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Volumn 14, Issue 10, 2017, Pages 3248-3257

Enhanced Brain Delivery of 2-(Phosphonomethyl)pentanedioic Acid Following Intranasal Administration of Its γ-Substituted Ester Prodrugs

Author keywords

2 PMPA; glutamate carboxypeptidase II; intranasal; neurological disease; pharmacokinetics; prodrugs

Indexed keywords

2 (PHOSPHONOMETHYL)PENTANEDIOIC ACID; ESTER DERIVATIVE; GAMMA (4 ACETOXYBENZYL) 2 (PHOSPHONOMETHYL)PENTANEDIOC ACID; PRODRUG; UNCLASSIFIED DRUG; 2-(PHOSPHONOMETHYL)PENTANEDIOIC ACID; ESTER; GLUTAMATE CARBOXYPEPTIDASE II; NEUROPROTECTIVE AGENT; ORGANOPHOSPHORUS COMPOUND;

EID: 85030650975     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/acs.molpharmaceut.7b00231     Document Type: Article
Times cited : (10)

References (39)
  • 1
    • 33645310629 scopus 로고    scopus 로고
    • Structure of glutamate carboxypeptidase II, a drug target in neuronal damage and prostate cancer
    • Mesters, J. R.; Barinka, C.; Li, W.; Tsukamoto, T.; Majer, P.; Slusher, B. S.; Konvalinka, J.; Hilgenfeld, R. Structure of glutamate carboxypeptidase II, a drug target in neuronal damage and prostate cancer EMBO J. 2006, 25 (6) 1375-84 10.1038/sj.emboj.7600969
    • (2006) EMBO J. , vol.25 , Issue.6 , pp. 1375-1384
    • Mesters, J.R.1    Barinka, C.2    Li, W.3    Tsukamoto, T.4    Majer, P.5    Slusher, B.S.6    Konvalinka, J.7    Hilgenfeld, R.8
  • 3
    • 77956798187 scopus 로고    scopus 로고
    • Endogenous N-acetylaspartylglutamate (NAAG) inhibits synaptic plasticity/transmission in the amygdala in a mouse inflammatory pain model
    • Adedoyin, M. O.; Vicini, S.; Neale, J. H. Endogenous N-acetylaspartylglutamate (NAAG) inhibits synaptic plasticity/transmission in the amygdala in a mouse inflammatory pain model Mol. Pain 2010, 6, 60 10.1186/1744-8069-6-60
    • (2010) Mol. Pain , vol.6 , pp. 60
    • Adedoyin, M.O.1    Vicini, S.2    Neale, J.H.3
  • 6
    • 3242750466 scopus 로고    scopus 로고
    • Antinociceptive effects of N-acetylaspartylglutamate (NAAG) peptidase inhibitors ZJ-11, ZJ-17 and ZJ-43 in the rat formalin test and in the rat neuropathic pain model
    • Yamamoto, T.; Hirasawa, S.; Wroblewska, B.; Grajkowska, E.; Zhou, J.; Kozikowski, A.; Wroblewski, J.; Neale, J. H. Antinociceptive effects of N-acetylaspartylglutamate (NAAG) peptidase inhibitors ZJ-11, ZJ-17 and ZJ-43 in the rat formalin test and in the rat neuropathic pain model Eur. J. Neurosci. 2004, 20 (2) 483-94 10.1111/j.1460-9568.2004.03504.x
    • (2004) Eur. J. Neurosci. , vol.20 , Issue.2 , pp. 483-494
    • Yamamoto, T.1    Hirasawa, S.2    Wroblewska, B.3    Grajkowska, E.4    Zhou, J.5    Kozikowski, A.6    Wroblewski, J.7    Neale, J.H.8
  • 7
    • 0035863534 scopus 로고    scopus 로고
    • Inhibition of spinal N-acetylated-alpha-linked acidic dipeptidase produces an antinociceptive effect in the rat formalin test
    • Yamamoto, T.; Nozaki-Taguchi, N.; Sakashita, Y.; Inagaki, T. Inhibition of spinal N-acetylated-alpha-linked acidic dipeptidase produces an antinociceptive effect in the rat formalin test Neuroscience 2001, 102 (2) 473-9 10.1016/S0306-4522(00)00502-9
    • (2001) Neuroscience , vol.102 , Issue.2 , pp. 473-479
    • Yamamoto, T.1    Nozaki-Taguchi, N.2    Sakashita, Y.3    Inagaki, T.4
  • 8
    • 0344441376 scopus 로고    scopus 로고
    • Effects of GCP-II inhibition on responses of dorsal horn neurones after inflammation and neuropathy: An electrophysiological study in the rat
    • Carpenter, K. J.; Sen, S.; Matthews, E. A.; Flatters, S. L.; Wozniak, K. M.; Slusher, B. S.; Dickenson, A. H. Effects of GCP-II inhibition on responses of dorsal horn neurones after inflammation and neuropathy: an electrophysiological study in the rat Neuropeptides 2003, 37 (5) 298-306 10.1016/j.npep.2003.08.001
    • (2003) Neuropeptides , vol.37 , Issue.5 , pp. 298-306
    • Carpenter, K.J.1    Sen, S.2    Matthews, E.A.3    Flatters, S.L.4    Wozniak, K.M.5    Slusher, B.S.6    Dickenson, A.H.7
  • 9
    • 33748052336 scopus 로고    scopus 로고
    • The preventive and therapeutic effects of GCPII (NAALADase) inhibition on painful and sensory diabetic neuropathy
    • Zhang, W.; Murakawa, Y.; Wozniak, K. M.; Slusher, B.; Sima, A. A. The preventive and therapeutic effects of GCPII (NAALADase) inhibition on painful and sensory diabetic neuropathy J. Neurol. Sci. 2006, 247 (2) 217-23 10.1016/j.jns.2006.05.052
    • (2006) J. Neurol. Sci. , vol.247 , Issue.2 , pp. 217-223
    • Zhang, W.1    Murakawa, Y.2    Wozniak, K.M.3    Slusher, B.4    Sima, A.A.5
  • 10
    • 0037082872 scopus 로고    scopus 로고
    • GCPII (NAALADase) inhibition prevents long-term diabetic neuropathy in type 1 diabetic BB/Wor rats
    • Zhang, W.; Slusher, B.; Murakawa, Y.; Wozniak, K. M.; Tsukamoto, T.; Jackson, P. F.; Sima, A. A. GCPII (NAALADase) inhibition prevents long-term diabetic neuropathy in type 1 diabetic BB/Wor rats J. Neurol. Sci. 2002, 194 (1) 21-8 10.1016/S0022-510X(01)00670-0
    • (2002) J. Neurol. Sci. , vol.194 , Issue.1 , pp. 21-28
    • Zhang, W.1    Slusher, B.2    Murakawa, Y.3    Wozniak, K.M.4    Tsukamoto, T.5    Jackson, P.F.6    Sima, A.A.7
  • 11
    • 84858001721 scopus 로고    scopus 로고
    • MGluR3 and not mGluR2 receptors mediate the efficacy of NAAG peptidase inhibitor in validated model of schizophrenia
    • Olszewski, R. T.; Bzdega, T.; Neale, J. H. mGluR3 and not mGluR2 receptors mediate the efficacy of NAAG peptidase inhibitor in validated model of schizophrenia Schizophrenia research 2012, 136 (1-3) 160-1 10.1016/j.schres.2012.01.007
    • (2012) Schizophrenia Research , vol.136 , Issue.13 , pp. 160-161
    • Olszewski, R.T.1    Bzdega, T.2    Neale, J.H.3
  • 12
    • 0033766443 scopus 로고    scopus 로고
    • NAALADase inhibition reduces alcohol consumption in the alcohol-preferring (P) line of rats
    • McKinzie, D. L.; Li, T. K.; McBride, W. J.; Slusher, B. S. NAALADase inhibition reduces alcohol consumption in the alcohol-preferring (P) line of rats Addict. Biol. 2000, 5 (4) 411-6 10.1111/j.1369-1600.2000.tb00209.x
    • (2000) Addict. Biol. , vol.5 , Issue.4 , pp. 411-416
    • McKinzie, D.L.1    Li, T.K.2    McBride, W.J.3    Slusher, B.S.4
  • 13
    • 0033779648 scopus 로고    scopus 로고
    • Modulation of behavioral sensitization to cocaine by NAALADase inhibition
    • Shippenberg, T. S.; Rea, W.; Slusher, B. S. Modulation of behavioral sensitization to cocaine by NAALADase inhibition Synapse (Hoboken, NJ, U. S.) 2000, 38 (2) 161-6 10.1002/1098-2396(200011)38:2<161::AID-SYN7>3.0.CO;2-G
    • (2000) Synapse (Hoboken, NJ, U. S.) , vol.38 , Issue.2 , pp. 161-166
    • Shippenberg, T.S.1    Rea, W.2    Slusher, B.S.3
  • 14
    • 71549170805 scopus 로고    scopus 로고
    • N-acetylaspartylglutamate (NAAG) inhibits intravenous cocaine self-administration and cocaine-enhanced brain-stimulation reward in rats
    • Xi, Z. X.; Kiyatkin, M.; Li, X.; Peng, X. Q.; Wiggins, A.; Spiller, K.; Li, J.; Gardner, E. L. N-acetylaspartylglutamate (NAAG) inhibits intravenous cocaine self-administration and cocaine-enhanced brain-stimulation reward in rats Neuropharmacology 2010, 58 (1) 304-13 10.1016/j.neuropharm.2009.06.016
    • (2010) Neuropharmacology , vol.58 , Issue.1 , pp. 304-313
    • Xi, Z.X.1    Kiyatkin, M.2    Li, X.3    Peng, X.Q.4    Wiggins, A.5    Spiller, K.6    Li, J.7    Gardner, E.L.8
  • 15
    • 84987936728 scopus 로고    scopus 로고
    • Blocking glutamate carboxypeptidase II inhibits glutamate excitotoxicity and regulates immune responses in experimental autoimmune encephalomyelitis
    • Ha, D.; Bing, S. J.; Ahn, G.; Kim, J.; Cho, J.; Kim, A.; Herath, K. H.; Yu, H. S.; Jo, S. A.; Cho, I. H.; Jee, Y. Blocking glutamate carboxypeptidase II inhibits glutamate excitotoxicity and regulates immune responses in experimental autoimmune encephalomyelitis FEBS J. 2016, 283 (18) 3438-56 10.1111/febs.13816
    • (2016) FEBS J. , vol.283 , Issue.18 , pp. 3438-3456
    • Ha, D.1    Bing, S.J.2    Ahn, G.3    Kim, J.4    Cho, J.5    Kim, A.6    Herath, K.H.7    Yu, H.S.8    Jo, S.A.9    Cho, I.H.10    Jee, Y.11
  • 16
    • 84959472444 scopus 로고    scopus 로고
    • Dose-dependent inhibition of GCPII to prevent and treat cognitive impairment in the EAE model of multiple sclerosis
    • Hollinger, K. R.; Alt, J.; Riehm, A. M.; Slusher, B. S.; Kaplin, A. I. Dose-dependent inhibition of GCPII to prevent and treat cognitive impairment in the EAE model of multiple sclerosis Brain Res. 2016, 1635, 105-12 10.1016/j.brainres.2016.01.035
    • (2016) Brain Res. , vol.1635 , pp. 105-112
    • Hollinger, K.R.1    Alt, J.2    Riehm, A.M.3    Slusher, B.S.4    Kaplin, A.I.5
  • 18
    • 84864740583 scopus 로고    scopus 로고
    • NAAG peptidase inhibitor reduces cellular damage in a model of TBI with secondary hypoxia
    • Feng, J. F.; Gurkoff, G. G.; Van, K. C.; Song, M.; Lowe, D. A.; Zhou, J.; Lyeth, B. G. NAAG peptidase inhibitor reduces cellular damage in a model of TBI with secondary hypoxia Brain Res. 2012, 1469, 144-52 10.1016/j.brainres.2012.06.021
    • (2012) Brain Res. , vol.1469 , pp. 144-152
    • Feng, J.F.1    Gurkoff, G.G.2    Van, K.C.3    Song, M.4    Lowe, D.A.5    Zhou, J.6    Lyeth, B.G.7
  • 20
    • 79960558038 scopus 로고    scopus 로고
    • N-acetylaspartylglutamate is an agonist at mGluR(3) in vivo and in vitro
    • Neale, J. H. N-acetylaspartylglutamate is an agonist at mGluR(3) in vivo and in vitro J. Neurochem. 2011, 119 (5) 891-5 10.1111/j.1471-4159.2011.07380.x
    • (2011) J. Neurochem. , vol.119 , Issue.5 , pp. 891-895
    • Neale, J.H.1
  • 21
    • 84963558348 scopus 로고    scopus 로고
    • Glutamate carboxypeptidase II gene knockout attenuates oxidative stress and cortical apoptosis after traumatic brain injury
    • Cao, Y.; Gao, Y.; Xu, S.; Bao, J.; Lin, Y.; Luo, X.; Wang, Y.; Luo, Q.; Jiang, J.; Neale, J. H.; Zhong, C. Glutamate carboxypeptidase II gene knockout attenuates oxidative stress and cortical apoptosis after traumatic brain injury BMC Neurosci. 2016, 17, 15 10.1186/s12868-016-0251-1
    • (2016) BMC Neurosci. , vol.17 , pp. 15
    • Cao, Y.1    Gao, Y.2    Xu, S.3    Bao, J.4    Lin, Y.5    Luo, X.6    Wang, Y.7    Luo, Q.8    Jiang, J.9    Neale, J.H.10    Zhong, C.11
  • 22
    • 84857589525 scopus 로고    scopus 로고
    • Glutamate carboxypeptidase II in diagnosis and treatment of neurologic disorders and prostate cancer
    • Barinka, C.; Rojas, C.; Slusher, B.; Pomper, M. Glutamate carboxypeptidase II in diagnosis and treatment of neurologic disorders and prostate cancer Curr. Med. Chem. 2012, 19 (6) 856-70 10.2174/092986712799034888
    • (2012) Curr. Med. Chem. , vol.19 , Issue.6 , pp. 856-870
    • Barinka, C.1    Rojas, C.2    Slusher, B.3    Pomper, M.4
  • 23
    • 84962173335 scopus 로고    scopus 로고
    • Discovery of Orally Available Prodrugs of the Glutamate Carboxypeptidase II (GCPII) Inhibitor 2-Phosphonomethylpentanedioic Acid (2-PMPA)
    • Majer, P.; Jancarik, A.; Krecmerova, M.; Tichy, T.; Tenora, L.; Wozniak, K.; Wu, Y.; Pommier, E.; Ferraris, D.; Rais, R.; Slusher, B. S. Discovery of Orally Available Prodrugs of the Glutamate Carboxypeptidase II (GCPII) Inhibitor 2-Phosphonomethylpentanedioic Acid (2-PMPA) J. Med. Chem. 2016, 59, 2810-9 10.1021/acs.jmedchem.6b00062
    • (2016) J. Med. Chem. , vol.59 , pp. 2810-2819
    • Majer, P.1    Jancarik, A.2    Krecmerova, M.3    Tichy, T.4    Tenora, L.5    Wozniak, K.6    Wu, Y.7    Pommier, E.8    Ferraris, D.9    Rais, R.10    Slusher, B.S.11
  • 24
    • 85018235686 scopus 로고    scopus 로고
    • Selective CNS Uptake of the GCP-II Inhibitor 2-PMPA following Intranasal Administration
    • Rais, R.; Wozniak, K.; Wu, Y.; Niwa, M.; Stathis, M.; Alt, J.; Giroux, M.; Sawa, A.; Rojas, C.; Slusher, B. S. Selective CNS Uptake of the GCP-II Inhibitor 2-PMPA following Intranasal Administration PLoS One 2015, 10 (7) e0131861 10.1371/journal.pone.0131861
    • (2015) PLoS One , vol.10 , Issue.7 , pp. e0131861
    • Rais, R.1    Wozniak, K.2    Wu, Y.3    Niwa, M.4    Stathis, M.5    Alt, J.6    Giroux, M.7    Sawa, A.8    Rojas, C.9    Slusher, B.S.10
  • 26
  • 27
    • 77949833508 scopus 로고    scopus 로고
    • Intranasal delivery to the central nervous system: Mechanisms and experimental considerations
    • Dhuria, S. V.; Hanson, L. R.; Frey, W. H., 2nd Intranasal delivery to the central nervous system: mechanisms and experimental considerations J. Pharm. Sci. 2010, 99 (4) 1654-73 10.1002/jps.21924
    • (2010) J. Pharm. Sci. , vol.99 , Issue.4 , pp. 1654-1673
    • Dhuria, S.V.1    Hanson, L.R.2    Frey, W.H.3
  • 28
    • 0037131338 scopus 로고    scopus 로고
    • Facile synthesis of alpha-substituted acrylate esters
    • Hin, B.; Majer, P.; Tsukamoto, T. Facile synthesis of alpha-substituted acrylate esters J. Org. Chem. 2002, 67 (21) 7365-8 10.1021/jo026101s
    • (2002) J. Org. Chem. , vol.67 , Issue.21 , pp. 7365-7368
    • Hin, B.1    Majer, P.2    Tsukamoto, T.3
  • 29
    • 0036488137 scopus 로고    scopus 로고
    • Substrate specificity, inhibition and enzymological analysis of recombinant human glutamate carboxypeptidase II
    • Barinka, C.; Rinnova, M.; Sacha, P.; Rojas, C.; Majer, P.; Slusher, B. S.; Konvalinka, J. Substrate specificity, inhibition and enzymological analysis of recombinant human glutamate carboxypeptidase II J. Neurochem. 2002, 80 (3) 477-87 10.1046/j.0022-3042.2001.00715.x
    • (2002) J. Neurochem. , vol.80 , Issue.3 , pp. 477-487
    • Barinka, C.1    Rinnova, M.2    Sacha, P.3    Rojas, C.4    Majer, P.5    Slusher, B.S.6    Konvalinka, J.7
  • 30
    • 0023761465 scopus 로고
    • Testing for the equality of area under the curves when using destructive measurement techniques
    • Bailer, A. J. Testing for the equality of area under the curves when using destructive measurement techniques J. Pharmacokinet. Biopharm. 1988, 16 (3) 303-9 10.1007/BF01062139
    • (1988) J. Pharmacokinet. Biopharm. , vol.16 , Issue.3 , pp. 303-309
    • Bailer, A.J.1
  • 31
    • 0028859126 scopus 로고
    • Applying Bailer's Method for AUC Confidence Intervals to Sparse Sampling
    • Nedelman, J. R.; Gibiansky, E.; Lau, D. T. W. Applying Bailer's Method for AUC Confidence Intervals to Sparse Sampling Pharm. Res. 1995, 12 (1) 124-128 10.1023/A:1016255124336
    • (1995) Pharm. Res. , vol.12 , Issue.1 , pp. 124-128
    • Nedelman, J.R.1    Gibiansky, E.2    Lau, D.T.W.3
  • 32
    • 0027359671 scopus 로고
    • Estimation of variance for AUC in animal studies
    • Yuan, J. Estimation of variance for AUC in animal studies J. Pharm. Sci. 1993, 82 (7) 761-3 10.1002/jps.2600820718
    • (1993) J. Pharm. Sci. , vol.82 , Issue.7 , pp. 761-763
    • Yuan, J.1
  • 34
    • 0033795553 scopus 로고    scopus 로고
    • Enhancement of the systemic and CNS specific delivery of L-dopa by the nasal administration of its water soluble prodrugs
    • Kao, H. D.; Traboulsi, A.; Itoh, S.; Dittert, L.; Hussain, A. Enhancement of the systemic and CNS specific delivery of L-dopa by the nasal administration of its water soluble prodrugs Pharm. Res. 2000, 17 (8) 978-84 10.1023/A:1007583422634
    • (2000) Pharm. Res. , vol.17 , Issue.8 , pp. 978-984
    • Kao, H.D.1    Traboulsi, A.2    Itoh, S.3    Dittert, L.4    Hussain, A.5
  • 36
    • 0036016980 scopus 로고    scopus 로고
    • Testosterone 17β-N, N-dimethylglycinate hydrochloride: A prodrug with a potential for nasal delivery of testosterone
    • Hussain, A. A.; AL-Bayatti, A. A.; Dakkuri, A.; Okochi, K.; Hussain, M. A. Testosterone 17β-N, N-dimethylglycinate hydrochloride: A prodrug with a potential for nasal delivery of testosterone J. Pharm. Sci. 2002, 91 (3) 785-789 10.1002/jps.10083
    • (2002) J. Pharm. Sci. , vol.91 , Issue.3 , pp. 785-789
    • Hussain, A.A.1    Al-Bayatti, A.A.2    Dakkuri, A.3    Okochi, K.4    Hussain, M.A.5
  • 37
    • 84884220816 scopus 로고    scopus 로고
    • Bioanalytical method for evaluating the pharmacokinetics of the GCP-II inhibitor 2-phosphonomethyl pentanedioic acid (2-PMPA)
    • Rais, R.; Rojas, C.; Wozniak, K.; Wu, Y.; Zhao, M.; Tsukamoto, T.; Rudek, M. A.; Slusher, B. S. Bioanalytical method for evaluating the pharmacokinetics of the GCP-II inhibitor 2-phosphonomethyl pentanedioic acid (2-PMPA) J. Pharm. Biomed. Anal. 2014, 88, 162-9 10.1016/j.jpba.2013.08.028
    • (2014) J. Pharm. Biomed. Anal. , vol.88 , pp. 162-169
    • Rais, R.1    Rojas, C.2    Wozniak, K.3    Wu, Y.4    Zhao, M.5    Tsukamoto, T.6    Rudek, M.A.7    Slusher, B.S.8
  • 38
    • 84860193946 scopus 로고    scopus 로고
    • Intranasal delivery of biologics to the central nervous system
    • Lochhead, J. J.; Thorne, R. G. Intranasal delivery of biologics to the central nervous system Adv. Drug Delivery Rev. 2012, 64 (7) 614-628 10.1016/j.addr.2011.11.002
    • (2012) Adv. Drug Delivery Rev. , vol.64 , Issue.7 , pp. 614-628
    • Lochhead, J.J.1    Thorne, R.G.2
  • 39
    • 84957990714 scopus 로고    scopus 로고
    • Investigation of utility of cerebrospinal fluid drug concentration as a surrogate for interstitial fluid concentration using microdialysis coupled with cisternal cerebrospinal fluid sampling in wild-type and Mdr1a(-/-) rats
    • Nagaya, Y.; Nozaki, Y.; Takenaka, O.; Watari, R.; Kusano, K.; Yoshimura, T.; Kusuhara, H. Investigation of utility of cerebrospinal fluid drug concentration as a surrogate for interstitial fluid concentration using microdialysis coupled with cisternal cerebrospinal fluid sampling in wild-type and Mdr1a(-/-) rats Drug Metab. Pharmacokinet. 2016, 31 (1) 57-66 10.1016/j.dmpk.2015.10.003
    • (2016) Drug Metab. Pharmacokinet. , vol.31 , Issue.1 , pp. 57-66
    • Nagaya, Y.1    Nozaki, Y.2    Takenaka, O.3    Watari, R.4    Kusano, K.5    Yoshimura, T.6    Kusuhara, H.7


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