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Year 2025, Volume: 29 Issue: 3, 1098 - 1110, 04.06.2025

Elif İnce , Pınar Eraslan-elma Atilla Akdemir Nilgün Karalı , Hande Gürer-orhan

https://doi.org/10.12991/jrespharm.1694239

Abstract

References

  • [1] Anand P, Kunnumakkara AB, Sundaram C, Harikumar KB, Tharakan ST, Lai OS, Sung B, Aggarwal BB. Cancer is a preventable disease that requires major lifestyle changes. Pharm Res. 2008; 25(9): 2097-2116. https://doi.org/10.1007/S11095-008-9661-9.
  • [2] Cavalieri E, Rogan E. The molecular etiology and prevention of estrogen-initiated cancers: Ockham's Razor: Pluralitas non est ponenda sine necessitate. Plurality should not be posited without necessity. Mol Aspects Med. 2014; 36: 1–55. https://doi.org/10.1016/j.mam.2013.08.002
  • [3] McFadyen, MC, McLeod HL, Jackson FC, Melvin WT, Doehmer J, Murray GI. Cytochrome P450 CYP1B1 protein expression: A novel mechanism of anticancer drug resistance. Biochem Pharmacol. 2001; 62(2): 207–212. https://doi.org/10.1016/s0006-2952(01)00643-8
  • [4] Kim T, Park H, Yue, W, Wang, JP, Atkins KA, Zhang Z, Rogan EG, Cavalieri EL, Mohammad KS, Kim S, Santen RJ, Aiyar SE. Tetra-methoxystilbene modulates ductal growth of the developing murine mammary gland. Breast Cancer Res Treat. 2011; 126(3): 779–789. https://doi.org/10.1007/s10549-010-1301-5
  • [5] Chun YJ, Kim S. Discovery of cytochrome P450 1B1 inhibitors as new promising anti-cancer agents. Med Res Rev. 2003; 23(6): 657-668. https://doi.org/10.1002/med.10050.
  • [6] Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin. 2018; 68: 394–424. https://doi.org/10.3322/CAAC.21492.
  • [7] Perou CM, Borresen-Dale AL. Systems Biology and Genomics of Breast Cancer. Cold Spring Harb Perspect Biol. 2011; 3: a003293–a003293. https://doi.org/10.1101/cshperspect.a003293.
  • [8] Leung YK, Lau KM, Mobley J, Jiang Z, Ho SM. Overexpression of cytochrome P450 1A1 and its novel spliced variant in ovarian cancer cells: Alternative subcellular enzyme compartmentation may contribute to carcinogenesis. Cancer Res. 2005; 65(9): 3726-3734. https://doi.org/10.1158/0008-5472.CAN-04-3771.
  • [9] Stocco C. Aromatase expression in the ovary: hormonal and molecular regulation. Steroids. 2008; 73(5): 473-487. https://doi.org/10.1016/J.steroids.2008.01.017.
  • [10] Lazaros L, Xita N, Kaponis A, et al. The association of aromatase (CYP19) gene variants with sperm concentration and motility. Asian J Androl. 2011; 13(2): 292-297. https://doi.org/10.1038/AJA.2010.144.
  • [11] Kharb R, Haider K, Neha, Yar MS. Aromatase inhibitors: Role in postmenopausal breast cancer. Arch Pharm. (Weinheim). 2020; 353(8): e2000081. https://doi.org/10.1002/ARDP.202000081.
  • [12] Miller WR, Larionov AA. Understanding the mechanisms of aromatase inhibitor resistance. Breast Cancer Res. 2012; 14: 201. https://doi.org/10.1186/BCR2931.
  • [13] Leoni A, Locatelli A, Morigi R, Rambaldi M. 2-Indolinone a versatile scaffold for treatment of cancer: a patent review (2008-2014). Expert Opin Ther Pat. 2016; 26: 149–173. https://doi.org/10.1517/13543776.2016.1118059.
  • [14] Motzer RJ, Hutson TE, Tomczak P, Michaelson MD, Bukowski RM, Rixe O, Oudard S, Negrier S, Szczylik C, Kim ST, Chen I, Bycott PW, Baum CM, Figlin RA. Sunitinib versus interferon alfa in metastatic renal-cell carcinoma. N Engl J Med. 2007; 356: 115–124. https://doi.org/10.1056/NEJMOA065044.
  • [15] Sternberg CN, Davis ID, Mardiak J, Szczylik C, Lee E, Wagstaff J, Barrios CH, Salman P, Gladkov OA, Kavina A, Zarbá JJ, Chen M, McCann L, Pandite L, Roychowdhury DF, Hawkins RE. Pazopanib in locally advanced or metastatic renal cell carcinoma: Results of a randomized phase III trial. J Clin Oncol. 2023; 41: 1957–1964. https://doi.org/10.1200/JCO.22.02622.
  • [16] Varun, Sonam, Kakkar R. Isatin and its derivatives: A survey of recent syntheses, reactions, and applications. Medchemcomm. 2019; 10: 351–368. https://doi.org/10.1039/C8MD00585K.
  • [17] Eldeeb M, Sanad EF, Ragab A, Ammar YA, Mahmoud K, Ali MM, Hamdy NM. Anticancer effects with molecular docking confirmation of newly synthesized isatin sulfonamide molecular hybrid derivatives against hepatic cancer cell lines. Biomedicines. 2022; 10(3):722.
  • [18] Chaudhari P, Bari S, Surana S, Shirkhedkar A, Wakode S, Shelar S, Racharla S, Ugale V, Ghodke M. Logical synthetic strategies and structure-activity relationship of indolin-2-one hybrids as small molecule anticancer agents: An overview. J Mol Struct. 2022; 1247 : 131280. https://doi.org/10.1016/J.MOLSTRUC.2021.131280.
  • [19] Güzel-Akdemir Ö, Akdemir A, Karalı N, Supuran CT. Discovery of novel isatin-based sulfonamides with potent and selective inhibition of the tumor-associated carbonic anhydrase isoforms IX and XII. Org Biomol Chem. 2015; 13(23): 6493-6499. https://doi.org/10.1039/C5OB00688K.
  • [20] Eldehna WM, Fares M, Ceruso M, Ghabbour HA, Abou-Seri SM, Abdel-Aziz HA, Abou El Ella DA, Supuran CT. Amido/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII. Eur J Med Chem. 2016; 110: 259-266. https://doi.org/10.1016/J.EJMECH.2016.01.030.
  • [21] Karalı N, Akdemir A, Göktaş F, Eraslan Elma P, Angeli A, Kızılırmak M, Supuran CT. Novel sulfonamide-containing 2-indolinones that selectively inhibit tumor-associated alpha carbonic anhydrases. Bioorg Med Chem. 2017; 25(14): 3714-3718. https://doi.org/10.1016/j.bmc.2017.05.029
  • [22] Eldehna WM, Al-Ansary GH, Bua S, Nocentini A, Gratteri P, Altoukhy A, Ghabbour H, Ahmed HY, Supuran C T. Novel indolin-2-one-based sulfonamides as carbonic anhydrase inhibitors: Synthesis, in vitro biological evaluation against carbonic anhydrases isoforms I, II, IV and VII and molecular docking studies. Eur J Med Chem. 2017; 127: 521-530. https://doi.org/10.1016/j.ejmech.2017.01.017.
  • [23] Eldehna WM, Nocentini A, Al-Rashood ST, Hassan GS, Alkahtani HM, Almehizia AA, Reda AM, Abdel-Aziz HA, Supuran CT. Tumor-associated carbonic anhydrase isoform IX and XII inhibitory properties of certain isatin-bearing sulfonamides endowed with in vitro antitumor activity towards colon cancer. Bioorg Chem. 2018; 81: 425-432. https://doi.org/10.1016/j.bioorg.2018.09.007
  • [24] Abo-Ashour MF, Eldehna WM, Nocentini A, Ibrahim HS, Bua S, Abou-Seri SM, Supuran CT. Novel hydrazido benzenesulfonamides-isatin conjugates: Synthesis, carbonic anhydrase inhibitory activity and molecular modeling studies. Eur J Med Chem. 2018; 157: 28-36. https://doi.org/10.1016/j.ejmech.2018.07.054
  • [25] Eldehna WM, Abo-Ashour MF, Nocentini A, El-Haggar RS, Bua S, Bonardi A, Al-Rashood ST, Hassan GS, Gratteri P, Abdel-Aziz HA, Supuran CT.Enhancement of the tail hydrophobic interactions within the carbonic anhydrase IX active site via structural extension: Design and synthesis of novel N-substituted isatins-SLC-0111 hybrids as carbonic anhydrase inhibitors and antitumor agents. Eur J Med Chem. 2019; 162: 147-160. https://doi.org/10.1016/j.ejmech.2018.10.068
  • [26] George RF, Bua S, Supuran CT, Awadallah FM. Synthesis of some N-aroyl-2-oxindole benzenesulfonamide conjugates with carbonic anhydrase inhibitory activity. Bioorg Chem. 2020; 96: 103635. https://doi.org/10.1016/j.bioorg.2020.103635
  • [27] Eraslan-Elma P, Akdemir A, Berrino E, Bozdağ M, Supuran CT, Karalı N. New 1H-indole-2,3-dione 3-thiosemicarbazones with 3-sulfamoylphenyl moiety as selective carbonic anhydrase inhibitors. Arch Pharm (Weinheim). 2022; 355(8): e2200023. https://doi.org/10.1002/ardp.202200023
  • [28] Jordan C, Furr BJA, An Introduction to the Regulation of Sex Steroids for the Treatment of Cancer, in: B.J.A. Jordan, V.C and Furr (Ed.), Horm. Breast Prostate Cancer, Humana Press, 2006: pp. 1–16.
  • [29] Santen RJ, Brodie H, Simpson ER, Siiteri PK, Brodie A. History of aromatase: saga of an important biological mediator and therapeutic target. Endocr Rev. 2009;30(4):343-375. https://doi.org/10.1210/er.2008-0016.
  • [30] Bhatia N, Thareja S. Aromatase inhibitors for the treatment of breast cancer: An overview (2019-2023). Bioorg Chem, 2024; 151: 107607. https://doi.org/10.1016/j.bioorg.2024.107607
  • [31] Wouters W, De Coster R, Goeminne N, Beerens D, van Dun J. Aromatase inhibition by the antifungal ketoconazole. J Steroid Biochem. 1988; 30(1-6): 387-389. https://doi.org/10.1016/0022-4731(88)90128-8
  • [32] Fabris M, Silva ML, de Santiago-Silva KM, de Lima Ferreira Bispo M, Goes Camargo P. CYP1B1: A promising target in cancer drug discovery. Anticancer Agents Med Chem. 2023; 23: 981–988. https://doi.org/10.2174/1871520623666230119103914.
  • [33] Yi L, Huang X, Yang M, Cai J, Jia J, Peng Z, Zhao Z, Yang F, Qiu D. A new class of CYP1B1 inhibitors derived from bentranil, Bioorganic Med Chem Lett. 2023; 80: 129112. https://doi.org/10.1016/j.bmcl.2022.129112.
  • [34] Ozcan-Sezer S, Ince E, Akdemir A, Ceylan ÖÖ, Suzen S, Gurer-Orhan H. Aromatase inhibition by 2-methyl indole hydrazone derivatives evaluated via molecular docking and in vitro activity studies. Xenobiotica. 2019; 49(5): 549-556. https://doi.org/10.1080/00498254.2018.1482029
  • [35] Burke MD, Mayer RT. Ethoxyresorufin: direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcholanthrene. Drug Metab Dispos. 1974; 2(6): 583-588.
  • [36] Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983; 65(1-2): 55-63. https://doi.org/10.1016/0022-1759(83)90303-4
  • [37] Labute P. Protonate3D: assignment of ionization states and hydrogen coordinates to macromolecular structures. Proteins. 2009; 75(1): 187-205. https://doi.org/10.1002/prot.22234https://doi.org/10.3390/BIOMEDICINES10030722.

Novel sulfonamide-based compounds as dual inhibitors of hCYP1B1 and hCYP19A1 with anticancer activity against breast cancer cells

Year 2025, Volume: 29 Issue: 3, 1098 - 1110, 04.06.2025

Elif İnce , Pınar Eraslan-elma Atilla Akdemir Nilgün Karalı , Hande Gürer-orhan

https://doi.org/10.12991/jrespharm.1694239

Abstract

Cancer remains a critical global health challenge, driven by multifactorial etiologies, including oxidative stress, hormonal imbalances, and procarcinogen bioactivation. The cytochrome P450 enzymes CYP1B1 and CYP19A1 play significant roles in these processes, with CYP1B1 involved in the bioactivation of carcinogens such as DMBA and estrogens, and CYP19A1 being crucial in estrogen biosynthesis, particularly in hormone-dependent cancers. In this study, we synthesized a novel sulfonamide-based 2-indolinone compound (7h) and evaluated its inhibitory activity against human CYP1B1 and CYP19A1 enzymes, along with previously reported 1H-indole-2,3-dione 3-[4-(3- sulfamoylphenyl)thiosemicarbazones] (compounds 7-9). Additionally, the cytotoxic effects of these compounds were tested on the MCF-7 human breast cancer cell line. R2 trifluoromethoxy-substituted compound 7c emerged as the most potent inhibitor of both hCYP1B1 (IC50 = 0.97 μM) and hCYP19A1 (IC50 = 6.46 μM) and demonstrated significant cytotoxicity, reducing MCF-7 cell viability to below 70% at 10 μM. R1 methyl- substituted compound 7b, R1 and R2 dimethyl- substituted compound 8b and R2 ethyl- substituted compound 9a reduced MCF-7 cell viability below 60% after 24 hours of incubation at 10 μM. Molecular docking studies revealed key interactions between the compounds and enzyme active sites, correlating with their inhibitory potency. These findings suggest that the sulfonamide-based 2- indolinone derivatives, particularly compound 7c, hold promise as dual inhibitors of CYP1B1 and CYP19A1, offering potential therapeutic benefits in the treatment of hormone-dependent and other cancers. Further studies are warranted to explore their full clinical potential.

Keywords

Aromatase CYP1B1 sulfonamides docking

References

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  • [2] Cavalieri E, Rogan E. The molecular etiology and prevention of estrogen-initiated cancers: Ockham's Razor: Pluralitas non est ponenda sine necessitate. Plurality should not be posited without necessity. Mol Aspects Med. 2014; 36: 1–55. https://doi.org/10.1016/j.mam.2013.08.002
  • [3] McFadyen, MC, McLeod HL, Jackson FC, Melvin WT, Doehmer J, Murray GI. Cytochrome P450 CYP1B1 protein expression: A novel mechanism of anticancer drug resistance. Biochem Pharmacol. 2001; 62(2): 207–212. https://doi.org/10.1016/s0006-2952(01)00643-8
  • [4] Kim T, Park H, Yue, W, Wang, JP, Atkins KA, Zhang Z, Rogan EG, Cavalieri EL, Mohammad KS, Kim S, Santen RJ, Aiyar SE. Tetra-methoxystilbene modulates ductal growth of the developing murine mammary gland. Breast Cancer Res Treat. 2011; 126(3): 779–789. https://doi.org/10.1007/s10549-010-1301-5
  • [5] Chun YJ, Kim S. Discovery of cytochrome P450 1B1 inhibitors as new promising anti-cancer agents. Med Res Rev. 2003; 23(6): 657-668. https://doi.org/10.1002/med.10050.
  • [6] Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin. 2018; 68: 394–424. https://doi.org/10.3322/CAAC.21492.
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  • [8] Leung YK, Lau KM, Mobley J, Jiang Z, Ho SM. Overexpression of cytochrome P450 1A1 and its novel spliced variant in ovarian cancer cells: Alternative subcellular enzyme compartmentation may contribute to carcinogenesis. Cancer Res. 2005; 65(9): 3726-3734. https://doi.org/10.1158/0008-5472.CAN-04-3771.
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  • [10] Lazaros L, Xita N, Kaponis A, et al. The association of aromatase (CYP19) gene variants with sperm concentration and motility. Asian J Androl. 2011; 13(2): 292-297. https://doi.org/10.1038/AJA.2010.144.
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  • [12] Miller WR, Larionov AA. Understanding the mechanisms of aromatase inhibitor resistance. Breast Cancer Res. 2012; 14: 201. https://doi.org/10.1186/BCR2931.
  • [13] Leoni A, Locatelli A, Morigi R, Rambaldi M. 2-Indolinone a versatile scaffold for treatment of cancer: a patent review (2008-2014). Expert Opin Ther Pat. 2016; 26: 149–173. https://doi.org/10.1517/13543776.2016.1118059.
  • [14] Motzer RJ, Hutson TE, Tomczak P, Michaelson MD, Bukowski RM, Rixe O, Oudard S, Negrier S, Szczylik C, Kim ST, Chen I, Bycott PW, Baum CM, Figlin RA. Sunitinib versus interferon alfa in metastatic renal-cell carcinoma. N Engl J Med. 2007; 356: 115–124. https://doi.org/10.1056/NEJMOA065044.
  • [15] Sternberg CN, Davis ID, Mardiak J, Szczylik C, Lee E, Wagstaff J, Barrios CH, Salman P, Gladkov OA, Kavina A, Zarbá JJ, Chen M, McCann L, Pandite L, Roychowdhury DF, Hawkins RE. Pazopanib in locally advanced or metastatic renal cell carcinoma: Results of a randomized phase III trial. J Clin Oncol. 2023; 41: 1957–1964. https://doi.org/10.1200/JCO.22.02622.
  • [16] Varun, Sonam, Kakkar R. Isatin and its derivatives: A survey of recent syntheses, reactions, and applications. Medchemcomm. 2019; 10: 351–368. https://doi.org/10.1039/C8MD00585K.
  • [17] Eldeeb M, Sanad EF, Ragab A, Ammar YA, Mahmoud K, Ali MM, Hamdy NM. Anticancer effects with molecular docking confirmation of newly synthesized isatin sulfonamide molecular hybrid derivatives against hepatic cancer cell lines. Biomedicines. 2022; 10(3):722.
  • [18] Chaudhari P, Bari S, Surana S, Shirkhedkar A, Wakode S, Shelar S, Racharla S, Ugale V, Ghodke M. Logical synthetic strategies and structure-activity relationship of indolin-2-one hybrids as small molecule anticancer agents: An overview. J Mol Struct. 2022; 1247 : 131280. https://doi.org/10.1016/J.MOLSTRUC.2021.131280.
  • [19] Güzel-Akdemir Ö, Akdemir A, Karalı N, Supuran CT. Discovery of novel isatin-based sulfonamides with potent and selective inhibition of the tumor-associated carbonic anhydrase isoforms IX and XII. Org Biomol Chem. 2015; 13(23): 6493-6499. https://doi.org/10.1039/C5OB00688K.
  • [20] Eldehna WM, Fares M, Ceruso M, Ghabbour HA, Abou-Seri SM, Abdel-Aziz HA, Abou El Ella DA, Supuran CT. Amido/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII. Eur J Med Chem. 2016; 110: 259-266. https://doi.org/10.1016/J.EJMECH.2016.01.030.
  • [21] Karalı N, Akdemir A, Göktaş F, Eraslan Elma P, Angeli A, Kızılırmak M, Supuran CT. Novel sulfonamide-containing 2-indolinones that selectively inhibit tumor-associated alpha carbonic anhydrases. Bioorg Med Chem. 2017; 25(14): 3714-3718. https://doi.org/10.1016/j.bmc.2017.05.029
  • [22] Eldehna WM, Al-Ansary GH, Bua S, Nocentini A, Gratteri P, Altoukhy A, Ghabbour H, Ahmed HY, Supuran C T. Novel indolin-2-one-based sulfonamides as carbonic anhydrase inhibitors: Synthesis, in vitro biological evaluation against carbonic anhydrases isoforms I, II, IV and VII and molecular docking studies. Eur J Med Chem. 2017; 127: 521-530. https://doi.org/10.1016/j.ejmech.2017.01.017.
  • [23] Eldehna WM, Nocentini A, Al-Rashood ST, Hassan GS, Alkahtani HM, Almehizia AA, Reda AM, Abdel-Aziz HA, Supuran CT. Tumor-associated carbonic anhydrase isoform IX and XII inhibitory properties of certain isatin-bearing sulfonamides endowed with in vitro antitumor activity towards colon cancer. Bioorg Chem. 2018; 81: 425-432. https://doi.org/10.1016/j.bioorg.2018.09.007
  • [24] Abo-Ashour MF, Eldehna WM, Nocentini A, Ibrahim HS, Bua S, Abou-Seri SM, Supuran CT. Novel hydrazido benzenesulfonamides-isatin conjugates: Synthesis, carbonic anhydrase inhibitory activity and molecular modeling studies. Eur J Med Chem. 2018; 157: 28-36. https://doi.org/10.1016/j.ejmech.2018.07.054
  • [25] Eldehna WM, Abo-Ashour MF, Nocentini A, El-Haggar RS, Bua S, Bonardi A, Al-Rashood ST, Hassan GS, Gratteri P, Abdel-Aziz HA, Supuran CT.Enhancement of the tail hydrophobic interactions within the carbonic anhydrase IX active site via structural extension: Design and synthesis of novel N-substituted isatins-SLC-0111 hybrids as carbonic anhydrase inhibitors and antitumor agents. Eur J Med Chem. 2019; 162: 147-160. https://doi.org/10.1016/j.ejmech.2018.10.068
  • [26] George RF, Bua S, Supuran CT, Awadallah FM. Synthesis of some N-aroyl-2-oxindole benzenesulfonamide conjugates with carbonic anhydrase inhibitory activity. Bioorg Chem. 2020; 96: 103635. https://doi.org/10.1016/j.bioorg.2020.103635
  • [27] Eraslan-Elma P, Akdemir A, Berrino E, Bozdağ M, Supuran CT, Karalı N. New 1H-indole-2,3-dione 3-thiosemicarbazones with 3-sulfamoylphenyl moiety as selective carbonic anhydrase inhibitors. Arch Pharm (Weinheim). 2022; 355(8): e2200023. https://doi.org/10.1002/ardp.202200023
  • [28] Jordan C, Furr BJA, An Introduction to the Regulation of Sex Steroids for the Treatment of Cancer, in: B.J.A. Jordan, V.C and Furr (Ed.), Horm. Breast Prostate Cancer, Humana Press, 2006: pp. 1–16.
  • [29] Santen RJ, Brodie H, Simpson ER, Siiteri PK, Brodie A. History of aromatase: saga of an important biological mediator and therapeutic target. Endocr Rev. 2009;30(4):343-375. https://doi.org/10.1210/er.2008-0016.
  • [30] Bhatia N, Thareja S. Aromatase inhibitors for the treatment of breast cancer: An overview (2019-2023). Bioorg Chem, 2024; 151: 107607. https://doi.org/10.1016/j.bioorg.2024.107607
  • [31] Wouters W, De Coster R, Goeminne N, Beerens D, van Dun J. Aromatase inhibition by the antifungal ketoconazole. J Steroid Biochem. 1988; 30(1-6): 387-389. https://doi.org/10.1016/0022-4731(88)90128-8
  • [32] Fabris M, Silva ML, de Santiago-Silva KM, de Lima Ferreira Bispo M, Goes Camargo P. CYP1B1: A promising target in cancer drug discovery. Anticancer Agents Med Chem. 2023; 23: 981–988. https://doi.org/10.2174/1871520623666230119103914.
  • [33] Yi L, Huang X, Yang M, Cai J, Jia J, Peng Z, Zhao Z, Yang F, Qiu D. A new class of CYP1B1 inhibitors derived from bentranil, Bioorganic Med Chem Lett. 2023; 80: 129112. https://doi.org/10.1016/j.bmcl.2022.129112.
  • [34] Ozcan-Sezer S, Ince E, Akdemir A, Ceylan ÖÖ, Suzen S, Gurer-Orhan H. Aromatase inhibition by 2-methyl indole hydrazone derivatives evaluated via molecular docking and in vitro activity studies. Xenobiotica. 2019; 49(5): 549-556. https://doi.org/10.1080/00498254.2018.1482029
  • [35] Burke MD, Mayer RT. Ethoxyresorufin: direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcholanthrene. Drug Metab Dispos. 1974; 2(6): 583-588.
  • [36] Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983; 65(1-2): 55-63. https://doi.org/10.1016/0022-1759(83)90303-4
  • [37] Labute P. Protonate3D: assignment of ionization states and hydrogen coordinates to macromolecular structures. Proteins. 2009; 75(1): 187-205. https://doi.org/10.1002/prot.22234https://doi.org/10.3390/BIOMEDICINES10030722.
There are 37 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences (Other)
Journal Section Articles
Authors

Elif İnce

Pınar Eraslan-elma

Atilla Akdemir

Nilgün Karalı

Hande Gürer-orhan

Publication Date June 4, 2025
Submission Date August 28, 2024
Acceptance Date November 23, 2024
Published in Issue Year 2025 Volume: 29 Issue: 3

Cite

APA İnce, E., Eraslan-elma, P., Akdemir, A., Karalı, N., et al. (2025). Novel sulfonamide-based compounds as dual inhibitors of hCYP1B1 and hCYP19A1 with anticancer activity against breast cancer cells. Journal of Research in Pharmacy, 29(3), 1098-1110. https://doi.org/10.12991/jrespharm.1694239
AMA İnce E, Eraslan-elma P, Akdemir A, Karalı N, Gürer-orhan H. Novel sulfonamide-based compounds as dual inhibitors of hCYP1B1 and hCYP19A1 with anticancer activity against breast cancer cells. J. Res. Pharm. June 2025;29(3):1098-1110. doi:10.12991/jrespharm.1694239
Chicago İnce, Elif, Pınar Eraslan-elma, Atilla Akdemir, Nilgün Karalı, and Hande Gürer-orhan. “Novel Sulfonamide-Based Compounds As Dual Inhibitors of hCYP1B1 and hCYP19A1 With Anticancer Activity Against Breast Cancer Cells”. Journal of Research in Pharmacy 29, no. 3 (June 2025): 1098-1110. https://doi.org/10.12991/jrespharm.1694239.
EndNote İnce E, Eraslan-elma P, Akdemir A, Karalı N, Gürer-orhan H (June 1, 2025) Novel sulfonamide-based compounds as dual inhibitors of hCYP1B1 and hCYP19A1 with anticancer activity against breast cancer cells. Journal of Research in Pharmacy 29 3 1098–1110.
IEEE E. İnce, P. Eraslan-elma, A. Akdemir, N. Karalı, and H. Gürer-orhan, “Novel sulfonamide-based compounds as dual inhibitors of hCYP1B1 and hCYP19A1 with anticancer activity against breast cancer cells”, J. Res. Pharm., vol. 29, no. 3, pp. 1098–1110, 2025, doi: 10.12991/jrespharm.1694239.
ISNAD İnce, Elif et al. “Novel Sulfonamide-Based Compounds As Dual Inhibitors of hCYP1B1 and hCYP19A1 With Anticancer Activity Against Breast Cancer Cells”. Journal of Research in Pharmacy 29/3 (June 2025), 1098-1110. https://doi.org/10.12991/jrespharm.1694239.
JAMA İnce E, Eraslan-elma P, Akdemir A, Karalı N, Gürer-orhan H. Novel sulfonamide-based compounds as dual inhibitors of hCYP1B1 and hCYP19A1 with anticancer activity against breast cancer cells. J. Res. Pharm. 2025;29:1098–1110.
MLA İnce, Elif et al. “Novel Sulfonamide-Based Compounds As Dual Inhibitors of hCYP1B1 and hCYP19A1 With Anticancer Activity Against Breast Cancer Cells”. Journal of Research in Pharmacy, vol. 29, no. 3, 2025, pp. 1098-10, doi:10.12991/jrespharm.1694239.
Vancouver İnce E, Eraslan-elma P, Akdemir A, Karalı N, Gürer-orhan H. Novel sulfonamide-based compounds as dual inhibitors of hCYP1B1 and hCYP19A1 with anticancer activity against breast cancer cells. J. Res. Pharm. 2025;29(3):1098-110.