Preclinical evaluation of a 64Cu-labeled disintegrin for PET imaging of prostate cancer.

Abstract:

:A novel recombinant disintegrin, vicrostatin (VCN), displays high binding affinity to a broad range of human integrins in substantial competitive biological advantage over other integrin-based antagonists. In this study, we synthesized a new 64Cu-labeled VCN probe and evaluated its imaging properties for prostate cancer in PC-3 tumor-bearing mice. Macrocyclic chelating agent 1,8-diamino-3,6,10,13,16,19-hexaazabicyclo[6.6.6]-eicosine (DiAmSar) was conjugated with PEG unit and followed by coupling with VCN. The precursor was then radiolabeled with positron emitter 64Cu (t1/2 = 12.7 h) in ammonium acetate buffer to provide 64Cu-Sar-PEG-VCN, which was subsequently subjected to in vitro studies, small animal PET, and biodistribution studies. The PC-3 tumor-targeting efficacy of 64Cu-Sar-PEG-VCN was compared to a cyclic RGD peptide-based PET probe (64Cu-Sar-RGD). 64Cu labeling was achieved in 75% decay-corrected yield with radiochemical purity of  > 98%. The specific activity of 64Cu-Sar-PEG-VCN was estimated to be 37 MBq/nmol. MicroPET imaging results showed that 64Cu-Sar-PEG-VCN has preferential tumor uptake and good tumor retention in PC-3 tumor xenografts. As compared to 64Cu-Sar-RGD, 64Cu-Sar-PEG-VCN produces higher tumor-to-muscle (T/M) imaging contrast ratios at 2 h (4.66 ± 0.34 vs. 2.88 ± 0.46) and 24 h (4.98 ± 0.80 vs. 3.22 ± 0.30) post-injection (pi) and similar tumor-to-liver ratios at 2 h (0.43 ± 0.09 vs. 0.37 ± 0.04) and 24 h (0.57 ± 0.13 vs. 0.52 ± 0.07) pi. The biodistribution results were consistent with the quantitative analysis of microPET imaging, demonstrating good T/M ratio (2.73 ± 0.36) of 64Cu-Sar-PEG-VCN at 48 h pi in PC-3 tumor xenografts. For both microPET and biodistribution studies at 48 h pi, the PC-3 tumor uptake of 64Cu-Sar-PEG-VCN is lower than that of 64Cu-Sar-RGD. 64Cu-Sar-PEG-VCN has the potential for in vivo imaging of prostate cancer with PET, which may provide a unique non-invasive method to quantitatively localize and characterize prostate cancer.

journal_name

Amino Acids

journal_title

Amino acids

authors

Jadvar H,Chen K,Park R,Yap LP,Vorobyova I,Swenson S,Markland FS

doi

10.1007/s00726-019-02794-3

subject

Has Abstract

pub_date

2019-11-01 00:00:00

pages

1569-1575

issue

10-12

eissn

0939-4451

issn

1438-2199

pii

10.1007/s00726-019-02794-3

journal_volume

51

pub_type

杂志文章
  • Plasma levels and urinary excretion of amino acids by subjects with renal calculi.

    abstract::Plasma levels and urinary amino acid excretions were estimated by high-performance liquid chromatography in 15 control subjects and 36 stone formers (SFs) classified according to the stone type: (1) 22 cases with calcium oxalate stones; (2) four cases with pure uric acid stones; (3) 10 cases with magnesium-ammonium ph...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-009-0359-z

    authors: Atanassova SS,Panchev P,Ivanova M

    更新日期:2010-05-01 00:00:00

  • The chemistry of natural enzyme-induced cross-links of proteins.

    abstract::The cross-linking of protein molecules to form stable supramolecular aggregates capable of acting as protective and supporting structures is a common feature of organisms coping with the stresses of life. These new polymeric forms range from thick rigid structures to thin flexible membranes. The formation of such cros...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00813999

    authors: Bailey AJ

    更新日期:1991-10-01 00:00:00

  • Optimization of hydrolysis conditions, isolation, and identification of neuroprotective peptides derived from seahorse Hippocampus trimaculatus.

    abstract::Hippocampus trimaculatus is one of the most heavily traded seahorse species for traditional medicine purposes in many countries. In the present study, we showed neuroprotective effects of peptide derived from H. trimaculatus against amyloid-β42 (Aβ42) toxicity which are central to the pathogenesis of Alzheimer's disea...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-013-1510-4

    authors: Pangestuti R,Ryu B,Himaya S,Kim SK

    更新日期:2013-08-01 00:00:00

  • Enhanced flux of substrates into polyamine biosynthesis but not ethylene in tomato fruit engineered with yeast S-adenosylmethionine decarboxylase gene.

    abstract::S-adenosylmethionine (SAM), a major substrate in 1-C metabolism is a common precursor in the biosynthetic pathways of polyamines and ethylene, two important plant growth regulators, which exhibit opposing developmental effects, especially during fruit ripening. However, the flux of various substrates including SAM int...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-013-1624-8

    authors: Lasanajak Y,Minocha R,Minocha SC,Goyal R,Fatima T,Handa AK,Mattoo AK

    更新日期:2014-03-01 00:00:00

  • Screening system for D-Asp-containing proteins using D-aspartyl endopeptidase and two-dimensional gel electrophoresis.

    abstract::D-Asp-containing proteins have been implicated in many aging-related diseases. To clarify the role of D-Asp-containing proteins in such diseases, we developed a screening system for these proteins using a D-aspartyl endopeptidase that specifically cleaves the proteins at the C-terminus. The digested proteins were dete...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-008-0040-y

    authors: Sakai-Kato K,Kinouchi T,Fujii N,Imai K,Utsunomiya-Tate N

    更新日期:2009-01-01 00:00:00

  • Determination of the protooncogene ets-2 gene transcript in human brain at the atto-gram-level by the use of competitive RT/PCR.

    abstract::Protooncogenes (PO) play a crucial role for brain biology and pathology. Only the concerted action of protooncogenes enables normal brain development. The reliable and sensitive quantification of brain PO is still holding centre stage in neurobiological research. The aim of our study was therefore the determination of...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF01318881

    authors: Schatzmann-Turhani D,Greber-Platzer S,Cairns N,Lubec G

    更新日期:1999-01-01 00:00:00

  • Synthesis of a bicyclic delta-amino acid as a constrained Gly-Asn dipeptide isostere.

    abstract::Delta-amino acids are very attractive in drug discovery, especially in the peptidomimetic area, because of their capability to act as dipeptide isosteres and reverse turn mimetics. Herein we report the synthesis of a rigid delta-amino acid constrained by a 3-aza-6,8-dioxabicyclo[3.2.1]octane-based scaffold, which can ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-007-0636-7

    authors: Trabocchi A,Menchi G,Danieli E,Guarna A

    更新日期:2008-06-01 00:00:00

  • High clinical accuracy of asymmetric dimethylarginine and symmetric dimethylarginine in patients with ischemic heart disease.

    abstract::Elevated plasma concentrations of asymmetric dimethylarginine (ADMA) and symmetric dimethylarginine (SDMA) were found in various clinical settings including coronary heart disease. To assess ADMA and SDMA diagnostic validity in patients with different stages of ischemic heart disease, we studied these markers in patie...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1307-x

    authors: Djordjević BV,Pavlović R,Ćosić V,Deljanin-Ilić M,Ristić T,Krstić N,Jevtović-Stoimenov T

    更新日期:2012-12-01 00:00:00

  • A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid.

    abstract::3-Hydroxyaspartic acid and its derivatives are found both in the free form and as peptide constituents in various microorganisms and fungi. Considering the biological importance of this amino acid and its potential utility as a multifunctional building block in organic syntheses, we have developed a short-step, asymme...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-007-0595-z

    authors: Khalaf JK,Datta A

    更新日期:2008-08-01 00:00:00

  • A refined synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids.

    abstract::The synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids has been refined to improve both the efficiency and the simplicity. These improvements provide a shorter and easier access to the racemic cis-cyclobutane β-amino acid core. Derivatization of this material with a chiral non-racemic oxazolidin-2-o...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-0918-y

    authors: Declerck V,Aitken DJ

    更新日期:2011-08-01 00:00:00

  • A dual action of taurine on the delayed rectifier K(+) current in embryonic chick cardiomyocytes.

    abstract::Effects of taurine on the delayed rectifier K(+) channel in isolated 10-day-old embryonic chick ventricular cardiomyocytes were examined at different intracellular Ca(2+) concentrations ([Ca]i), using whole-cell voltage and current clamp techniques. Experiments were performed at room temperature (22°C). Test pulses we...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00805955

    authors: Satoh H

    更新日期:1995-09-01 00:00:00

  • Functional roles of agmatinase during the peri-implantation period of pregnancy in sheep.

    abstract::This study investigated the effect of agmatine (Agm) in proliferation of ovine trophecdoderm cells (oTr1) as well as the importance of the arginine decarboxylase (ADC) and agmatinase (AGMAT) alternative pathway for synthesis of polyamines in ovine conceptuses during the peri-implantation period of pregnancy. Morpholin...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-017-2515-1

    authors: Lenis YY,Elmetwally MA,Tang W,Satterfield C,Dunlap K,Wu G,Bazer FW

    更新日期:2018-02-01 00:00:00

  • Cardiovascular actions of L-cysteine and L-cysteine sulfinic acid in the nucleus tractus solitarius of the rat.

    abstract::The sulfur-containing excitatory amino acid (EAA) L-cysteine sulfinic acid (CSA), a neurotransmitter candidate, is endogenously synthesized from L-cysteine (Cys). Exogenous Cys administration into the brain produces cardiovascular effects; these effects likely occur via synaptic stimulation of central nervous system (...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-014-1733-z

    authors: Takemoto Y

    更新日期:2014-07-01 00:00:00

  • No peptide left behind: the "out of range" recovery in IPG-IEF fractionation.

    abstract::IEF is often used in multidimensional shotgun proteomics and the narrow range of 3.5-4.5 is the recommended pH interval for the fractionation of tryptic peptides. Usually, even if IEF is performed in IPG strip with a narrow range pH, the entire sample must be loaded onto the strip, including the "out of IPG range" pep...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-014-1720-4

    authors: Iori E,Rattazzi M,Millioni R

    更新日期:2014-05-01 00:00:00

  • Classification of G proteins and prediction of GPCRs-G proteins coupling specificity using continuous wavelet transform and information theory.

    abstract::The coupling between G protein-coupled receptors (GPCRs) and guanine nucleotide-binding proteins (G proteins) regulates various signal transductions from extracellular space into the cell. However, the coupling mechanism between GPCRs and G proteins is still unknown, and experimental determination of their coupling sp...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-1133-6

    authors: Li Z,Zhou X,Dai Z,Zou X

    更新日期:2012-08-01 00:00:00

  • Direct access to side chain N,N'-diaminoalkylated derivatives of basic amino acids suitable for solid-phase peptide synthesis.

    abstract::A simple and efficient one-pot procedure that enables rapid access to orthogonally protected N,N'-diaminoalkylated basic amino acid building blocks fully compatible with standard Boc and Fmoc solid-phase peptide synthesis is reported. Described synthetic approach includes double reductive alkylation of N (α)-protected...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1336-5

    authors: Pitteloud JP,Bionda N,Cudic P

    更新日期:2013-02-01 00:00:00

  • Neurofilament proteins NF-L, NF-M and NF-H in brain of patients with Down syndrome and Alzheimer's disease.

    abstract::Neurofilaments (NFs) are integral constituents of the neuron playing a major role in brain development, maintenance, regeneration and the pattern of expression for NFs suggests their contribution to plasticity of the neuronal cytoskeleton and creating and maintaining neuronal architecture. Using immune-histochemical t...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s007260170015

    authors: Bajo M,Yoo BC,Cairns N,Gratzer M,Lubec G

    更新日期:2001-01-01 00:00:00

  • Cis-trans isomerization of omega dihedrals in proteins.

    abstract::Peptide bonds in protein structures are mainly found in trans conformation with a torsion angle ω close to 180°. Only a very low proportion is observed in cis conformation with ω angle around 0°. Cis-trans isomerization leads to local conformation changes which play an important role in many biological processes. In t...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-013-1511-3

    authors: Craveur P,Joseph AP,Poulain P,de Brevern AG,Rebehmed J

    更新日期:2013-08-01 00:00:00

  • Dakin-West reaction on 1-thyminyl acetic acid for the synthesis of 1,3-bis(1-thyminyl)-2-propanone, a heteroaromatic compound with nucleopeptide-binding properties.

    abstract::This work deals with the Dakin-West synthesis, starting from the nucleoamino acid 1-thyminyl acetic acid, as well the NMR, ESI MS, and X-ray characterization of a heteroaromatic compound denominated by us T(2)CO, comprising two thymine moieties anchored to a 2-propanonic unit, the spectroscopic properties of which wer...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1237-7

    authors: Roviello GN,Roviello G,Musumeci D,Bucci EM,Pedone C

    更新日期:2012-10-01 00:00:00

  • Cancer therapy and prevention by green tea: role of ornithine decarboxylase.

    abstract::Green tea which is widely consumed in China, Japan and India, contains polyphenolic compounds, which account for 30% of the dry weight of the leaves. Most of the polyphenols are flavanols, of which (-)-epigallocatechin-3-gallate (EGCG) is most abundant. Epidemiological studies revealed that the incidences of stomach a...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s726-002-8197-9

    authors: Bachrach U,Wang YC

    更新日期:2002-01-01 00:00:00

  • Distribution of L-tryptophan in normal and glucose - loaded mice.

    abstract::L-tryptophan is an essential amino acid in food, but is also widely used as a drug on the basis of several physiological actions. Lately, tryptophan's uses as a drug and as a food supplement have been discontinued in several countries due to its severe side-effects.In the present study, the distribution of tryptophan ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00806494

    authors: Sainio EL,Närvänen S,Sainio P,Tuohimaa P

    更新日期:1995-06-01 00:00:00

  • Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation-alkylation sequence of a chiral γ-lactam.

    abstract::Starting from a chiral 4-hydroxymethyl pyrrolidin-2-one, an isostere of α-methyl homoserine tethered on a γ-lactam ring was prepared exploiting a stereoselective acylation-methylation sequence, followed by Curtius rearrangement, and structural assignment was confirmed by n.O.e. experiments. By reverting the sequence, ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-014-1671-9

    authors: Civitavecchia A,Martelli G,Orena M,Rinaldi S

    更新日期:2014-04-01 00:00:00

  • Anti-tissue transglutaminase antibodies activate intracellular tissue transglutaminase by modulating cytosolic Ca2+ homeostasis.

    abstract::Anti-tissue transglutaminase (tTG) antibodies are specifically produced in the small-intestinal mucosa of celiac disease (CD) patients. It is now recognized that these antibodies, acting on cell-surface tTG, may play an active role in CD pathogenesis triggering an intracellular response via the activation of different...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-1120-y

    authors: Caputo I,Lepretti M,Secondo A,Martucciello S,Paolella G,Sblattero D,Barone MV,Esposito C

    更新日期:2013-01-01 00:00:00

  • Real-time heterogeneous protein-protein interaction between αA-crystallin N-terminal mutants and αB-crystallin using quartz crystal microbalance (QCM).

    abstract::The lens transparency depends on higher concentration of lens proteins and their interactions. α-Crystallin is one of the predominant lens proteins, responsible for proper structural and functional architecture of the lens microenvironment, and any alteration of which results in cataract formation. The R12C, R21L, R49...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-1935-z

    authors: Ramkumar S,Fujii N,Sakaue H,Fujii N,Thankappan B,kumari RP,Natarajaseenivasan K,Anbarasu K

    更新日期:2015-05-01 00:00:00

  • Applications of chemically defined diets to the solution of nutrition problems.

    abstract::Chemically defined amino acid diets have been developed for most laboratory and meat-producing animal species as well as for humans. In many cases, growth performance of animals fed these diets equals that obtained with standard intact-protein diets. The pattern of both essential and nonessential amino acids is critic...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00806073

    authors: Baker DH

    更新日期:1992-02-01 00:00:00

  • Synthesis and electrochemical behaviour of beta-halodehydroamino acid derivatives.

    abstract::Several new beta,beta-dihalo and beta-halo-beta-substituted dehydroalanines and dehydrodipeptides were synthesized by reacting the corresponding dehydroamino acid derivative with a N-halosuccinimide or in the case of beta,beta-di-iododehydroalanines with iodine. The results obtained confirmed that the stereochemical o...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0466-x

    authors: Ferreira PM,Monteiro LS,Pereira G

    更新日期:2010-07-01 00:00:00

  • Pathways involved in alanyl-glutamine-induced changes in neutrophil amino- and alpha-keto acid homeostasis or immunocompetence.

    abstract::We examined the effects of DON [glutamine-analogue and inhibitor of glutamine-requiring enzymes], alanyl-glutamine (regarding its role in neutrophil immunonutrition) and alanyl-glutamine combined with L-NAME, SNAP, DON, beta-alanine and DFMO on neutrophil amino and alpha-keto acid concentrations or important neutrophi...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-006-0395-x

    authors: Mühling J,Burchert D,Langefeld TW,Matejec R,Harbach H,Engel J,Wolff M,Welters ID,Fuchs M,Menges T,Krüll M,Hempelmann G

    更新日期:2007-09-01 00:00:00

  • Principal component analysis of the relationship between the D-amino acid concentrations and the taste of the sake.

    abstract::We performed sensory evaluations on 141 bottles of sake and analyzed the relationship between the D-amino acid concentrations, and the taste of the sake using principal component analysis, which yielded seven principal components (PC1-7) that explained 100 % of the total variance in the data. PC1, which explains 33.6 ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1359-y

    authors: Okada K,Gogami Y,Oikawa T

    更新日期:2013-02-01 00:00:00

  • Acetaminophen reduces the protein levels of high affinity amino acid permeases and causes tryptophan depletion.

    abstract::In yeast, toxicity of acetaminophen (APAP), a frequently used analgesic and antipyretic drug, depends on ubiquitin-controlled processes. Previously, we showed a remarkable overlap in toxicity profiles between APAP and tyrosine, and a similarity with drugs like rapamycin and quinine, which induce degradation of the ami...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2613-8

    authors: Huseinovic A,Dekker SJ,Boogaard B,Vermeulen NPE,Kooter JM,Vos JC

    更新日期:2018-10-01 00:00:00

  • Acute regulation of IGF-I by alterations in post-exercise macronutrients.

    abstract::This investigation sought to examine the contributions of exercise and nutrient replenishment on in vivo regulation of the insulin-like growth factor-I (IGF-I) axis components. Eight college-aged males completed three high-intensity interval training (HIIT) protocols followed by three post-exercise nutritional protoco...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-0837-y

    authors: Foster EB,Fisher G,Sartin JL,Elsasser TH,Wu G,Cowan W,Pascoe DD

    更新日期:2012-04-01 00:00:00