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An Insight into Symmetrical Cyanine Dyes as Promising Selective Antiproliferative Agents in Caco-2 Colorectal Cancer Cells.

التفاصيل البيبلوغرافية
العنوان: An Insight into Symmetrical Cyanine Dyes as Promising Selective Antiproliferative Agents in Caco-2 Colorectal Cancer Cells.
المؤلفون: Serrano JL; CICS-UBI-Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal.; Department of Chemistry, University of Beira Interior, Rua Marquês de Ávila e Bolama, 6201-001 Covilhã, Portugal., Maia A; CICS-UBI-Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal.; Department of Chemistry, University of Beira Interior, Rua Marquês de Ávila e Bolama, 6201-001 Covilhã, Portugal., Santos AO; CICS-UBI-Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal., Lima E; CICS-UBI-Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal.; CQVR-Chemistry Centre of Vila Real, University of Trás-os-Montes and Alto Douro, Quinta de Prados, 5001-801 Vila Real, Portugal., Reis LV; CQVR-Chemistry Centre of Vila Real, University of Trás-os-Montes and Alto Douro, Quinta de Prados, 5001-801 Vila Real, Portugal., Nunes MJ; Department of Chemistry, University of Beira Interior, Rua Marquês de Ávila e Bolama, 6201-001 Covilhã, Portugal., Boto REF; CICS-UBI-Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal.; Department of Chemistry, University of Beira Interior, Rua Marquês de Ávila e Bolama, 6201-001 Covilhã, Portugal., Silvestre S; CICS-UBI-Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal.; Department of Chemistry, University of Beira Interior, Rua Marquês de Ávila e Bolama, 6201-001 Covilhã, Portugal.; CNC-Center for Neuroscience and Cell Biology, University of Coimbra, Rua Larga, 3004-517 Coimbra, Portugal., Almeida P; CICS-UBI-Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal.; Department of Chemistry, University of Beira Interior, Rua Marquês de Ávila e Bolama, 6201-001 Covilhã, Portugal.
المصدر: Molecules (Basel, Switzerland) [Molecules] 2022 Sep 07; Vol. 27 (18). Date of Electronic Publication: 2022 Sep 07.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI, c1995-
مواضيع طبية MeSH: Antineoplastic Agents*/pharmacology , Colorectal Neoplasms* , Quinolines*, Benzoxazoles ; Caco-2 Cells ; Fluorescent Dyes ; Humans
مستخلص: Cancer remains one of the diseases with the highest worldwide incidence. Several cytotoxic approaches have been used over the years to overcome this public health threat, such as chemotherapy, radiotherapy, and photodynamic therapy (PDT). Cyanine dyes are a class of compounds that have been extensively studied as PDT sensitisers; nevertheless, their antiproliferative potential in the absence of a light source has been scarcely explored. Herein, the synthesis of eighteen symmetric mono-, tri-, and heptamethine cyanine dyes and their evaluation as potential anticancer agents is described. The influences of the heterocyclic nature, counterion, and methine chain length on the antiproliferative effects and selectivities were analysed, and relevant structure-activity relationship data were gathered. The impact of light on the cytotoxic activity of the most promising dye was also assessed and discussed. Most of the monomethine and trimethine cyanine dyes under study demonstrated a high antiproliferative effect on human tumour cell lines of colorectal (Caco-2), breast (MCF-7), and prostate (PC-3) cancer at the initial screening (10 µM). However, concentration-viability curves showed higher potency and selectivity for the Caco-2 cell line. A monomethine cyanine dye derived from benzoxazole was the most promising compound (IC 50 for Caco-2 = 0.67 µM and a selectivity index of 20.9 for Caco-2 versus normal human dermal fibroblasts (NHDF)) and led to Caco-2 cell cycle arrest at the G0/G1 phase. Complementary in silico studies predicted good intestinal absorption and oral bioavailability for this cyanine dye.
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معلومات مُعتمدة: UIDB/00709/2020 Fundação para a Ciência e Tecnologia; UIDP/00709/2020 Fundação para a Ciência e Tecnologia; UID/QUI/UI0616/2019 Fundação para a Ciência e Tecnologia; SFRH/BD/147645/2019 Fundação para a Ciência e Tecnologia; SFRH/BD/148028/2019 Fundação para a Ciência e Tecnologia; 022161 Fundo Europeu de Desenvolvimento Regional (FEDER)
فهرسة مساهمة: Keywords: Caco-2 cells; antiproliferative agents; cell cycle arrest; colorectal cancer; cyanine dyes
المشرفين على المادة: 0 (Antineoplastic Agents)
0 (Benzoxazoles)
0 (Fluorescent Dyes)
0 (Quinolines)
تواريخ الأحداث: Date Created: 20220923 Date Completed: 20220926 Latest Revision: 20230320
رمز التحديث: 20231215
مُعرف محوري في PubMed: PMC9503608
DOI: 10.3390/molecules27185779
PMID: 36144515
قاعدة البيانات: MEDLINE
الوصف
تدمد:1420-3049
DOI:10.3390/molecules27185779