当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY LETTERS期刊下所有文献 > Chemical space screening around Phe3 in opioid peptides: Modulating µ versus δ agonism by Suzuki-Miyaura cross-couplings.

Chemical space screening around Phe3 in opioid peptides: Modulating µ versus δ agonism by Suzuki-Miyaura cross-couplings.

Abstract：

:In this study, affinities and activities of derivatized analogues of Dmt-dermorphin[1-4] (i.e. Dmt-d-Ala-Phe-GlyNH2, Dmt = 2',6'-dimethyl-(S)-tyrosine) for the µ opioid receptor (MOP) and δ opioid receptor (DOP) were evaluated using radioligand binding studies, functional cell-based assays and isolated organ bath experiments. By means of solid-phase or solution-phase Suzuki-Miyaura cross-couplings, various substituted regioisomers of the phenylalanine moiety in position 3 of the sequence were prepared. An 18-membered library of opioid tetrapeptides was generated via screening of the chemical space around the Phe3 side chain. These substitutions modulated bioactivity, receptor subtype selectivity and highly effective ligands with subnanomolar binding affinities, contributed to higher functional activities and potent analgesic actions. In search of selective peptidic ligands, we show here that the Suzuki-Miyaura reaction is a versatile and robust tool which could also be deployed elsewhere.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Willemse T,Eiselt E,Hollanders K,Schepens W,van Vlijmen HWT,Chung NN,Blais V,Holleran B,Longpré JM,Schiller PW,Maes BUW,Sarret P,Gendron L,Ballet S

doi

10.1016/j.bmcl.2018.05.015

subject

Has Abstract

pub_date

2018-07-15 00:00:00

pages

2320-2323

issue

13

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(18)30404-9

journal_volume

28

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS文献大全
  • Protective effect of Opuntia ficus-indica L. cladodes against UVA-induced oxidative stress in normal human keratinocytes.

    abstract：:Opuntia ficus-indica L. is known for its beneficial effects on human health, but still little is known on cladodes as a potent source of antioxidants. Here, a direct, economic and safe method was set up to obtain water extracts from Opuntia ficus-indica cladodes rich in antioxidant compounds. When human keratinocytes ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2017.10.043

    authors： Petruk G,Di Lorenzo F,Imbimbo P,Silipo A,Bonina A,Rizza L,Piccoli R,Monti DM,Lanzetta R

    更新日期：2017-12-15 00:00:00

  • Dumbbell-shaped circular oligonucleotides as inhibitors of human topoisomerase I.

    abstract：:A dumbbell-shaped circular oligonucleotide containing topoisomerase I-binding sites and two mismatched base pairs in its sequence has been designed and synthesized. Our further studies demonstrate that this particularly designed oligonucleotide displays an IC(50) value of 9 nM in its inhibition on the activity of huma...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.06.035

    authors： Li X,Tao Ng MT,Wang Y,Liu X,Li T

    更新日期：2007-09-01 00:00:00

  • Synthesis and anti-leishmanial activity of 1-aryl-β-carboline derivatives against Leishmania donovani.

    abstract：:β-carbolines from various natural and synthetic sources have been known to show diverse biological activities. As a part of our current ongoing project to search for potent natural product-derived anti-leishmanial compounds, we have synthesized a series of substituted 1-aryl-β-carboline derivatives. A total of 22 comp...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.04.115

    authors： Gohil VM,Brahmbhatt KG,Loiseau PM,Bhutani KK

    更新日期：2012-06-15 00:00:00

  • Synthesis, fungicidal activity and SAR of 3,4-dichloroisothiazole-based cycloalkylsulfonamides.

    abstract：:To develop more valuable and effective fungicide candidates, a novel series of 3,4-dichloroisothioxazole-based cycloalkylsulfonamides were synthesized and their structures were identified by 1H NMR, 13C NMR, MS and elemental analysis. Compound 3k was further confirmed by X-ray single crystal diffraction. The in vitro ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2019.03.047

    authors： Zhang Y,Wang M,Ahmed M,He L,Ji M,Qi Z,Li X

    更新日期：2019-06-01 00:00:00

  • Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents.

    abstract：:A series of novel quinoline-oxadiazole hybrid compounds was designed based on stepwise rational modification of the lead molecules reported previously, in order to enhance bioactivity and improve druglikeness. The hybrid compounds synthesized were screened for biological activity against Mycobacterium tuberculosis H37...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2015.11.057

    authors： Jain PP,Degani MS,Raju A,Anantram A,Seervi M,Sathaye S,Ray M,Rajan MGR

    更新日期：2016-01-15 00:00:00

  • A selective phosphine-based fluorescent probe for nitroxyl in living cells.

    abstract：:A novel fluorescein-based fluorescent probe for nitroxyl (HNO) based on the reductive Staudinger ligation of HNO with an aromatic phosphine was prepared. This probe reacts with HNO derived from Angeli's salt and 4-bromo Piloty's acid under physiological conditions without interference by other biological redox species...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.11.041

    authors： Miao Z,Reisz JA,Mitroka SM,Pan J,Xian M,King SB

    更新日期：2015-01-01 00:00:00

  • Enhancing the activity of membrane remodeling epsin-peptide by trimerization.

    abstract：:Modulating the structural dynamics of biomembranes by inducing bilayer curvature and lipid packing defects has been highlighted as a practical tool to modify membrane-dependent cellular processes. Previously, we have reported on an amphipathic helical peptide derived from the N-terminal segment (residues 1-18, EpN18) ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2020.127190

    authors： Hsu WY,Masuda T,Afonin S,Sakai T,Arafiles JVV,Kawano K,Hirose H,Imanishi M,Ulrich AS,Futaki S

    更新日期：2020-06-15 00:00:00

  • Identification of urine metabolites of TFAP, a cyclooxygenase-1 inhibitor.

    abstract：:Only a few COX-1-selective inhibitors are currently available, and the research on COX-1 selective inhibitors is not fully developed. The authors have produced several COX-1 selective inhibitors including N-(5-amino-2-pyridinyl)-4-trifluoromethylbenzamide: TFAP (3). Although 3 shows potent analgesic effect without gas...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.01.161

    authors： Kakuta H,Fukai R,Xiaoxia Z,Ohsawa F,Bamba T,Hirata K,Tai A

    更新日期：2010-03-15 00:00:00

  • Radanamycin, a macrocyclic chimera of radicicol and geldanamycin.

    abstract：:Radicicol and geldanamycin are potent inhibitors of the Hsp90 protein folding machinery, which is an emerging target for the development of cancer chemotherapeutics. However, radicicol is inactive in vivo and geldanamycin suffers from its redox-active behavior that produces toxicity unrelated to Hsp90 inhibition. It w...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.01.086

    authors： Wang M,Shen G,Blagg BS

    更新日期：2006-05-01 00:00:00

  • Differential signaling properties at the kappa opioid receptor of 12-epi-salvinorin A and its analogues.

    abstract：:The kappa opioid receptor (KOPR) has been identified as a potential drug target to prevent or alter the course of mood, anxiety and addictive disorders or reduce response to stress. In a search for highly potent and selective KOPR partial agonists as pharmacological tools, we have modified 12-epi-salvinorin A, a compo...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.11.128

    authors： Béguin C,Potuzak J,Xu W,Liu-Chen LY,Streicher JM,Groer CE,Bohn LM,Carlezon WA Jr,Cohen BM

    更新日期：2012-01-15 00:00:00

  • Inhaled Janus Kinase (JAK) inhibitors for the treatment of asthma.

    abstract：:Multiple asthma-relevant cytokines including IL-4, IL-5, IL-13, and TSLP depend upon JAKs for signaling. JAK inhibition may, therefore, offer a novel intervention strategy for patients with disease refractory to current standards of care. Multiple systemically delivered JAK inhibitors have been approved for human use ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章,评审

    doi：10.1016/j.bmcl.2019.126658

    authors： Zak M,Dengler HS,Rajapaksa NS

    更新日期：2019-10-15 00:00:00

  • Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of 5-amino-1,3,4-thiadiazole-2-sulfonamide and 5-(4-amino-3-chloro-5-fluorophenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide to human isoform II.

    abstract：:The X-ray crystal structures of 5-amino-1,3,4-thiadiazole-2-sulfonamide (the acetazolamide precursor) and 5-(4-amino-3-chloro-5-fluorophenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide in complex with the human isozyme II of carbonic anhydrase (CA, EC 4.2.1.1) are reported. The thiadiazole-sulfonamide moiety of the tw...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.09.022

    authors： Menchise V,De Simone G,Di Fiore A,Scozzafava A,Supuran CT

    更新日期：2006-12-15 00:00:00

  • Achieving structural diversity using the perpendicular conformation of alpha-substituted phenylcyclopropanes to mimic the bioactive conformation of ortho-substituted biphenyl P4 moieties: discovery of novel, highly potent inhibitors of Factor Xa.

    abstract：:Ortho-substituted biphenyl moieties are widely used in drug design. We herein report a successful use of the perpendicular conformation of the alpha-substituted phenylcyclopropyl groups to mimic the aplanar, biologically active conformation of the ortho-substituted biphenyl moieties to achieve structural diversity. Th...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2008.05.095

    authors： Qiao JX,Cheney DL,Alexander RS,Smallwood AM,King SR,He K,Rendina AR,Luettgen JM,Knabb RM,Wexler RR,Lam PY

    更新日期：2008-07-15 00:00:00

  • 4-Phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives as non-peptidic selective delta-opioid agonists with potential anxiolytic/antidepressant properties. Part 2.

    abstract：:Novel 4-phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives have been prepared and their synthesis described herein. In vitro affinities for delta-, micro-, and kappa-opioid receptors are reported. Evaluation of some representative compounds from this series in the mouse neonatal ultrasonic vocalization test and the mo...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.05.012

    authors： Trabanco AA,Aerts N,Alvarez RM,Andrés JI,Boeckx I,Fernández J,Gómez A,Janssens FE,Leenaerts JE,De Lucas AI,Matesanz E,Steckler T,Pullan S

    更新日期：2007-07-15 00:00:00

  • Synthesis and antiproliferative activity of unnatural enantiomers of 7-epi-goniofufurone and crassalactone C.

    abstract：:A facile synthesis of 7-epi-(-)-goniofufurone as well as the first synthesis of (-)-crassalactone C was achieved starting from D-xylose. A comparison of their in vitro antitumour activities with those observed for the corresponding naturally occurring enantiomers was provided. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2008.08.093

    authors： Popsavin V,Benedeković G,Srećo B,Popsavin M,Francuz J,Kojić V,Bogdanović G

    更新日期：2008-10-01 00:00:00

  • Syntheses of certain 3-aryl-2-propenoates and evaluation of their cytotoxicity.

    abstract：:A series of 3-aryl-2-propenoates including cinnamates, (E)-methyl/ethyl 3-[2-(1,4-dimethoxy-5,8-dione)naphthalenyl]-2-propenoates (8ba, 8bb) and (E)-methyl/ethyl 3-[2-(1,4-dihydroxy-9,10-dione)anthracenyl]-2-propenoates (9aa,9ab) was synthesized and evaluated for antitumor cytotoxicity. It was found that the ortho- or...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(01)00165-2

    authors： Nam NH,You YJ,Kim Y,Hong DH,Kim HM,Ahn BZ

    更新日期：2001-05-07 00:00:00

  • Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.

    abstract：:Nobiletin, a major component of polymethoxyflavones in citrus fruits, has a broad spectrum of health beneficial properties including anti-inflammatory and anti-carcinogenic activities. The metabolite identification of nobiletin in mouse urine has concluded that it undergoes mono-demethylation (3'- and 4'-demethylnobil...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.06.096

    authors： Li S,Sang S,Pan MH,Lai CS,Lo CY,Yang CS,Ho CT

    更新日期：2007-09-15 00:00:00

  • Copper dipicolinates as peptidomimetic ligands for the Src SH2 domain.

    abstract：:The introduction of copper chelates into peptide mimetics creates the Src SH2 binding ligands and paramagnetic complexes suitable for EPR studies of peptide protein interactions. The dipicolinic acid was attached to SH2 domain targeting fragments by two different linkers. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2004.06.018

    authors： Schmidt B,Jiricek J,Titz A,Ye G,Parang K

    更新日期：2004-08-16 00:00:00

  • N-(pyrimidin-4-yl) and N-(pyridin-2-yl) phenylalanine derivatives as VLA-4 integrin antagonists.

    abstract：:The SAR studies to optimise both potency and rate of clearance in the rat for a series of pyrimidine and pyridine based VLA-4 antagonists are described. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(02)00241-x

    authors： Porter JR,Archibald SC,Brown JA,Childs K,Critchley D,Head JC,Hutchinson B,Parton TA,Robinson MK,Shock A,Warrellow GJ,Zomaya A

    更新日期：2002-06-17 00:00:00

  • Anti-herpes simplex virus efficacies of 2-aminobenzamide derivatives as novel HSP90 inhibitors.

    abstract：:After the widespread use of the acyclic purine nucleoside analogues for therapy of herpes simplex virus (HSV) infection since the 1980s, new antiviral strategies are urgently needed to counter the emergence of drug-resistant clinical isolates. In this report, we define the anti-HSV efficacies of three optimized 2-amin...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.05.079

    authors： Xiang YF,Qian CW,Xing GW,Hao J,Xia M,Wang YF

    更新日期：2012-07-15 00:00:00

  • Discovery of 'molecular switches' within a GIRK activator scaffold that afford selective GIRK inhibitors.

    abstract：:This letter describes a multi-dimensional SAR campaign based on a potent, efficacious and selective GIRK1/2 activator (~10-fold versus GIRK1/4 and inactive on nonGIRK 1-containing GIRKs, GIRK 2 or GIRK2/3). Further chemical optimization through an iterative parallel synthesis effort identified multiple 'molecular swit...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2013.06.023

    authors： Wen W,Wu W,Romaine IM,Kaufmann K,Du Y,Sulikowski GA,Weaver CD,Lindsley CW

    更新日期：2013-08-15 00:00:00

  • Oxidative stimuli-responsive nanoprodrug of camptothecin kills glioblastoma cells.

    abstract：:The purpose of this study was to prepare and characterize nanometer-sized prodrug (nanoprodrug) of camptothecin. The camptothecin prodrug was synthesized using tetraethylene glycol spacer linked via carbonate bond to camptothecin and via ester bond to alpha-lipoic acid. The nanoprodrug was prepared through the spontan...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.06.144

    authors： Lee BS,Nalla AK,Stock IR,Shear TC,Black KL,Yu JS

    更新日期：2010-09-01 00:00:00

  • A chemically stable fluorescent marker of the ureter.

    abstract：:Surgical methods guided by exogenous fluorescent markers have the potential to define tissue types in real time. Small molecule dyes with efficient and selective renal clearance could enable visualization of the ureter during surgical procedures involving the abdomen and pelvis. These studies report the design and syn...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2018.02.040

    authors： Cha J,Nani RR,Luciano MP,Kline G,Broch A,Kim K,Namgoong JM,Kulkarni RA,Meier JL,Kim P,Schnermann MJ

    更新日期：2018-09-01 00:00:00

  • Generation of novel radiolabeled opiates through site-selective iodination.

    abstract：:Tritiated opioid radioligands have proven valuable in exploring opioid binding sites. However, tritium has many limitations. Its low specific activity and limited counting efficiency makes it difficult to examine low abundant, high affinity sites and its disposal is problematic due to the need to use organic scintilla...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.05.008

    authors： Majumdar S,Burgman M,Haselton N,Grinnell S,Ocampo J,Pasternak AR,Pasternak GW

    更新日期：2011-07-01 00:00:00

  • Hybrid anticancer agents: isothiocyanate-progesterone conjugates as chemotherapeutic agents and insights into their cytotoxicities.

    abstract：:New hybrid molecules of isothiocyanate and progesterone and their metal complexes were synthesized exhibiting promising anti-proliferative and pro-apoptotic activity against breast and prostate cancer cells. These metal complex compounds exploited an existing cellular transport pathway for delivery of cytotoxic isothi...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.11.128

    authors： Adsule S,Banerjee S,Ahmed F,Padhye S,Sarkar FH

    更新日期：2010-02-01 00:00:00

  • 4-Amino-2-cyanopyrimidines: novel scaffold for nonpeptidic cathepsin S inhibitors.

    abstract：:We describe here a novel 4-amino-2-cyanopyrimidine scaffold for nonpeptidomimetic cathepsin S selective inhibitors. Some of the synthesized compounds have sub-nanomolar potency and high selectivity toward cathepsin S along with promising pharmacokinetic and physicochemical properties. The key structural features of th...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2008.07.011

    authors： Irie O,Yokokawa F,Ehara T,Iwasaki A,Iwaki Y,Hitomi Y,Konishi K,Kishida M,Toyao A,Masuya K,Gunji H,Sakaki J,Iwasaki G,Hirao H,Kanazawa T,Tanabe K,Kosaka T,Hart TW,Hallett A

    更新日期：2008-08-15 00:00:00

  • Synthesis and molecular docking study of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential antitumor agents.

    abstract：:A series of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 3d exhibited potentially high activity against human gastric cancer cell SGC-7901 with IC(50) value of 2.69 ± 0.60 μg/mL. All title compounds were assa...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.08.017

    authors： Liu XH,Liu HF,Chen J,Yang Y,Song BA,Bai LS,Liu JX,Zhu HL,Qi XB

    更新日期：2010-10-01 00:00:00

  • The bioisosteric modification of pyrazinamide derivatives led to potent antitubercular agents: Synthesis via click approach and molecular docking of pyrazine-1,2,3-triazoles.

    abstract：:Tuberculosis remains as a major public health risk which causes the highest mortality rate globally and an improved regimen is required to treat the drug-resistant strains. Pyrazinamide is a first-line antitubercular drug used in combination therapy with other anti-TB drugs. Herein, we describe the modification of pyr...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2019.126846

    authors： Reddyrajula R,Dalimba U

    更新日期：2020-01-15 00:00:00

  • Peptide chemistry applied to a new family of phenothiazine-containing inhibitors of human farnesyltransferase.

    abstract：:Novel phenothiazine derivatives bearing an amino acid residue were synthesized via peptide chemistry, and evaluated for their inhibitory potential on human farnesyltransferase. The phenothiazine unit proved to be an important bulky unit in the structure of the synthesized inhibitors. Propargyl ester 20 bearing a tyros...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.04.102

    authors： Dumitriu GM,Ghinet A,Bîcu E,Rigo B,Dubois J,Farce A,Belei D

    更新日期：2014-07-15 00:00:00

  • Pyrazoles, 1,2,4-triazoles, and tetrazoles as surrogates for cis-amide bonds in boronate ester thrombin inhibitors.

    abstract：:Substituted pyrazoles, 1,2,4-triazoles, and tetrazoles are good surrogates for cis-amide bonds in a series of boronate ester thrombin inhibitors. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(98)00104-8

    authors： Duncia JV,Santella JB 3rd,Higley CA,VanAtten MK,Weber PC,Alexander RS,Kettner CA,Pruitt JR,Liauw AY,Quan ML,Knabb RM,Wexler RR

    更新日期：1998-04-07 00:00:00