Cyclic hydroxamic acid inhibitors of prostate cancer cell growth: Selectivity and structure activity relationships

Roberts, Kenneth P.; Iyer, Ramaswamy A.; Prasad, Girija; Liu, Lee T.; Lind, Robert E.; Hanna, Patrick E.

doi:10.1002/(sici)1097-0045(19980201)34:2<92::aid-pros3>3.0.co;2-l

Cited by 21 publications

(22 citation statements)

References 12 publications

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“…They are considered to be capable of lowering cancer risk (Zhang et al 1995;Roberts et al 1998) and insulin secretion (Landberg et al 2010). Moreover, they have antiallergic properties (Otsuka et al1988;Poupaert et al 2005), appetite suppression and weight reduction effects (Rosenfeld and Forsberg 2009).…”

Section: Bxs Classmentioning

confidence: 99%

The genetic background of benzoxazinoid biosynthesis in cereals

2015

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Benzoxazinoids (BXs) are important compounds in plant defense. Their allelopathic, nematode suppressive and antimicrobial properties are well known. BXs are found in monocot plants and in a few species of dicots. Over 50 years of study have led to the characterization of the chromosomal locations and coding sequences of almost all the genes involved in BX biosynthesis in a number of cereal species: ZmBx1-ZmBx10a7c in maize, TaBx1-TaBx5, TaGT and Taglu in wheat, ScBx17ScBx5, ScBx6-like, ScGT and Scglu in rye. So far, the ortholog of the maize Bx7 gene has not been identified in the other investigated species. This review aims to summarize the available data on the genetic basis of BXs biosynthesis in cereals.

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Section: Bxs Classmentioning

confidence: 99%

The genetic background of benzoxazinoid biosynthesis in cereals

2015

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“…18 are derivatives of a natural benzoxazinone compound that has been shown to cause symptomatic improvements in patients with benign prostatic hyperplasia, chronic prostatitis and prostatodynia. Compounds 74a and b showed potent inhibitory effects on DU-145 prostate cancer cell growth, although they were not selective for this cell line because they inhibited MCF-7 cell growth at a concentration of 10 μg/mL [126]. …”

Section: N-hydroxy-substituted Fused Six-membered Ring Systemsmentioning

confidence: 99%

Bioactive heterocycles containing endocyclic N-hydroxy groups

Rani

Granchi

2015

European Journal of Medicinal Chemistry

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Drug-likeness rules consider N-O single bonds as “structural alerts” which should not be present in a perspective drug candidate. In most cases this concern is correct, since it is known that N-hydroxy metabolites of branded drugs produce reactive species that cause serious side effects. However, this dangerous reactivity of the N-OH species generally takes place when the nitrogen atom is not comprised in a cyclic moiety. In fact, the same type of metabolic behavior should not be expected when the nitrogen atom is included in the ring of an aromatic heterocyclic scaffold. Nevertheless, heterocycles bearing endocyclic N-hydroxy portions have so far been poorly studied as chemical classes that may provide new therapeutic agents. This review provides an overview of N-OH-containing heterocycles with reported bioactivities that may be considered as therapeutically relevant and, therefore, may extend the chemical space available for the future development of novel pharmaceuticals. A systematic treatment of the various chemical classes belonging to this particular family of molecules is described along with a discussion of the biological activities associated to the most important examples.

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“…A number of publications have reported the beneficial effects of benzoxazinoids in vitro; these include the inhibitory effect of DI-BOA on prostate cancer cell growth Zhang et al, 1995), breast cancer cell growth (Roberts et al, 1998), prostatic inflammation disease and benign prostate hyperplasia (Roberts et al, 1998;Rugendorff, Weidner, Ebeling, & Buck, 1993). The inhibitory effect of MBOA on human immunodeficiency virus reverse transcriptase (Wang & Ng, 2002) and the inhibitory effects of HMBOA and MBOA on the key biological process of allergic inflammation by the IgE-receptor mediated histamine release from mast cells (Otsuka, Hirai, Nagao, & Yamasaki, 1988) have also been reported.…”

Section: Beneficial Biological Effects Of Benzoxazinoidsmentioning

confidence: 99%

“…Bread is consumed in large quantities all over the world, especially rye bread throughout the Nordic countries. Considering that DIBOA has been known for some time to inhibit cancer cell growth in vitro (Habib, Ross, Lewenstein, Zhang, & Jaton, 1995;Roberts et al, 1998;Zhang et al, 1995), our present discovery of an array of benzoxazinoids in cereal grains therefore indicates a need for detailed studies of these compounds. This study aimed to map quantitatively the presence of 10 benzoxazinoid compounds in mature grains of selected cultivars of rye and wheat before and after five-day HTP treatment, as well as in bread baked with the corresponding HTP and conventional flours.…”

Section: Introductionmentioning

confidence: 99%