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Abdel-Malek, Z., Kreutzfeld, K. L., Marwan, M. M., Hadley, M. E., Hruby, V. J., and Wilkes, B. C., 1985, Prolonged stimulation of S91 melanoma tyrosinase by [Nie4, d-Phe7]-substituted α-melanotropins, Cancer Res. 45:4735–4740.
Adan, R. A. H., Oosterom, J., Ludvigsdolter, G., Brabbee, J. H., Beerbach, J. R. H., and Gispen, W. H., 1994, Identification of antagonists for MC3, MC4 and MC5 receptors, Eur. J. Pharmacol. 269:331–338.
Al-Obeidi, F., Hruby, V. J., Pettitt, B. M., and Hadley, M. E., 1989a, Design of a new class of superpotent cyclic α-melanotropins based on quenched dynamic simulations, J. Am. Chem. Soc. 111:3413–3416.
Al-Obeidi, F., Hruby, V. J., Castrucci, A. M. L., and Hadley, M. E., 1989b, Potent and prolonged acting cyclic lactam analogues of α-melanotropin: Design based on molecular dynamics, J. Med. Chem. 32:2555–2561.
Al-Obeidi, F., Hruby, V. J., Hadley, M. E., Sawyer, T. K., and Castrucci, A. M. L., 1990, Design, synthesis, and biological activities of a potent and a selective α-melanotropin antagonist, Int. J. Pept. Protein Res. 35:228–234
Barret, P., MacDonald, A., Helliwell, R., Davidson, G., and Morgan, P., 1994, Cloning and expression of a new member of the melanocyte-stimulating hormone receptor family, J. Mol. Endocrinol. 12:203–213.
Bhardwaj, R., and Blanchard, J., 1996, Controlled-release delivery system for the α-MSH analog Melanotan-I using poloxamer 407, J. Pharm. Sci. 85:915–919.
Bhardwaj, R., and Blanchard, J., 1997, In vitro evaluation of poly(D,L-lactide-co-glycolide) polymer-based implants containing the a α-Melanocyte stimulating hormone analog, Melanotan-I, J. Control. Ret. 45:49–55.
Bhardwaj, R., and Blanchard, J., 1998, In vitro characterization and in vivo release profile of a poly(d, L-lactide-co-glycolide)-based implant delivery system for the α-MSH analog, melanotan-I, Int. J. Pharm. 170.
Bolognia, J. L., Murray, M. S., and Pawelek, J. M., 1990, Hairless pigmented guinea pigs: A new model for the study of mammalian pigmentation, Pigment Cell Res. 3:150–156.
Bool, A. M., Gray, G. H., II, Hadley, M. E., Heward, C. B., Hruby, V. J., Sawyer, T. K., and Yang, Y. C. S., 1981, Racemization effects on melanocyte stimulating hormones and related peptides, J. Endocrinol. 88:57–65.
Bronaugh, R. L., Stewart, R. F., and Coudgon, E. L., 1982, Methods for in vitro percutaneous absorption studies, Toxicol. Appl. Pharmacol. 62:481–488.
Castrucci, A. M. L., Hadley, M. E., and Hruby, V. J., 1984, Melanotropin bioassays: In vitro and in vivo comparisons. Gen. Comp. Endocrinol. 55:104–111.
Castrucci, A. M. L., Hadley, M. E., Sawyer, T. K., Wilkes, B. C., Al-Obeidi, F., Staples, D. J., DeVaux, A. E., Dym, O., Hintz, M. F, Riehm, J., Rao, K. R., and Hruby, V. J., 1989, α-Melanotropin: The minimal active sequence in the lizard skin bioassay, Gen. Comp. Endocrinol. 73:157–163.
Chhajlani, V., Muceniece, R., and Wikberg, J. E. S., 1993, Molecular cloning of a novel human melanocortin receptor, Biochem. Biophys. Res. Commun. 195:866–873.
Cody, W. L., Stevenson, J. W. S., Al-Obeidi, F., Sugg, E. E., and Hruby, V. J., 1988, Melanotropin three-dimensional structural studies by physical methods and computer-assisted molecular modeling, in: The Melanotropic Peptides (M. E. Hadley, ed.), Volume III, pp. 93–109, CRC Press, Boca Raton.
Dawson, B. V., Hadley, M. E., Kreutzfeld, K., Dorr, R. T., Hruby, V. J., Al-Obeidi, F., and Don, S., 1988, Transdermal delivery of a melanotropic peptide hormone analog, Life Sci. 43:1111–1117.
Dawson, B. V., Ford, C. A., Holloway, H., Dorr, R. T., and Johnson, P., 1993, Administration of melanotropic peptides during gestation in the rodent, Toxicology 77:91–101.
Desarnaud, F., Labbé, O., Eggerickx, D., Vassart, G., and Parmentier, M., 1994, Molecular cloning, functional expression and pharmacological characterization of a mouse melanocortin receptor gene, Biochem. J. 299:367–373.
Dorr, R. T., Dawson, B. V., Hadley, M. E., Levine, N., and Hruby, V. J., 1988, Toxicological studies of a superpotent melanotropin, Invest. New Drugs 6:251–258.
Dorr, R. T., Lines, T., Levine, N., Brooks, C., Xiang, L., Hruby, V. J., and Hadley, M. E., 1995, Pilot phase-1 trial of a superpotent melanotropic peptide in 3 normal volunteers, Life Sci. 58:1777–1784.
Drewe, J., Flicker, G. W., Vonderscher, J. G., and Beglinger, C., 1993, Enteral absorption of octreotide absorption enhancement by polyoxyethylene-24-cholesterol ether, Br. J. Pharmacol. 108:298–303.
Engel, M. H., Sawyer, T. K., Hadley, M. E., and Hruby, V. J., 1981, Quantitative determination of amino acid racemization in heat-alkali treated melanotropins: Implications for peptide hormone structure-function studies, Anal. Biochem. 116:303–311.
Fathi, Z., Lawrence, G. I., and Parker, E. M., 1995, Cloning, expression, and tissue distribution of a fifth melanocortin receptor subtype, Neurochem. Res. 20:107–113.
Frandberg, P.-A., Muceniece, R., Prusis, P., Wikberg, J., and Chhajlani, V., 1994. Evidence for alternate points of attachment for α-MSH and its stereoisomer [Nle4, D-Phe7]-α-MSH at the melanocortin-1 receptor, Biochem. Biophys. Res. Commun. 202:1266–1271.
Gantz, I., Konda, Y., Tashiro, T., Shimoto, Y, Miwa, H., Munzert, G., Watson, S. J., DelValle, J., and Yamada, T., 1993a, Molecular cloning of a novel melanocortin receptor, J. Biol. Chem. 268:8246–8250.
Gantz, I., Miwa, H., Konda, Y., Shimoto, Y., Tashiro, T., Watson, S. J., DelValle, J., and Yamada, T., 1993b, Molecular cloning, expression, and gene localization of a fourth melanocortin receptor, J. Biol. Chem. 268:15174–15179.
Gantz, I., Shimoto, Y., Konda, Y, Miwa, H., Dickinson, C. J., and Yamada, T., 1994, Molecular cloning, expression, and characterization of a fifth melanocortin receptor, Biochem. Biophys. Res. Commun. 200:1214–1220.
Gee, C. E., Chen, C. L. C., Roberts, J. L., Thompson, R., and Waston, S. J., 1983, Identification of proopiomelanocortin neurons in the rat hypothalamus by in situ cDNA-mRNA hybridization. Nature 306:374–375.
Geschwind, I.I., Huseby, R. A., and Nishioka, R., 1972, The effect of melanocyte-stimulating hormone on coat color in the mouse, Recent Prog. Horm. Res. 28:91–130.
Griffon, N., Mignon, V, Facchinetti, R, Diaz, J., Schwartz, J.-C, and Sokoloff, P., 1994, Molecular cloning and characterization of the rat fifth melanocortin receptor, Biochem. Biophys. Res. Commun. 200:1007–1014.
Hadley, M. E., 1996, Endocrinology, 4th ed., Prentice-Hall, Englewood Cliffs, NJ.
Hadley, M. E., Anderson, B., Heward, C. B., Sawyer, T. K., and Hruby, V. J., 1981, Calcium-dependent, irreversible effects of [4-norIeucine, 7-D-phenylalanine]melanotropin on melanophores, Science 213:1025–1027.
Hadley, M. E., Abdel-Malek, Z., Marwan, M. M., Kreutzfeld, K. L., and Hruby, V. J., 1985, [Nle4, d-Phe7]α-MSH: A superpotent melanotropin that “irreversibly” activates melanoma tyrosinase, Endoer. Res. 11:157–170.
Hadley, M. E., Sharma, S. D., Hruby, V. J., Levine, N., and Dorr, R. T., 1993, Melanotropic peptides for therapeutic and cosmetic tanning of the skin, Ann. N. Y. Acad. Sci. 680:424–439.
Hadley, M. E., Hruby, V. J., Jiang, J., Sharma, S. D., Fink, J. L., Haskell-Luevano, C., Bentley, D. L., Al-Obeidi, F. A., and Sawyer, T. K., 1996, Melanocortin receptors: Identification and characterization by melanotropic agonists and antagonists, Pigment Cell Res. 9:213–234.
Haskell-Luevano, C., Miwa, H., Dickinson, C., Hruby, V. J., Yamada, T., and Gantz, I., 1994, Binding and cAMP studies of melanotropin peptides with the cloned human peripheral melanocortin receptor, hMClR, Biochem. Biophys. Res. Commun. 204:1337–1342.
Haskell-Luevano, C., Miwa, H., Dickinson, C., Hadley, M. E., Hruby, V. J., Yamada, T, and Gantz, I., 1996a, Characterization of the unusual dissociation properties of melanotropin peptides from the melanocortin receptor, hMClR, J. Med. Chem. 39:432–435.
Haskell-Luevano, C., Sawyer, T. K., Hendrata, S., North, C., Panahinia, L., Stum, M., Staples, D. J., Castrucci, A. M. L., Hadley, M. E., and Hruby, V. J., 1996b, Truncation studies of melanotropin peptides identify tripeptide analogues exhibiting prolonged agonist bioactivity, Peptides 17:995–1002.
Haskell-Luevano, C., Sawyer, T. K., Trumpp-Kallmeyer, S., Bikker, J. A., Humblet, C., Gantz, I., and Hruby, V. J., 1996c, Three-dimensional molecular models of the hMC IR melanocortin receptor: Complexes with melanotropin peptide agonists, Drug Des. Disc. 14:197–211.
Haskell-Luevano, C., Nikiforovich, G., Sharma, S. D., Yang, Y.-K., Dickinson, C., Hruby, V. J., and Gantz, I., 1997, Biological and conformational examination of stereochemical modifications using the template melanotropin peptide, Ac-Nle-c[Asp-His-Phe-Arg-Trp-Ala-Lys]-NH2, on human melanocortin receptors, J. Med. Chem. 40:1738–1748.
Hruhy, V. J., Wilkes, B. C., Cody, W. L., Sawyer, T. K., and Hadley, M. E., 1984a, Melanotropins: Structural, conformational and biological considerations in the development of superpotent and super-prolonged analogs, Pep. Protein Rev. 3:1–64.
Hruby, V. J., Wilkes, B. C., Hadley, M. E., Al-Obeidi, R, Sawyer, T. K., Staples, D. J., deVaux, A. E., Dym, O., Castrucci, A. M. L., Hintz, M. E., Riehm, J. P., and Rao, R., 1987, α-Melanotropin: The minimal active sequence. I. Frog skin bioassay, J. Med. Chem. 30:2126–2130.
Hruby, V. J., Sharma, S. D., Lu, D., Castrucci, A. M. L., Al-Obeidi, F. A., Cone, R., and Hadley, M. E., 1995, Cyclic lactam α-Melanotropin analogues of Ac-c[Nle4, Asp5, d-Phe7, Lys10]α-MSH(4–10)-NH2 with bulky aromatic amino acids at position 7 show high antagonist potency and selectivity at melanocortin receptors, J. Med. Chem. 38:3454–3461.
Ito, S., and Wakamatsu, K., 1994, An improved modification of permanganate oxidation of eumelanin that gives a constant yield of pyrrole-2,3,5-tricarboxylic acid, Pigment Cell Res. 7:141–144.
Jiang, J., Sharma, S. D., Nakamura, S., Lai, J.-Y., Fink, J., Hadley, M. E., Hruby, V. J., and Hendrix, M. J. C., 1995, The melanotropic peptide, [Nle4, d-Phe7]α-MSH, stimulates human melanoma tyrosinase activity and inhibits cell proliferation, Pigment Cell Res. 8:301–323.
Kreutzfeld, K. L., and Bagnara, J. T, 1989, Application of α-Melanocyte stimulating hormone (α-MSH) radioimmunoassay to the detection of the superpotent analog, [Nle4, d-Phe7]α-MSH. Pigment Cell Res. 2:65–69.
Labbé, O., Desarnaud, F., Eggerickx, D., Vassart, G., and Parmentier, M., 1994, Molecular cloning of a mouse melanocortin 5 receptor gene widely distributed in peripheral tissues, Biochemistry 33:4543–4549.
Lan, E.-L., Ugwu, S. O., Blanchard J., Fang, X., Hruby, V. J., and Sharma, S., 1994, Preformulation studies with Melanotan-II: A potential skin cancer chemo preventative peptide, J. Pharm. Sci. 83:1081–1084.
Levine, N., Lemus-Wilson, A., Wood, S. H., Abdel-Malek, A. Z., Hruby, V. J., and Hadley, M. E., 1987, Follicular melanogenesis in the mouse: Stimulation by injected and topical melanotropins, J. Invest. Dermatol. 89:269–273.
Levine, N., Sheftel, S. N., Eytan, T., Dorr, R. T., Hadley, M. E., Weinrach, J. C., Ertl, G. A., Toth, K., McGee, D. L., and Hruby, V. J., 1991, Induction of skin tanning by the subcutaneous administration of a potent synthetic melanotropin, J. Am. Med. Assoc. 266:2730–2736.
Moore, K. L., 1982, The circulatory system, in: The Developing Human, 3rd ed., pp. 298–322 and 333–343, Saunders, Philadelphia.
Mountjoy, K. G., Mortrud, M. T., Low, M. J., Simerly, R. B., and Cone, R. D., 1994, Localization of the melanocortin-4 receptor (MC4-R) in neuro endocrine and autonomic control circuits in the brain, Mol Endocrinol. 8:1298–1308.
O’Donohue, T. L., and Dorsa, D. M., 1982, The opiomelanotropinergic neuronal and endocrine system, Peptides 3:353–395.
Robbins, L. S., Nadeau, J. H., Johnson, K. R., Kelly, M. A., Roselli-Rehfuss, L., Baack, E., Mountjoy, K. G., and Cone, R. D., 1993, Pigmentation phenotypes of variant extension locus alleles result from point mutations that alter MSH receptor function, Cell 72:827–834.
Roselli-Rehfuss, L., Mountjoy, K. G., Robbins, L. S., Mortrud, M. T., Low, M. J., Tatro, J. B., Entwistle, M. L., Simedy, R. B., and Cone, R. D., 1993, Identification of a receptor for melanotropin and other proopiomelanocortin peptides in the hypothalamus and limbic system, Proc. Natl Acad. Sci. USA 90:8856–8860.
Sawyer, T. K., Sanfilippo, P. J., Hruby, V. J., Engel, M. H., Heward, C. B., Burnett, J. B., and Hadley, M. E., 1980, 4-Norleucine, 7-D-phenylalanine-α-Melanocyte stimulating hormone: A highly potent melanotropin with ultralong biological activity, Proc. Natl. Acad. Sci. USA 77:5754–5758.
Sawyer, T. K., Hruby, V. J., Wilkes, B. C., Draelos, M. T, Hadley, M. E., and Bergsneider, M., 1982, Comparative biological activities of highly potent analogues of α-melanotropin(4–10), J. Med. Chem. 25:1022–1027.
Sawyer, T. K., Castrucci, A. M. L., Staples, D. J., Affholter, J. A., deVaux, A. E., Hruby, V. J., and Hadley, M. E., 1993, Structure-activity relationships of [Nle4, d-Phe7]α-MSH: Discovery of a tripeptidyl agonist exhibiting sustained biological activity, Ann. N. Y. Acad. Sci. 680:597–599.
Shaw, J. E., Chandrasekaran, S. K., Michaels, A. S., and Taskovict, L., 1975, Controlled transdermal delivery in vitro and in vivo, in: Animal Models in Dermatology (H.I. Maibach, ed.), pp. 138–146, Churchill-Livingstone, Edinburgh.
Smith, P. E., and Graeser, J. B., 1924, A differential response of the melanophore stimulant and oxytocic autocord of the posterior pituitary, Anat. Rec. 27:187.
Surendran, N., Ugwu, S. O., Sterling, E. J., and Blanchard, J., 1995a, A HPLC assay for the determination of [Nle4, d-Phe7]α-MSH analog (MT-I) in biological matrices, J. Chromatogr. 670:235–242.
Surendran, N., Ugwu, S. O., Nguyen, L. D., Sterling, E. J., Dorr, R. T., and Blanchard, J., 1995b, Absorption enhancement of Melanotan-I: Comparison of the Caco-2 and rat in situ models, Drug Delivery 2:49–55.
Surendran, N., Bhardwaj, R., Ugwu, S. O., Sterling, E. J., and Blanchard, J., 1996, Partitioning properties and degradation kinetics of [Nle4, D-Phe7]α-MSH analog Melanotan-I (MT-I), Int. J. Pharm. 135:81–89.
Ugwu, S. O., and Blanchard, J., 1992, High-performance liquid chromatographic assay for the α-Melanotropin(4–10) fragment analog (Melanotan-II) in rat plasma, J. Chromatogr. 584:175–180.
Ugwu, S. O., Lan, E.-L., Sharma, S., Hruby, V., and Blanchard, J., 1994a, Kinetics of degradation of a cyclic lactam analog of α-Melanotropin (MT-II) in aqueous solution, Int. J. Pharm. 102:193–199.
Ugwu, S. O., Blanchard, J., Nguyen, L. D., Hadley, M. E., and Dorr, R. T., 1994b, Comparison of HPLC and bioassay methods for plasma Melanotan-II (MT-II) determination: Application to pharmacokinetic study in rats, Biopharm. Drug Dispos. 15:383–390.
Ugwu, S. O., Blanchard, J., Dorr, R. T., Levine, N., Brooks, C., Hadley, M., Aikin, M., and Hruby, V., 1997, Skin pigmentation and pharmacokinetics of Melanotan-I in humans, Biopharm. Drug Dispos. 18:259–269.
Wilson, J. G., 1965, Methods for administering agents and detecting malformations in experimental animals, in: Teratology Principles and Techniques (J. G. Wilson and T. Warkan, eds.), pp. 262–277, University of Chicago Press, Chicago.
Wilson, J. G., 1965b, Developmental abnormalities, rats, in: Pathology of Laboratory Animals (V. Benirschke, F. M. Garner, and T. C. Jones, eds.). Volume 2, pp. 1840–1847, Springer-Verlag, Berlin.
Witchi, E., 1962, Development: Rat, in: Growth, Including Reproduction and Morphologic Development (P. L. Altman and D. S. Dittmer, eds.), pp. 304–314, FASEB, Washington, DC.
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Hadley, M.E. et al. (2002). Discovery and Development of Novel Melanogenic Drugs. In: Borchardt, R.T., Freidinger, R.M., Sawyer, T.K., Smith, P.L. (eds) Integration of Pharmaceutical Discovery and Development. Pharmaceutical Biotechnology, vol 11. Springer, Boston, MA. https://doi.org/10.1007/0-306-47384-4_25
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