A new selective fluorescent probe based on tamoxifen.


:Developing targeted validation probes that can interrogate biology is of interest for both chemists and biologists. The synthesis of suitable compounds provides a means for avoiding the costly labeling of cells with specific antibodies and the bias associated with the interpretation of biological validation experiments. The chemotherapeutic agent, tamoxifen has been routinely used in the treatment of breast cancer for decades. Once metabolized, the active form of tamoxifen (4-hydroxytamoxifen) competes with the binding of estrogens to the estrogen receptors (ER). Its selectivity in ER modulation makes it an ideal candidate for the development of materials to be used as chemical probes. Here we report the synthesis of a fluorescent BODIPY®FL conjugate of tamoxifen linked through an ethylene glycol moiety, and present proof-of-principle results in ER positive and ER negative cell lines. Optical microscopy indicates that the fluorescent probe binds selectively to tamoxifen sensitive breast cancer cell lines. The compound showed no affinity for the tamoxifen resistant breast cancer lines. The specificity of the new compound make it a valuable addition to the chemical probe tool kit for estrogen receptors.


Bioorg Med Chem Lett


Ho LA,Thomas E,McLaughlin RA,Flematti GR,Fuller RO




Has Abstract


2016-10-15 00:00:00














  • Synthesis and antifungal activity of the 2,2,5-tetrahydrofuran regioisomers of SCH 51048.

    abstract::The four 2,2,5-regioisomer counterparts of SCH 51048 were synthesized and evaluated. As with the parent series, only the two cis isomers possessed any in vitro activity, and only the activity of the isomer with the R-configuration at the tetrahydrofuran 2-carbon was significant. The activity data suggests that oxygen ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Lovey RG,Saksena AK,Girijavallabhan VM,Blundell P,Guzik H,Loebenberg D,Parmegiani RM,Cacciapuoti A

    更新日期:2002-07-08 00:00:00

  • Synthesis and activities of naphthalimide azoles as a new type of antibacterial and antifungal agents.

    abstract::Naphthalimide-derived azoles as a new type of antimicrobial agents were synthesized and evaluated for their efficiency in vitro against eight bacteria and two fungi by two fold serial dilution technique. Most title compounds exhibited good antimicrobial potency with low MIC values ranging from 1 to 16μg/mL. Notably, s...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zhang YY,Zhou CH

    更新日期:2011-07-15 00:00:00

  • Discovery of 4-anilino α-carbolines as novel Brk inhibitors.

    abstract::Dysregulation of cell signalling processes caused by an enhanced activity of protein kinases mainly contributes to cancer progression. Protein kinase inhibitors have been established as promising drugs that inhibit such overactive protein kinases in cancer cells. The formation of metastases, which makes a therapy diff...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Mahmoud KA,Krug M,Wersig T,Slynko I,Schächtele C,Totzke F,Sippl W,Hilgeroth A

    更新日期:2014-04-15 00:00:00

  • Discovery of a small molecular compound simultaneously targeting RXR and HADC: design, synthesis, molecular docking and bioassay.

    abstract::Retinoid X receptor (RXR) and Histone deacetylase (HDAC) are considered important targets for anti-cancer therapy due to their crucial roles in genetic or epigenetic regulations of cancer development and progression. Here, we have designed and synthesized a novel compound which targets both RXR and HADC. This dual-tar...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Chen GL,Wang LH,Wang J,Chen K,Zhao M,Sun ZZ,Wang S,Zheng HL,Yang JY,Wu CF

    更新日期:2013-07-01 00:00:00

  • Rational design of novel, potent piperazinone and imidazolidinone BACE1 inhibitors.

    abstract::Guided by structure-based design, we synthesized two novel series of potent inhibitors of BACE1 and generated extensive SAR around both the prime and non-prime side binding pockets. The key feature of both series is a cyclic amine motif specifically crafted to achieve interactions with both the flap and with the S2' p...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Cumming JN,Le TX,Babu S,Carroll C,Chen X,Favreau L,Gaspari P,Guo T,Hobbs DW,Huang Y,Iserloh U,Kennedy ME,Kuvelkar R,Li G,Lowrie J,McHugh NA,Ozgur L,Pan J,Parker EM,Saionz K,Stamford AW,Strickland C,Tadesse D,

    更新日期:2008-06-01 00:00:00

  • Synthesis and antifungal evaluation of pyrido[1,2-a]indole-1,4-diones and benzo[f]pyrido[1,2-a]indole-6,11-diones.

    abstract::Pyrido[1,2-a]indole-1,4-diones and benzo[f]pyrido[1,2-a]indole-6,11-diones were synthesized and tested for in vitro antifungal activity against two pathogenic strains of fungi. Among them tested, many compounds showed good antifungal activity. The results suggest that pyrido[1,2-a]indole-1,4-diones and benzo[f]pyrido[...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Ryu CK,Yoon JH,Song AL,Im HA,Kim JY,Kim A

    更新日期:2012-01-01 00:00:00

  • Biotransformations of 6',7'-dihydroxybergamottin and 6',7'-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity.

    abstract::Penicillium digitatum, as well as five other citrus pathogenic species, (Penicillium ulaiense Link, Geotrichum citri Link, Botrytis cinerea P. Micheli ex Pers., Lasiodiplodia theobromae (Pat.) Griffon & Maubl., and Phomopsis citri (teleomorph Diaporthe citri)) were observed to convert 6',7'-epoxybergamottin (1) into 6...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Myung K,Manthey JA,Narciso JA

    更新日期:2012-03-15 00:00:00

  • Antitumor activity of resveratrol is independent of Cu(II) complex formation in MCF-7 cell line.

    abstract::Resveratrol (Rsv) is widely reported to possess anticarcinogenic properties in a plethora of cellular and animal models having limited toxicity toward normal cells. In the molecular level, Rsv can act as a suppressive agent for several impaired signaling pathways on cancer cells. However, Fukuhara and Miyata have show...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Andrade Volkart P,Benedetti Gassen R,Mühlen Nogueira B,Nery Porto B,Eduardo Vargas J,Arigony Souto A

    更新日期:2017-08-01 00:00:00

  • Kinase domain inhibition of leucine rich repeat kinase 2 (LRRK2) using a [1,2,4]triazolo[4,3-b]pyridazine scaffold.

    abstract::Leucine rich repeat kinase 2 (LRRK2) has been genetically linked to Parkinson's disease (PD). The most common mutant, G2019S, increases kinase activity, thus LRRK2 kinase inhibitors are potentially useful in the treatment of PD. We herein disclose the structure, potential ligand-protein binding interactions, and pharm...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Galatsis P,Henderson JL,Kormos BL,Han S,Kurumbail RG,Wager TT,Verhoest PR,Noell GS,Chen Y,Needle E,Berger Z,Steyn SJ,Houle C,Hirst WD

    更新日期:2014-09-01 00:00:00

  • Antiproliferative and apoptotic effects of the oxidative dimerization product of methyl caffeate on human breast cancer cells.

    abstract::Caffeic acid derivatives are increasingly regarded as potential oncoprotective that could inhibit both the initiation and progression of cancer. Here we have synthesized seven 1-arylnaphthalene lignans and related compounds and tested their impact on breast cancer cell growth in tissue culture. The product of the oxid...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Bailly F,Toillon RA,Tomavo O,Jouy N,Hondermarck H,Cotelle P

    更新日期:2013-01-15 00:00:00

  • Synthesis and characterization of bis(mu-hydroxo)diiron(III) complex of N-(4-nitro-2-hydroxy)phenylmethyl-N-(2-pyridylethyl)-N-(2-pyridylmethyl)amine and hydroxylation reaction of alkane.

    abstract::Bis(mu-hydroxo)diiron(III) complex, [Fe2III(mu-OH)2(NE)2](NO3)2 x 3H2O (3) (N-(4-nitro-2-hydroxy)phenylmethyl-N-(2-pyridylethyl)-N-(2-pyridylmethyl)amine = HNE, where H denotes a dissociable proton of the p-nitrophenol group), has been prepared and characterized by X-ray crystallography, electronic and magnetic spectr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kurosaki H,Yoshida H,Ito M,Koike H,Higuchi E,Goto M

    更新日期:2001-03-26 00:00:00

  • Synthesis of doxorubicin-peptide conjugate with multidrug resistant tumor cell killing activity.

    abstract::Cell penetrating peptide TAT was introduced into doxorubicin structure. Synthesized doxorubicin-TAT conjugate showed different intracellular distribution pattern and cell killing activity from those of free doxorubicin. Unlike free doxorubicin, doxorubicin-TAT conjugate was highly permeable to drug-resistant cells and...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Liang JF,Yang VC

    更新日期:2005-11-15 00:00:00

  • Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as mu opioid receptor antagonists with improved opioid receptor selectivity profiles.

    abstract::A series of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, mu opioid receptor antagonists, analogs of alvimopan, were prepared using solid phase methodology. This study led to the identification of a highly selective mu opioid receptor antagonist, which interacts selectively with mu peripheral recept...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Le Bourdonnec B,Barker WM,Belanger S,Wiant DD,Conway-James NC,Cassel JA,O'Neill TJ,Little PJ,DeHaven RN,DeHaven-Hudkins DL,Dolle RE

    更新日期:2008-03-15 00:00:00

  • Tags for labeling protein N-termini with subtiligase for proteomics.

    abstract::The peptide ligase subtiligase, derived from subtilisin, has been employed in the identification of protein N-termini in complex mixtures. Here, the peptide ester substrates for the ligation reaction were optimized with respect to solubility, resulting in greater incorporation of the N-terminal tags. Additionally, the...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Yoshihara HA,Mahrus S,Wells JA

    更新日期:2008-11-15 00:00:00

  • Investigation of factor Xa inhibitors containing non-amidine S1 elements.

    abstract::Several non-amidino S1 derivatives of the 1,2-diaminobenzene-based scaffold (4) were synthesized and evaluated for their ability to bind to the active site and inhibit the human protease factor Xa. A subset of these compounds were also evaluated for their anticoagulant effects in human plasma as measured by prothrombi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Franciskovich JB,Masters JJ,Tinsley JM,Craft TJ,Froelich LL,Gifford-Moore DS,Klimkowski VJ,Smallwood JK,Smith GF,Smith T,Towner RR,Weir LC,Wiley MR

    更新日期:2005-11-01 00:00:00

  • Remarkably fast and selective aromatization of Hantzsch esters with MoOCl4 and MoCl5: a chemical model for possible biologically relevant properties of molybdenum-containing enzymes.

    abstract::Mo(VI) and Mo(V) salts both react selectively with Hantzsch esters to produce substitute pyridines in good-to-excellent yield (75-99%). The remarkable reactivity and selectivity of MoOCl(4) under reflux of acetonitrile and MoCl(5) in dichloromethane at room temperature encouraged us to propose that molybdenum-containi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Litvić M,Regović M,Smic K,Lovrić M,Filipan-Litvić M

    更新日期:2012-06-01 00:00:00

  • Design of riboflavin-presenting PAMAM dendrimers as a new nanoplatform for cancer-targeted delivery.

    abstract::This communication describes the synthesis and in vitro biological evaluation of novel generation 5 PAMAM dendrimers conjugated with riboflavin as a targeting ligand. Cell-based experiments demonstrated that a dendrimer conjugated with riboflavin is able to undergo cellular binding and uptake in KB cells, and when the...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Thomas TP,Choi SK,Li MH,Kotlyar A,Baker JR Jr

    更新日期:2010-09-01 00:00:00

  • Isoxazole carboxylic acids as protein tyrosine phosphatase 1B (PTP1B) inhibitors.

    abstract::Guided by X-ray crystallography, we have extended the structure-activity relationship (SAR) study on an isoxazole carboxylic acid-based PTP1B inhibitor (1) and more potent and equally selective (>20-fold selectivity over the highly homologous T-cell PTPase, TCPTP) PTP1B inhibitors were identified. Inhibitor 7 demonstr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zhao H,Liu G,Xin Z,Serby MD,Pei Z,Szczepankiewicz BG,Hajduk PJ,Abad-Zapatero C,Hutchins CW,Lubben TH,Ballaron SJ,Haasch DL,Kaszubska W,Rondinone CM,Trevillyan JM,Jirousek MR

    更新日期:2004-11-15 00:00:00

  • New adjuvants to enhance anticoagulant activity of warfarin.

    abstract::New adjuvants of warfarin anticoagulant activity have been developed. These compounds, which are 1,4-methano-1,2,3,4-tetrahydroanthracene-9,10-diol derivatives, act synergistically with warfarin to potentiate its anticoagulant effect. None of the compounds tested is an effective oral anticoagulant in the absence of wa...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Stromich JJ,Weber AK,Mirzaei YR,Caldwell MD,Lewis DE

    更新日期:2010-03-15 00:00:00

  • Arylmethoxypyridines as novel, potent and orally active mGlu5 receptor antagonists.

    abstract::Optimisation of affinity, chemical stability, metabolic stability and solubility led from a chemically labile HTS hit 1 to mGlu5 receptor antagonists (24-26) with high affinity for the allosteric MPEP binding site, improved microsomal metabolic stability and anxiolytic-like activity in vivo as assessed by the Vogel co...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Büttelmann B,Peters JU,Ceccarelli S,Kolczewski S,Vieira E,Prinssen EP,Spooren W,Schuler F,Huwyler J,Porter RH,Jaeschke G

    更新日期:2006-04-01 00:00:00

  • Synthesis and biological evaluation of copper (II) complexes of sterically hindered o-aminophenol derivatives as antimicrobial agents.

    abstract::Cu(II) complexes with 4,6-di(tert-butyl)-2-aminophenol (I) and 2-anilino-4,6-di(tert-butyl)phenol (II) have been synthesized and characterized by means of elemental analysis, TG/DTA, FT-IR, UV-vis, ESR, and conductance measurements. The compounds I and II can coordinate in their singly deprotonated forms and behave as...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Loginova NV,Koval'chuk TV,Zheldakova RA,Osipovich NP,Sorokin VL,Polozov GI,Ksendzova GA,Glushonok GK,Chernyavskaya AA,Shadyro OI

    更新日期:2006-10-15 00:00:00

  • Synthesis and evaluation of pretomanid (PA-824) oxazolidinone hybrids.

    abstract::Pretomanid (PA-824) is an important nitroimidazole antitubercular agent in late stage clinical trials. However, pretomanid is limited by poor solubility and high protein binding, which presents opportunities for improvement in its physiochemical properties. Conversely, the oxazolidinone linezolid has excellent physico...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Rakesh,Bruhn DF,Scherman MS,Singh AP,Yang L,Liu J,Lenaerts AJ,Lee RE

    更新日期:2016-01-15 00:00:00

  • The design of phenylglycine containing benzamidine carboxamides as potent and selective inhibitors of factor Xa.

    abstract::Factor Xa, a critical serine protease in the blood coagulation cascade, has become a target for inhibition as a strategy for the invention of novel anti-thrombotic agents. Here we describe the development of phenylglycine containing benzamidine carboxamides as novel, potent and selective inhibitors of factor Xa. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Jones SD,Liebeschuetz JW,Morgan PJ,Murray CW,Rimmer AD,Roscoe JM,Waszkowycz B,Welsh PM,Wylie WA,Young SC,Martin H,Mahler J,Brady L,Wilkinson K

    更新日期:2001-03-12 00:00:00

  • Identification and SAR around N-{2-[4-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-[1,4]diazepan-1-yl]-ethyl}-2-phenoxy-nicotinamide, a selective alpha2C adrenergic receptor antagonist.

    abstract::The discovery of the CNS-penetrant and selective alpha(2C) adrenergic receptor antagonist N-{2-[4-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-[1,4]diazepan-1-yl]-ethyl}-2-phenoxy-nicotinamide, 13 is described. Structure-activity studies demonstrate the structural requirements for binding affinity, functional activity, a...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Patel SD,Habeski WM,Min H,Zhang J,Roof R,Snyder B,Bora G,Campbell B,Li C,Hidayetoglu D,Johnson DS,Chaudhry A,Charlton ME,Kablaoui NM

    更新日期:2008-10-15 00:00:00

  • Synthesis and biological evaluation of novel 4-(hetero) aryl-2-piperazino quinazolines as anti-leishmanial and anti-proliferative agents.

    abstract::A series of new class of 4-(hetero)aryl-2-piperazino quinazolines were synthesized and assessed for in vitro activity against extracellular promastigotes and intracellular amastigotes of Leishmania donovani. Among the compounds evaluated, compound 4bb and 4cb showed the selectivity index (SI) value>8.03 and 4.21, resp...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kumar S,Shakya N,Gupta S,Sarkar J,Sahu DP

    更新日期:2009-05-01 00:00:00

  • A concise synthesis and antimicrobial activities of 3-polyamino-23,24-bisnorcholanes as steroid-polyamine conjugates.

    abstract::A series of steroid-polyamine conjugates were synthesized and evaluated for their antimicrobial activity. This study was focused on the effect of stereochemistry at the C-3 and C-5 of steroids and types of polyamine at C-3 on activity against various human pathogens. All the conjugates exhibited strong antimicrobial a...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kim HS,Khan SN,Jadhav JR,Jeong JW,Jung K,Kwak JH

    更新日期:2011-07-01 00:00:00

  • Thiophene-based vitronectin receptor antagonists.

    abstract::A series of alpha(v)beta(3) antagonists based on a thiophene scaffold were synthesized via two routes and evaluated for in vitro biological activity. We have identified several structurally similar antagonists with different selectivities towards alpha(IIb)beta(3), alpha(v)beta(5) and alpha(5)beta(1) at the cellular l...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Bubenik M,Meerovitch K,Bergeron F,Attardo G,Chan L

    更新日期:2003-02-10 00:00:00

  • 2-Amino-aryl-7-aryl-benzoxazoles as potent, selective and orally available JAK2 inhibitors.

    abstract::A series of novel benzoxazole derivatives has been designed and shown to exhibit attractive JAK2 inhibitory profiles in biochemical and cellular assays, capable of delivering compounds with favorable PK properties in rats. Synthesis and structure-activity relationship data are also provided. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Gerspacher M,Furet P,Pissot-Soldermann C,Gaul C,Holzer P,Vangrevelinghe E,Lang M,Erdmann D,Radimerski T,Regnier CH,Chene P,De Pover A,Hofmann F,Baffert F,Buhl T,Aichholz R,Blasco F,Endres R,Trappe J,Drueckes P

    更新日期:2010-03-01 00:00:00

  • Discovery of BRD4 bromodomain inhibitors by fragment-based high-throughput docking.

    abstract::Bromodomains (BRDs) recognize acetyl-lysine modified histone tails mediating epigenetic processes. BRD4, a protein containing two bromodomains, has emerged as an attractive therapeutic target for several types of cancer as well as inflammatory diseases. Using a fragment-based in silico screening approach, we identifie...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zhao H,Gartenmann L,Dong J,Spiliotopoulos D,Caflisch A

    更新日期:2014-06-01 00:00:00

  • Synthesis and antitubercular activity of monocyclic nitroimidazoles: insights from econazole.

    abstract::We have designed and synthesized econazole-derived nitroimidazoles to investigate the antitubercular activity of the nitroimidazole compounds. The introduction of a nitro group at the 4-position of the imidazole on econazole abolished the antitubercular activity. However, alcoholic nitroimidazoles 4 and 6 compounds we...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Lee SH,Kim S,Yun MH,Lee YS,Cho SN,Oh T,Kim P

    更新日期:2011-03-01 00:00:00