Keywords: Backbone Modification, Conformational Constraints, Peptidomimetics, Macrocyclic Compound, Peptidomimetic Agent, Synthetic Peptide, Amino Acid Substitution, Article, Chemical Bond, Cyclization, Drug Design, Drug Structure, Drug Synthesis, Human, Medicinal Chemistry, Molecular Biology, Nonhuman, Priority Journal, Protein Conformation, Protein Modification, Biomimetic Materials, Small Molecule Libraries, Models,
Affiliations: *** IBB - CNR ***
Department of Pharmacy, CIRPEB: Centro Interuniversitario di Ricerca sui Peptidi Bioattivi, DFM-Scarl, University of Naples "Federico II", 80134, Naples, Italy, liana.sco@gmail.com.
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Hefti, F. F., Requirements for a lead compound to become a clinical candidate (2008) BMC Neurosci
Thaker, H. D., Sgolastra, F., Clements, D., Synthetic mimics of antimicrobial peptides from triaryl scaffolds (2011) J Med Chem, 54, pp. 2241-2254
Yang, S. Y., Pharmacophore modeling and applications in drug discovery: Challenges and recent advances (2010) Drug Discov Today, 15, pp. 444-450
Scognamiglio, P. L., Di Natale, C., Perretta, G., From peptides to small molecules: An intriguing but intricated way to new drugs (2013) Curr Med Chem, 20, pp. 3803-3817
Karle, I. L., Flexibility in peptide molecules and restraints imposed by hydrogen bonds, the AiB residue, and core inserts (1996) Biopolymers, 1, pp. 157-180
Ramachandran, G. N., Ramakrishnan, C., Sasisekharan, V., Stereochemistry of polypeptide chain configurations (1963) J Mol Biol, 4, pp. 95-99
Grauer, A., K nig, B., Peptidomimetics- a versatile route to biologically active compounds (2009) Eur J Org Chem, 30, pp. 5099-5111
Hruby, V. J., Li, G. G., Haskell Luevano, C., Design of peptides, proteins, and peptidomimetics in chi space (1997) Biopolymers, 3, pp. 219-266
Komarov, I. V., Grigorenko, A. O., Turov, A. V., Conformationally rigid cyclic -amino acids in the design of peptidomimetics, peptide models and biologically active compounds (2004) Usp Khim, 73, pp. 849-876
Silverman, R. B., Drug discovery design and development E7 peptidomimetics (2004) The organic chemistry of drug design and drug action, pp. 47-50. , In: Silver man RB, Elsevier Academic, Evanston, IL
Hruby, V. J., Balse, P. M., Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads (2000) Curr Med Chem, 7, pp. 945-970
Abdou, W. M., Barghash, R. F., Bekheit, M. S., Carbodiimides in the synthesis of enaminoand -aminophosphonates as peptidomimetics of analgesic/antiinfl ammatory and anticancer agents (2012) Arch Pharm, 345, pp. 884-895
Ibrahim, I. A. A., Shahzad, N., Al-joudi, F. S., In vitro and in vivo study of effect of -adrenergic agonist-methyldopa on the serum biochemical laboratory findings (2013) Clin Exp Pharmacol
Choi, W. T., Duggineni, S., Xu, Y., Targeting the CXC chemokine receptor 4 (CXCR4) (2012) J Med Chem, 55, pp. 977-994
Zuckermann, R. N., Kodadek, T., Peptoids as potential therapeutics (2009) Curr Opin Mol Ther, 11, pp. 299-307
Miller, S. M., Simon, R. J., Zuckermann, R. N., Comparison of the proteolytic susceptibilities of homologous L-amino acid, D-amino acid, and N-substituted glycine peptide and peptoid oligomers (1995) Drug Dev Res, 35, pp. 20-32
Bach, A. C., Eyermann, C. J., Groos, J. D., Structural studies of a family of high affinity ligands for IIb/IIIa (1994) J Am Chem Soc, 116, pp. 3207-3219
Huang, Z., He, Y. B., Raynor, K., Mainchain and side-chain chiral methylated somatostatin analogs: Synthesis and conformational analyses (1992) J Am Chem Soc, 114, pp. 9390-9401
Mosberg, H. I., Hurst, R., Hruby, V. J., Bis-penicillamine enkephalins possess highly improved specificity toward delta opioid receptors (1983) Proc Natl Acad Sci U S A, 80, pp. 5871-5874
Spear, K. L., Brown, M. S., Reinhard, E. J., Conformational restriction of angiotensin II: Cyclic analogues having high potency (1990) J Med Chem, 33, pp. 1935-1940
Lu, Y., Nguyen, T. M., Weltrowska, G., [2, 6 -Dimethyltyrosine] dynorphin A (1- 11) - NH2 analogues lacking an N-terminal amino group: Potent and selective kappa opioid antagonists (2001) J Med Chem, 44, pp. 3048-3053
Moussa, C. E. H., Mitrovic, A. D., Vandenberg, R. J., Effects of L-glutamate transport inhibition by a conformationally restricted glutamate analogue (2S, 1 S, 2 R) -2- (carboxycyclopropyl) glycine (L-CCG III) on metabolism in brain tissue in vitro analysed by NMR spectroscopy (2002) Neurochem Res, 27, pp. 27-35
Stewart, D. E., Sarkar, A., Wampler, J. E., Occurrence and role of cis peptide bonds in protein structures (1990) J Mol Biol, 214, pp. 253-260
Olsen, B. R., Ninomiya, Y., Collagens (1998) Guidebook to the extracellular matrix and adhesion proteins, p. 40. , In: Kreis T, Vale R, Oxford University Press, Oxford
Perni, R. B., Chandorkar, G., Cottrell, K. M., Inhibitors of hepatitis C virus NS3. 4A protease. Effect of P4 capping groups on inhibitory potency and pharmacokinetics (2007) Bioorg Med Chem Lett, 17, pp. 3406-3411
Chavan, A. S., Deng, J. C., Chuang, S. C., () -Michael addition of alkyl amines to dimethyl (E) -hex-2-en-4-ynedioate: Synthesis of, -dehydroamino acid derivatives (2013) Molecules, 18, pp. 2611-2622
Fisher, G. H., Berryer, P., Ryan, J. W., Dehydrophenylalanyl analogs of bradykinin: Synthesis and biological activities (1981) Arch Biochem Biophys, 211, pp. 269-275
Appella, D. H., Christianson, L. A., Karle, I. L., -peptide foldamers: Robust helix formation in a new family of amino acid oligomers (1996) J Am Chem Soc, 118, pp. 13071-13072
Weiner, B., Szyma ski, W., Janssen, D. B., Recent advances in the catalytic asymmetric synthesis of -amino acids (2010) Chem Soc Rev, 39, pp. 1656-1691
Murray, J. K., Farooqi, B., Sadowsky, J. D., Efficient synthesis of a beta-peptide combinatorial library with microwave irradiation (2005) J Am Chem Soc, 127, pp. 13271-13280
Cheng, R. P., Gellman, S. H., Degrado, W. F., Beta-Peptides: From structure to function (2001) Chem Rev, 101, pp. 3219-3232
M ller, A., Vogt, C., Sewald, N., Synthesis of Fmoc- -homoamino acids by ultrasoundspromoted Wolff rearrangement (2006) Synthesis, pp. 837-841
Schiller, P. W., Nguyen, T. M., Weltrowska, G., Differential stereochemical requirements of mu vs. delta opioid receptors for ligand binding and signal transduction: Development of a class of potent and highly deltaselective peptide antagonists (1993) Proc Natl Acad Sci U S A, 89, pp. 11871-11875
Hah, J. M., Mart sek, P., Roman, L. J., Aromatic reduced amide bond peptidomimetics as selective inhibitors of neuronal nitric oxide synthase (2003) J Med Chem, 46, pp. 1661-1669
Edwards, J. V., Spatola, A. F., Lemieux, C., In vitro activity profiles of cyclic and linear enkephalin pseudopeptide analogs (1986) Biochem Biophys Res Commun, 136, pp. 730-736
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Synthetic and structural routes for the rational conversion of peptides into small molecules