Prodrugs of butyric acid from bench to bedside: Synthetic design, mechanisms of action, and clinical applications

Drug Development Research

Volumn 50, Issue 3-4, 2000, Pages 379-391

  Rephaeli, Ada ^a   Zhuk, Regina ^b   Nudelman, Abraham ^b  

^a TEL AVIV UNIVERSITY   (Israel)

^b BAR ILAN UNIVERSITY   (Israel)

Author keywords

Alopecia; Anticancer drugs; Butyric acid; Differentiation; Prodrugs; Retinoic acid; hemoglobinopathies

Indexed keywords

1 (2,2 DIMETHYLPROPYLIDENE) DIBUTYRATE; 1 BUTYROYLOXYMETHYL GLUTARATE; 1 BUTYROYLOXYMETHYLDIETHYL PHOSPHATE; 1 ETHYLIDENE DIBUTYRATE; 1 GLUTAROYLOXYMETHYL BUTYRATE LYSINE; 2 METHOXYETHOXYACETYLOXYMETHYL BUTYRATE; 2 METHOXYETHOXYETOXYACETYLOXYMETHYL BUTYRATE; 3 PYRIDYLCARBOXYMETHYL BUTYRATE; 4 AMINOBENZOYLOXYMETHYL BUTYRATE; AMPHETAMINIL; AN 10; AN 11; AN 2; AN 21; AN 22; AN 23; AN 24; AN 36; AN 37; AN 38; AN 39; AN 40; AN 41; AN 42; AN 46; AN 48; AN 7; AN 85; AN 88; AN 90; AN 96; AN 97; BUTYLIDENE DIBUTYRATE; BUTYRIC ACID DERIVATIVE; BUTYROYLOXYMETHYL (4 TERT BUTOXYCARBONYLAMIDO)BUTYRATE; BUTYROYLOXYMETHYL 4 AMINOBUTYRATE; BUTYROYLOXYMETHYL GLUTARATE; BUTYROYLOXYMETHYLDIETHYL PHOSPHATE; GLUTAROYLOXYMETHYL BUTYRATE LYSINE; HEMOGLOBIN; ISOBUTYROYLOXYMETHYL BUTYRATE; PIVALOYLOXYMETHYL (4 TERT BUTOXYCARBONYLAMINO)BUTYRATE; PIVALOYLOXYMETHYL 4 AMINOBUTYRATE; PIVALOYLOXYMETHYL BUTYRATE; PIVALOYLOXYMETHYL ISOBUTYRATE; PIVALOYLOXYMETHYL PROPIONATE; PIVALOYLOXYMETHYL VALERATE; PRODRUG; RETINOIC ACID DERIVATIVE; RETINOYLOXYMETHYL BUTYRATE; RN 1; UNCLASSIFIED DRUG;

ALOPECIA; ANTINEOPLASTIC ACTIVITY; BETA THALASSEMIA; CELL TRANSPORT; CLINICAL TRIAL; CYTOTOXICITY; DRUG ACTIVITY; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG SAFETY; DRUG SCREENING; DRUG SYNTHESIS; HAIR FOLLICLE; HEMOGLOBINOPATHY; HUMAN; LEUKEMIA; LUNG NON SMALL CELL CANCER; NONHUMAN; PROTEIN EXPRESSION; REVIEW; SICKLE CELL ANEMIA; STRUCTURE ACTIVITY RELATION;

EID: 0033819869     PISSN: 02724391     EISSN: None     Source Type: Journal    
DOI: 10.1002/1098-2299(200007/08)50:3/4<379::AID-DDR20>3.0.CO;2-8     Document Type: Review

References (50)

1. Sustained induction of fetal hemoglobin by pulse butyrate therapy in sielde cell disease
2. Effect of the cytostatic butyric acid pro-drug, pivaloyloxymethyl butyrate, on the tumorigenicity of cancer cells
3. Comparison between the effect of butyric acid and its prodrug pivaloyloxymethyl butyrate on byperactylation of histones in HL-60 cell lines
4. Selective hypermethylation of transcribed nucleosomal DNA by sodium butyrate
5. Manifold effects of sodium butyrate on nuclear function. Selective and reversible inhibition of phosphorylation of histones H1 and H2A and impaired methylation of lysine and arginine in nuclear protein fractions
6. Short chain fatty acid rectal irrigation therapy for left-sided ulcerative colitis: A randomized, placebo-controlled clinical trial
7. Esters of N,N-disubstituted 2-hydroxyacetamides as novel highly biolabile prodrug type for carboxylic acid agents
8. Induction of fetal hemoglobin in sickle cell disease
9. Effect of hydroxyurea on the frequency of painful crises in sickle cell anemia: Investigators of the multicenter study of hydroxyurea in sickle cell anemia
10. Clofilium, a potassium channel blocker, induces apoptosis of human promyelocytic leukemia (HL-60) cells via Bcl-2-insensitive activation of caspase-3
11. Phase I study of the orally administered butyrate prodrug, tributyrin, in patients with solid tumors
12. Short chain fatty acids in the human colon
13. A phase I study of AN-9, pivaloyloxymethyl butyrate (Pivanex) a lipophilic butyric acid analog, in patients with advanced solid tumors
14. Butyrate in the treatment of sickle cell disease and β-thalassemia
15. Role of histone deacetylases in acute leukemia
16. Fusion proteins of the retinoic acid receptor-alpha recruit histone deacetylase in promyelocytic Leukaemia
17. A phase I trial of topical topitriol (calcitriol, 1,25-dihydrovitamin D-3) to prevent chemotherapy-induced alopecia
18. Alteration in protein-DNA interactions in the γ-globin gene promotor in response to butyrate therapy
19. An anti-cancer derivative of butyric acid (pivaloyloxymethyl butyrate) and daunorubicin cooperatively prolong survival of mice inoculated with monocytic leukemia cells
20. Effects of sodium butyrate, a new pharmacological agent, on cells in culture
21. Induction of histone acetylation and growth regulation in eryrthroleukemia cells by 4-phenylbutyrate and structural analogs
22. Treatment with azacytidine of patients with end-stage β-thalassemia
23. Induction of caspase-3 protease activity and apoptosis by butyrate and thichostatin A (inhibitors of histone deacetylase): Dependence on cytochrome c-dependent pathway
24. Clinical pharmacology of sodium butyrate in patients with acute leukemia
25. Effect of polar organic compounds on leukemic cells. Butyrate-induced partial remission of acute myelogenous leukemia in a child
26. A novel mutual prodrug of retinoic and butyric acids with enhanced anti-cancer activity
27. Novel anticancer prodrugs of butyric acid
28. Reactivation of fetal hemoglobin in patients with beta-thalassemia
29. α-Amino butyric acid cannot reactivate the silence γ gene of the β locus YAC transgenic mouse
30. Treatment of refractory distal ulcerative colitis with short chain fatty enemas
31. Topical calcitriol enhances normal hair regrowth but does not prevent chemotherapy-induced alopecia in mice
32. Pharmacokinetic studies of n-butyric acid mono-and polyesters derived from monosaccharides
33. Butyric acid: A small fatty acid with diverse biological functions
34. Esterase inhibitors diminish the modulation of gene expression by butyric acid derivative, pivaloyloxymethyl butyrate (AN-9)
35. Rapid alteration of c-myc and c-jun expression in leukemic cells induced to differentiate by a butyric acid prodrug
36. Butyrate induced differentiation in leukemic myeloid cells in-vitro and in-vivo studies
37. Derivatives of butyric acid as potential anti-neoplastic agents
38. A novel butyric acid derivative stimulate fetal hemoglobin expression: Sickle cell disease and thalassaemias
39. Pharmacokinetic studies with mecillinam and pivmecillinam
40. Therapeutic targeting of transcription in acute promyelocytic leukemia by use of an inhibitor of histone deacetylase
41. Activity of pivaloyloxymethyl butyrate, a novel anticancer agent, on primary, human tumor colony-forming units
42. Potentiation of retinoic acid-induced differentiation of human acute promyelocytic leukemia NB4 cells by butyric acid, tributyrin, and hexamethylene bisacetamide
43. Molecular analysis of sodium butyrate-induced growth arrest
44. Therapeutic targeting of transcription in acute promyelocytic leukemia by use of an inhibitor of histone deacetylase
45. Butyric acid in the treatment of cancer
46. Transcriptional control: Sinful repression
47. Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A
48. Pivaloyloxymethyl butyrate (AN-9) exhibits higher anticancer activity than butyric acid (BA): It penetrates taster than the acid and induces apoptosis in HL-60 cells
49. Butyric acid and pivaloyloxymethyl butyrate, AN-9, a novel butyric acid derivative, induce apoptosis in HL-60 cells