Pre-microRNA binding aminoglycosides and antitumor drugs as inhibitors of Dicer catalyzed microRNA processing.

Abstract:

:Over-expressions of miRNAs are being increasingly linked with many diseases including different types of cancer. In this study, the role of some known small molecular therapeutics has been investigated for their ability to bind with the pre-miRNA target (hsa-mir-155) and thereby to interfere with the Dicer catalyzed miRNA processing. Potential binding and inhibition effects have been demonstrated by some of these analogs. They can be used as leads for further development of potent small molecular miRNA-antagonists.

journal_name

Bioorg Med Chem Lett

authors

Maiti M,Nauwelaerts K,Herdewijn P

doi

10.1016/j.bmcl.2011.12.103

subject

Has Abstract

pub_date

2012-02-15 00:00:00

pages

1709-11

issue

4

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(11)01785-9

journal_volume

22

pub_type

杂志文章
  • Identification of a new biaryl scaffold generating potent renin inhibitors.

    abstract::The discovery and SAR of a series of potent renin inhibitors possessing a novel biaryl scaffold are described herein. Molecular modeling revealed that the cyclopropylamide spacer present in 1 can be replaced by a simple, substituted aromatic ring such as a toluene in 2. The resulting compounds exhibit subnanomolar ren...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.07.127

    authors: Lacombe P,Aspiotis R,Bayly C,Chen A,Dubé D,Fortin R,Gallant M,Juteau H,Liu S,McKay D,Roy P,Wu T

    更新日期:2010-10-01 00:00:00

  • Synthesis and properties of prodrugs activated in hypoxia to give bleomycin analogues.

    abstract::Prodrugs bioreductively activated to bleomycin analogues are reported. The production of hydroxyl radicals in the presence of FE(II) and dioxygen by both the prodrugs and the activated products are determined and their in vitro cytotoxicity measured. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00467-3

    authors: Highfield JA,Mehta LK,Parrick J,Candeias LP,Wardman P

    更新日期:1998-09-22 00:00:00

  • Heterocyclic substituted anthralin derivatives as inhibitors of keratinocyte growth and inducers of differentiation.

    abstract::Heterocyclic substituted derivatives of the antipsoriatic anthralin were synthesized and evaluated in vitro for their antiproliferative action against keratinocytes and their ability to induce keratinocyte differentiation. The indole-2-carboxylic acid analogue 2e exhibited the same excellent antiproliferative activity...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00599-0

    authors: Müller K,Reindl H,Breu K

    更新日期:2001-01-08 00:00:00

  • The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines.

    abstract::The synthesis of potent 4-aryl methoxypiperidinol inhibitors of the dopamine transporter is described. Symmetrical para substituents of the benzene rings are important for high potency in binding to the dopamine transporter. 4-[Bis(4-fluorophenyl) methoxy]-1-methylpiperidine has an IC50 of 22.1+/-5.73 nM and increases...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.08.028

    authors: Lapa GB,Byrd GD,Lapa AA,Budygin EA,Childers SR,Jones SR,Harp JJ

    更新日期:2005-11-15 00:00:00

  • Lead generation and optimization of novel GPR119 agonists with a spirocyclic cyclohexane structure.

    abstract::We describe here the generation of a lead compound and its optimization studies that led to the identification of a novel GPR119 agonist. Based on a spirocyclic cyclohexane structure reported in our previous work, we identified compound 8 as a lead compound, being guided by ligand-lipophilicity efficiency (LLE), which...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.12.041

    authors: Harada K,Mizukami J,Watanabe T,Mori G,Ubukata M,Suwa K,Fukuda S,Negoro T,Sato M,Inaba T

    更新日期:2019-02-01 00:00:00

  • Preparation and optimization of new 4-(2-(indolin-1-yl)-2-oxoethyl)-2-morpholinothiazole-5-carboxylic acid and amide derivatives as potent and selective PI3Kβ inhibitors.

    abstract::In our continuous efforts to identify and develop novel targeted cancer treatments, a new morpholino-thiazole scaffold active against PI3Kβ has been identified. This Letter reports the optimization of this compound class to develop PI3Kβ isoform-selective inhibitors with suitable pharmacological properties. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.02.004

    authors: Certal V,Halley F,Virone-Oddos A,Filoche-Rommé B,Carry JC,Gruss-Leleu F,Bertin L,Guizani H,Pilorge F,Richepin P,Karlsson A,Charrier V,Abecassis PY,Vincent L,Nicolas JP,Lengauer C,Garcia-Echeverria C,Schio L

    更新日期:2014-03-15 00:00:00

  • Discovery of new peptide-based catalysts for the direct asymmetric aldol reaction.

    abstract::A series of oligo-peptide based catalysts were prepared using Fmoc solid-phase peptide synthesis. It was found that peptides with N-terminal proline residues catalyzed an aldol reaction yielding enantiomeric enriched product. Peptide H-Pro-Glu-Leu-Phe-OH catalyzed the reaction with good activity and moderate enantiose...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00498-0

    authors: Kofoed J,Nielsen J,Reymond JL

    更新日期:2003-08-04 00:00:00

  • Structure activity relationships of benzylproline-derived inhibitors of the glutamine transporter ASCT2.

    abstract::The glutamine transporter ASCT2 has been identified as a promising target to inhibit rapid growth of cancer cells. However, ASCT2 pharmacology is not well established. In this report, we performed a systematic structure activity analysis of a series of substituted benzylproline derivatives. Substitutions on the phenyl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.12.063

    authors: Singh K,Tanui R,Gameiro A,Eisenberg G,Colas C,Schlessinger A,Grewer C

    更新日期:2017-02-01 00:00:00

  • Antileishmanial potential of fused 5-(pyrazin-2-yl)-4H-1,2,4-triazole-3-thiols: Synthesis, biological evaluations and computational studies.

    abstract::A series of newer 1,2,4-triazole-3-thiol derivatives 5(a-m) and 6(a-i) containing a triazole fused with pyrazine moiety of pharmacological significance have been synthesized. All the synthesized compounds were screened for their in vitro antileishmanial and antioxidant activities. Compounds 5f (IC50=79.0µM) and 6f (IC...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.06.053

    authors: Patil SR,Asrondkar A,Patil V,Sangshetti JN,Kalam Khan FA,Damale MG,Patil RH,Bobade AS,Shinde DB

    更新日期:2017-08-15 00:00:00

  • Synthesis and biological evaluation of a new series of N-acyldiamines as potential antibacterial and antifungal agents.

    abstract::In continuation of our efforts to find new antimicrobial compounds, series of fatty N-acyldiamines were prepared from fatty methyl esters and 1,2-ethylenediamine, 1,3-propanediamine or 1,4-butanediamine. The synthesized compounds were screened for their antibacterial activity against Gram-positive bacteria (Staphyloco...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.08.047

    authors: Ferreira BDS,de Almeida AM,Nascimento TC,de Castro PP,Silva VL,Diniz CG,Le Hyaric M

    更新日期:2014-10-01 00:00:00

  • Synthetic ligand promotes gene expression by affecting GC sequence in promoter.

    abstract::A naphthyridine carbamate tetramer (NCT8) is a synthetic compound, which selectively binds to nucleic acids containing CGG/CGG sequence. Although NCT8 is a promising compound for a wide range of DNA and RNA based biotechnology such as modulation of specific gene expression, little is known about its behavior in human ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.06.006

    authors: Matsumoto S,Iida K,Murata A,Denawa M,Hagiwara M,Nakatani K

    更新日期:2017-08-01 00:00:00

  • Design and synthesis of o-trifluoromethylbiphenyl substituted 2-amino-nicotinonitriles as inhibitors of farnesyltransferase.

    abstract::A non-methionine FT inhibitor lead structure (1) was designed through computer modeling of the peptidomimetic FT inhibitor ABT839. Optimization of this lead resulted in compounds 2e and 2g, with FT IC(50) values of 1.3 and 1.8 nM, GGT IC(50) of 1400 nM, and EC(50) (Ras processing) values of 13 and 11 nM, respectively....

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.10.014

    authors: Wang GT,Wang X,Wang W,Hasvold LA,Sullivan G,Hutchins CW,O'Conner S,Gentiles R,Sowin T,Cohen J,Gu WZ,Zhang H,Rosenberg SH,Sham HL

    更新日期:2005-01-03 00:00:00

  • Synthesis of novel keto-ACE analogues as domain-selective angiotensin I-converting enzyme inhibitors.

    abstract::Novel analogues of the angiotensin I-converting enzyme (ACE) inhibitor keto-ACE were synthesized via a facile Horner-Emmons olefination of a phosphonoketone precursor with ethyl glyoxylate. Introduction of a bulky aromatic tryptophan at the P(2)(') position of keto-ACE resulted in a significant increase in C-domain-se...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.06.003

    authors: Nchinda AT,Chibale K,Redelinghuys P,Sturrock ED

    更新日期:2006-09-01 00:00:00

  • Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates.

    abstract::The esterase, phosphatase, and sulfatase activities of carbonic anhydrase (CA, EC 4.2.1.1) isozymes, CA I, II, and XIII with 4-nitrophenyl esters as substrates was investigated. These enzymes show esterase activity with 4-nitrophenyl acetate as substrate, with second order rate constants in the range of 753-7706M(-1)s...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.03.012

    authors: Innocenti A,Scozzafava A,Parkkila S,Puccetti L,De Simone G,Supuran CT

    更新日期:2008-04-01 00:00:00

  • trans-3,4-Disubstituted pyrrolidines as inhibitors of the human aspartyl protease renin. Part II: prime site exploration using an oxygen linker.

    abstract::Inhibition of the aspartyl protease renin is considered as an efficient approach for treating hypertension. Lately, we described the discovery of a novel class of direct renin inhibitors which comprised a pyrrolidine scaffold (e.g., 2). Based on the X-ray structure of the lead compound 2 bound to renin we predicted th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.02.040

    authors: Sellner H,Cottens S,Cumin F,Ehrhardt C,Kosaka T,Lorthiois E,Ostermann N,Webb RL,Rigel DF,Wagner T,Maibaum J

    更新日期:2015-04-15 00:00:00

  • Substituted tetrahydro-beta-carbolines as potential agents for the treatment of human papillomavirus infection.

    abstract::The identification and optimization of a series of substituted tetrahydro-beta-carbolines with potent activity against human papillomavirus is described. Structure-activity studies focused on the substitution pattern and chirality of the beta-carboline ring system are discussed. Optimization of these parameters led to...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.10.123

    authors: Miller JF,Turner EM,Sherrill RG,Gudmundsson K,Spaltenstein A,Sethna P,Brown KW,Harvey R,Romines KR,Golden P

    更新日期:2010-01-01 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

  • The solid phase synthesis of a series of tri-substituted hydantoin ligands for the somatostatin SST5 receptor.

    abstract::A series of trisubstituted hydantoins has been prepared by a versatile solid phase route employing primary alcohols, amines and amino acids as the monomeric building blocks. Several compounds showed submicromolar affinity in binding assays at recombinant human somatostatin receptors. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00647-7

    authors: Sciciński JJ,Barker MD,Murray PJ,Jarvie EM

    更新日期:1998-12-15 00:00:00

  • Identification of novel estrogen receptor (ER) agonists that have additional and complementary anti-cancer activities via ER-independent mechanism.

    abstract::In this study, a series of bis(4-hydroxy)benzophenone oxime ether derivatives such as 12c, 12e and 12h were identified as novel estrogen receptor (ER) agonists that have additional and complementary anti-proliferative activities via ER-independent mechanism in cancer cells. These compounds are expected to overcome the...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.01.089

    authors: Kim T,Kim HI,An JY,Lee J,Lee NR,Heo J,Kim JE,Yu J,Lee YS,Inn KS,Kim NJ

    更新日期:2016-04-01 00:00:00

  • In vitro evolution of an HIV integrase binding protein from a library of C-terminal domain γS-crystallin variants.

    abstract::A protein without natural binding functions was engineered to bind HIV-1 integrase. Phage display selections applied a library of variants based on the C-terminal domain of the eye lens protein human γS-crystallin. Multiple loop regions were altered to encode libraries with ≈3.6 × 10(11) different variants. A crystall...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.07.008

    authors: Moody IS,Verde SC,Overstreet CM,Edward Robinson W Jr,Weiss GA

    更新日期:2012-09-01 00:00:00

  • Synthesis, SAR and pharmacology of CP-293,019: a potent, selective dopamine D4 receptor antagonist.

    abstract::A series of novel, potent and selective pyrido[1,2-a]pyrazine dopamine D4 receptor antagonists are reported including CP-293,019 (D4 Ki = 3.4 nM, D2 Ki > 3,310 nM), which also inhibits apomorphine-induced hyperlocomotion in rats after oral dosing. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00108-5

    authors: Sanner MA,Chappie TA,Dunaiskis AR,Fliri AF,Desai KA,Zorn SH,Jackson ER,Johnson CG,Morrone JM,Seymour PA,Majchrzak MJ,Faraci WS,Collins JL,Duignan DB,Prete Di CC,Lee JS,Trozzi A

    更新日期:1998-04-07 00:00:00

  • Redox-responsive and calcium-dependent switching of glycosyldisulfide interactions with Concanavalin A.

    abstract::Glycosyldisulfides can interact efficiently with carbohydrate-binding entities. This has been shown for a range of thiosaccharide dimers when tested for their effects against the lectin Concanavalin A using a modified quartz crystal microbalance-technique. Contrary to the thiosaccharide monomers, showing no significan...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.04.024

    authors: Pei Z,Aastrup T,Anderson H,Ramström O

    更新日期:2005-06-02 00:00:00

  • Imidazolopyrazinones as potential antioxidants.

    abstract::A series of imidazolopyrazinones 3, substituted at C-2, and C-2/C-6, has been prepared. The compounds behaved as quenchers of superoxide anion. The more active compounds are structurally related to coelenterazine, a natural substrate of marine bioluminescence. Theoretical parameters based on Hartree-Fock instabilities...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00445-0

    authors: Devillers I,Dive G,De Tollenaere C,Falmagne B,de Wergifosse B,Rees JF,Marchand-Brynaert J

    更新日期:2001-09-03 00:00:00

  • Optimization of anti-proliferative activity using a screening approach with a series of bis-heterocyclic G-quadruplex ligands.

    abstract::Using a phenotypic screening and SAR optimization approach, a phenyl-bis-oxazole derivative has been identified with anti-proliferative activity, optimized with the use of a panel of cancer cell lines. The lead compound was synthesized by means of a short and effective two-step synthesis using Pd-catalyzed direct aryl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.07.057

    authors: Ohnmacht SA,Ciancimino C,Vignaroli G,Gunaratnam M,Neidle S

    更新日期:2013-10-01 00:00:00

  • Adamantyl N-benzylbenzamide: new series of depigmentation agents with tyrosinase inhibitory activity.

    abstract::A new series of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety has been synthesized, and the depigmenting and tyrosinase inhibitory activities of the molecules were evaluated. The lipophilic character of the adamantyl moiety appeared to confer greater depigmentation power on the benzamid...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.12.144

    authors: Baek HS,Hong YD,Lee CS,Rho HS,Shin SS,Park YH,Joo YH

    更新日期:2012-03-01 00:00:00

  • Melanocortin subtype-4 receptor agonists containing a piperazine core with substituted aryl sulfonamides.

    abstract::The biological activity for a set of melanocortin-4 receptor (MC4R) agonists containing a piperazine core with an ortho-substituted aryl sulfonamide is described. Compounds from this set had binding and functional activities at MC4R less than 30 nM. The most selective compound in this series was >25,000-fold more pote...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.01.060

    authors: Fotsch C,Han N,Arasasingham P,Bo Y,Carmouche M,Chen N,Davis J,Goldberg MH,Hale C,Hsieh FY,Kelly MG,Liu Q,Norman MH,Smith DM,Stec M,Tamayo N,Xi N,Xu S,Bannon AW,Baumgartner JW

    更新日期:2005-03-15 00:00:00

  • HY251, a novel decahydrocyclopenta[a]indene analog, from Aralia continentalis induces apoptosis via down-regulation of AR expression in human prostate cancer LNCaP cells.

    abstract::In the course of screening for a novel anticancer drug candidate, we previously isolated HY251 with the molecular structure of 3-propyl-2-vinyl-1,2,3,3a,3b,6,7,7a,8,8a-decahydrocyclopenta[a]indene-3,3a,7a,8a-tetraol from the roots of Aralia continentalis. The current study was designed to evaluate the detailed mechani...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.01.045

    authors: Oh HL,Lee CH

    更新日期:2011-03-01 00:00:00

  • Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors.

    abstract::Several chemical modifications in the N(1)-benzenesulfonamide ring of celecoxib are presented. The series with a hydroxymethyl group adjacent to the sulfonamide was found to be the most potent modification that yielded many compounds selectively active against COX-2 enzyme in vitro. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.10.027

    authors: Singh SK,Reddy PG,Rao KS,Lohray BB,Misra P,Rajjak SA,Rao YK,Venkateswarlu A

    更新日期:2004-01-19 00:00:00

  • Vitamin B6s inhibit oxidative stress caused by Alzheimer's disease-related Cu(II)-β-amyloid complexes-cooperative action of phospho-moiety.

    abstract::Cu(II) complexes of Alzheimer's disease-related β-amyloid (Aβ) peptides exhibit metal-centered oxidation chemistry. The metallo-Aβ complexes are the hallmark of the disease and have been attributed to the generation of reactive oxygen species (ROS), causing oxidative stress. In this communication, the inhibitions of t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.08.123

    authors: Hashim A,Wang L,Juneja K,Ye Y,Zhao Y,Ming LJ

    更新日期:2011-11-01 00:00:00

  • Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents.

    abstract::A series of optically pure phenyl-and non-phenyl-substituted 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines was synthesized and their binding affinity for dopamine transporter (DAT) was investigated. The analogues with a hydroxyl group in the S configuration were more selective for the DAT over...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00940-x

    authors: Hsin LW,Prisinzano T,Wilkerson CR,Dersch CM,Horel R,Jacobson AE,Rothman RB,Rice KC

    更新日期:2003-02-10 00:00:00