(2R-trans)-2-Butyl-5-heptylpyrrolidine as a Potent Sigma Receptor Ligand Produced by Streptomyces longispororuber
A potent sigma (σ) receptor ligand was isolated from the culture broth of Streptomyces longispororuber #525. The active compound was identified to be (2R-trans)-2-butyl-5-heptylpyrrolidine by spectroscopic and chemical studies. The compound exhibited high affinity and selectivity for σ receptors. Th...
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| Published in | Journal of antibiotics Vol. 53; no. 5; pp. 467 - 473 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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TOKYO
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
2000
Japan Antibiotics Research Assoc Japan Antibiotics Research Association |
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| Abstract | A potent sigma (σ) receptor ligand was isolated from the culture broth of Streptomyces longispororuber #525. The active compound was identified to be (2R-trans)-2-butyl-5-heptylpyrrolidine by spectroscopic and chemical studies. The compound exhibited high affinity and selectivity for σ receptors. The IC50 values toward σ1, σ2 and dopamine D2 receptors were 2.0, 22.7 and more than 40, 000 nM, respectively. Its (2S-trans)- and (±)-cis-isomers, both synthesized, were also found to be high affinity σ ligands. |
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| AbstractList | A potent sigma ( sigma ) receptor ligand was isolated from the culture broth of Streptomyces longispororuber #525. The active compound was identified to be (2R-trans)-2-butyl-5-heptylpyrrolidine by spectroscopic and chemical studies. The compound exhibited high affinity and selectivity for sigma receptors. The IC sub(50) values toward sigma sub(1), sigma sub(2) and dopamine D sub(2) receptors were 2.0, 22.7 and more than 40,000 nM, respectively. Its (2S-trans)- and ( plus or minus )-cis-isomers, both synthesized, were also found to be high affinity sigma ligands. A potent sigma (sigma) receptor ligand was isolated from the culture broth of Streptomyces longispororuber #525. The active compound was identified to be (2R-trans)-2-butyl-5-heptylpyrrolidine by spectroscopic and chemical studies. The compound exhibited high affinity and selectivity for sigma receptors. The IC50 values toward sigma(1), sigma(2) and dopamine D-2 receptors were 2.0, 22.7 and more than 40,000 nM, respectively. Its (2S-trans)- and (+/-)-cis-isomers, both synthesized, were also found to be high affinity sigma ligands. A potent sigma (sigma) receptor ligand was isolated from the culture broth of Streptomyces longispororuber #525. The active compound was identified to be (2R-trans)-2-butyl-5-heptylpyrrolidine by spectroscopic and chemical studies. The compound exhibited high affinity and selectivity for sigma receptors. The IC50 values toward sigma1, sigma2 and dopamine D2 receptors were 2.0, 22.7 and more than 40,000 nM, respectively. Its (2S-trans)- and (+/-)-cis-isomers, both synthesized, were also found to be high affinity sigma ligands. A potent sigma (σ) receptor ligand was isolated from the culture broth of Streptomyces longispororuber #525. The active compound was identified to be (2R-trans)-2-butyl-5-heptylpyrrolidine by spectroscopic and chemical studies. The compound exhibited high affinity and selectivity for σ receptors. The IC50 values toward σ1, σ2 and dopamine D2 receptors were 2.0, 22.7 and more than 40, 000 nM, respectively. Its (2S-trans)- and (±)-cis-isomers, both synthesized, were also found to be high affinity σ ligands. |
| Author | NAKAYAMA, HIROSHI SHONO, KAZUSHIGE KUMAGAI, KAZUO OHNO, YUKIHIRO SAJI, IKUTARO |
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| DOI | 10.7164/antibiotics.53.467 |
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| Keywords | VENOM ANT ANTIPSYCHOTIC-DRUGS MEMBRANES SITES OPIATES GUINEA-PIG BRAIN BINDING Streptomycetaceae Ligand Opioid receptor Sigma receptor Fermentation In vitro Pyrrolidine derivatives Actinomycetales Biological fixation D2 Dopamine receptor Enantiomer Microorganism culture Bacteria Actinomycetes Structural analysis |
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(BCI:BCI19664700103325) 1966; 16 Hanner, M (WOS:A1996UY93000119) 1996; 93 HASHIMOTO, K (WOS:A1993LC38000023) 1993; 236 WALKER, JM (WOS:A1990EQ14900003) 1990; 42 ARSENIYADIS, S (WOS:A1988N516800008) 1988; 44 ABOUGHARBIA, M (WOS:A1993BA26B00001) 1993; 28 BLUM, MS (WOS:A1980JL37700011) 1980; 67 TUFARIELLO, JJ (WOS:A1986A514800019) 1986; 27 Moebius, FF (WOS:A1997WU15000001) 1997; 18 DEHAVENHUDKINS, DL (WOS:A1992KA02500002) 1992; 227 TAM, SW (WOS:A1984TK56500072) 1984; 81 OPPOLZER, W (WOS:A1994PH43300016) 1994; 35 |
| References_xml | – volume: 18 start-page: 67 year: 1997 ident: WOS:A1997WU15000001 article-title: The mysteries of sigma receptors: New family members reveal a role in cholesterol synthesis publication-title: TRENDS IN PHARMACOLOGICAL SCIENCES contributor: fullname: Moebius, FF – volume: 30 start-page: 225 year: 1980 ident: WOS:A1980JG46200030 article-title: APPROVED LISTS OF BACTERIAL NAMES publication-title: INTERNATIONAL JOURNAL OF SYSTEMATIC BACTERIOLOGY contributor: fullname: SKERMAN, VBD – volume: 12 start-page: 421 year: 1964 ident: WOS:A19645142A00001 article-title: RAPID DIFFERENTIATION BETWEEN NOCARDIA + STREPTOMYCES BY PAPER CHROMATOGRAPHY OF WHOLE-CELL HYDROLYSATES publication-title: APPLIED MICROBIOLOGY contributor: fullname: BECKER, B – volume: 83 start-page: 8784 year: 1986 ident: WOS:A1986E906700073 article-title: 1,3-DI(2-[5-H-3]TOLYL)GUANIDINE - A SELECTIVE LIGAND THAT LABELS SIGMA-TYPE RECEPTORS FOR PSYCHOTOMIMETIC OPIATES AND ANTIPSYCHOTIC-DRUGS publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA contributor: fullname: WEBER, E – volume: 1 start-page: 561 year: 1990 ident: WOS:A1990DV03800012 article-title: AN EFFICIENT ROUTE TO CHIRAL TRANS-2,5-DIALKYLPYRROLIDINES VIA STEREOSELECTIVE INTRAMOLECULAR AMIDOMERCURATION publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: TAKAHATA, H – volume: 398 start-page: 701 year: 1999 ident: WOS:000079920100049 article-title: Fungus-growing ants use antibiotic-producing bacteria to control garden parasites publication-title: NATURE contributor: fullname: Currie, CR – volume: 55 start-page: 215 year: 1979 ident: WOS:A1979GT84400015 article-title: H-3-SPIROPERIDOL BINDING TO DOPAMINE RECEPTORS IN RAT STRIATAL MEMBRANES - INFLUENCE OF LOXAPINE AND ITS HYDROXYLATED METABOLITES publication-title: EUROPEAN JOURNAL OF PHARMACOLOGY contributor: fullname: COUPET, J – volume: 67 start-page: 144 year: 1980 ident: WOS:A1980JL37700011 article-title: ALKALOIDAL VENOM MACE - OFFENSIVE USE BY A THIEF ANT publication-title: NATURWISSENSCHAFTEN contributor: fullname: BLUM, MS – volume: 16 start-page: 313 year: 1966 ident: BCI:BCI19664700103325 article-title: Methods for characterization of Streptomyces Bpecies publication-title: INT J SYST BACTERIOL contributor: fullname: SHIRLING, E. B. – year: 1973 ident: WOS:000087276800003.1 publication-title: COL TON MAN contributor: fullname: NIPP SHIK KENK – volume: 44 start-page: 2457 year: 1988 ident: WOS:A1988N516800008 article-title: ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING publication-title: TETRAHEDRON contributor: fullname: ARSENIYADIS, S – volume: 236 start-page: 159 year: 1993 ident: WOS:A1993LC38000023 article-title: FURTHER CHARACTERIZATION OF [H-3] IFENPRODIL BINDING TO SIGMA-RECEPTORS IN RAT-BRAIN publication-title: EUROPEAN JOURNAL OF PHARMACOLOGY contributor: fullname: HASHIMOTO, K – volume: 35 start-page: 7015 year: 1994 ident: WOS:A1994PH43300016 article-title: DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESES OF (-)-CONIINE, (-)-SOLENOPSIN-A, (-)-SOLENOPSIS-FUGAX VENOM AND (-)-XENOVENINE VIA DEOXYGENATIVE DECARBOXYLATION OF 2-CARBONYLSULTAM-SUBSTITUTED N-HYDROXY-PIPERIDINES AND N-HYDROXY-PYRROLIDINES publication-title: TETRAHEDRON LETTERS contributor: fullname: OPPOLZER, W – volume: 42 start-page: 355 year: 1990 ident: WOS:A1990EQ14900003 article-title: SIGMA-RECEPTORS - BIOLOGY AND FUNCTION publication-title: PHARMACOLOGICAL REVIEWS contributor: fullname: WALKER, JM – volume: 13 start-page: 85 year: 1992 ident: WOS:A1992HH39800001 article-title: A PROPOSAL FOR THE CLASSIFICATION OF SIGMA BINDING-SITES publication-title: TRENDS IN PHARMACOLOGICAL SCIENCES contributor: fullname: QUIRION, R – volume: 93 start-page: 8072 year: 1996 ident: WOS:A1996UY93000119 article-title: Purification, molecular cloning, and expression of the mammalian sigma(1)-binding site publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA contributor: fullname: Hanner, M – volume: 27 start-page: 1489 year: 1986 ident: WOS:A1986A514800019 article-title: THE ALPHA, ALPHA-'-DIALKYLATION OF CYCLIC AMINES - THE SYNTHESIS OF SOLENOPSIS ANT VENOMS publication-title: TETRAHEDRON LETTERS contributor: fullname: TUFARIELLO, JJ – volume: 1 start-page: 7 year: 1989 ident: MEDLINE:2577720 article-title: Receptor mechanisms in antipsychotic drug action: focus on sigma receptors. publication-title: The Journal of neuropsychiatry and clinical neurosciences contributor: fullname: Snyder, S H – volume: 227 start-page: 371 year: 1992 ident: WOS:A1992KA02500002 article-title: CHARACTERIZATION OF THE BINDING OF [H-3] (+)-PENTAZOCINE TO SIGMA-RECOGNITION SITES IN GUINEA-PIG BRAIN publication-title: EUROPEAN JOURNAL OF PHARMACOLOGY-MOLECULAR PHARMACOLOGY SECTION contributor: fullname: DEHAVENHUDKINS, DL – volume: 81 start-page: 5618 year: 1984 ident: WOS:A1984TK56500072 article-title: SIGMA-OPIATES AND CERTAIN ANTIPSYCHOTIC-DRUGS MUTUALLY INHIBIT (+)-[H-3]SKF-10,047 AND [H-3]HALOPERIDOL BINDING IN GUINEA-PIG BRAIN MEMBRANES publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES contributor: fullname: TAM, SW – volume: 11 start-page: 105 year: 1988 ident: WOS:A1988M621100002 article-title: THE SIGMA-RECEPTOR - A NOVEL SITE IMPLICATED IN PSYCHOSIS AND ANTIPSYCHOTIC DRUG EFFICACY publication-title: CLINICAL NEUROPHARMACOLOGY contributor: fullname: DEUTSCH, SI – volume: 28 start-page: 1 year: 1993 ident: WOS:A1993BA26B00001 article-title: SIGMA-RECEPTORS AND THEIR LIGANDS - THE SIGMA-ENIGMA publication-title: ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 28 contributor: fullname: ABOUGHARBIA, M |
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| SubjectTerms | 2-Butyl-5-heptylpyrrolidine Animals Biological and medical sciences Biotechnology & Applied Microbiology Fermentation Immunology In Vitro Techniques Life Sciences & Biomedicine Ligands Medical sciences Microbiology Molecular Structure Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology & Pharmacy Pharmacology. Drug treatments Pyrrolidines - metabolism Rats Receptors, sigma - metabolism Science & Technology Spectrum Analysis Streptomyces - metabolism |
| Title | (2R-trans)-2-Butyl-5-heptylpyrrolidine as a Potent Sigma Receptor Ligand Produced by Streptomyces longispororuber |
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| ispartofPNX | The Journal of Antibiotics, 2000/05/25, Vol.53(5), pp.467-473 |
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