoglobin (Mb) and hemoglobin (Hb) have not been reported. We demonstrate that the reactions of AmphNHOH with ferric Mb and Hb generate the respective heme-nitrosoamphetamine derivatives characterized by UV-vis spectroscopy. We have determined the X-ray crystal structure of the H64A Mb-nitrosoamphetamine complex to 1.73 {\AA} resolution. The structure reveals the N-binding of the nitroso-d-amphetamine isomer, with no significant H-bonding interactions between the ligand and the distal pocket amino acid residues.",
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Nitrosoamphetamine binding to myoglobin and hemoglobin : Crystal structure of the H64A myoglobin-nitrosoamphetamine adduct. / Wang, Bing; Powell, Samantha M.; Guan, Ye; Xu, Nan; Thomas, Leonard M.; Richter-Addo, George B.

In: Nitric Oxide - Biology and Chemistry, Vol. 67, 01.07.2017, p. 26-29.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Nitrosoamphetamine binding to myoglobin and hemoglobin

T2 - Crystal structure of the H64A myoglobin-nitrosoamphetamine adduct

AU - Wang, Bing

AU - Powell, Samantha M.

AU - Guan, Ye

AU - Xu, Nan

AU - Thomas, Leonard M.

AU - Richter-Addo, George B.

PY - 2017/7/1

Y1 - 2017/7/1

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AB - N-hydroxyamphetamine (AmphNHOH) is an oxidative metabolite of amphetamine and methamphetamine. It is known to form inhibitory complexes upon binding to heme proteins. However, its interactions with myoglobin (Mb) and hemoglobin (Hb) have not been reported. We demonstrate that the reactions of AmphNHOH with ferric Mb and Hb generate the respective heme-nitrosoamphetamine derivatives characterized by UV-vis spectroscopy. We have determined the X-ray crystal structure of the H64A Mb-nitrosoamphetamine complex to 1.73 Å resolution. The structure reveals the N-binding of the nitroso-d-amphetamine isomer, with no significant H-bonding interactions between the ligand and the distal pocket amino acid residues.

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