Straightforward synthesis of cytosporone analogs AMS35AA and AMS35BB

Vitor, Neimar; Meza, Alisson; Gomes, Roberto da Silva; Rafique, Jamal; Lima, Dênis Pires de; Beatriz, Adilson

doi:10.1590/0001-3765202120201347

Cited by 5 publications

(7 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Phthalide 1 was readily prepared by treating 3,5-dimethoxybenzoic acid with octanoyl chloride in the presence of AlCl 3 . This compound has been characterized by 1 H and 13 C NMR spectroscopy, and the data match those reported in the literature [ 1 ].…”

Section: Methodssupporting

confidence: 66%

“…Resorcinolic lipids, such as cytosporones and their precursors, can interact with the phospholipid bilayers [ 1 ], help in the formation of liposomes [ 2 ], promote protection against oxidative stress [ 3 ], and inhibit bacterial growth [ 1 , 2 ] and tumor cells [ 4 ]. In addition, the resorcinol lipid cytosporone B induced apoptosis in tumor cells by interacting with the nuclear orphan receptor Nur77 [ 2 , 4 ].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

3-Heptylidene-4,6-Dimethoxy-3H-Isobenzofuran-1-One Is Genotoxic, Increases the Frequency of Cell Death, and Potentiates the Effects of Cyclophosphamide and Cisplatin

et al. 2023

Self Cite

View full text Add to dashboard Cite

3-heptylidene-4,6-dimethoxy-3H-isobenzofuran-1-one (Phthalide 1) is the precursor of three resorcinol lipids that have been described as potential chemotherapeutic agents and capable of potentiating the effects of cyclophosphamide. In this study, we evaluated the genotoxic potential, cell-killing potential, and interactions with cyclophosphamide and cisplatin of phthalide 1. Twelve groups were created from 120 mice: Negative Control, cyclophosphamide (100 mg/kg), cisplatin (6 mg/kg), Phthalide 1 (5, 10 and 20 mg/kg), and associations of 1 with cyclophosphamide and 1 with cisplatin. The results demonstrate that 1 increases (p < 0.05) the frequency of chromosomal damage, liver and kidney cell death, and splenic phagocytosis. The association of 1 with cyclophosphamide and cisplatin demonstrated a chemopreventive effect and, therefore, a reduction (p < 0.05) in the frequency of chromosomal damage. However, cell death and splenic phagocytosis did not suffer significant variations. As a result of the above, 1 has potential chemotherapeutic application and may be a candidate for developing a new generation of chemotherapeutics. In addition, it has characteristics to be used as a chemotherapy adjuvant in association with cyclophosphamide and cisplatin since it increases the frequency of cell death induced by chemotherapy. We also reported that the chemopreventive effect of 1, in association with cyclophosphamide and cisplatin, can prevent adverse effects (induction of DNA damage in non-tumor cells) without interfering with the mode of action of chemotherapy drugs and, therefore, without reducing the induction of cell death.

show abstract

Section: Methodssupporting

confidence: 66%

Section: Introductionmentioning

confidence: 99%

3-Heptylidene-4,6-Dimethoxy-3H-Isobenzofuran-1-One Is Genotoxic, Increases the Frequency of Cell Death, and Potentiates the Effects of Cyclophosphamide and Cisplatin

et al. 2023

Self Cite

View full text Add to dashboard Cite

show abstract

“…8,9,19 Additionally, the analogs are neither genotoxic nor mutagenic and do not affect biochemical parameters. 8,9,19 Strong evidence has recently shown that AMS35AA, alone or associated with CYC, has no toxic effects on spermatogenesis, suggesting that it might be used in association with CYC in chemotherapy without adverse effects on testicular function. 20 In line with previous research endeavors, this study aimed to assess the effects of CYC in conjunction with AMS35BB on genetic toxicology models and several other biological characteristics.…”

Section: ■ Introductionmentioning

confidence: 99%

“…In recent investigations, our group has demonstrated that three synthetic cytosporone analogs, termed AMS35AA , AMS35BB , and AMS049 , can enhance the mutagenic effect of cyclophosphamide ( CYC ) and induce apoptosis in mice (Figure ). ,, Additionally, the analogs are neither genotoxic nor mutagenic and do not affect biochemical parameters. ,, Strong evidence has recently shown that AMS35AA , alone or associated with CYC , has no toxic effects on spermatogenesis, suggesting that it might be used in association with CYC in chemotherapy without adverse effects on testicular function …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Chemotherapeutic Mechanism of Action of the Synthetic Resorcinolic Methyl 3,5-dimethoxy-2-octanoylbenzoate

Correa,

das Neves,

Oliveira

et al. 2024

Chem. Res. Toxicol.

Self Cite

View full text Add to dashboard Cite

Resorcinolic lipids are described as potential examples of selective chemotherapeutic adjuvants that can enhance the effects of cyclophosphamide (CYC) while promoting cell death without causing DNA damage. Therefore, the current study attempted to describe how the resorcinolic lipid methyl 3,5-dimethoxy-2-octanoylbenzoate (AMS35BB) interacted with DNA (DNA docking) and how this compound affected genetic toxicology models and other biological characteristics when combined with CYC. We observed that AMS35BB, used alone (7.5 and 10 mg/kg), increases the frequency of genomic damage (comet assay) but not chromosomal damage (micronuclei assay), lowers phagocytosis, and promotes cell death in Swiss male mice. When used in association with CYC, AMS35BB can reduce the risk of genomic damage by up to 33.8% as well as chromosomal damage, splenic phagocytosis, cell death, and lymphocyte frequency. Molecular docking showed that AMS35BB had a higher affinity than the active metabolite of CYC for binding to the DNA double helix major groove. As a result, AMS35BB has the potential to be both an adjuvant when used in association with CYC and a therapeutic candidate for the development of a selective chemotherapeutic drug.

show abstract

Synthetic drives for useful drug molecules through organocatalytic methods

Banik

Sahoo

Tiwari

et al. 2022

Physical Sciences Reviews

View full text Add to dashboard Cite

The treatment of various pathological conditions in human beings involves the use of safe and efficacious drug substances. But there are different complications associated with the treatment of various disease states including drug resistance, adverse drug reactions, toxicity, etc. To minimize these problems, there is an urgent need to develop new therapeutics with suitable pharmacokinetic and pharmacodynamic properties. So, the organocatalytic methods are emerged as a potential synthetic tool to accelerate the design of new drug candidates with improved physicochemical and pharmacological properties, selectivity, and efficiency for the treatment of life-threatening diseases. Organocatalytic reactions refer to the chemical reaction that is accelerated by organic catalysts instead of using organometallic catalysts. Organocatalysts are more advantageous in comparison to metallic catalysts because organocatalysts are cost-effective, stable, efficient, non-toxic, readily available, and easy to handle. In addition to this, the organocatalysis method involves an eco-friendly reaction by minimizing the formation of by-products and reducing the chemical hazards. Organocatalysts are categorized into four classes such as Lewis acids, Lewis bases, Bronsted acids, and Bronsted bases. These catalysts are generally involved in various reactions mechanisms such as Aldol reaction, Diels–Alder reactions, Michael Addition and Knoevenagal reactions, etc. The utility of organocatalyst in synthetic chemistry results in the development of medicinally active compounds with diverse structural features.

show abstract

Straightforward synthesis of cytosporone analogs AMS35AA and AMS35BB

Cited by 5 publications

References 15 publications

3-Heptylidene-4,6-Dimethoxy-3H-Isobenzofuran-1-One Is Genotoxic, Increases the Frequency of Cell Death, and Potentiates the Effects of Cyclophosphamide and Cisplatin

3-Heptylidene-4,6-Dimethoxy-3H-Isobenzofuran-1-One Is Genotoxic, Increases the Frequency of Cell Death, and Potentiates the Effects of Cyclophosphamide and Cisplatin

Chemotherapeutic Mechanism of Action of the Synthetic Resorcinolic Methyl 3,5-dimethoxy-2-octanoylbenzoate

Synthetic drives for useful drug molecules through organocatalytic methods

Contact Info

Product

Resources

About