Summary: Reagent used as an intermediate in the manufacture of beta-alanine and pantothenic acid.

Top Publications

  1. Ahsan T, Lottman L, Harwood F, Amiel D, Sah R. Integrative cartilage repair: inhibition by beta-aminopropionitrile. J Orthop Res. 1999;17:850-7 pubmed
    The effects of beta-aminopropionitrile, a known inhibitor of lysyl oxidase, on the extractability of newly synthesized collagen and integrative cartilage repair were determined in explant cultures of adult bovine articular cartilage...
  2. Oxlund H, Barckman M, Ortoft G, Andreassen T. Reduced concentrations of collagen cross-links are associated with reduced strength of bone. Bone. 1995;17:365S-371S pubmed
    ..No changes were found in ash or collagen concentrations of the cortical bone.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  3. Keles G, Basoglu T, Yapici O, Cetinkaya B, Acikgoz G, Firatli E. Periodontal & systemic bone changes in rats with experimental lathyrism. Indian J Med Res. 2006;123:541-6 pubmed
    ..We therefore undertook a study to observe periodontal and systemic bone changes by performing radiological, metabolic, and bone densitometric evaluations in rats with experimental lathyrism...
  4. Marsh R, Gallin W. Toxic effects of beta-aminopropionitrile treatment on developing chicken skin. J Exp Zool. 1994;268:381-9 pubmed
    beta-aminopropionitrile (BAPN), a compound that inhibits crosslinking of collagen, has been widely used to examine the function of collagen in developing tissues...
  5. Awasthi S, Boor P. Allylamine and beta-aminopropionitrile-induced vascular injury: enhanced expression of high-molecular-weight proteins. J Toxicol Environ Health A. 1998;53:61-76 pubmed
    ..the present study we describe changes in aorta at the protein level associated with allylamine (AA) and beta-aminopropionitrile (beta APN) induced vascular toxicity in a rat model...
  6. Kirschmann D, Seftor E, Fong S, Nieva D, Sullivan C, Edwards E, et al. A molecular role for lysyl oxidase in breast cancer invasion. Cancer Res. 2002;62:4478-83 pubmed
    ..In addition, treatment of MDA-MB-231 and Hs578T cells with beta-aminopropionitrile (an irreversible inhibitor of LOX enzymatic activity) decreased invasive activity...
  7. Turecek C, Fratzl Zelman N, Rumpler M, Buchinger B, Spitzer S, Zoehrer R, et al. Collagen cross-linking influences osteoblastic differentiation. Calcif Tissue Int. 2008;82:392-400 pubmed publisher
    ..Lathyrogens, like ss-aminopropionitrile (ssAPN), inhibit the formation of a stable matrix...
  8. Akita M, Lee S, Kaneko K. Electron microscopic observations of elastic fibres in the lung and aorta of tight-skin and beta-aminopropionitrile-fed mice. Histol Histopathol. 1992;7:39-45 pubmed
    ..In the lung of the beta-aminopropionitrile (BAPN)-fed mouse, enlargement of the alveolar air spaces was not prominent compared with the TSK mouse...
  9. Yamaguchi S. Analysis of stress-strain curves at fast and slow velocities of loading in vitro in the transverse section of the rat incisor periodontal ligament following the administration of beta-aminopropionitrile. Arch Oral Biol. 1992;37:439-44 pubmed
    ..2% of beta-aminopropionitrile (BAPN) for 20 days, and between the velocity of loading at 10(4) and 1 mm/24 h...

More Information


  1. McGowan K, Sah R. Treatment of cartilage with beta-aminopropionitrile accelerates subsequent collagen maturation and modulates integrative repair. J Orthop Res. 2005;23:594-601 pubmed
    Integrative repair of cartilage was previously found to depend on collagen synthesis and maturation. beta-aminopropionitrile (BAPN) treatment, which irreversibly blocks lysyl oxidase, inhibited the formation of collagen crosslinks, ..
  2. Yang X, Li S, Li W, Chen J, Xiao X, Wang Y, et al. Inactivation of lysyl oxidase by ?-aminopropionitrile inhibits hypoxia-induced invasion and migration of cervical cancer cells. Oncol Rep. 2013;29:541-8 pubmed publisher
    ..Treatment of tumor cells with ?-aminopropionitrile (BAPN), an active site inhibitor of LOX, blocked the hypoxia-induced EMT morphological and marker protein ..
  3. Bondareva A, Downey C, Ayres F, Liu W, Boyd S, Hallgrimsson B, et al. The lysyl oxidase inhibitor, beta-aminopropionitrile, diminishes the metastatic colonization potential of circulating breast cancer cells. PLoS ONE. 2009;4:e5620 pubmed publisher
    ..With this background, we studied the ability of beta-aminopropionitrile (BAPN), an irreversible inhibitor of LOX, to regulate the metastatic colonization potential of the human ..
  4. Di Donato A, Lacal J, Di Duca M, Giampuzzi M, Ghiggeri G, Gusmano R. Micro-injection of recombinant lysyl oxidase blocks oncogenic p21-Ha-Ras and progesterone effects on Xenopus laevis oocyte maturation. FEBS Lett. 1997;419:63-8 pubmed
    ..Further investigation showed that lysyl oxidase action depends on protein synthesis and is therefore probably mediated by a newly synthesized protein. ..
  5. Lazarus H, Cruikshank W, Narasimhan N, Kagan H, Center D. Induction of human monocyte motility by lysyl oxidase. Matrix Biol. 1995;14:727-31 pubmed
    ..response was prevented by prior heat inactivation of the enzyme, by treatment of the enzyme with beta-aminopropionitrile or ethylenediamine, which are active site-directed inhibitors of lysyl oxidase, and by a competing, lysine-..
  6. Asanbaeva A, Masuda K, Thonar E, Klisch S, Sah R. Cartilage growth and remodeling: modulation of balance between proteoglycan and collagen network in vitro with beta-aminopropionitrile. Osteoarthritis Cartilage. 2008;16:1-11 pubmed
    To examine the effect of beta-aminopropionitrile (BAPN), an inhibitor of lysyl oxidase, on growth and remodeling of immature articular cartilage in vitro...
  7. Payne S, Fogelgren B, Hess A, Seftor E, Wiley E, Fong S, et al. Lysyl oxidase regulates breast cancer cell migration and adhesion through a hydrogen peroxide-mediated mechanism. Cancer Res. 2005;65:11429-36 pubmed
    ..Treatment of the invasive breast cancer cell lines, Hs578T and MDA-MB-231, with beta-aminopropionitrile (betaAPN), an irreversible inhibitor of LOX catalytic activity, leads to a significant decrease in cell ..
  8. Giampuzzi M, Botti G, Di Duca M, Arata L, Ghiggeri G, Gusmano R, et al. Lysyl oxidase activates the transcription activity of human collagene III promoter. Possible involvement of Ku antigen. J Biol Chem. 2000;275:36341-9 pubmed
    ..Moreover, lysyl oxidase effect was abolished by beta-aminopropionitrile, a specific inhibitor of its catalytic activity...
  9. Li W, Liu G, Chou I, Kagan H. Hydrogen peroxide-mediated, lysyl oxidase-dependent chemotaxis of vascular smooth muscle cells. J Cell Biochem. 2000;78:550-7 pubmed
    ..LO-dependent chemotaxis, but not chemokinesis, was abolished by beta-aminopropionitrile, an active site inhibitor of LO, or by catalase, as well as by prior heat denaturation...
  10. Wilmarth K, Froines J. In vitro and in vivo inhibition of lysyl oxidase by aminopropionitriles. J Toxicol Environ Health. 1992;37:411-23 pubmed
    ..Organic nitriles, including beta-aminopropionitrile (BAPN), have been shown to irreversibly inhibit lysyl oxidase in vitro...
  11. Mercier N, Kakou A, Challande P, Lacolley P, Osborne Pellegrin M. Comparison of the effects of semicarbazide and beta-aminopropionitrile on the arterial extracellular matrix in the Brown Norway rat. Toxicol Appl Pharmacol. 2009;239:258-67 pubmed publisher
    ..arteries of growing Brown Norway (BN) rats after chronic administration of semicarbazide (SCZ) and beta-aminopropionitrile (BAPN), two inhibitors with different properties and relative specificities for SSAO and lysyl oxidase (LOX)...
  12. Jackson L, Faris B, Martin B, Jones H, Rich C, Foster J, et al. The effect of beta-aminopropionitrile on elastin gene expression in smooth muscle cell cultures. Biochem Biophys Res Commun. 1991;179:939-44 pubmed
    When beta-aminopropionitrile (BAPN) is added to neonatal rat aortic smooth muscle cell cultures there is a decrease in insoluble elastin accumulation with a concomitant increase in tropoelastin and tropoelastin fragments in the culture ..
  13. Thaler R, Spitzer S, Rumpler M, Fratzl Zelman N, Klaushofer K, Paschalis E, et al. Differential effects of homocysteine and beta aminopropionitrile on preosteoblastic MC3T3-E1 cells. Bone. 2010;46:703-9 pubmed publisher
    Compounds, like beta-aminopropionitrile (bAPN) and homocysteine (hcys), are known to inhibit a stable matrix formation. Osteoblast-synthesized collagen matrix regulates the differentiation of precursor cells into mature osteoblasts...
  14. Komatsu K, Kanazashi M, Arai T, Chiba M. Effects of hydrocortisone and beta-aminopropionitrile on stress-strain and stress-relaxation behaviors, and birefringent retardation of collagen fibers in the rat incisor periodontal ligament. Connect Tissue Res. 2002;43:581-8 pubmed
    ..rats received daily subcutaneous injections of 10 mg/kg of hydrocortisone (HC group), 300 mg/kg of beta-aminopropionitrile (BAPN group), or saline (control group), for 10 days...
  15. Kim M, Kim S, Jung S, Park J, Yoo H, Ko J, et al. Expression and purification of enzymatically active forms of the human lysyl oxidase-like protein 4. J Biol Chem. 2003;278:52071-4 pubmed
    ..The purified LOXL4 proteins showed beta-aminopropionitrile-inhibitable activity of 0.022-0.032 units/mg toward a nonpeptidyl substrate, benzylamine...
  16. Levene C, Heale G, Robins S. Collagen cross-link synthesis in cultured vascular endothelium. Br J Exp Pathol. 1989;70:621-6 pubmed
    ..Treatment of the cultures with the lathyrogen beta-aminopropionitrile (BAPN), which inhibits lysyl oxidase, inhibited synthesis of this cross-link...
  17. Blank J, Glasgow J, Pietra G, Burdette L, Weinbaum G. Nitrogen-dioxide-induced emphysema in rats. Lack of worsening by beta-aminopropionitrile treatment. Am Rev Respir Dis. 1988;137:376-9 pubmed
    We evaluated the effect of beta-aminopropionitrile (beta APN) on the nitrogen dioxide (NO2) animal model of emphysema...
  18. Wright G, Wei X, McDevitt C, Lane B, Sokoloff L. Stimulation of matrix formation in rabbit chondrocyte cultures by ascorbate. 1. Effect of ascorbate analogs and beta-aminopropionitrile. J Orthop Res. 1988;6:397-407 pubmed
    ..Ascorbate increased the hypro:pro ratio of newly synthesized proteins. beta-Aminopropionitrile (1 mM) reduced the proportion of [3H]hydroxyproline and [35S]O4-proteoglycans in the ascorbate-supplemented ..
  19. Nelson J, Diegelmann R, Cohen I. Effect of beta-aminopropionitrile and ascorbate on fibroblast migration. Proc Soc Exp Biol Med. 1988;188:346-52 pubmed
    Ascorbate and beta-aminopropionitrile (BAPN) have direct, but diverse affects on collagen matrix production...
  20. Palamakumbura A, Jeay S, Guo Y, Pischon N, Sommer P, Sonenshein G, et al. The propeptide domain of lysyl oxidase induces phenotypic reversion of ras-transformed cells. J Biol Chem. 2004;279:40593-600 pubmed
    ..beta-aminopropionitrile, the selective inhibitor of lysyl oxidase enzyme activity, was remarkably unable to block suramin-induced ..
  21. Kim Y, Kim E, Kim Y. The human lysyl oxidase-like 2 protein functions as an amine oxidase toward collagen and elastin. Mol Biol Rep. 2011;38:145-9 pubmed publisher
    ..Further, amine oxidase activity of LOXL2 was not susceptible to inhibition by ?-aminopropionitrile, an irreversible inhibitor of LOX, suggesting a different enzymatic mechanism between these two paralogues.
  22. Cengiz M, Kirtiloglu T, Acikgoz G, Trisi P, Wang H. Effect of defective collagen synthesis on epithelial implant interface: lathyritic model in dogs. An experimental preliminary study. J Oral Implantol. 2012;38:105-14 pubmed publisher
    ..Defective collagen metabolism such as lathyrism may negatively influence the interface between implant and surrounding soft tissue attachment...
  23. Martin J, Sosa Melgarejo J, Swash M, Mather K, Leigh P, Berry C. Purkinje cell toxicity of beta-aminopropionitrile in the rat. Virchows Arch A Pathol Anat Histopathol. 1991;419:403-8 pubmed
    ..beta-Aminopropionitrile (BAPN) is one such compound...
  24. McGowan S, Liu R, Harvey C. Effects of heparin and other glycosaminoglycans on elastin production by cultured neonatal rat lung fibroblasts. Arch Biochem Biophys. 1993;302:322-31 pubmed
    ..Proteoglycans, which are present in most elastic tissues, may participate in the regulation of elastin synthesis and deposition during periods of new elastin formation. ..
  25. Brasselet C, Durand E, Addad F, Al Haj Zen A, Smeets M, Laurent Maquin D, et al. Collagen and elastin cross-linking: a mechanism of constrictive remodeling after arterial injury. Am J Physiol Heart Circ Physiol. 2005;289:H2228-33 pubmed
    ..After 1 mo, balloon angioplasty was performed in both femoral arteries. Fourteen rabbits were fed beta-aminopropionitrile (beta-APN, 100 mg/kg) and compared with 14 untreated animals. The remodeling index, i.e...
  26. Miller E, Rhodes R. Preparation and characterization of the different types of collagen. Methods Enzymol. 1982;82 Pt A:33-64 pubmed
  27. Lees S, Eyre D, Barnard S. BAPN dose dependence of mature crosslinking in bone matrix collagen of rabbit compact bone: corresponding variation of sonic velocity and equatorial diffraction spacing. Connect Tissue Res. 1990;24:95-105 pubmed
    Crosslinking density in demineralized bone matrix collagen was found to depend on the beta-aminopropionitrile (BAPN) dose level for compact bone from rabbit femurs...
  28. Ohmura H, Yasukawa H, Minami T, Sugi Y, Oba T, Nagata T, et al. Cardiomyocyte-specific transgenic expression of lysyl oxidase-like protein-1 induces cardiac hypertrophy in mice. Hypertens Res. 2012;35:1063-8 pubmed publisher
    ..A LOX inhibitor, beta-aminopropionitrile (BAPN), inhibited agonist-induced leucine incorporation in cardiomyocytes in vitro, suggesting the ..
  29. Dawson D, Cotter M, Policz D, Stoffer D, Nichols J, Poch G. Comparative evaluation of the combined osteolathyritic effects of two nitrile combinations on xenopus embryos. Toxicology. 2000;147:193-207 pubmed
    Two nitrile combinations, beta-aminopropionitrile (beta APN) with aminoacetonitrile (AAN) and betaAPN with beta APN (as a sham combination), were evaluated using the frog embryo mixture toxicity assay to determine their combined ..
  30. Capo M, Sevil B, Frejo M, Anadon Baselga M, Alonso C. In vitro neuronal changes induced by beta-aminopropionitrile. J Environ Pathol Toxicol Oncol. 1994;13:259-64 pubmed
    beta-Aminopropionitrile (beta APN), a peptide found in leguminous plants, is a multifunctional aminonitrile because it has some action on collagen, elastin, and nervous cells...
  31. Benson S, Rawson R, Killian C, Wilt F. Role of the extracellular matrix in tissue-specific gene expression in the sea urchin embryo. Mol Reprod Dev. 1991;29:220-6 pubmed
    ..These results demonstrate a differential effect of the ECM on expression of tissue-specific molecular markers. ..
  32. Yeowell H, Marshall M, Walker L, Ha V, Pinnell S. Regulation of lysyl oxidase mRNA in dermal fibroblasts from normal donors and patients with inherited connective tissue disorders. Arch Biochem Biophys. 1994;308:299-305 pubmed
    ..of penicillamine (100 microM), which interferes with collagen cross-linking, nor the administration of beta-aminopropionitrile, which is a strong irreversible inhibitor of LO, to fibroblasts significantly changed the levels of LO mRNA ..
  33. Patterson J, Bullock A, MacNeil S, Chapple C. Methods to reduce the contraction of tissue-engineered buccal mucosa for use in substitution urethroplasty. Eur Urol. 2011;60:856-61 pubmed publisher
    ..The techniques assessed were pretreatment of de-epidermised dermis (DED) with glutaraldehyde, culture with ?-aminopropionitrile (?-APN; a lysyl oxidase inhibitor), and physical restraint of TEBM grafts during culture...
  34. Mumtaz M, Farooqui M, Ghanayem B, Rajaraman S, Frankenberg L, Ahmed A. Studies on the mechanism of urotoxic effects of N,N'-dimethylaminopropionitrile in rats and mice. 1. Biochemical and morphologic characterization of the injury and its relationship to metabolism. J Toxicol Environ Health. 1991;33:1-17 pubmed
    ..These studies indicate that there are species differences in DMAPN toxicity. The differences may be due to differences in the formation of reactive metabolic intermediates of DMAPN. ..
  35. Kanematsu Y, Kanematsu M, Kurihara C, Tsou T, Nuki Y, Liang E, et al. Pharmacologically induced thoracic and abdominal aortic aneurysms in mice. Hypertension. 2010;55:1267-74 pubmed publisher
    ..acetate-salt hypertension; degeneration of elastic lamina was induced by infusion of beta-aminopropionitrile, a lysyl oxidase inhibitor...
  36. Yamane A, Fukui T, Chiba M. In vitro measurement of orthodontic tooth movement in rats given beta-aminopropionitrile or hydrocortisone using a time-lapse videotape recorder. Eur J Orthod. 1997;19:21-8 pubmed
    ..Rats received daily s.c. injections of beta-aminopropionitrile (BAPN, 300 mg/kg/day) or hydrocortisone (10 mg/kg/day) for a period of 7 days...
  37. Taverne A. Collagen responsible for tooth eruption? A study of the eruption of rat incisors. Aust Orthod J. 1993;12:199-206 pubmed
    ..As the collagen protein seems to play a key role in tooth eruption, the investigation concentrated on the presence and maturation of collagen and its possible function in the process of tooth eruption. ..
  38. Peterszegi G, Andres E, Molinari J, Ravelojaona V, Robert L. Effect of cellular aging on collagen biosynthesis: I. Methodological considerations and pharmacological applications. Arch Gerontol Geriatr. 2008;47:356-67 pubmed
    ..To further refine the procedure, we tempted to completely inhibit collagen synthesis by beta-aminopropionitrile (beta APN) added to cultures in order to obtain a negative control...
  39. Mentzer R, Smith N, Poch G, Dawson D. Combined osteolathyric effects of beta-aminopropionitrile and penicillamine on Xenopus embryos: statistical comparison with dose-addition and independence. Drug Chem Toxicol. 1999;22:359-74 pubmed
    The combined osteolathyric effects of beta-aminopropionitrile (beta APN) and penicillamine (PNC) on developing Xenopus embryos were determined and compared with theoretical effects for the dose-addition and independence models...
  40. Haque A, Hossain M, Lambein F, Bell E. Evidence of osteolathyrism among patients suffering from neurolathyrism in Bangladesh. Nat Toxins. 1997;5:43-6 pubmed
    ..a compound that chemically and metabolically can produce the osteolathyrogen beta-aminopropionitrile (BAPN), as well as foods made from the seeds of the same plant which contain the neurotoxin 3-N-oxalyl-2,3-..
  41. Chowdhury S, Davis R. Lathyrism in laying hens and increases in egg weight. Vet Rec. 1988;123:272-5 pubmed
    ..egg weight in hens with lathyrism was investigated by feeding laying birds with diets containing beta-aminopropionitrile, the toxic principle of certain legume seeds in the genus Lathyrus...
  42. Hamilton A, Heikkila J. Examination of the stress-induced expression of the collagen binding heat shock protein, hsp47, in Xenopus laevis cultured cells and embryos. Comp Biochem Physiol A Mol Integr Physiol. 2006;143:133-41 pubmed
    ..but not hsp70 or BiP mRNA accumulation was enhanced by treatment with a procollagen-specific stressor, beta-aminopropionitrile. In Xenopus embryos hsp47 mRNA was present constitutively throughout development...
  43. Godin R, Klinzing D, Porcaro W, Ernst S. Specification of endoderm in the sea urchin embryo. Mech Dev. 1997;67:35-47 pubmed
    ..These results indicate that early signaling events mediated by cell-cell contact are required for the initial specification and maintenance of the endoderm in the developing embryo. ..
  44. Hashimoto N, Kim C, Kikuchi H, Kojima M, Kang Y, Hazama F. Experimental induction of cerebral aneurysms in monkeys. J Neurosurg. 1987;67:903-5 pubmed two monkeys treated with ligation of the common carotid artery, experimental hypertension, and beta-aminopropionitrile feeding...
  45. Kwong Hing A, Teasdale R, Sandhu H. Local effects of impaired mechanical properties of collagen on bone formation and resorption. Anat Embryol (Berl). 1991;184:93-7 pubmed
    ..25% Beta aminopropionitrile (B-APN), a potent inhibitor of collagen crosslink formation, for 3 weeks...
  46. Kurobe H, Matsuoka Y, Hirata Y, Sugasawa N, Maxfield M, Sata M, et al. Azelnidipine suppresses the progression of aortic aneurysm in wild mice model through anti-inflammatory effects. J Thorac Cardiovasc Surg. 2013;146:1501-8 pubmed publisher
    ..Angiotensin II and ?-aminopropionitrile (a lysyl oxidase inhibitor) were administrated subcutaneously in 7-week-old C57BL/6J mice using an osmotic ..
  47. Claud P, Artur Y, Guichard J, Laine R. Metabolism of tresperimus by rat aorta semicarbazide-sensitive amine oxidase (SSAO). Fundam Clin Pharmacol. 2002;16:461-70 pubmed
  48. Conklin D, Trent M, Boor P. The role of plasma semicarbazide-sensitive amine oxidase in allylamine and beta-aminopropionitrile cardiovascular toxicity: mechanisms of myocardial protection and aortic medial injury in rats. Toxicology. 1999;138:137-54 pubmed
    Allylamine (AA; 3-aminopropene) and beta-aminopropionitrile (betaAPN) combined treatment (AA + betaAPN) results in myocardial protection from AA-induced subendocardial necrosis and a rapid and extensive aortic medial smooth muscle injury ..
  49. Ikeda H, Ogata I, Fujiwara K. Evidence that impaired intracellular collagen synthesis reduces proliferation in cultured rat hepatocytes. Biochem Biophys Res Commun. 1994;200:1701-7 pubmed
    ..However, the DNA synthesis was not affected by beta-aminopropionitrile fumarate, which inhibits cross linking in extracellular collagen maturation, nor by purified bacterial ..
  50. Norton T. Experimental myopia in tree shrews. Ciba Found Symp. 1990;155:178-94; discussion 194-9 pubmed
    ..Recovery may occur by a slowing of axial expansion while the optical surfaces proceed toward adult values. ..
  51. Joseph H, Roisen F, Anderson G, Barker J, Weiner L, Tobin G. Inhibition of wound contraction with locally injected lathyrogenic drugs. Am J Surg. 1997;174:347-50 pubmed
    ..Animals were divided into groups receiving daily local injections of beta-aminopropionitrile or D-penicillamine, or both beta-aminopropionitrile and D-penicillamine and normal saline vehicle (control ..
  52. Rodriguez H, Vaysberg M, Mikels A, McCauley S, Velayo A, Garcia C, et al. Modulation of lysyl oxidase-like 2 enzymatic activity by an allosteric antibody inhibitor. J Biol Chem. 2010;285:20964-74 pubmed publisher
    ..also show that LOXL2 is capable of being inhibited by a known suicide inhibitor of lysyl oxidase (LOX), beta-aminopropionitrile, which we find is a potent inhibitor of LOXL2 activity...
  53. Kim S, Kim Y. Variations in LOXL1 associated with exfoliation glaucoma do not affect amine oxidase activity. Mol Vis. 2012;18:265-70 pubmed
    ..To evaluate the impact of the R141L and G153D variations on the amine oxidase activity of LOXL1, we generated four different haplotypes of LOXL1 with R141L and G153D and assessed the amine oxidase activity of the LOXL1 variant proteins...