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.
N1 - Funding Information:
We are grateful to the National Science Foundation (Grants CHE-1213674 and CHE-1566509 to GBR-A) for funding for this work. This paper reports data obtained in the University of Oklahoma Macromolecular Crystallography Laboratory, which is supported, in part, by an Institutional Development Award (IDeA) from the National Institute of General Medical Sciences of the National Institutes of Health under grant number P20GM103640, and by a Major Research Instrumentation award from the National Science Foundation under award number 092269. We also thank Dr. Jun (Eva) Yi for her assistance with hemoglobin isolation and purification protocols, and Dr. Paul Sims for assistance with the spectral deconvolution analysis.
Publisher Copyright:
© 2017 Elsevier Inc.
PY - 2017/7/1
Y1 - 2017/7/1
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=85018315520&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85018315520&partnerID=8YFLogxK
U2 - 10.1016/j.niox.2017.04.012
DO - 10.1016/j.niox.2017.04.012
M3 - Article
C2 - 28450187
AN - SCOPUS:85018315520
SN - 1089-8603
VL - 67
SP - 26
EP - 29
JO - Nitric Oxide - Biology and Chemistry
JF - Nitric Oxide - Biology and Chemistry
ER -