ArticleJournal of medicinal chemistry2009
Rhodamine inhibitors of P-glycoprotein: an amide/thioamide "switch" for ATPase activity.
Article in Journal of medicinal chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 71 citations in OpenAlex.
- Diversification of the 10th core atom of 9-cyanopyronins expands the resonance Raman vibrational palette.Communications chemistry · 2026Article
- Rhodamine 19 Alkyl Esters as Effective Antibacterial Agents.International journal of molecular sciences · 2024Article
- Structure-ATPase Activity Relationship of Rhodamine Derivatives as Potent Inhibitors of P-Glycoprotein CmABCB1.ACS medicinal chemistry letters · 2024Article
- An efficient metal-free and catalyst-free C-S/C-O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides.Beilstein journal of organic chemistry · 2023Article
- Disruption of small molecule transporter systems by Transporter-Interfering Chemicals (TICs).FEBS letters · 2020Review
- A general method to optimize and functionalize red-shifted rhodamine dyes.Nature methods · 2020Article
- Theoretical insights on helix repacking as the origin of P-glycoprotein promiscuity.Scientific reports · 2020Article
- Advances in blood-brain barrier modeling in microphysiological systems highlight critical differences in opioid transport due to cortisol exposure.Fluids and barriers of the CNS · 2020Article
- Aptamer-functionalized Hybrid Nanoparticles to Enhance the Delivery of Doxorubicin into Breast Cancer Cells by Silencing P-glycoprotein.Journal of cancer treatment & diagnosis · 2020Article
- Friedel-Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts.Beilstein journal of organic chemistry · 2019Article
- Targeting T Cell Bioenergetics by Modulating P-Glycoprotein Selectively Depletes Alloreactive T Cells To Prevent Graft-versus-Host Disease.Journal of immunology (Baltimore, Md. : 1950) · 2016Article
- Selective photodepletion of malignant T cells in extracorporeal photopheresis with selenorhodamine photosensitizers.Bioorganic & medicinal chemistry · 2016Article
- Selenorhodamine photosensitizers for photodynamic therapy of P-glycoprotein-expressing cancer cells.Journal of medicinal chemistry · 2014Article
- Cysteines introduced into extracellular loops 1 and 4 of human P-glycoprotein that are close only in the open conformation spontaneously form a disulfide bond that inhibits drug efflux and ATPase activity.The Journal of biological chemistry · 2014Article
- Glyceollin transport, metabolism, and effects on p-glycoprotein function in Caco-2 cells.Journal of medicinal food · 2014Article
- Identification of the distance between the homologous halves of P-glycoprotein that triggers the high/low ATPase activity switch.The Journal of biological chemistry · 2014Article
- Chalcogenopyrylium dyes as differential modulators of organic anion transport by multidrug resistance protein 1 (MRP1), MRP2, and MRP4.Drug metabolism and disposition: the biological fate of chemicals · 2013Article
- P-glycoprotein trafficking at the blood-brain barrier altered by peripheral inflammatory hyperalgesia.Journal of neurochemistry · 2012Article
- Biomimetic Design of Protein Nanomaterials for Hydrophobic Molecular Transport.Advanced functional materials · 2012Article
- Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1).Bioorganic & medicinal chemistry · 2012Article
Corrections and comments
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Authors and funding
12 authors at 4 institutions in 2 countries.
Funding
Abstract
We have examined 46 tetramethylrosamine/rhodamine derivatives with structural diversity in the heteroatom of the xanthylium core, the amino substituents of the 3- and 6-positions, and the alkyl, aryl, or heteroaryl group at the 9-substituent. These compounds were examined for affinity and ATPase stimulation in isolated MDR3 CL P-gp and human P-gp-His(10), for their ability to promote uptake of calcein AM and vinblastine in multidrug-resistant MDCKII-MDR1 cells, and for transport in monolayers of MDCKII-MDR1 cells. Thioamide 31-S gave K(M) of 0.087 microM in human P-gp. Small changes in structure among this set of compounds affected affinity as well as transport rate (or flux) even though all derivatives examined were substrates for P-gp. With isolated protein, tertiary amide groups dictate high affinity and high stimulation while tertiary thioamide groups give high affinity and inhibition of ATPase activity. In MDCKII-MDR1 cells, the tertiary thioamide-containing derivatives promote uptake of calcein AM and have very slow passive, absorptive, and secretory rates of transport relative to transport rates for tertiary amide-containing derivatives. Thioamide 31-S promoted uptake of calcein AM and inhibited efflux of vinblastine with IC(50)'s of approximately 2 microM in MDCKII-MDR1 cells.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.