Etymology
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en- (1)

word-forming element meaning "in; into," from French and Old French en-, from Latin in- "in, into" (from PIE root *en "in"). Typically assimilated before -p-, -b-, -m-, -l-, and -r-. Latin in- became en- in French, Spanish, Portuguese, but remained in- in Italian.

Also used with native and imported elements to form verbs from nouns and adjectives, with a sense "put in or on" (encircle), also "cause to be, make into" (endear), and used as an intensive (enclose). Spelling variants in French that were brought over into Middle English account for parallels such as ensure/insure, and most en- words in English had at one time or another a variant in in-, and vice versa.

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pro- 

word-forming element meaning "forward, forth, toward the front" (as in proclaim, proceed); "beforehand, in advance" (prohibit, provide); "taking care of" (procure); "in place of, on behalf of" (proconsul, pronoun); from Latin pro (adv., prep.) "on behalf of, in place of, before, for, in exchange for, just as," which also was used as a first element in compounds and had a collateral form por-.

Also in some cases from cognate Greek pro "before, in front of, sooner," which also was used in Greek as a prefix (as in problem). Both the Latin and Greek words are from PIE *pro- (source also of Sanskrit pra- "before, forward, forth;" Gothic faura "before," Old English fore "before, for, on account of," fram "forward, from;" Old Irish roar "enough"), extended form of root *per- (1) "forward," hence "in front of, before, toward, near," etc.

The common modern sense of "in favor of, favoring" (pro-independence, pro-fluoridation, pro-Soviet, etc.) was not in classical Latin and is attested in English from early 19c.

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