Abstract
Breast cancer is the most prevalent diagnosed cancer among women and the main cause of morbidity and mortality. As for breast cancer, MCF-7 cells are an important candidate since they are widely utilized in research for estrogen receptor (ER)-positive breast cancer cell assays, and various sub-clones have been identified to reflect different classes of ER-positive tumors with varied levels of nuclear receptor expression. Rhodamines and its derivatives have shown a great interest over the past two decades due to their excellent structural and spectroscopic properties. Rhodamine derivatives have been widely investigated for their mitochondrial targeting and chemotherapeutic properties. Rhodamine derivatives, in particular, have been widely investigated for their therapeutic properties. In this regard, several studies have shown that rhodamine dye derivatives have promising in vitro and in vivo therapeutic efficacy. The present study deals with potential anticancer activity of few synthesized rhodamine derivatives against MCF-7 cell lines.
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References
Bag B, Biswal B (2012) Alteration of selectivity in rhodamine-based probes for Fe(III) and Hg(II) ion induced dual mode signalling responses. Org Biomol Chem 10:2733
Bag B, Pal A (2011a) Rhodamine-based probes for metal ion-induced chromo-/fluorogenic dual signaling and their selectivity towards Hg(II) ion. Org Biomol Chem 9:4467–4480
Bag B, Pal A (2011b) Water induced chromogenic and fluorogenic signal modulation in a bi-fluorophore appended acyclic amino-receptor system. Org Biomol Chem 9:915–925
Battula H, Bommi S, Bobbe Y, Patel T, Ghosh B, Jayanty S (2021) Distinct rhodamine B derivatives exhibiting dual effect of anticancer activity and fluorescence property. J Photochem Photobiol 6:100026. https://doi.org/10.1016/j.jpap.2021.100026
Belostotsky I, DaSilva S, Paez M, Indig G (2011) Mitochondrial targeting for photochemotherapy. Can selective tumor cell killing be predicted based on n-octanol/water distribution coefficients? Biotech Histochem 86(5):302–314
Biswal B, Bag B (2013) Preferences of rhodamine coupled (aminoalkyl)-piperazine probes towards Hg(II) ion and their FRET mediated signaling. Org Biomol Chem 11:4975–4992
Biswal B, Bag B (2015) Photophysical investigations of a FRET-based bifluorophoric conjugate and its Hg(II) specific ratiometric ‘turn-on’ signalling. J Photochem Photobiol A 311:127–136
Fearon KC, Plumb JA, Burns HJ, Calman KC (1987) Reduction of the growth rate of the Walker 256 tumor in rats by rhodamine 6G together with hypoglycemia. Cancer Res 47(14):3684–3687
Garcia-Martinez L, Zhang Y, Nakata Y, Chan HL, Morey L (2021) Epigenetic mechanisms in breast cancer therapy and resistance. Nat Commun 12(1):1786
Hajian R, Tavakol M, Club YR, Branch B, Branch G (2012) Interaction of anticancer drug methotrexate with DS-DNA analyzed by spectroscopic and electrochemical methods. J Chem 9:471–480
Hathaway HJ, Buttler KS, Adolphi NL, Lovarto DM, Belfon R, Fegan D, Monson JE, Trujillo JE, Tessier TE, Braynt HC, Huber DL, Larson RS, Flynn ER (2011) Detection of breast cancer cells using targeted magnetic nanoparticles and ultra-sensitive magnetic field sensors. Breast Cancer Res 13:R108
Johnson LV, Walsh ML, Chen LB (1980) Localization of mitochondria in living cells with rhodamine 123. Proc Natl Acad Sci USA 77:990–994
Li X, Yin Y, Du B, Li N, Li Y (2016) The synthesis and evaluations of the 68Ga-lissamine rhodamine B (LRB) as a new radiotracer for imaging tumors by positron emission tomography. Biomed Res Int 8549635
Ma W, Tian Z, Zang S, He X, Li JJ, Xia X, Chen X, Liu Z (2018) Lysosome targeted drugs: rhodamine B modified N^N-chelating ligands for half-sandwich iridium(III) anticancer complexes. Inorg Chem Front 5:2587–2597
Macașoi I, Pavel IZ, Moacă AE, Avram Ș, David VL, Coricovac D, Mioc A, Spandidos DA, Tsatsakis A, Șoica C, Dumitrașcu V, Dehelean C (2020) Mechanistic investigations of antitumor activity of a rhodamine B-oleanolic acid derivative bioconjugate. Oncol Rep 44(3):1169–1183
Modica-Napolitano JS, Aprille JR (2001) Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells. Adv Drug deliV Rev 49(1):63–70
Oza G, Ravichandran M, Jagadale P, Velumani S (2016) Inorganic nanoflotillas as engineered particles for drug and gene delivery. Eng Nanobiomater 2:429–483
Rezaei-Seresht H, Cheshomi H, Falanji F, Movahedi-Motlagh F, Hashemian M, Mireskandari E (2019) Cytotoxic activity of caffeic acid and gallic acid against MCF-7 human breast cancer cells: an in silico and in vitro study. Avicenna J Phytomed 9(6):574–586
Rueda OM et al (2019) Dynamics of breast-cancer relapse reveal late-recurring ER-positive genomic subgroups. Nature 567(7748):399–404
Semina SE, Pal P, Kansara NS, Huggins RJ, Alarid ET, Greene GL, Frasor J (2022) Selective pressure of endocrine therapy activates the integrated stress response through NFκB signaling in a subpopulation of ER positive breast cancer cells. Breast Cancer Res 24(1):19
Toogood SH, Scrutton NS (2020) Thermal, electrochemical and photochemical reactions involving catalytically versatile ene reductase enzymes. The Enzymes 47:491–515
Wu Z, Zhu C, Bai X, Wu Y (2018) Preparation of rhodamine B 6-[3-(2-methoxy-5-methylphenylcarbamoyloxy)-9-azabicyclo[3.3.1]nonane-9-yl-]-hexylamide compound and its application in diagnosis of breast cancer. Chinese Patent CN 108676002
Yan X, Zhou Y, Liu S (2012) Optical imaging of tumors with copper-labeled rhodamine derivatives by targeting mitochondria. Theranostics 2:988–998.s
Acknowledgements
BB wishes to thank the Director, CSIR-IMMT for requisite permissions to carry out this work. The authors wish to thank Dr. Jyoti Kode, Advance Centre for Treatment Research & Education in Cancer (ACTREC), India, for screening through in vitro SRB assay for anti-cancer activity evaluation of the compounds.
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This work was supported by SERB, New Delhi (Grant number: EEQ/2020/00004) to BB.
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PB and BB conceived and designed research. BB conducted synthetic experiments and compound characterization. PB, VK, and AG conducted the experiments and contributed new reagents or analytical tools. BB, SD, and NKR analyzed data. PB wrote the draft manuscript; BB prepared and edited the version of manuscript. All authors read and approved the manuscript and all data were generated in-house and that no paper mill was used.
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Behera, P.C., Karmakar, V., Ghosh, A. et al. Anti-cancer potential of substituted “amino-alkyl-rhodamine” derivatives against MCF-7 human breast cancer cell line. Naunyn-Schmiedeberg's Arch Pharmacol 396, 1001–1007 (2023). https://doi.org/10.1007/s00210-022-02376-3
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DOI: https://doi.org/10.1007/s00210-022-02376-3