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99566-27-5,MFCD00076704
Catalog No.:AA01E9J5

99566-27-5 | Neuropeptide FF H-Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2

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1mg
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA01E9J5
Chemical Name:
Neuropeptide FF H-Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2
CAS Number:
99566-27-5
Molecular Formula:
C56H77F3N14O12
Molecular Weight:
1195.2924
MDL Number:
MFCD00076704
SMILES:
OC(=O)C(F)(F)F.NC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)CCCNC(=N)N)CCC(=O)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)N)CC(C)C)Cc1ccccc1
Properties
Computed Properties
 
Complexity:
2050  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Heavy Atom Count:
78  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
12  
Rotatable Bond Count:
32  
XLogP3:
-0.3  

Literature

Title: Selective mode of action of guanidine-containing non-peptides at human NPFF receptors.

Journal: Journal of medicinal chemistry 20120712

Title: Crypteins derived from the mouse neuropeptide FF (NPFF)A precursor display NPFF-like effects in nociceptive tests in mice.

Journal: Peptides 20120701

Title: Effects of neuropeptide FF system on CB₁ and CB₂ receptors mediated antinociception in mice.

Journal: Neuropharmacology 20120201

Title: Modulation of neuropeptide FF (NPFF) receptors influences the expression of amphetamine-induced conditioned place preference and amphetamine withdrawal anxiety-like behavior in rats.

Journal: Peptides 20120101

Title: Central administration of neuropeptide FF and related peptides attenuate systemic morphine analgesia in mice.

Journal: Protein and peptide letters 20110401

Title: Neuropeptide FF receptor modulates potassium currents in a dorsal root ganglion cell line.

Journal: Pharmacological reports : PR 20110101

Title: Electrophysiological analysis of the inhibitory effects of FMRFamide-like peptides on the pacemaker activity of gonadotropin-releasing hormone neurons.

Journal: Journal of neurophysiology 20101201

Title: Nutritional markers, not markers of bone turnover, are related predictors of bone mineral density in chronic peritoneal dialysis patients.

Journal: Clinical nephrology 20101101

Title: Opposite control of body temperature by NPFF1 and NPFF2 receptors in mice.

Journal: Neuropeptides 20101001

Title: Effects of pain controlling neuropeptides on human fat cell lipolysis.

Journal: International journal of obesity (2005) 20100801

Title: Neuropeptide FF receptors have opposing modulatory effects on nociception.

Journal: The Journal of pharmacology and experimental therapeutics 20100701

Title: Pressor and tachycardic responses to intrathecal administration of neuropeptide FF in anesthetized rats.

Journal: Peptides 20100401

Title: Pharmacological characterization of the mouse NPFF2 receptor.

Journal: Peptides 20100201

Title: Multiple primary cilia modulate the fluid transcytosis in choroid plexus epithelium.

Journal: Traffic (Copenhagen, Denmark) 20100201

Title: Modulation by neuropeptide FF of the interaction of mu-opioid (MOP) receptor with G-proteins.

Journal: Neurochemistry international 20100101

Title: Opioid-modulating properties of the neuropeptide FF system.

Journal: BioFactors (Oxford, England) 20100101

Title: Characterization of two novel tritiated radioligands for labelling Neuropeptide FF (NPFF(1) and NPFF(2)) receptors.

Journal: Neurochemistry international 20091201

Title: Intracerebroventricular administration of 26RFa produces an analgesic effect in the rat formalin test.

Journal: Peptides 20090901

Title: [Modification of the FF neuropeptide enhances its hypertensive effect].

Journal: Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20090501

Title: [Progress in fundamental research: perspectives of cardiology].

Journal: Terapevticheskii arkhiv 20090101

Title: RFamide neuropeptides inhibit murine and human adipose differentiation.

Journal: Biochemical and biophysical research communications 20081205

Title: Neuropeptide FF-sensitive confinement of mu opioid receptor does not involve lipid rafts in SH-SY5Y cells.

Journal: Biochemical and biophysical research communications 20080815

Title: Short-term anorexigenic effects of central neuropeptide VF are associated with hypothalamic changes in chicks.

Journal: Journal of neuroendocrinology 20080801

Title: Neuropeptide FF (NPFF) reduces the expression of cocaine-induced conditioned place preference and cocaine-induced sensitization in animals.

Journal: Peptides 20080601

Title: Inhibition of neuropeptide FF (NPFF)-induced hypothermia and anti-morphine analgesia by RF9, a new selective NPFF receptors antagonist.

Journal: Regulatory peptides 20080410

Title: Immunohistochemical localization of neuropeptide FF-like in the brain of the turtle: relation to catecholaminergic structures.

Journal: Brain research bulletin 20080318

Title: A novel cryptic peptide derived from the rat neuropeptide FF precursor reverses antinociception and conditioned place preference induced by morphine.

Journal: Peptides 20080301

Title: Modulatory role of neuropeptide FF system in nociception and opiate analgesia.

Journal: Neuropeptides 20080201

Title: Rat RFRP-3 alters hypothalamic GHRH expression and growth hormone secretion but does not affect KiSS-1 gene expression or the onset of puberty in male rats.

Journal: Neuroendocrinology 20080101

Title: Anoretic effects of neuropeptide FF are mediated via central mu and kappa subtypes of opioid receptors and receptor ligands.

Journal: General and comparative endocrinology 20080101

Title: Central neuropeptide FF reduces feed consumption and affects hypothalamic chemistry in chicks.

Journal: Neuropeptides 20071201

Title: Neuropeptide FF (NPFF) reduces the expression of morphine- but not of ethanol-induced conditioned place preference in rats.

Journal: Peptides 20071101

Title: Pharmacological effects of the dansylated neuropeptide FF analogues on body temperature and morphine analgesia.

Journal: Neuropeptides 20071001

Title: Neuropeptide FF and neuropeptide VF inhibit GABAergic neurotransmission in parvocellular neurons of the rat hypothalamic paraventricular nucleus.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20070501

Title: Staurosporine differentiation of NPFF2 receptor-transfected SH-SY5Y neuroblastoma cells induces selectivity of NPFF activity towards opioid receptors.

Journal: Peptides 20070501

Title: Physical association between neuropeptide FF and micro-opioid receptors as a possible molecular basis for anti-opioid activity.

Journal: The Journal of biological chemistry 20070316

Title: The role of neuropeptide FF (NPFF) in the expression of sensitization to hyperlocomotor effect of morphine and ethanol.

Journal: Neuropeptides 20070201

Title: Prolactin-releasing Peptide mediates cholecystokinin-induced satiety in mice.

Journal: Endocrinology 20061001

Title: In vivo inhibition of neuropeptide FF agonism by BIBP3226, an NPY Y1 receptor antagonist.

Journal: Peptides 20060901

Title: Distribution of neuropeptide FF-like immunoreactivity in the brain of the lizard Gekko gecko and its relation to catecholaminergic structures.

Journal: The Journal of comparative neurology 20060901

Title: Neuropeptide FF distribution in the human and rat forebrain: a comparative immunohistochemical study.

Journal: The Journal of comparative neurology 20060601

Title: Modulatory roles of the NPFF system in pain mechanisms at the spinal level.

Journal: Peptides 20060501

Title: Distribution of neuropeptide FF-like immunoreactive structures in the lamprey central nervous system and its relation to catecholaminergic neuronal structures.

Journal: Peptides 20060501

Title: Cardiovascular effects of neuropeptide FF antagonists.

Journal: Peptides 20060501

Title: Structure-activity relationships of neuropeptide FF and related peptidic and non-peptidic derivatives.

Journal: Peptides 20060501

Title: Rat NPFF(1) receptor-mediated signaling: functional comparison of neuropeptide FF (NPFF), FMRFamide and PFR(Tic)amide.

Journal: Peptides 20060501

Title: A neuropeptide FF agonist blocks the acquisition of conditioned place preference to morphine in C57Bl/6J mice.

Journal: Peptides 20060501

Title: Spatiotemporal sequence of appearance of NPFF-immunoreactive structures in the developing central nervous system of Xenopus laevis.

Journal: Peptides 20060501

Title: Identification of transcriptional regulators of neuropeptide FF gene expression.

Journal: Peptides 20060501

Title: Neuropeptide FF (NPFF) control of magnocellular neurosecretory cells of the rat hypothalamic paraventricular nucleus (PVN).

Journal: Peptides 20060501

Title: Changes in neuropeptide FF and NPY immunohistochemical patterns in rat brain under heroin treatment.

Journal: Brain research 20060414

Title: Evolutionary origin and divergence of PQRFamide peptides and LPXRFamide peptides in the RFamide peptide family. Insights from novel lamprey RFamide peptides.

Journal: The FEBS journal 20060401

Title: Regulation of endogenous human NPFF2 receptor by neuropeptide FF in SK-N-MC neuroblastoma cell line.

Journal: Journal of neurochemistry 20060101

Title: Distribution of neuropeptide FF-like immunoreactivity in the brain of Dermophis mexicanus (Amphibia; Gymnophiona): comparison with FMRFamide immunoreactivity.

Journal: Brain, behavior and evolution 20060101

Title: Neuropeptide FF receptors exert contractile activity via inhibition of nitric oxide release in the mouse distal colon.

Journal: Peptides 20050501

Title: Neuropeptide FF (NPFF) analogs functionally antagonize opioid activities in NPFF2 receptor-transfected SH-SY5Y neuroblastoma cells.

Journal: Molecular pharmacology 20050301

Title: Functional modulation of human delta opioid receptor by neuropeptide FF.

Journal: BMC neuroscience 20050101

Title: Opioid-modulating peptides: mechanisms of action.

Journal: Current topics in medicinal chemistry 20050101

Title: Pain- and morphine-associated transcriptional regulation of neuropeptide FF and the G-protein-coupled NPFF2 receptor gene.

Journal: Neurobiology of disease 20040601

Title: Co-localization of endomorphin-2 and substance P in primary afferent nociceptors and effects of injury: a light and electron microscopic study in the rat.

Journal: The European journal of neuroscience 20040401

Title: Neuropeptide FF, but not prolactin-releasing peptide, mRNA is differentially regulated in the hypothalamic and medullary neurons after salt loading.

Journal: Neuroscience 20040101

Title: Neuropeptide FF exerts pro- and anti-opioid actions in the parabrachial nucleus to modulate food intake.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20031101

Title: Identification of proNeuropeptide FFA peptides processed in neuronal and non-neuronal cells and in nervous tissue.

Journal: European journal of biochemistry 20031001

Title: Expression of neuropeptide FF, prolactin-releasing peptide, and the receptor UHR1/GPR10 genes during embryogenesis in the rat.

Journal: Developmental dynamics : an official publication of the American Association of Anatomists 20030301

Title: Molecular properties of endogenous RFamide-related peptide-3 and its interaction with receptors.

Journal: Biochimica et biophysica acta 20030217

Title: Central administration of neuropeptide FF causes activation of oxytocin paraventricular hypothalamic neurones that project to the brainstem.

Journal: Journal of neuroendocrinology 20030101

Title: Comparative analysis of neuropeptide FF-like immunoreactivity in the brain of anuran (Rana perezi, Xenopus laevis) and urodele (Pleurodeles waltl) amphibians.

Journal: Journal of chemical neuroanatomy 20030101

Title: Activation of spinal neuropeptide FF and the neuropeptide FF receptor 2 during inflammatory hyperalgesia in rats.

Journal: Neuroscience 20030101

Title: Identification of neuropeptide FF-related peptides in human cerebrospinal fluid by mass spectrometry.

Journal: FEBS letters 20021218

Title: Neuropeptide AF and FF modulation of adipocyte metabolism. Primary insights from functional genomics and effects on beta-adrenergic responsiveness.

Journal: The Journal of biological chemistry 20021018

Title: A neuropeptide FF-related gene is expressed selectively in neurons of the terminal nerve in Danio rerio.

Journal: Mechanisms of development 20020901

Title: Analysis of human neuropeptide FF gene expression.

Journal: Journal of neurochemistry 20020901

Title: Immobilized artificial membrane chromatography coupled with atmospheric pressure ionization mass spectrometry.

Journal: Journal of chromatography. A 20020809

Title: Dissociation of pharmacological pro- and anti-opioid effects by neuropeptide FF analogs.

Journal: European journal of pharmacology 20020802

Title: Central administration of neuropeptide FF (NPFF) causes increased neuronal activation and up-regulation of NPFF gene expression in the rat brainstem.

Journal: The Journal of comparative neurology 20020603

Title: Peptide nucleic acids targeted to the mouse proNPFF(A) reveal an endogenous opioid tonus.

Journal: Peptides 20020601

Title: Molecular characterization and cell-specific expression of a Manduca sexta FLRFamide gene.

Journal: The Journal of comparative neurology 20020513

Title: The neuropeptide FF analogue, 1DMe, reduces in vivo dynorphin release from the rat spinal cord.

Journal: Journal of neurochemistry 20020501

Title: Interaction between neuropeptide FF and opioids in the ventral tegmental area in the behavioral response to novelty.

Journal: Neuroscience 20020101

Title: Intracerebroventricular injection of neuropeptide FF, an opioid modulating neuropeptide, acutely reduces food intake and stimulates water intake in the rat.

Journal: Neuroscience letters 20011109

Title: Identification and characterization of novel mammalian neuropeptide FF-like peptides that attenuate morphine-induced antinociception.

Journal: The Journal of biological chemistry 20011005

Title: Selective modulation of heteromeric ASIC proton-gated channels by neuropeptide FF.

Journal: Neuropharmacology 20011001

Title: Structure-activity relationships of neuropeptide FF: role of C-terminal regions.

Journal: Peptides 20010901

Title: Identification of neuropeptide FF-related peptides in rodent spinal cord.

Journal: Peptides 20010701

Title: Modulation of pain by [1DMe]NPYF, a stable analogue of neuropeptide FF, in neuropathic rats.

Journal: Brain research 20010511

Title: Combinatorial lead optimization of a neuropeptide FF antagonist.

Journal: Journal of medicinal chemistry 20010510

Title: Functional characterization of a human receptor for neuropeptide FF and related peptides.

Journal: British journal of pharmacology 20010501

Title: Effects of intracerebroventricularly administered chimeric peptide of metenkephalin and FMRFa--[D-Ala2]YFa-on antinociception and its modulation in mice.

Journal: Brain research bulletin 20010501

Title: Cholera and pertussis toxins inhibit differently hypothermic and anti-opioid effects of neuropeptide FF.

Journal: Regulatory peptides 20010402

Title: New central projections of neuropeptide FF: colateral branching pathways in the brainstem and hypothalamus in the rat.

Journal: Journal of chemical neuroanatomy 20010301

Title: Neuropeptide FF: new molecular insights.

Journal: Trends in pharmacological sciences 20010201

Title: Role of the delta-opioid receptor in (1DMe)NPYF mediated antinociception.

Journal: Peptides 20010101

Title: Response properties of neurons in the rostroventromedial medulla of neuropathic rats: attempted modulation of responses by [1DMe]NPYF, a neuropeptide FF analogue.

Journal: Neuroscience 20010101

Title: [Modulation of calcium conductance by opioid and anti-opioid peptides].

Journal: Journal de la Societe de biologie 20010101

Title: Identification and characterization of two G protein-coupled receptors for neuropeptide FF.

Journal: The Journal of biological chemistry 20001215

Title: Relevance of the C-terminal Arg-Phe sequence in gamma(2)-melanocyte-stimulating hormone (gamma(2)-MSH) for inducing cardiovascular effects in conscious rats.

Journal: British journal of pharmacology 20001201

Title: Synaptic actions of neuropeptide FF in the rat parabrachial nucleus: interactions with opioid receptors.

Journal: Journal of neurophysiology 20000801

Title: Role of opioid receptors in the spinal antinociceptive effects of neuropeptide FF analogues.

Journal: British journal of pharmacology 19960201

Title: Mechanisms underlying the cardiovascular responses to peripheral administration of NPFF in the rat.

Journal: The Journal of pharmacology and experimental therapeutics 19950701

Title: Low affinity of FMRFamide and four FaRPs (FMRFamide-related peptides), including the mammalian-derived FaRPs F-8-Famide (NPFF) and A-18-Famide, for opioid mu, delta, kappa 1, kappa 2a, or kappa 2b receptors.

Journal: Peptides 19940101

Title: Comparative action of Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2 analogs on intestinal motility and nociception in rats.

Journal: The Journal of pharmacology and experimental therapeutics 19930401

Title: Chronic intracerebroventricular infusion of the antiopioid peptide, Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2 (NPFF), downregulates mu opioid binding sites in rat brain.

Journal: Peptides 19930101

Title: Biphasic effect on nociception and antiopiate activity of the neuropeptide FF (FLFQPQRFamide) in the rat.

Journal: Peptides 19930101

Title: Analogues of F8Famide resistant to degradation, with high affinity and in vivo effects.

Journal: European journal of pharmacology 19921103

Title: Modulation of human lymphocyte proliferation by FLFQPQRFamide, a FMRFamide-like peptide with anti-opiate properties.

Journal: Journal of neuroimmunology 19920501

Title: Characterization and localization of a putative morphine-modulating peptide, FLFQPQRFamide, in the rat spinal cord: biochemical and immunocytochemical studies.

Journal: Neuroscience 19910101

Title: FMRF-NH2-like peptide is deficient in the pituitary gland of the Brattleboro rat.

Journal: Peptides 19900101

Title: Immunohistochemical distribution and partial characterization of FLFQPQRFamidelike peptides in the central nervous system of rats.

Journal: The Journal of comparative neurology 19890808

Title: Rat brain regional distribution and spinal cord neuronal pathway of FLFQPQRF-NH2, a mammalian FMRF-NH2-like peptide.

Journal: Brain research 19890807

Title: IgG from antiserum against endogenous mammalian FMRF-NH2-related peptides augments morphine- and stress-induced analgesia in mice.

Journal: Peptides 19890101

Title: Biochemical characterization of FMRF-NH2-like peptides in spinal cords of various mammalian species using specific radioimmunoassays.

Journal: Peptides 19880101

Title: Elevation of arterial pressure in rats by two new vertebrate peptides FLFQPQRF-NH2 and AGEGLSSPFWSLAAPQRF-NH2 which are immunoreactive to FMRF-NH2 antiserum.

Journal: Neuropeptides 19870701

Title: Distribution and characterization of two putative endogenous opioid antagonist peptides in bovine brain.

Journal: Peptides 19870101

Title: Isolation, sequencing, synthesis, and pharmacological characterization of two brain neuropeptides that modulate the action of morphine.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19851101

Title: Mankus JV, et al. Nonpeptide ligands of neuropeptide FF: current status and structural insights. Future Med Chem. 2012 Jun;4(9):1085-92.

Title: Jhamandas JH, et al. Role of neuropeptide FF in central cardiovascular and neuroendocrine regulation. Front Endocrinol (Lausanne). 2013 Feb 7;4:8.

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Tags:99566-27-5 Molecular Formula|99566-27-5 MDL|99566-27-5 SMILES|99566-27-5 Neuropeptide FF H-Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2