Induction of tumor cell apoptosis by a novel class of N-thiolated β-lactam antibiotics with structural modifications at N1 and C3 of the lactam ring

International Journal of Molecular Medicine

Volumn 21, Issue 6, 2008, Pages 689-695

  Frezza, Michael ^a   Garay, Julio ^b   Chen, Di ^a   Cui, Cindy ^a   Turos, Edward ^b   Dou, Q Ping ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

Apoptosis; DNA damage; Structure activity relationship; Tumor cell death; lactams

Indexed keywords

ANTINEOPLASTIC AGENT; BETA LACTAM ANTIBIOTIC; DNA; JG 1; JG 10; JG 11; JG 12; JG 13; JG 14; JG 15; JG 16; JG 17; JG 18; JG 19; JG 2; JG 20; JG 21; JG 22; JG 23; JG 24; JG 3; JG 4; JG 5; JG 6; JG 7; JG 8; JG 9; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; BETA LACTAM; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; SINGLE HETEROCYCLIC RINGS;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CANCER GROWTH; CANCER INHIBITION; CELL DEATH; CHEMICAL MODIFICATION; CONTROLLED STUDY; DNA DAMAGE; DRUG DOSE ESCALATION; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA; MOUSE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT; ANIMAL; BREAST TUMOR; CELL STRAIN HL 60; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; EXPERIMENTAL NEOPLASM; LEUKEMIA CELL LINE; METABOLISM; NICK END LABELING; NUDE MOUSE; PATHOLOGY; T LYMPHOCYTE; TUMOR CELL LINE; TUMOR VOLUME; WESTERN BLOTTING;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BETA-LACTAMS; BLOTTING, WESTERN; BREAST NEOPLASMS; CELL LINE, TUMOR; FEMALE; HETEROCYCLIC COMPOUNDS, 1-RING; HL-60 CELLS; HUMANS; IN SITU NICK-END LABELING; JURKAT CELLS; MAMMARY NEOPLASMS, EXPERIMENTAL; MICE; MICE, NUDE; MOLECULAR STRUCTURE; POLY(ADP-RIBOSE) POLYMERASES; STRUCTURE-ACTIVITY RELATIONSHIP; T-LYMPHOCYTES; TUMOR BURDEN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 47649116323     PISSN: 11073756     EISSN: None     Source Type: Journal    
DOI: 10.3892/ijmm.21.6.689     Document Type: Article

References (22)

1. Danial NN and Korsmeyer SJ: Cell death: critical control points. Cell 116: 205-219,2004.
2. Fesik SW: Promoting apoptosis as a strategy for cancer drug discovery. Nat Rev Cancer 5: 876-885, 2005.
3. Hengartner MO: The biochemistry of apoptosis. Nature 407: 770-776, 2000.
4. Earnshaw WC: Nuclear changes in apoptosis. Curr Opin Cell Biol 7: 337-343, 1995.
5. Fulda S and Debatin KM: Extrinsic versus intrinsic apoptosis pathways in anticancer chemotherapy. Oncogene 25: 4798-4811, 2006.
6. Kaufmann SH and Earnshaw WC: Induction of apoptosis by cancer chemotherapy. Exp Cell Res 256: 42-49, 2000.
7. Fulda S and Debatin KM: Targeting apoptosis pathways in cancer therapy. Curr Cancer Drug Targets 4: 569-576, 2004.
8. Makin G and Dive C: Apoptosis and cancer chemotherapy. Trends Cell Biol 11: S22-S26, 2001.
9. Nicholson DW: From bench to clinic with apoptosis-based therapeutic agents. Nature 407: 810-816, 2000.
10. Nathwani D and Wood MJ: Penicillins. A current review of their clinical pharmacology and therapeutic use. Drugs 45: 866-894, 1993.
11. Abraham EP: The beta-lactam antibiotics. Sci Am 244: 76-86, 1981.
12. Kidwai M, Sapra P and Bhushan KR: Synthetic strategies and medicinal properties of beta-lactams. Curr Med Chem 6: 195-215, 1999.
13. Turos E, Long TE, Heldreth B, et al: N-thiolated beta-lactams: a new family of anti-Bacillus agents. Bioorg Med Chem Lett 16: 2084-2090, 2006.
14. Turos E, Long TE, Konaklieva MI, et al: N-thiolated beta-lactams: novel antibacterial agents for methicillin-resistant Staphylococcus aureus. Bioorg Med Chem Lett 12: 2229-2231, 2002.
15. Kazi A, Hill R, Long TE, Kuhn DJ, Turos E and Dou QP: Novel N-thiolated beta-lactam antibiotics selectively induce apoptosis in human tumor and transformed, but not normal or non-transformed, cells. Biochem Pharmacol 67: 365-374, 2004.
16. Kuhn DJ, Wang Y, Minic V, et al: Structure-activity relationships of N-methylthiolated beta-lactam antibiotics with C3 substitutions and their selective induction of apoptosis in human cancer cells. Front Biosci 10: 1183-1190, 2005.
17. Smith DM, Kazi A, Smith L, et al: A novel beta-lactam antibiotic activates tumor cell apoptotic program by inducing DNA damage. Mol Pharmacol 61: 1349-1358, 2002.
18. Ren XF, Konaklieva MI, Shi H, Dickey S, Lim DV, Gonzalez J and Turos E: Studies on nonconventionally fused bicyclic beta-lactams. J Org Chem 63: 8898-8917, 1998.
19. Daniel KG, Gupta P, Harbach RH, Guida WC and Don QP: Organic copper complexes as a new class of proteasome inhibitors and apoptosis inducers in human cancer cells. Biochem Pharmacol 67: 1139-1151, 2004.
20. An B, Goldfarb RH, Siman R and Dou QP: Novel dipeptidyl proteasome inhibitors overcome Bcl-2 protective function and selectively accumulate the cyclin-dependent kinase inhibitor p27 and induce apoptosis in transformed, but not normal, human fibroblasts. Cell Death Differ 5: 1062-1075, 1998.
21. Kuhn D, Coates C, Daniel K, et al: Beta-lactams and their potential use as novel anticancer chemotherapeutic s drugs. Front Biosci 9: 2605-2617, 2004.
22. Revell KD, Heldreth B, Long TE, Jang S and Turos E: N-thiolated beta-lactams: Studies on the mode of action and identification of a primary cellular target in Staphylococcus aureus. Bioorg Med Chem 15: 2453-2467, 2007.