当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Triterpenoids from Momordica balsamina: Reversal of ABCB1-mediated multidrug resistance.

Triterpenoids from Momordica balsamina: Reversal of ABCB1-mediated multidrug resistance.

Abstract：

:The ability as P-glycoprotein (P-gp, ABCB1) modulators of thirty (1-30) triterpenoids of the cucurbitane-type was evaluated on human L5178 mouse T-lymphoma cell line transfected with the human MDR1 gene, through the rhodamine-123 exclusion assay. Compounds (1-26, and 29, 30) were previously obtained from the African medicinal plant Momordica balsamina, through both isolation (1-15) and molecular derivatization (16-26 and 29, 30). Compounds 27-28 are two new karavilagenin C (34) derivatives having succinic acid moieties. Apart from 4, 6, 8, 10 and 11, most of the isolated compounds (1-15) displayed strong MDR reversing activity in a dose-dependent mode, exhibiting a many-fold activity when compared with verapamil, used as positive control. At the lowest concentration tested, compounds 2 and 7 were the most active. However, a decrease of activity was found for the acyl derivatives (16-30). In a chemosensitivity assay, the MDR reversing activity of some of the most active compounds (1-3, 5, 7, 12-15) was further assessed on the same cell model. All the tested compounds, excepting 15, corroborated the results of the transport assay, revealing to synergistically interact with doxorubicin. Structure-activity relationship studies, taking into account previous results, showed that different substitution patterns, at both the tetracyclic nucleus and the side chain, play important role in ABCB1 reversal activity. An optimal lipophilicity was also recognized.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Ramalhete C,Mulhovo S,Molnar J,Ferreira MU

doi

10.1016/j.bmc.2016.08.022

subject

Has Abstract

pub_date

2016-11-01 00:00:00

pages

5061-5067

issue

21

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(16)30629-0

journal_volume

24

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • Prediction of hERG potassium channel affinity by the CODESSA approach.

    abstract：:The problem of predicting torsadogenic cardiotoxicity of drugs is afforded in this work. QSAR studies on a series of molecules, acting as hERG K+ channel blockers, were carried out for this purpose by using the CODESSA program. Molecules belonging to the analyzed dataset are characterized by different therapeutic targ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.12.030

    authors： Coi A,Massarelli I,Murgia L,Saraceno M,Calderone V,Bianucci AM

    更新日期：2006-05-01 00:00:00

  • Coordination of iron ions in the form of histidinyl dinitrosyl complexes does not prevent their genotoxicity.

    abstract：:Formation of dinitrosyl iron complexes (DNICs) was observed in a wide spectrum of pathophysiological conditions associated with overproduction of NO. To gain insight into the possible genotoxic effects of DNIC, we examined the interaction of histidinyl dinitrosyl iron complexes (HIS-DNIC) with DNA by means of circular...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.09.032

    authors： Lewandowska H,Stępkowski TM,Sadło J,Wójciuk GP,Wójciuk KE,Rodger A,Kruszewski M

    更新日期：2012-11-15 00:00:00

  • Cyanocobalamin (vitamin B12) conjugates with enhanced solubility.

    abstract：:Cyanocobalamin (vitamin B12) is an essential nutrient as well as a very useful carrier in drug delivery. Conjugates of vitamin B12 are investigated due to their wide range of therapeutic applications. We report the synthesis of six vitamin B12 conjugates, and the effect of conjugation on their solubilities and stabili...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.11.036

    authors： Wang X,Wei L,Kotra LP

    更新日期：2007-02-15 00:00:00

  • Design, synthesis and anti-inflammatory activity of imidazol-5-yl pyridine derivatives as p38α/MAPK14 inhibitor.

    abstract：:P38α/MAPK14 is intracellular signalling regulator involved in biosynthesis of inflammatory mediator cytokines (TNF-α, IL-1, IL-6, and IL-1b), which induce the production of inflammatory proteins (iNOS, NF-kB, and COX-2). In this study, drug repurposing strategies were followed to repositioning of a series of B-RAF V60...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2020.115969

    authors： Ali EMH,Abdel-Maksoud MS,Hassan RM,Mersal KI,Ammar UM,Se-In C,He-Soo H,Kim HK,Lee A,Lee KT,Oh CH

    更新日期：2021-02-01 00:00:00

  • Development of a potent 2-oxoamide inhibitor of secreted phospholipase A2 guided by molecular docking calculations and molecular dynamics simulations.

    abstract：:Inhibition of group IIA secreted phospholipase A2 (GIIA sPLA2) has been an important objective for medicinal chemists. We have previously shown that inhibitors incorporating the 2-oxoamide functionality may inhibit human and mouse GIIA sPLA2s. Herein, the development of new potent inhibitors by molecular docking calcu...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.02.040

    authors： Vasilakaki S,Barbayianni E,Leonis G,Papadopoulos MG,Mavromoustakos T,Gelb MH,Kokotos G

    更新日期：2016-04-15 00:00:00

  • Synthesis and evaluation of imidazole-dioxolane compounds as selective heme oxygenase inhibitors: effect of substituents at the 4-position of the dioxolane ring.

    abstract：:Several imidazole-dioxolane compounds were synthesized and evaluated as novel inhibitors of heme oxygenase (HO). These compounds, which include a series of substituted thiophenol and substituted phenol derivatives of (2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(phenylsulfanyl)methyl]-1,3-dioxol...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.01.078

    authors： Vlahakis JZ,Hum M,Rahman MN,Jia Z,Nakatsu K,Szarek WA

    更新日期：2009-03-15 00:00:00

  • Aurine tricarboxylic acid, a potent metal-chelating inhibitor of NFkappaB-DNA binding.

    abstract：:The metal-interaction of aurine tricarboxylic acid (ATA) and its inhibitory effect on the DNA binding of NFkappaB were studied. Chemical speciation and spectroscopic studies have shown the strong interaction of ATA with metal ions present in the biological systems. EPR, FTIR and electronic spectral studies indicated t...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00109-7

    authors： Sharma RK,Garg BS,Kurosaki H,Goto M,Otsuka M,Yamamoto T,Inoue J

    更新日期：2000-07-01 00:00:00

  • Synthesis and biological evaluation of pyrimidine derivatives as novel human Pin1 inhibitors.

    abstract：:Pin1 (Protein interacting with NIMA1) is a cis-trans isomerase and promotes the amide bond rotation of phosphoSer/Thr-Pro motifs in its substrates. Inhibition of Pin1 might be a novel strategy for developing anticancer agents. Herein, a series of pyrimidine derivatives were synthesized and their Pin1 inhibitory activi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.03.024

    authors： Cui G,Jin J,Chen H,Cao R,Chen X,Xu B

    更新日期：2018-05-01 00:00:00

  • Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.

    abstract：:A series of arylidene N-alkoxydiketopiperazines was designed and stereoselectively synthesized via oxime-ether formation and intramolecular acylation. Possible cyclization and acid-catalyzed rearrangement-fragmentation mechanisms were discussed. The crystal structure of the novel diketopiperazine further confirmed the...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.08.038

    authors： Tian X,Feng J,Fan SM,Zhen XL,Han JR,Liu SX

    更新日期：2016-11-01 00:00:00

  • A new modification of anti-tubercular active molecules.

    abstract：:The connection of two active molecules across an easily released bridge as a new type of potentially active molecule has been studied. The synthesis is based on derivatives that originate from isonicotinoyl hydrazide, pyrazinamide, p-aminosalicylic acid (PAS), ethambutol, and ciprofloxacin. The lipophilicity, hydrolys...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.01.051

    authors： Imramovský A,Polanc S,Vinsová J,Kocevar M,Jampílek J,Recková Z,Kaustová J

    更新日期：2007-04-01 00:00:00

  • Dolastatin 11 conformations, analogues and pharmacophore.

    abstract：:Twenty analogues of the natural antitumor agent dolastatin 11, including majusculamide C, were synthesized and tested for cytotoxicity against human cancer cells and stimulation of actin polymerization. Only analogues containing the 30-membered ring were active. Molecular modeling and NMR evidence showed the low-energ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.04.040

    authors： Ali MA,Bates RB,Crane ZD,Dicus CW,Gramme MR,Hamel E,Marcischak J,Martinez DS,McClure KJ,Nakkiew P,Pettit GR,Stessman CC,Sufi BA,Yarick GV

    更新日期：2005-07-01 00:00:00

  • Antimicrobial and cytotoxic arylazoenamines. Part III: antiviral activity of selected classes of arylazoenamines.

    abstract：:Eighty-five arylazoenamines, characterized by different types of aryl and basic moieties, have been synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of ten RNA and DNA viruses. The most commonly affected viruses were, in decreasing order, CVB-2, RSV, BVDV, YFV, and...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.08.028

    authors： Tonelli M,Boido V,Canu C,Sparatore A,Sparatore F,Paneni MS,Fermeglia M,Pricl S,La Colla P,Casula L,Ibba C,Collu D,Loddo R

    更新日期：2008-09-15 00:00:00

  • Insights into the mechanism of streptonigrin-induced protein arginine deiminase inactivation.

    abstract：:Protein citrullination is just one of more than 200 known PTMs. This modification, catalyzed by the protein arginine deiminases (PADs 1-4 and PAD6 in humans), converts the positively charged guanidinium group of an arginine residue into a neutral ureido-group. Given the strong links between dysregulated PAD activity a...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.12.064

    authors： Dreyton CJ,Anderson ED,Subramanian V,Boger DL,Thompson PR

    更新日期：2014-02-15 00:00:00

  • The use of aminoglycoside derivatives to study the mechanism of aminoglycoside 6'-N-acetyltransferase and the role of 6'-NH2 in antibacterial activity.

    abstract：:Aminoglycoside antibiotics act by binding to 16S rRNA. Resistance to these antibiotics occurs via drug modifications by enzymes such as aminoglycoside 6'-N-acetyltransferases (AAC(6')s). We report here the regioselective and efficient synthesis of N-6'-acylated aminoglycosides and their use as probes to study AAC(6')-...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.02.009

    authors： Yan X,Gao F,Yotphan S,Bakirtzian P,Auclair K

    更新日期：2007-04-15 00:00:00

  • 4-Fluoro-N-butylphenylacetamide (H6) inhibits cell growth via cell-cycle arrest and apoptosis in human cervical cancer cells.

    abstract：:Phenylacetate induced tumor cytostasis and differentiation. The chemotherapeutic function of the compound in lung cancer has been previously reported, however, whether or not phenylacetate performs other activities is not known. In this study, the potential usage of synthetic phenylacetate derivatives, 4-fluoro-N-buty...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.11.028

    authors： Liu CH,Huang LJ,Kuo SC,Lee TH,Tsai KJ,Chan HC

    更新日期：2009-01-01 00:00:00

  • Synthesis and biological activity of previtamin D(3) analogues with A-ring modifications.

    abstract：:Synthesis of two novel 6-s-cis analogues of 1alpha,25-dihydroxyvitamin D3 are described using shikimic acid and its 4-epi isomer as versatile chiral starting materials. These derivatives contain a 2beta-(3'-hydroxypropoxy) moiety or a 2beta,3beta-epoxy group into 1alpha,25-OH(2)-19-nor-pre-D3. The synthesized analogue...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.10.053

    authors： Sánchez-Abella L,Fernández S,Verstuyf A,Verlinden L,Gotor V,Ferrero M

    更新日期：2008-12-15 00:00:00

  • Synthesis, 3D-QSAR, and docking studies of 1-phenyl-1H-1,2,3-triazoles as selective antagonists for beta3 over alpha1beta2gamma2 GABA receptors.

    abstract：:A series of 16 1-phenyl-1H-1,2,3-triazoles with substituents at both the 4- and 5-positions of the triazole ring were synthesized, and a total of 49 compounds, including previously reported 4- or 5-monosubstituted analogues, were examined for their ability to inhibit the specific binding of [(3)H]4'-ethynyl-4-n-propyl...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.05.039

    authors： Alam MS,Huang J,Ozoe F,Matsumura F,Ozoe Y

    更新日期：2007-08-01 00:00:00

  • N-substituted aminohydroxypyridines as potential non-opioid analgesic agents.

    abstract：:A series of new N-substituted aminohydroxypyridines have been synthesized, pharmacologically evaluated and compared with their N-substituted oxazolopyridone analogs. The compound with the maximal combination of safety and analgesic efficacy was 3-[2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl]amino-2-hydroxypyridine (comp...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/0968-0896(95)00080-z

    authors： Viaud MC,Jamoneau P,Bizot-Espiard JG,Pfeiffer B,Renard P,Caignard DH,Adam G,Guillaumet G

    更新日期：1995-07-01 00:00:00

  • Novel hexadentate and pentadentate chelators for ⁶⁴Cu-based targeted PET imaging.

    abstract：:A series of new hexadentate and pentadentate chelators were designed and synthesized as chelators of (64)Cu. The new pentadentate and hexadentate chelators contain different types of donor groups and are expected to form neutral complexes with Cu(II). The new chelators were evaluated for complex kinetics and stability...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.02.041

    authors： Sin I,Kang CS,Bandara N,Sun X,Zhong Y,Rogers BE,Chong HS

    更新日期：2014-04-15 00:00:00

  • Structure-activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors.

    abstract：:The structure-activity relationship of a number of synthetic green tea polyphenol analogs involving modifications of A ring and B ring of epi-gallocatechin gallate (EGCG) as proteasome inhibitors has been examined. It was found that in B ring, a decrease in the number of OH groups led to decreased potency. Introductio...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.12.056

    authors： Wan SB,Landis-Piwowar KR,Kuhn DJ,Chen D,Dou QP,Chan TH

    更新日期：2005-03-15 00:00:00

  • Synthesis of indomethacin analogues for evaluation as modulators of MRP activity.

    abstract：:Synthesis of a range of indomethacin analogues, required for investigation in combination toxicity assays, bearing both N-benzyl and N-benzoyl groups, is described. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00292-3

    authors： Maguire AR,Plunkett SJ,Papot S,Clynes M,O'Connor R,Touhey S

    更新日期：2001-03-01 00:00:00

  • Glyconanobiotics: Novel carbohydrated nanoparticle antibiotics for MRSA and Bacillus anthracis.

    abstract：:This report describes the synthesis and evaluation of glycosylated polyacrylate nanoparticles that have covalently-bound antibiotics within their framework. The requisite glycosylated drug monomers were prepared from one of three known antibiotics, an N-sec-butylthio beta-lactam, ciprofloxacin, and a penicillin, by ac...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.11.052

    authors： Abeylath SC,Turos E,Dickey S,Lim DV

    更新日期：2008-03-01 00:00:00

  • Fluorinated methylenecyclopropane analogues of nucleosides. Synthesis and antiviral activity of (Z)- and (E)-9-{[(2-fluoromethyl-2-hydroxymethyl)-cyclopropylidene]methyl}adenine and -guanine.

    abstract：:Synthesis and antiviral activity of the title fluoromethylenecyclopropane analogues 15a, 15b, 16a, and 16b is described. Methylenecyclopropane carboxylate was first transformed to 2,2-bis-hydroxymethylmethylenecyclopropane. Selective monoacetylation followed by introduction of fluorine gave 2-acetoxymethyl-2-fluoromet...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.11.082

    authors： Li C,Prichard MN,Korba BE,Drach JC,Zemlicka J

    更新日期：2008-03-01 00:00:00

  • Bisbenzylisoquinoline alkaloids and P-glycoprotein function: A structure activity relationship study.

    abstract：:Conflicts with the notion that specific substrate interactions were required in the control of reaction path in active transport systems, P-glycoprotein showed extraordinarily low specificity. Therefore, overexpression P-glycoprotein excluded a large number of anticancer agents from cancer cells, and multidrug resista...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2020.115553

    authors： Xu W,Chen S,Wang X,Wu H,Yamada H,Hirano T

    更新日期：2020-06-15 00:00:00

  • Discovery and synthesis of novel luteolin derivatives as DAT agonists.

    abstract：:Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.09.049

    authors： Zhang J,Liu X,Lei X,Wang L,Guo L,Zhao G,Lin G

    更新日期：2010-11-15 00:00:00

  • PNA-Based Dynamic Combinatorial Libraries (PDCL) and screening of lectins.

    abstract：:Selections from dynamic combinatorial libraries (DCL) benefit from the dynamic nature of the library that can change constitution upon addition of a selection pressure, such as ligands binding to a protein. This technology has been predominantly used with small molecules interacting with each other through reversible ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2020.115458

    authors： Farrera-Soler L,Daguer JP,Raunft P,Barluenga S,Imberty A,Winssinger N

    更新日期：2020-05-15 00:00:00

  • Design, synthesis and biological evaluation of novel hydroxamic acid based histone deacetylase 6 selective inhibitors bearing phenylpyrazol scaffold as surface recognition motif.

    abstract：:In recent years, inhibition of HDAC6 became a promising therapeutic strategy for the treatment of cancer and HDAC6 inhibitors were considered to be potent anti-cancer agents. In this work, celecoxib showed moderate degree of HDAC6 inhibition activity and selectivity in preliminary enzyme inhibition activity assay. A s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.08.029

    authors： Yang J,Cheng G,Xu Q,Luan S,Wang S,Liu D,Zhao L

    更新日期：2018-05-01 00:00:00

  • Novel p-carborane-containing multitarget anticancer agents inspired by the metabolism of 17β-estradiol.

    abstract：:The female hormone 17 β-estradiol (E2) is synthesized from estrone by steroid sulfatase (STS), and metabolized into 2-methoxyestradiol (2-ME), whereby the biological activity of the latter is substantially different from that of E2. Based on the metabolic pathways of E2, a carborane-containing 2-ME mimic (1c) and its ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.10.006

    authors： Kaise A,Ohta K,Endo Y

    更新日期：2017-12-15 00:00:00

  • Functionalized 3-benzylidene-indolin-2-ones: inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity.

    abstract：:Functionalized benzylidene-indolin-2-ones are widely associated with antiproliferative activity. The scaffold is not normally associated with chemoprevention in spite of the presence of a nitrogen-linked Michael acceptor moiety that may predispose members to induction of NQO1, a widely used biomarker of chemopreventiv...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.12.052

    authors： Zhang W,Go ML

    更新日期：2009-03-01 00:00:00

  • Cryptadines A and B, novel C27N3-type pentacyclic alkaloids from Lycopodium cryptomerinum.

    abstract：:Two novel C(27)N(3)-type Lycopodium alkaloids, cryptadines A (1) and B (2) consisting of two octahydroquinoline rings (C(11)N) and a piperidine ring (C(5)N), have been isolated from the club moss Lycopodium cryptomerinum, and their structures and relative stereochemistry were elucidated on the basis of spectroscopic d...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.08.043

    authors： Koyama K,Hirasawa Y,Kobayashi J,Morita H

    更新日期：2007-12-15 00:00:00