The selective concentration of sulphadiazine and related compounds in malignant tissue

Abel, George; Connors, T. A.; Ross, W. C. J.; Nguyen‐Hoang‐Nam,; Hoellinger, H.; Pichat, L.

doi:10.1016/0014-2964(73)90042-x

Cited by 38 publications

(6 citation statements)

References 5 publications

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“…The research also found that CUL4-DCAF15 E3 ubiquitin ligase can be recruited by sulfonamide compounds such as indisulam, tasisulam, and chloroquinoxaline sulfonamide (CQS) ( Figure 1) to trigger ubiquitination and degradation of RBM39 protein, resulting in an antitumor effect [10]. Besides, sulfonamides can be selectively concentrated in tumor tissues [11][12][13] and are expected to be useful for the development of tumor-targeting drugs. for many years, and the research on quinone-based anticancer drugs is still ongoing [15,16].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antitumor Activity of a Series of Novel 4-(Aromatic Sulfonyl)-1-oxa-4-azaspiro[4.5]deca-6,9-dien-8-ones

et al. 2020

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Many sulfonamides show anticancer activity. Based on benzenesulfonylazaspirodienone (HL-X9) identified in our previous work, we optimized the lead compound for better efficacy, thereby synthesizing a series of novel 4-(aromatic sulfonyl)-1-oxa-4-azaspiro[4.5]deca-6,9-dien-8-one derivatives through a key step of metal-catalyzed cascade cyclization. The preliminary antiproliferative tests have shown that the anticancer activities of acetyl-protected mannose-linked sulfonylazaspirodienone derivatives (7i–7l) have been greatly improved. Among them, 7j is the most potent derivative, with IC50 values of 0.17 µM, 0.05 µM, and 0.07 µM for A549, MDA-MB-231, and HeLa cell lines, respectively. Flow cytometry analysis shows that 7j arrests MDA-MB-231 cells in the G2/M phase and has a certain effect on the apoptosis of MDA-MB-231 cells. In addition, the acute toxicity of 7j was lower than that of adriamycin.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antitumor Activity of a Series of Novel 4-(Aromatic Sulfonyl)-1-oxa-4-azaspiro[4.5]deca-6,9-dien-8-ones

et al. 2020

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“…The study also proved that such new nano-anti-cancer drug be able to kill human cervical HeLa cells effectively and induce tumor cells apoptosis, but without toxic effect on normal cells. Bartulin et al (1974) and Abel et al (1973) reported that the concentrations of sulfonamide and its derivatives in Walke cancer or Yoshida cancer were two to three times higher than that of liver. The sulfadiazine can selectively be taken in by …”

Section: Introductionmentioning

confidence: 99%

Studies on Interactions between Sulfadiazine and Peptide Amides

Wang¹,

Zhang²,

Du³

et al. 2015

Biotechnology

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A B S T R A C T In this study, the optimal structures and binding energies of 14 hydrogen bonded complexes, which contained the sulfadiazine, N-methylacetamide, a glycine dipeptide and an alanine dipeptide, were obtained. The sites preference of sulfadiazine hydrogen bonding to peptide amides were explored. The interaction energies of all the complexes were corrected by Basis Set Superposition Error (BSSE). By the analysis interaction energy, charge density and second-order interaction energies E(2) of the complexes, it is found that N-methylacetamide can use three binding sites (site NMA1, NMA2 and NMA3) to form N-H…O=C or N-H…N hydrogen-bonded complexes with sulfadiazine, the N-H…O=C hydrogen-bonded complexes formed at site NMA1 of N-methylacetamide are more stable. The calculation results also show that the glycine dipeptide can use either site Gly1 or Gly2 and the alanine dipeptide can use either site Ala1 or Ala2 to form hydrogen-bonded complexes with sulfadiazine, the hydrogen-bonded complexes formed at site Gly2 of the glycine dipeptide and at site Ala2 of the alanine dipeptide are more stable. The interaction between sulfadiazine and the peptide is preferred to that between sulfadiazine and N-methylacetamide.

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“…5,6 Sulfonamides have been also well-known as an important class of drugs not only retaining a pharmacological efficacy such as antibacterial and/or anti-cancer effect but also exhibiting the different pH values in relation with the pK a values depending on the structures. [7][8][9][10][11] In addition, hydrogel obtained from copolymerization of N-isopropylacrylamide (NiPAM) and N-[4-((2,6-dimethyl-4-pyrimidinyl)sulfamoyl)phenyl] methacrylamide carrying sulfamethazine group (pK a = 7.4) with N,N'-methylenebis(acrylamide) has been found to exhibit the pH-sensitive phase transition behavior. 12 Many amphiphilic polymeric micelles as colloidal nanoparticles have been used as the nanocontainers carrying drugs for antimicrobial chemotherapy and diagonosis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new pH-sensitive amphiphilic block copolymers and study for the micellization using a fluorescence probe

et al. 2008

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This paper reports a facile synthesis of new water-soluble poly(ethylene oxide) (PEO)-based amphiphilic block copolymers showing pH sensitive phase transition behaviors. The copolymers were prepared by atom transfer radical polymerization (ATRP) of methacrylamide type of monomers carrying a sulfonamide group using a PEObased macroinitiator and a Cu(I)Br/Me 6 TREN catalytic system in aqueous media. The resulting polymers were characterized by a combination of 1 H-NMR, size exclusion chromatography, and UV/Visible spectrophotometeric analysis. The micellization of the block copolymers as a drug-loading mechanism in aqueous media using fluorescein salt was examined as a function of pH. The stable micelle formation and its loading efficacy suggest that the block copolymers can be used as precursors for drug-nanocontainers.

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The selective concentration of sulphadiazine and related compounds in malignant tissue

Cited by 38 publications

References 5 publications

Design, Synthesis, and Antitumor Activity of a Series of Novel 4-(Aromatic Sulfonyl)-1-oxa-4-azaspiro[4.5]deca-6,9-dien-8-ones

Design, Synthesis, and Antitumor Activity of a Series of Novel 4-(Aromatic Sulfonyl)-1-oxa-4-azaspiro[4.5]deca-6,9-dien-8-ones

Studies on Interactions between Sulfadiazine and Peptide Amides

Synthesis of new pH-sensitive amphiphilic block copolymers and study for the micellization using a fluorescence probe

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