Reductive activation of mitomycins A and C by vitamin C

Paz, Manuel M.

doi:10.1016/j.bioorg.2013.03.002

Cited by 8 publications

(1 citation statement)

References 53 publications

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“…Vitamin C (Vc) is an indispensable nutrient required to maintain healthy physiological processes in humans because it removes harmful free radicals and accelerates collagen synthesis. , Vc also exhibits a wide range of pharmacological properties, including anti-aging, anti-oxidation, anti-hypertension, and anti-cancer. , However, the sustainability of Vc is low, and most of its functionality is lost during processing and storage of food and feeds due to the exposure to light, heat, moisture, and oxygen. , The utilization of more-stable forms of Vc is therefore crucial for human nutrition. To overcome the drawbacks, encapsulation techniques have recently been utilized to extend the shelf-life of Vc, such as liposome encapsulation, , nanoparticle encapsulation, and microencapsulation .…”

Section: Introductionmentioning

confidence: 99%

Preparation and Self-Assembly Mechanism of Bovine Serum Albumin–Citrus Peel Pectin Conjugated Hydrogel: A Potential Delivery System for Vitamin C

Peng

Chen

Luo

et al. 2016

J. Agric. Food Chem.

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In this study, a novel hydrogel (BSA-pectin hydrogel, BPH) was prepared via a self-assembly method by using the natural polymers of bovine serum albumin (BSA) and citrus peel pectin (pectin). The rheological properties and gel conformational structures were determined and showed that electrostatic and covalent interactions between BSA and pectin were the main mechanisms for the formation of BPH. The morphological characteristics of BPH included a stable and solid three-dimensional network structure with a narrow size distribution (polydispersity index <0.06). BPH was used as a delivery system to load the functional agent vitamin C (Vc). The encapsulation efficiency (EE) and release properties of Vc from BPH were also investigated. The results revealed that the EE of Vc into BPH was approximately 65.31%, and the in vitro Vc release from BPH was governed by two distinct stages (i.e., burst release and sustained release) in different pH solutions, with release mechanisms involving diffusion, swelling, and erosion. Meanwhile, the stability results showed that BPH was a stable system with an enhanced Vc retention (73.95%) after 10 weeks of storage. Thus, this three-dimensional network system of BPH may be a potential delivery system to improve the stability and bioavailability of functional agents in both food and non-food fields.

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Section: Introductionmentioning

confidence: 99%

Preparation and Self-Assembly Mechanism of Bovine Serum Albumin–Citrus Peel Pectin Conjugated Hydrogel: A Potential Delivery System for Vitamin C

Peng

Chen

Luo

et al. 2016

J. Agric. Food Chem.

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Information processing through a bio-based redox capacitor: Signatures for redox-cycling

Liu

Kim

White

et al. 2014

Bioelectrochemistry

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Synthesis of Mitomycin C and Decarbamoylmitomycin C N2 deoxyguanosine-adducts

Champeil

Cheng

Huang

et al. 2016

Bioorganic Chemistry

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Mitomycin C (MC) and Decarbamoylmitomycin C (DMC) -a derivative of MC lacking the carbamate on C10- are DNA alkylating agents. Their cytotoxicity is attributed to their ability to generate DNA monoadducts as well as intrastrand and interstrand cross-links (ICLs). The major monoadducts generated by MC and DMC in tumor cells have opposite stereochemistry at carbon one of the guanine-mitosene bond: trans (or alpha) for MC and cis (or beta) for DMC. We hypothesize that local disruptions of DNA structure from trans or cis adducts are responsible for the different biochemical responses produced by MC and DMC. Access to DNA substrates bearing cis and trans MC/DMC lesions is essential to verify this hypothesis. Synthetic oligonucleotides bearing trans lesions can be obtained by bio-mimetic methods. However, this approach does not yield cis adducts. This report presents the first chemical synthesis of a cis mitosene DNA adduct. We also examined the stereopreference exhibited by the two drugs at the mononucleotide level by analyzing the formation of cis and trans adducts in the reaction of deoxyguanosine with MC or DMC using a variety of activation conditions. In addition, we performed Density Functional Theory calculations to evaluate the energies of these reactions. Direct alkylation under autocatalytic or bifunctional conditions yielded preferentially alpha adducts with both MC and DMC. DFT calculations showed that under bifunctional activation, the thermodynamically favored adducts are alpha, trans, for MC and beta, cis, for DMC. This suggests that the duplex DNA structure may stabilize/oriente the activated pro-drugs so that, with DMC, formation of the thermodynamically favored beta products are possible in a cellular environment.

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Reductive activation of mitomycins A and C by vitamin C

Cited by 8 publications

References 53 publications

Preparation and Self-Assembly Mechanism of Bovine Serum Albumin–Citrus Peel Pectin Conjugated Hydrogel: A Potential Delivery System for Vitamin C

Preparation and Self-Assembly Mechanism of Bovine Serum Albumin–Citrus Peel Pectin Conjugated Hydrogel: A Potential Delivery System for Vitamin C

Information processing through a bio-based redox capacitor: Signatures for redox-cycling

Synthesis of Mitomycin C and Decarbamoylmitomycin C N2 deoxyguanosine-adducts

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