Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates - PubMed (original) (raw)

Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates

Y Zhang et al. Proc Natl Acad Sci U S A. 1994.

Abstract

Sulforaphane [1-isothiocyanato-4-(methyl-sulfinyl)butane] was recently isolated from one variety of broccoli as the major and very potent inducer of phase 2 detoxication enzymes in murine hepatoma cells in culture. Since phase 2 enzyme induction is often associated with reduced susceptibility of animals and their cells to the toxic and neoplastic effects of carcinogens and other electrophiles, it was important to establish whether sulforaphane could block chemical carcinogenesis. In this paper we report that sulforaphane and three synthetic analogues, designed as potent phase 2 enzyme inducers, block the formation of mammary tumors in Sprague-Dawley rats treated with single doses of 9,10-dimethyl-1,2-benzanthracene. The analogues are exo-2-acetyl-exo-6-isothiocyanatonorbornane, endo-2-acetyl-exo-6-isothiocyanatonorbornane, and exo-2-acetyl-exo-5-isothiocyanatonorbornane. When sulforaphane and exo-2-acetyl-exo-6-isothiocyanatonorbornane were administered by gavage (75 or 150 mumol per day for 5 days) around the time of exposure to the carcinogen, the incidence, multiplicity, and weight of mammary tumors were significantly reduced, and their development was delayed. The analogues endo-2-acetyl-exo-6-isothiocyanatonorbornane and exo-2-acetyl-exo-5-isothiocyanatonorbornane were less potent protectors. Thus, a class of functionalized isothiocyanates with anticarcinogenic properties has been identified. These results validate the thesis that inducers of phase 2 enzymes in cultured cells are likely to protect against carcinogenesis.

PubMed Disclaimer

Similar articles

• Broccoli sprouts: an exceptionally rich source of inducers of enzymes that protect against chemical carcinogens.
  Fahey JW, Zhang Y, Talalay P. Fahey JW, et al. Proc Natl Acad Sci U S A. 1997 Sep 16;94(19):10367-72. doi: 10.1073/pnas.94.19.10367. Proc Natl Acad Sci U S A. 1997. PMID: 9294217 Free PMC article.
• A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure.
  Zhang Y, Talalay P, Cho CG, Posner GH. Zhang Y, et al. Proc Natl Acad Sci U S A. 1992 Mar 15;89(6):2399-403. doi: 10.1073/pnas.89.6.2399. Proc Natl Acad Sci U S A. 1992. PMID: 1549603 Free PMC article.
• Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms.
  Zhang Y, Talalay P. Zhang Y, et al. Cancer Res. 1994 Apr 1;54(7 Suppl):1976s-1981s. Cancer Res. 1994. PMID: 8137323 Review.
• [Sulforaphane--a possible agent in prevention and therapy of cancer].
  Tomczyk J, Olejnik A. Tomczyk J, et al. Postepy Hig Med Dosw (Online). 2010 Nov 29;64:590-603. Postepy Hig Med Dosw (Online). 2010. PMID: 21160094 Review. Polish.

Cited by

• Immunomodulatory Effects and Regulatory Mechanisms of (R)-6-HITC, an Isothiocyanate from Wasabi (Eutrema japonicum), in an Ex Vivo Mouse Model of LPS-Induced Inflammation.
  Alcarranza M, Alarcón-de-la-Lastra C, Recio Jiménez R, Fernández I, Castejón Martínez ML, Villegas I. Alcarranza M, et al. J Agric Food Chem. 2024 Oct 2;72(39):21520-21532. doi: 10.1021/acs.jafc.4c02943. Epub 2024 Sep 19. J Agric Food Chem. 2024. PMID: 39298284 Free PMC article.
• The Immunomodulatory Effects of Sulforaphane in Exercise-Induced Inflammation and Oxidative Stress: A Prospective Nutraceutical.
  Ruhee RT, Suzuki K. Ruhee RT, et al. Int J Mol Sci. 2024 Feb 1;25(3):1790. doi: 10.3390/ijms25031790. Int J Mol Sci. 2024. PMID: 38339067 Free PMC article. Review.
• Phenylpropanoid-enriched broccoli seedling extract can reduce inflammatory markers and pain behavior.
  Gurgul AA, Najjar Y, Chee A, An H, Che CT, Park TJ, Warpeha KM. Gurgul AA, et al. J Transl Med. 2023 Dec 19;21(1):922. doi: 10.1186/s12967-023-04777-1. J Transl Med. 2023. PMID: 38115032 Free PMC article.
• A Spectrum of Solutions: Unveiling Non-Pharmacological Approaches to Manage Autism Spectrum Disorder.
  Mondal A, Sharma R, Abiha U, Ahmad F, Karan A, Jayaraj RL, Sundar V. Mondal A, et al. Medicina (Kaunas). 2023 Aug 31;59(9):1584. doi: 10.3390/medicina59091584. Medicina (Kaunas). 2023. PMID: 37763703 Free PMC article. Review.

References

1. 1. J Med Chem. 1994 Jan 7;37(1):170-6 - PubMed
2. 1. Cancer Res. 1988 Sep 1;48(17):4776-82 - PubMed
3. 1. Adv Enzyme Regul. 1989;28:237-50 - PubMed
4. 1. Nutr Cancer. 1992;18(1):1-29 - PubMed
5. 1. Anal Biochem. 1988 Mar;169(2):328-36 - PubMed

Publication types

MeSH terms

Substances

LinkOut - more resources

• Full Text Sources

  • Atypon
  • Europe PubMed Central
  • PubMed Central

• Other Literature Sources

  • The Lens - Patent Citations